811:
has shown to bind tightly to Cu, whereas other divalent ions are only loosely bound. The tridentate character contributes to this selectivity. The fourth coordination site on the copper is saturated by an oppositely arranged pyridine nucleobase. The asymmetric metal base pairing system is orthogonal to the Watson-Crick base pairs. Another example of an artificial nucleobase is that with hydroxypyridone nucleobases, which are able to bind Cu inside the DNA duplex. Five consecutive copper-hydroxypyridone base pairs were incorporated into a double strand, which were flanked by only one natural nucleobase on both ends. EPR data showed that the distance between copper centers was estimated to be 3.7 ± 0.1 Å, while a natural B-type DNA duplex is only slightly larger (3.4 Å). The appeal for stacking metal ions inside a DNA duplex is the hope to obtain nanoscopic self-assembling metal wires, though this has not been realized yet.
541:
single- and in double-strands irrespective of surrounding bases. Also the oxo-homologue of tC called tC (both commercially available), 1,3-diaza-2-oxophenoxazine, has a quantum yield of 0.2 in double-stranded systems. However, it is somewhat sensitive to surrounding bases in single-strands (quantum yields of 0.14–0.41). The high and stable quantum yields of these base analogues make them very bright, and, in combination with their good base analogue properties (leaves DNA structure and stability next to unperturbed), they are especially useful in fluorescence anisotropy and FRET measurements, areas where other fluorescent base analogues are less accurate. Also, in the same family of cytosine analogues, a FRET-acceptor base analogue, tC
644:
537:
sensitivity of 2-AP to immediate surroundings is shared by other promising and useful fluorescent base analogues like 3-MI, 6-MI, 6-MAP, pyrrolo-dC (also commercially available), modified and improved derivatives of pyrrolo-dC, furan-modified bases and many other ones (see recent reviews). This sensitivity to the microenvironment has been utilized in studies of e.g. structure and dynamics within both DNA and RNA, dynamics and kinetics of DNA-protein interaction and electron transfer within DNA.
38:
658:
170:
743:
736:
3799:
729:
356:
228:
472:
651:
342:
594:
587:
622:(DAP) is used instead of adenine. Diaminopurine basepairs perfectly with thymine as it is identical to adenine but has an amine group at position 2 forming 3 intramolecular hydrogen bonds, eliminating the major difference between the two types of basepairs (weak A-T vs strong C-G). This improved stability affects protein-binding interactions that rely on those differences. Other combination include:
807:
a duplex; this is an example where a Watson-Crick basepair mismatch is stabilized by the formation of the metal-base pair. Another example of a metal complexing to natural nucleobases is the formation of A-Zn-T and G-Zn-C at high pH; Co and Ni also form these complexes. These are Watson-Crick base pairs where the divalent cation in coordinated to the nucleobases. The exact binding is debated.
795:. Metal-complexing with DNA can occur by the formation of non-canonical base pairs from natural nucleobases with participation by metal ions and also by the exchanging the hydrogen atoms that are part of the Watson-Crick base pairing by metal ions. Introduction of metal ions into a DNA duplex has shown to have potential magnetic or conducting properties, as well as increased stability.
277:. These nucleoside triphosphates possess a non-canonical sugar, dideoxyribose, which lacks the 3' hydroxyl group normally present in DNA and therefore cannot bond with the next base. The lack of the 3' hydroxyl group terminates the chain reaction as the DNA polymerases mistake it for a regular deoxyribonucleotide. Another chain-terminating analogue that lacks a 3' hydroxyl and mimics
888:. Earlier, the artificial strings of DNA did not encode for anything, but scientists speculated they could be designed to manufacture new proteins which could have industrial or pharmaceutical uses. Transcription of DNA containing unnatural base pairs and translation of corresponding mRNA were actually achieved recently. In November 2017, the same team at the
900:: four canonical and two artificially added, dNaM and dTPT3 (these two form a pair). The bacteria had two corresponding RNA bases included in two new codons, additional tRNAs recognizing these new codons (these tRNAs also contained two new RNA bases within their anticodons) and additional amino acids, enabling the bacteria to synthesize "unnatural" proteins.
491:) are linked to the ring linked to the sugar (in para) via a flexible arm, presumably extruding from the major groove of the helix. Due to low processivity of the nucleotides linked to bulky adducts such as florophores by s, the sequence is typically copied using a nucleotide with an arm and later coupled with a reactive fluorophore (indirect labelling):
254:). Although these oligonucleotides have a different backbone sugar—or, in the case of PNA, an amino acid residue in place of the ribose phosphate—they still bind to RNA or DNA according to Watson and Crick pairing while being immune to nuclease activity. They cannot be synthesized enzymatically and can only be obtained synthetically using
911:
in transcription and translation, for the site-specific incorporation of non-standard amino acids into proteins. In 2006, they created 7-(2-thienyl)imidazopyridine (Ds) and pyrrole-2-carbaldehyde (Pa) as a third base pair for replication and transcription. Afterward, Ds and 4--2-nitropyrrole (Px) was
540:
A newly developed and very interesting group of fluorescent base analogues that has a fluorescence quantum yield that is nearly insensitive to their immediate surroundings is the tricyclic cytosine family. 1,3-Diaza-2-oxophenothiazine, tC, has a fluorescence quantum yield of approximately 0.2 both in
806:
nucleobases that are brought together by Hg and forms a connected metal-base pair. This motif does not accommodate stacked Hg in a duplex due to an intrastrand hairpin formation process that is favored over duplex formation. Two thymines across from each other do not form a Watson-Crick base pair in
810:
A large variety of artificial nucleobases have been developed for use as metal base pairs. These modified nucleobases exhibit tunable electronic properties, sizes, and binding affinities that can be optimized for a specific metal. For example, a nucleoside modified with a pyridine-2,6-dicarboxylate
714:
is considered. xDNA contains expanded bases, in which a benzene ring has been added, which may pair with canonical bases, resulting in four additional possible base-pairs (xA-T, xT-A, xC-G, xG-C) with eight bases (or 16 bases if the unused arrangements are used). Another form of benzene added bases
706:
Universal bases may pair indiscriminately with any other base, but, in general, lower the melting temperature of the sequence considerably; examples include 2'-deoxyinosine (hypoxanthine deoxynucleotide) derivatives, nitroazole analogues, and hydrophobic aromatic non-hydrogen-bonding bases (strong
536:
The most commonly used and commercially available fluorescent base analogue, 2-aminopurine (2-AP), has a high-fluorescence quantum yield free in solution (0.68) that is considerably reduced (appr. 100 times but highly dependent on base sequence) when incorporated into nucleic acids. The emission
553:
In a cell, there are several non-canonical bases present: CpG islands in DNA (often methylated), all eukaryotic mRNA (capped with a methyl-7-guanosine), and several bases of rRNAs (methylated). Often, tRNAs are heavily modified postranscriptionally in order to improve their conformation or base
924:
The possibility has been proposed and studied, both theoretically and experimentally, of implementing an orthogonal system inside cells independent of the cellular genetic material in order to make a completely safe system, with the possible increase in encoding potentials. Several groups have
865:, which successfully replicated the unnatural base pairs through multiple generations. This is the first known example of a living organism passing along an expanded genetic code to subsequent generations. This was in part achieved by the addition of a supportive algal gene that expresses a
91:. An analogue may have any of these altered. Typically the analogue nucleobases confer, among other things, different base pairing and base stacking properties. Examples include universal bases, which can pair with all four canonical bases, and phosphate-sugar backbone analogues such as
626:
Isoguanine and isocytosine, which have their amine and ketone inverted compared to standard guanine and cytosine. They are not used probably as tautomers are problematic for base pairing, but isoC and isoG can be amplified correctly with PCR even in the presence of the 4 canonical
574:(Watson-Crick base pairing) via hydrogen bonds (amine with ketone, purine with pyrimidine). Adenine and 2-aminoadenine have one/two amine group(s), whereas thymine has two carbonyl groups, and cytosine and guanine are mixed amine and carbonyl (inverted in respect to each other).
141:
into bacterial DNA, and by including individual artificial nucleotides in the culture media, were able to passage the bacteria 24 times; they did not create mRNA or proteins able to use the artificial nucleotides. The artificial nucleotides featured 2 fused aromatic rings.
545:, has been developed. Together with tC as a FRET-donor this constitutes the first nucleic acid base analogue FRET-pair ever developed. The tC-family has, for example, been used in studies related to polymerase DNA-binding and DNA-polymerization mechanisms.
2589:
Buncel E, Boone C, Joly H, Kumar R, Norris AR (1985). "Metal ion-biomolecule interactions. XII. 1H and 13C NMR evidence for the preferred reaction of thymidine over guanosine in exchange and competition reactions with mercury (II) and methylmercury (II)".
457:, which base pairs to cytosine instead of thymine. Cytosine is deaminated to uracil, which base pairs with adenine instead of guanine. Deamination of guanine is not mutagenic. Nitrous acid-induced mutations also are induced to mutate back to wild-type.
181:
Investigation of possible scenarios of the origin of life: By testing different analogs, researchers try to answer the question of whether life's use of DNA and RNA was selected over time due to its advantages, or if they were chosen by arbitrary
418:) have been inserted into bacterial DNA but these genes did not template mRNA or induce protein synthesis. The artificial nucleotides featured two fused aromatic rings which formed a (d5SICS–dNaM) complex mimicking the natural (dG–dC) base pair.
160:
polymerase incorporates these compounds with non-canonical bases. These compounds are activated in the cells by being converted into nucleotides, they are administered as nucleosides since charged nucleotides cannot easily cross cell membranes.
3005:
Hirao I, Ohtsuki T, Fujiwara T, Mitsui T, Yokogawa T, Okuni T, Nakayama H, Takio K, Yabuki T, Kigawa T, Kodama K, Yokogawa T, Nishikawa K, Yokoyama S (February 2002). "An unnatural base pair for incorporating amino acid analogs into proteins".
238:'s 2' hydroxy group reacts with the phosphate linked 3' hydroxy group, making RNA too unstable to be used or synthesized reliably. To overcome this, a ribose analogue can be used. The most common RNA analogues are 2'-O-methyl-substituted RNA,
442:. If this happens during DNA replication, a guanine will be inserted as the opposite base analog, and in the next DNA replication, that guanine will pair with a cytosine. This results in a change in one base pair of DNA, specifically a
430:(5BU), the abnormal base found in the mutagenic nucleotide analog BrdU. When a nucleotide containing 5-bromouracil is incorporated into the DNA, it is most likely to pair with adenine; however, it can spontaneously shift into another
778:
In metal base-pairing, the Watson-Crick hydrogen bonds are replaced by the interaction between a metal ion with nucleosides acting as ligands. The possible geometries of the metal that would allow for duplex formation with two
1107:
Petersson B, Nielsen BB, Rasmussen H, Larsen IK, Gajhede M, Nielsen PE, Kastrup JS (February 2005). "Crystal structure of a partly self-complementary peptide nucleic acid (PNA) oligomer showing a duplex-triplex network".
693:(analogues with same number of atoms) such as the thymine analogue 2,4-difluorotoluene (F) or the adenine analogue 4-methylbenzimidazole (Z). An alternative hydrophobic pair could be isoquinoline and pyrrolopyridine
1632:
Wojciechowski F, Hudson RH (September 2008). "Fluorescence and hybridization properties of peptide nucleic acid containing a substituted phenylpyrrolocytosine designed to engage
Guanine with an additional H-bond".
3049:
Hirao I, Kimoto M, Mitsui T, Fujiwara T, Kawai R, Sato A, Harada Y, Yokoyama S (September 2006). "An unnatural hydrophobic base pair system: site-specific incorporation of nucleotide analogs into DNA and RNA".
1604:
Berry DA, Jung KY, Wise DS, Sercel AD, Pearson WH, Mackie H, Randolph JB, Somers RL (2004). "Pyrrolo-dC and pyrrolo-C: fluorescent analogs of cytidine and 2 '-deoxycytidine for the study of oligonucleotides".
452:
Additionally, nitrous acid (HNO2) is a potent mutagen that acts on replicating and non-replicating DNA. It can cause deamination of the amino groups of adenine, guanine and cytosine. Adenine is deaminated to
558:
can base pair with C, U, and even with A, whereas thiouridine (with A) is more specific than uracil (with a purine). Other common tRNA base modifications are pseudouridine (which gives its name to the
618:
The precise reason why there are only four nucleotides is debated, but there are several unused possibilities. Furthermore, adenine is not the most stable choice for base pairing: in
Cyanophage S-2L,
703:
Metal-coordinated bases, such as pairing between a pyridine-2,6-dicarboxylate (tridentate ligand) and a pyridine (monodentate ligand) through square planar coordination to a central copper ion.
562:), dihydrouridine (which does not stack as it is not aromatic), queuosine, wyosine, and so forth. Nevertheless, these are all modifications to normal bases and are not placed by a polymerase.
2907:
689:
However, correct DNA structure can form even when the bases are not paired via hydrogen bonding; that is, the bases pair thanks to hydrophobicity, as studies have shown with DNA
570:
Canonical bases may have either a carbonyl or an amine group on the carbons surrounding the nitrogen atom furthest away from the glycosidic bond, which allows them to
884:
which can be encoded by DNA, from the existing 20 amino acids to a theoretically possible 172, thereby expanding the potential for living organisms to produce novel
861:
containing natural T-A and C-G base pairs along with the best-performing UBP Romesberg's laboratory had designed and inserted it into cells of the common bacterium
630:
Diaminopyrimidine and xanthine, which bind like 2-aminoadenine and thymine but with inverted structures. This pair is not used as xanthine is a deamination product.
130:(TNA) and hexitol nucleic acids (HNA). Each of these is distinguished from naturally occurring DNA or RNA by changes to the backbone of the molecule. However, the
1886:
Wilhelmsson LM, Holmén A, Lincoln P, Nielsen PE, Nordén B (2001). "A highly fluorescent DNA base analogue that forms Watson-Crick base pairs with guanine".
2110:
Kirnos MD, Khudyakov IY, Alexandrushkina NI, Vanyushin BF (November 1977). "2-aminoadenine is an adenine substituting for a base in S-2L cyanophage DNA".
833:
that is created in a laboratory and does not occur in nature. In 2012, a group of
American scientists led by Floyd Romesberg, a chemical biologist at the
289:
replication. Another analogue in sequencing is a nucleobase analogue, 7-deaza-GTP and is used to sequence CG rich regions, instead 7-deaza-ATP is called
185:
As a tool to detect particular sequences: XNA can be used to tag and identify a wide range of DNA and RNA components with high specificity and accuracy;
1923:"Fluorescent properties of DNA base analogue tC upon incorporation into DNA – negligible influence of neighbouring bases on fluorescence quantum yield"
1392:
3191:
Kimoto M, Yamashige R, Matsunaga K, Yokoyama S, Hirao I (May 2013). "Generation of high-affinity DNA aptamers using an expanded genetic alphabet".
1053:
1518:"Fluorescence studies of nucleotides and polynucleotides. I. Formycin, 2-aminopurine riboside, 2,6-diaminopurine riboside, and their derivatives"
907:
institute in Japan. In 2002, they developed an unnatural base pair between 2-amino-8-(2-thienyl)purine (s) and pyridine-2-one (y) that functions
707:
stacking effects). These are used as proof of concept and, in general, are not utilized in degenerate primers (which are a mixture of primers).
290:
3250:
Herdewijn P, Marlière P (June 2009). "Toward safe genetically modified organisms through the chemical diversification of nucleic acids".
2767:"Efficient and sequence-independent replication of DNA containing a third base pair establishes a functional six-letter genetic alphabet"
2210:
Taniguchi Y, Kool ET (July 2007). "Nonpolar isosteres of damaged DNA bases: effective mimicry of mutagenic properties of 8-oxopurines".
2881:
2679:
Lee JS, Latimer LJ, Reid RS (1993). "A cooperative conformational change in duplex DNA induced by Zn2+ and other divalent metal ions".
916:
selection (SELEX) and demonstrated the genetic alphabet expansion significantly augment DNA aptamer affinities to target proteins.
880:
The successful incorporation of a third base pair is a significant breakthrough toward the goal of greatly expanding the number of
3394:
1703:
Rist MJ, Marino JP (2002). "Fluorescent nucleotide base analogs as probes of nucleic acid structure, dynamics and interactions".
2511:
Aich P, Skinner RJ, Wettig SD, Steer RP, Lee JS (August 2002). "Long range molecular wire behaviour in a metal complex of DNA".
2714:
Tanaka K, Tengeiji A, Kato T, Toyama N, Shionoya M (February 2003). "A discrete self-assembled metal array in artificial DNA".
2063:"Structural and mechanistic basis for enhanced translational efficiency by 2-thiouridine at the tRNA anticodon wobble position"
1774:
2855:
2390:
Liu H, Gao J, Lynch SR, Saito YD, Maynard L, Kool ET (October 2003). "A four-base paired genetic helix with expanded size".
700:
Several fluorescent bases have also been made, such as the 2-amino-6-(2-thienyl)purine and pyrrole-2-carbaldehyde base pair.
912:
discovered as a high fidelity pair in PCR amplification. In 2013, they applied the Ds-Px pair to DNA aptamer generation by
510:
Thiol reactive: thiol-containing nucleotides react with the fluorophore linked to a reactive leaving group like maleimide.
2825:
2476:
Zhang HY, Calzolari A, Di Felice R (August 2005). "On the magnetic alignment of metal ions in a DNA-mimic double helix".
2061:
Rodriguez-Hernandez A, Spears JL, Gaston KW, Limbach PA, Gamper H, Hou YM, Kaiser R, Agris PF, Perona JJ (October 2013).
1730:
Wilson JN, Kool ET (December 2006). "Fluorescent DNA base replacements: Reporters and sensors for biological systems".
507:
dyes, which contain a reactive leaving group like succinimidyl ester (NHS). Base-pairing amino groups are not affected.
131:
2617:
Ono A, Togashi H (August 2004). "Highly selective oligonucleotide-based sensor for mercury(II) in aqueous solutions".
1080:
3480:
2021:"Nucleic acid base analog FRET-pair facilitating detailed structural measurements in nucleic acid containing systems"
1972:"Characterization and use of an unprecedentedly bright and structurally non-perturbing fluorescent DNA base analogue"
1299:
Summerton J (December 1999). "Morpholino antisense oligomers: the case for an RNase H-independent structural type".
3767:
1668:
Greco NJ, Tor Y (August 2005). "Simple fluorescent pyrimidine analogues detect the presence of DNA abasic sites".
3772:
857:
that form a d5SICS–dNaM complex or base pair in DNA. In 2014, the same team reported that they had synthesized a
516:-linked nucleotides rely on the same indirect labelling principle (and fluorescent streptavidin) and are used in
2932:
Zhang Y, Ptacin JL, Fischer EC, Aerni HR, Caffaro CE, San Jose K, Feldman AW, Turner CR, Romesberg FE (2017).
3669:
3555:
2652:
Meggers E, Holland PL, Tolman WB, Romesberg FE, Schultz PG (2000). "A Novel Copper-Mediated DNA Base Pair".
2554:
Clever GH, Polborn K, Carell T (2005). "Ein hochgradig DNA-Duplex-stabilisierendes Metall-Salen-Basenpaar".
892:
that first introduced two extra nucleobases into bacterial DNA reported having constructed a semi-synthetic
3234:
311:
may have been preceded by an "RNA-like world" where other nucleic acids with a different backbone, such as
193:
1256:
Summerton J, Weller D (June 1997). "Morpholino antisense oligomers: design, preparation, and properties".
3823:
3782:
3777:
3762:
3387:
17:
889:
834:
3095:"An unnatural base pair system for efficient PCR amplification and functionalization of DNA molecules"
3838:
1023:
950:
allowing the translation of only orthogonal mRNA with a matching altered Shine-Dalgarno sequence; and
525:
255:
3843:
2765:
Malyshev DA, Dhami K, Quach HT, Lavergne T, Ordoukhanian P, Torkamani A, Romesberg FE (July 2012).
2441:
Wettig SD, Lee JS (2003). "Thermodynamic investigation of M-DNA: a novel metal ion–DNA complex".
947:
866:
1970:
Sandin P, Börjesson K, Li H, Mårtensson J, Brown T, Wilhelmsson LM, Albinsson B (January 2008).
1459:
Malyshev DA, Dhami K, Lavergne T, Chen T, Dai N, Foster JM, Corrêa IR, Romesberg FE (May 2014).
873:
bacteria. Then, the natural bacterial replication pathways use them to accurately replicate the
3828:
3802:
3495:
3380:
820:
188:
As an enzyme acting on DNA, RNA and XNA substrates - XNA has been shown to have the ability to
837:
in San Diego, California, published that his team had designed two unnatural base pairs named
3523:
1146:
Taylor AI, Pinheiro VB, Smola MJ, Morgunov AS, Peak-Chew S, Cozens C, Weeks KM, Herdewijn P,
983:
954:
496:
443:
137:
In May 2014, researchers announced that they had successfully introduced two new artificial
3714:
3697:
3528:
2945:
2778:
2723:
2563:
2399:
2119:
1839:"Fluorescent analogs of biomolecular building blocks: design, properties, and applications"
1472:
1163:
854:
377:
316:
308:
302:
251:
243:
151:
111:
92:
3295:"The conserved active site motif A of Escherichia coli DNA polymerase I is highly mutable"
499:
contain a primary amine group on a linker that reacts with the amino-reactive dye such as
8:
3709:
3692:
3550:
3433:
869:
transporter which efficiently imports the triphosphates of both d5SICSTP and dNaMTP into
643:
239:
119:
3144:"Highly specific unnatural base pair systems as a third base pair for PCR amplification"
2988:
2949:
2782:
2727:
2567:
2403:
2123:
2019:
Börjesson K, Preus S, El-Sagheer AH, Brown T, Albinsson B, Wilhelmsson LM (April 2009).
1476:
1167:
802:. A well-documented example is the formation of T-Hg-T, which involves two deprotonated
383:
Naturally occurring bases can be divided into two classes according to their structure:
3603:
3598:
3473:
3359:
3275:
3216:
3168:
3143:
3142:
Yamashige R, Kimoto M, Takezawa Y, Sato A, Mitsui T, Yokoyama S, Hirao I (March 2012).
3119:
3094:
3075:
3031:
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2933:
2801:
2766:
2747:
2536:
2423:
2320:
2295:
2271:
2246:
2143:
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1996:
1971:
1947:
1922:
1863:
1838:
1819:
1586:
1493:
1460:
1434:
1368:
1335:
1281:
1233:
1208:
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1151:
320:
312:
270:
127:
123:
60:
2454:
2187:
2162:
1534:
1517:
1312:
3687:
3649:
3642:
3593:
3545:
3351:
3316:
3267:
3208:
3173:
3124:
3067:
3023:
2971:
2806:
2739:
2696:
2634:
2603:
2528:
2493:
2458:
2415:
2372:
2364:
2325:
2276:
2227:
2192:
2135:
2092:
2040:
2001:
1952:
1903:
1868:
1811:
1791:
1770:
1747:
1685:
1650:
1578:
1539:
1498:
1373:
1355:
1316:
1273:
1238:
1189:
1125:
1059:
1033:
998:
943:
936:
932:
259:
100:
3363:
3220:
3035:
2751:
2540:
2427:
2020:
1823:
1590:
1438:
1285:
3513:
3343:
3334:
Rackham O, Chin JW (August 2005). "A network of orthogonal ribosome x mRNA pairs".
3306:
3279:
3259:
3200:
3163:
3155:
3114:
3106:
3079:
3059:
3015:
2961:
2953:
2934:"A semi-synthetic organism that stores and retrieves increased genetic information"
2796:
2786:
2731:
2688:
2661:
2626:
2599:
2571:
2524:
2520:
2485:
2450:
2407:
2356:
2315:
2307:
2266:
2258:
2219:
2182:
2174:
2147:
2127:
2082:
2074:
2032:
1991:
1983:
1942:
1934:
1895:
1858:
1850:
1803:
1739:
1712:
1677:
1642:
1614:
1570:
1529:
1488:
1480:
1426:
1421:
1363:
1347:
1308:
1265:
1228:
1220:
1179:
1171:
1147:
1117:
1085:
657:
31:
742:
735:
3637:
3608:
1618:
728:
107:, the design of new-to-nature forms of life based on alternative biochemistries.
1351:
3729:
3632:
3449:
2771:
Proceedings of the
National Academy of Sciences of the United States of America
1574:
1397:
896:
bacteria able to make proteins using such DNA. Its DNA contained six different
650:
204:
2163:"A third base pair for the polymerase chain reaction: inserting isoC and isoG"
2078:
1807:
1430:
3817:
3664:
3654:
3535:
3490:
3468:
2368:
2344:
1921:
Sandin P, Wilhelmsson LM, Lincoln P, Powers VE, Brown T, Albinsson B (2005).
1716:
1359:
1269:
1048:
978:
973:
935:
artificial replication and transcription polymerases starting generally from
792:
758:
751:
680:
673:
666:
619:
609:
602:
427:
376:
For structures of the analogues that may be mentioned in the literature, see
189:
156:
Several nucleoside analogues are used as antiviral or anticancer agents. The
2791:
2735:
2411:
2343:
Atwell, Shane; Meggers, Eric; Spraggon, Glen; Schultz, Peter G. (Dec 2001).
1767:
Fluorescent
Analogs of Biomolecular Building Blocks: Design and Applications
593:
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2005:
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1502:
1377:
1320:
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788:
454:
177:
Nucleic acid analogues are used in molecular biology for several purposes:
96:
72:
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2700:
1987:
1543:
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3372:
3110:
2311:
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2139:
1938:
1038:
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138:
134:
proposes that a genetic molecule require a charged backbone to function.
104:
84:
3460:
3347:
3019:
2957:
2882:"First life forms to pass on artificial DNA engineered by US scientists"
2296:"Fluorescent probing for RNA molecules by an unnatural base-pair system"
1559:"Fluorescent pteridine nucleoside analogs: a window on DNA interactions"
1484:
1175:
37:
3719:
3428:
3423:
3418:
2109:
1018:
1013:
1008:
903:
Another demonstration of UBPs were achieved by Ichiro Hirao's group at
897:
881:
850:
826:
799:
517:
435:
387:
371:
361:
355:
282:
274:
247:
169:
115:
88:
45:
2665:
2489:
2360:
2262:
2247:"Unnatural substrate repertoire of A, B, and X family DNA polymerases"
2223:
2060:
2036:
1899:
1854:
1681:
1646:
1224:
1121:
390:
are six-membered heterocyclic with nitrogen atoms in position 1 and 3.
323:
existed, however, evidence for this hypothesis been called "tenuous".
3583:
3204:
3063:
2131:
1743:
1393:"Researchers Report Breakthrough in Creating Artificial Genetic Code"
780:
571:
484:
278:
227:
76:
2692:
1558:
471:
396:
are bicyclic, consisting of a pyrimidine fused to an imidazole ring.
3737:
3588:
3518:
2161:
Johnson SC, Sherrill CB, Marshall DJ, Moser MJ, Prudent JR (2004).
1301:
Biochimica et
Biophysica Acta (BBA) - Gene Structure and Expression
1209:"Molecular beacons of xeno-nucleic acid for detecting nucleic acid"
1028:
993:
690:
446:
341:
197:
3093:
Kimoto M, Kawai R, Mitsui T, Yokoyama S, Hirao I (February 2009).
2294:
Kimoto M, Mitsui T, Harada Y, Sato A, Yokoyama S, Hirao I (2007).
3742:
2908:"Scientists Add Letters to DNA's Alphabet, Raising Hope and Fear"
885:
874:
858:
803:
555:
500:
439:
3235:"Xenobiology: a new form of life as the ultimate biosafety tool"
3190:
601:
A GC basepair: purine carbonyl/amine forms three intermolecular
95:, which affect the properties of the chain (PNA can even form a
75:
are chains of nucleotides, which are composed of three parts: a
3757:
3752:
3702:
2826:"Scientists Create First Living Organism With 'Artificial' DNA"
1885:
1106:
968:
838:
672:
An X-DAP base: purine ketone/ketone forms three intermolecular
513:
431:
406:
393:
347:
235:
196:
DNA, RNA and other XNA molecules similar to the actions of RNA
80:
1920:
757:
An S-Pa base: purine thienyl/amine forms three intermolecular
3560:
2651:
2018:
1461:"A semi-synthetic organism with an expanded genetic alphabet"
904:
750:
A F-Z base: methylbenzimidazole does not form intermolecular
679:
A iG-iC base: purine amine/ketone forms three intermolecular
559:
157:
2342:
2160:
665:
A DAP-T base: purine amine/amine forms three intermolecular
3141:
1969:
1145:
1081:"Chemists Invent New Letters for Nature's Genetic Alphabet"
1043:
842:
711:
413:
3004:
2764:
213:
Investigation of the structural features of nucleic acids.
3622:
3443:
3092:
3048:
1458:
1419:
Callaway E (May 7, 2014). "First life with 'alien' DNA".
830:
798:
Metal complexing has been shown to occur between natural
286:
68:
64:
49:
41:
2713:
608:
An AT basepair: purine amine/- forms two intermolecular
331:
265:
2931:
2475:
825:
An unnatural base pair (UBP) is a designed subunit (or
2758:
2510:
2293:
71:, used in medicine and in molecular biology research.
715:
is yDNA, in which the base is widened by the benzene.
222:
27:
Compound analogous to naturally occurring RNA and DNA
2588:
2553:
1764:
1631:
1603:
710:The numbers of possible base pairs is doubled when
210:
Investigation of the mechanisms used by enzyme; and
953:Novel tRNA encoding non-natural aminoacids for an
929:Novel backbones and base pairs as discussed above;
3249:
2345:"Structure of a Copper-Mediated Base Pair in DNA"
1836:
554:pairing, in particular in or near the anticodon:
3815:
3292:
2513:Journal of Biomolecular Structure & Dynamics
2389:
1454:
1452:
1450:
1448:
1206:
1054:Artificially Expanded Genetic Information System
285:. Cordycepin is an anticancer drug that targets
1515:
1255:
2678:
2244:
1412:
1333:
548:
296:
63:(structurally similar) to naturally occurring
3388:
2209:
1445:
1334:Robertson, M. P.; Joyce, G. F. (2012-05-01).
1258:Antisense & Nucleic Acid Drug Development
1207:Wang Q, Chen L, Long Y, Tian H, Wu J (2013).
531:
2925:
2856:"Life engineered with expanded genetic code"
2154:
814:
783:nucleosides around a central metal atom are
3333:
3286:
2672:
1789:
1384:
1152:"Catalysts from synthetic genetic polymers"
3402:
3395:
3381:
3293:Shinkai A, Patel PH, Loeb LA (June 2001).
2616:
2103:
1837:Sinkeldam RW, Greco NJ, Tor Y (May 2010).
1729:
1702:
1340:Cold Spring Harbor Perspectives in Biology
99:). Nucleic acid analogues are also called
3310:
3167:
3118:
2965:
2800:
2790:
2440:
2319:
2270:
2186:
2086:
2056:
2054:
1995:
1946:
1862:
1792:"Fluorescent nucleic acid base analogues"
1533:
1516:Ward DC, Reich E, Stryer L (March 1969).
1492:
1367:
1298:
1232:
1183:
1072:
103:and represent one of the main pillars of
2849:
2847:
2823:
2349:Journal of the American Chemical Society
2251:Journal of the American Chemical Society
2245:Hwang GT, Romesberg FE (November 2008).
2212:Journal of the American Chemical Society
2025:Journal of the American Chemical Society
1670:Journal of the American Chemical Society
1667:
1635:Journal of the American Chemical Society
1418:
1110:Journal of the American Chemical Society
722:Novel basepairs with special properties
470:
226:
168:
36:
2905:
2899:
1556:
1390:
426:One of the most common base analogs is
14:
3816:
2879:
2873:
2051:
1078:
173:Common changes in nucleotide analogues
3376:
2989:'Unnatural' microbe can make proteins
2853:
2844:
845:. More technically, these artificial
332:Nucleobase structure and nomenclature
266:Other notable analogues used as tools
217:
2817:
1732:Organic & Biomolecular Chemistry
1141:
1139:
919:
164:
3299:The Journal of Biological Chemistry
2478:The Journal of Physical Chemistry B
1522:The Journal of Biological Chemistry
773:
24:
764:An xA-T base: same bonding as A-T
612:with pyrimidine carbonyl/carbonyl
223:Hydrolysis resistant RNA-analogues
132:polyelectrolyte theory of the gene
79:backbone, a pentose sugar, either
25:
3855:
3519:Micro
2443:Journal of Inorganic Biochemistry
1136:
326:
110:Artificial nucleic acids include
3798:
3797:
1563:Cell Biochemistry and Biophysics
741:
734:
727:
656:
649:
642:
592:
585:
354:
340:
231:Chemical structure of Morpholino
3474:precursor, heterogenous nuclear
3327:
3243:
3227:
3184:
3135:
3086:
3042:
2998:
2982:
2707:
2645:
2610:
2582:
2547:
2504:
2469:
2434:
2383:
2336:
2287:
2238:
2203:
2012:
1963:
1914:
1879:
1830:
1796:Quarterly Reviews of Biophysics
1783:
1758:
1723:
1696:
1661:
1625:
1597:
1550:
1509:
605:with pyrimidine amine/carbonyl
565:
475:Structure of aminoallyl-uridine
460:
307:It has been suggested that the
3604:Trans-acting small interfering
3568:Enhancer RNAs
3486:Transfer
2525:10.1080/07391102.2002.10506826
1336:"The Origins of the RNA World"
1327:
1292:
1249:
1200:
1100:
925:focused on different aspects:
669:with pyrimidine ketone/ketone
528:in medicine and biochemistry.
258:or, for PNA, other methods of
13:
1:
3491:Ribosomal
3469:Messenger
2681:Biochemistry and Cell Biology
2455:10.1016/S0162-0134(02)00624-4
1535:10.1016/S0021-9258(18)91833-8
1313:10.1016/s0167-4781(99)00150-5
1066:
683:with pyrimidine ketone/amine
637:Unused basepair arrangements
434:which pairs with a different
203:As a tool with resistance to
3252:Chemistry & Biodiversity
2604:10.1016/0162-0134(85)83009-9
2067:Journal of Molecular Biology
1765:Wilhelmsson and Tor (2016).
1619:10.1016/j.tetlet.2004.01.108
761:with pyrrole -/carbaldehyde
696:Other noteworthy basepairs:
676:with pyrimidine amine/amine
256:the phosphoramidite strategy
250:, and peptide nucleic acid (
7:
1790:Wilhelmsson LM (May 2010).
1352:10.1101/cshperspect.a003608
961:
549:Natural non-canonical bases
421:
297:Precursors to the RNA world
145:
10:
3860:
3670:Multicopy single-stranded
3514:Interferential
2824:Callaway E (May 7, 2014).
1079:Singer E (July 19, 2015).
890:Scripps Research Institute
835:Scripps Research Institute
818:
532:Fluorescent base analogues
464:
375:
369:
300:
149:
29:
3793:
3728:
3678:
3621:
3584:Guide
3576:
3504:
3459:
3442:
3411:
2906:Pollack A (May 7, 2014).
2079:10.1016/j.jmb.2013.05.018
1808:10.1017/s0033583510000090
1431:10.1038/nature.2014.15179
1391:Pollack A (May 7, 2014).
1024:Oligonucleotide synthesis
815:Unnatural base pair (UBP)
721:
636:
579:
3546:Small nuclear
2880:Sample I (May 7, 2014).
2854:Fikes BJ (May 8, 2014).
1717:10.2174/1385272023373914
1270:10.1089/oli.1.1997.7.187
948:Shine-Dalgarno sequences
877:containing d5SICS–dNaM.
400:Artificial nucleotides (
59:are compounds which are
30:Not to be confused with
3660:Genomic
3336:Nature Chemical Biology
2860:San Diego Union Tribune
2792:10.1073/pnas.1205176109
2736:10.1126/science.1080587
2412:10.1126/science.1088334
944:16S ribosomal sequences
867:nucleotide triphosphate
3763:Artificial chromosomes
3551:Small nucleolar
3312:10.1074/jbc.M011472200
3264:10.1002/cbdv.200900083
3148:Nucleic Acids Research
3099:Nucleic Acids Research
2631:10.1002/anie.200454172
2576:10.1002/ange.200501589
2300:Nucleic Acids Research
2167:Nucleic Acids Research
1976:Nucleic Acids Research
1927:Nucleic Acids Research
497:aminoallyl nucleotides
476:
232:
174:
57:Nucleic acid analogues
53:
3556:Small Cajal Body RNAs
1769:. New Jersey: Wiley.
984:Expanded genetic code
955:expanded genetic code
474:
230:
172:
128:threose nucleic acids
112:peptide nucleic acids
40:
3609:Subgenomic messenger
3524:Small interfering
3496:Transfer-messenger
3193:Nature Biotechnology
3008:Nature Biotechnology
2556:Angew. Chem. Int. Ed
1575:10.1385/cbb:34:2:257
849:bearing hydrophobic
524:Fluorophores find a
402:Unnatural Base Pairs
378:Simple aromatic ring
303:RNA world hypothesis
244:bridged nucleic acid
152:Nucleoside analogues
124:glycol nucleic acids
120:locked nucleic acids
3348:10.1038/nchembio719
3160:10.1093/nar/gkr1068
3020:10.1038/nbt0202-177
2995:. 29 November 2017.
2958:10.1038/nature24659
2950:2017Natur.551..644Z
2783:2012PNAS..10912005M
2728:2003Sci...299.1212T
2568:2005AngCh.117.7370C
2404:2003Sci...302..868L
2355:(49): 12364–12367.
2124:1977Natur.270..369K
1988:10.1093/nar/gkm1006
1557:Hawkins ME (2001).
1485:10.1038/nature13314
1477:2014Natur.509..385M
1176:10.1038/nature13982
1168:2015Natur.518..427T
821:Unnatural base pair
240:locked nucleic acid
3824:Molecular genetics
3638:Chloroplast
3481:modified Messenger
3444:Ribonucleic acids
3111:10.1093/nar/gkn956
2312:10.1093/nar/gkm508
2179:10.1093/nar/gkh522
1939:10.1093/nar/gki790
946:with altered anti-
853:feature two fused
580:Natural basepairs
477:
271:Dideoxynucleotides
233:
218:Backbone analogues
175:
122:(LNA), as well as
101:xeno nucleic acids
87:, and one of four
54:
3811:
3810:
3688:Xeno
3650:Complementary
3623:Deoxyribonucleic
3617:
3616:
3594:Small hairpin
2832:. Huffington Post
2722:(5610): 1212–13.
2666:10.1021/ja0025806
2619:Angewandte Chemie
2490:10.1021/jp052202t
2361:10.1021/ja011822e
2263:10.1021/ja803833h
2224:10.1021/ja071970q
2037:10.1021/ja806944w
1900:10.1021/ja0025797
1855:10.1021/cr900301e
1776:978-1-118-17586-6
1682:10.1021/ja052000a
1647:10.1021/ja804233g
1225:10.7150/thno.5935
1150:(February 2015).
1122:10.1021/ja0458726
1060:Xeno nucleic acid
1034:Synthetic biology
999:Molecular biology
937:T7 RNA polymerase
920:Orthogonal system
768:
767:
754:with toluene F/F
687:
686:
616:
615:
293:, an antibiotic.
260:peptide synthesis
165:Molecular biology
16:(Redirected from
3851:
3839:RNA interference
3801:
3800:
3778:Yeast
3599:Small temporal
3529:Piwi-interacting
3457:
3456:
3453:
3434:Deoxynucleotides
3397:
3390:
3383:
3374:
3373:
3368:
3367:
3331:
3325:
3324:
3314:
3305:(22): 18836–42.
3290:
3284:
3283:
3247:
3241:
3240:Vol 32(4):322–31
3231:
3225:
3224:
3205:10.1038/nbt.2556
3188:
3182:
3181:
3171:
3139:
3133:
3132:
3122:
3090:
3084:
3083:
3064:10.1038/nmeth915
3046:
3040:
3039:
3002:
2996:
2986:
2980:
2979:
2969:
2944:(7682): 644–47.
2929:
2923:
2922:
2920:
2918:
2903:
2897:
2896:
2894:
2892:
2877:
2871:
2870:
2868:
2866:
2851:
2842:
2841:
2839:
2837:
2821:
2815:
2814:
2804:
2794:
2777:(30): 12005–10.
2762:
2756:
2755:
2711:
2705:
2704:
2676:
2670:
2669:
2660:(43): 10714–15.
2654:J. Am. Chem. Soc
2649:
2643:
2642:
2614:
2608:
2607:
2586:
2580:
2579:
2551:
2545:
2544:
2508:
2502:
2501:
2484:(32): 15345–48.
2473:
2467:
2466:
2438:
2432:
2431:
2398:(5646): 868–71.
2387:
2381:
2380:
2340:
2334:
2333:
2323:
2291:
2285:
2284:
2274:
2257:(44): 14872–82.
2242:
2236:
2235:
2207:
2201:
2200:
2190:
2158:
2152:
2151:
2132:10.1038/270369a0
2118:(5635): 369–70.
2107:
2101:
2100:
2090:
2073:(20): 3888–906.
2058:
2049:
2048:
2016:
2010:
2009:
1999:
1967:
1961:
1960:
1950:
1918:
1912:
1911:
1888:J. Am. Chem. Soc
1883:
1877:
1876:
1866:
1843:Chemical Reviews
1834:
1828:
1827:
1787:
1781:
1780:
1762:
1756:
1755:
1744:10.1039/b612284c
1727:
1721:
1720:
1700:
1694:
1693:
1676:(31): 10784–85.
1665:
1659:
1658:
1641:(38): 12574–75.
1629:
1623:
1622:
1607:Tetrahedron Lett
1601:
1595:
1594:
1554:
1548:
1547:
1537:
1513:
1507:
1506:
1496:
1471:(7500): 385–88.
1456:
1443:
1442:
1416:
1410:
1409:
1407:
1405:
1388:
1382:
1381:
1371:
1331:
1325:
1324:
1296:
1290:
1289:
1253:
1247:
1246:
1236:
1204:
1198:
1197:
1187:
1162:(7539): 427–30.
1143:
1134:
1133:
1104:
1098:
1097:
1095:
1093:
1076:
774:Metal base-pairs
745:
738:
731:
719:
718:
660:
653:
646:
634:
633:
596:
589:
577:
576:
495:Amine reactive:
358:
344:
48:to the left and
32:degenerate bases
21:
3859:
3858:
3854:
3853:
3852:
3850:
3849:
3848:
3844:Gene expression
3814:
3813:
3812:
3807:
3789:
3730:Cloning vectors
3724:
3710:Locked
3674:
3624:
3613:
3572:
3500:
3447:
3446:
3438:
3407:
3401:
3371:
3332:
3328:
3291:
3287:
3248:
3244:
3232:
3228:
3189:
3185:
3154:(6): 2793–806.
3140:
3136:
3091:
3087:
3047:
3043:
3003:
2999:
2987:
2983:
2930:
2926:
2916:
2914:
2904:
2900:
2890:
2888:
2878:
2874:
2864:
2862:
2852:
2845:
2835:
2833:
2822:
2818:
2763:
2759:
2712:
2708:
2693:10.1139/o93-026
2687:(3–4): 162–68.
2677:
2673:
2650:
2646:
2625:(33): 4300–02.
2615:
2611:
2587:
2583:
2562:(44): 7370–74.
2552:
2548:
2509:
2505:
2474:
2470:
2439:
2435:
2388:
2384:
2341:
2337:
2306:(16): 5360–69.
2292:
2288:
2243:
2239:
2218:(28): 8836–44.
2208:
2204:
2159:
2155:
2108:
2104:
2059:
2052:
2031:(12): 4288–93.
2017:
2013:
1968:
1964:
1933:(16): 5019–25.
1919:
1915:
1894:(10): 2434–35.
1884:
1880:
1849:(5): 2579–619.
1835:
1831:
1788:
1784:
1777:
1763:
1759:
1738:(23): 4265–74.
1728:
1724:
1705:Curr. Org. Chem
1701:
1697:
1666:
1662:
1630:
1626:
1613:(11): 2457–61.
1602:
1598:
1555:
1551:
1514:
1510:
1457:
1446:
1417:
1413:
1403:
1401:
1389:
1385:
1332:
1328:
1297:
1293:
1254:
1250:
1205:
1201:
1144:
1137:
1105:
1101:
1091:
1089:
1077:
1073:
1069:
1064:
964:
922:
823:
817:
776:
770:
568:
551:
544:
534:
526:variety of uses
469:
463:
424:
381:
374:
368:
367:
366:
365:
364:
359:
351:
350:
345:
334:
329:
305:
299:
268:
225:
220:
167:
154:
148:
35:
28:
23:
22:
15:
12:
11:
5:
3857:
3847:
3846:
3841:
3836:
3831:
3826:
3809:
3808:
3806:
3805:
3794:
3791:
3790:
3788:
3787:
3786:
3785:
3780:
3775:
3770:
3760:
3755:
3750:
3745:
3740:
3734:
3732:
3726:
3725:
3723:
3722:
3717:
3715:Peptide
3712:
3707:
3706:
3705:
3700:
3695:
3693:Glycol
3684:
3682:
3676:
3675:
3673:
3672:
3667:
3662:
3657:
3652:
3647:
3646:
3645:
3640:
3629:
3627:
3619:
3618:
3615:
3614:
3612:
3611:
3606:
3601:
3596:
3591:
3586:
3580:
3578:
3574:
3573:
3571:
3570:
3565:
3564:
3563:
3558:
3553:
3548:
3538:
3533:
3532:
3531:
3526:
3521:
3510:
3508:
3502:
3501:
3499:
3498:
3493:
3488:
3483:
3478:
3477:
3476:
3465:
3463:
3454:
3440:
3439:
3437:
3436:
3431:
3426:
3421:
3415:
3413:
3409:
3408:
3405:nucleic acids
3400:
3399:
3392:
3385:
3377:
3370:
3369:
3326:
3285:
3258:(6): 791–808.
3242:
3226:
3183:
3134:
3085:
3052:Nature Methods
3041:
2997:
2981:
2924:
2912:New York Times
2898:
2872:
2843:
2816:
2757:
2706:
2671:
2644:
2609:
2592:Inorg. Biochem
2581:
2546:
2503:
2468:
2449:(1–2): 94–99.
2433:
2382:
2335:
2286:
2237:
2202:
2173:(6): 1937–41.
2153:
2102:
2050:
2011:
1962:
1913:
1878:
1829:
1782:
1775:
1757:
1722:
1695:
1660:
1624:
1596:
1549:
1528:(5): 1228–37.
1508:
1444:
1411:
1398:New York Times
1383:
1346:(5): a003608.
1326:
1291:
1248:
1219:(6): 395–408.
1199:
1135:
1116:(5): 1424–30.
1099:
1070:
1068:
1065:
1063:
1062:
1057:
1051:
1046:
1041:
1036:
1031:
1026:
1021:
1016:
1011:
1006:
1001:
996:
991:
986:
981:
976:
971:
965:
963:
960:
959:
958:
951:
940:
930:
921:
918:
855:aromatic rings
819:Main article:
816:
813:
775:
772:
766:
765:
762:
759:hydrogen bonds
755:
752:hydrogen bonds
747:
746:
739:
732:
724:
723:
717:
716:
708:
704:
701:
685:
684:
681:hydrogen bonds
677:
674:hydrogen bonds
670:
667:hydrogen bonds
662:
661:
654:
647:
639:
638:
632:
631:
628:
614:
613:
610:hydrogen bonds
606:
603:hydrogen bonds
598:
597:
590:
582:
581:
567:
564:
550:
547:
542:
533:
530:
522:
521:
511:
508:
465:Main article:
462:
459:
423:
420:
398:
397:
391:
370:Main article:
360:
353:
352:
346:
339:
338:
337:
336:
335:
333:
330:
328:
327:Base analogues
325:
301:Main article:
298:
295:
267:
264:
224:
221:
219:
216:
215:
214:
211:
208:
205:RNA hydrolysis
201:
186:
183:
166:
163:
150:Main article:
147:
144:
26:
9:
6:
4:
3:
2:
3856:
3845:
3842:
3840:
3837:
3835:
3832:
3830:
3829:Nucleic acids
3827:
3825:
3822:
3821:
3819:
3804:
3796:
3795:
3792:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3765:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3739:
3736:
3735:
3733:
3731:
3727:
3721:
3718:
3716:
3713:
3711:
3708:
3704:
3701:
3699:
3698:Threose
3696:
3694:
3691:
3690:
3689:
3686:
3685:
3683:
3681:
3677:
3671:
3668:
3666:
3663:
3661:
3658:
3656:
3655:Deoxyribozyme
3653:
3651:
3648:
3644:
3643:Mitochondrial
3641:
3639:
3636:
3635:
3634:
3631:
3630:
3628:
3626:
3620:
3610:
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3581:
3579:
3575:
3569:
3566:
3562:
3559:
3557:
3554:
3552:
3549:
3547:
3544:
3543:
3542:
3539:
3537:
3534:
3530:
3527:
3525:
3522:
3520:
3517:
3516:
3515:
3512:
3511:
3509:
3507:
3503:
3497:
3494:
3492:
3489:
3487:
3484:
3482:
3479:
3475:
3472:
3471:
3470:
3467:
3466:
3464:
3462:
3461:Translational
3458:
3455:
3451:
3445:
3441:
3435:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3416:
3414:
3410:
3406:
3398:
3393:
3391:
3386:
3384:
3379:
3378:
3375:
3365:
3361:
3357:
3353:
3349:
3345:
3342:(3): 159–66.
3341:
3337:
3330:
3322:
3318:
3313:
3308:
3304:
3300:
3296:
3289:
3281:
3277:
3273:
3269:
3265:
3261:
3257:
3253:
3246:
3239:
3236:
3230:
3222:
3218:
3214:
3210:
3206:
3202:
3199:(5): 453–57.
3198:
3194:
3187:
3179:
3175:
3170:
3165:
3161:
3157:
3153:
3149:
3145:
3138:
3130:
3126:
3121:
3116:
3112:
3108:
3104:
3100:
3096:
3089:
3081:
3077:
3073:
3069:
3065:
3061:
3058:(9): 729–35.
3057:
3053:
3045:
3037:
3033:
3029:
3025:
3021:
3017:
3014:(2): 177–82.
3013:
3009:
3001:
2994:
2990:
2985:
2977:
2973:
2968:
2963:
2959:
2955:
2951:
2947:
2943:
2939:
2935:
2928:
2913:
2909:
2902:
2887:
2883:
2876:
2861:
2857:
2850:
2848:
2831:
2827:
2820:
2812:
2808:
2803:
2798:
2793:
2788:
2784:
2780:
2776:
2772:
2768:
2761:
2753:
2749:
2745:
2741:
2737:
2733:
2729:
2725:
2721:
2717:
2710:
2702:
2698:
2694:
2690:
2686:
2682:
2675:
2667:
2663:
2659:
2655:
2648:
2640:
2636:
2632:
2628:
2624:
2620:
2613:
2605:
2601:
2597:
2593:
2585:
2577:
2573:
2569:
2565:
2561:
2557:
2550:
2542:
2538:
2534:
2530:
2526:
2522:
2518:
2514:
2507:
2499:
2495:
2491:
2487:
2483:
2479:
2472:
2464:
2460:
2456:
2452:
2448:
2444:
2437:
2429:
2425:
2421:
2417:
2413:
2409:
2405:
2401:
2397:
2393:
2386:
2378:
2374:
2370:
2366:
2362:
2358:
2354:
2350:
2346:
2339:
2331:
2327:
2322:
2317:
2313:
2309:
2305:
2301:
2297:
2290:
2282:
2278:
2273:
2268:
2264:
2260:
2256:
2252:
2248:
2241:
2233:
2229:
2225:
2221:
2217:
2213:
2206:
2198:
2194:
2189:
2184:
2180:
2176:
2172:
2168:
2164:
2157:
2149:
2145:
2141:
2137:
2133:
2129:
2125:
2121:
2117:
2113:
2106:
2098:
2094:
2089:
2084:
2080:
2076:
2072:
2068:
2064:
2057:
2055:
2046:
2042:
2038:
2034:
2030:
2026:
2022:
2015:
2007:
2003:
1998:
1993:
1989:
1985:
1982:(1): 157–67.
1981:
1977:
1973:
1966:
1958:
1954:
1949:
1944:
1940:
1936:
1932:
1928:
1924:
1917:
1909:
1905:
1901:
1897:
1893:
1889:
1882:
1874:
1870:
1865:
1860:
1856:
1852:
1848:
1844:
1840:
1833:
1825:
1821:
1817:
1813:
1809:
1805:
1802:(2): 159–83.
1801:
1797:
1793:
1786:
1778:
1772:
1768:
1761:
1753:
1749:
1745:
1741:
1737:
1733:
1726:
1718:
1714:
1711:(9): 775–93.
1710:
1706:
1699:
1691:
1687:
1683:
1679:
1675:
1671:
1664:
1656:
1652:
1648:
1644:
1640:
1636:
1628:
1620:
1616:
1612:
1608:
1600:
1592:
1588:
1584:
1580:
1576:
1572:
1569:(2): 257–81.
1568:
1564:
1560:
1553:
1545:
1541:
1536:
1531:
1527:
1523:
1519:
1512:
1504:
1500:
1495:
1490:
1486:
1482:
1478:
1474:
1470:
1466:
1462:
1455:
1453:
1451:
1449:
1440:
1436:
1432:
1428:
1424:
1423:
1415:
1400:
1399:
1394:
1387:
1379:
1375:
1370:
1365:
1361:
1357:
1353:
1349:
1345:
1341:
1337:
1330:
1322:
1318:
1314:
1310:
1307:(1): 141–58.
1306:
1302:
1295:
1287:
1283:
1279:
1275:
1271:
1267:
1264:(3): 187–95.
1263:
1259:
1252:
1244:
1240:
1235:
1230:
1226:
1222:
1218:
1214:
1210:
1203:
1195:
1191:
1186:
1181:
1177:
1173:
1169:
1165:
1161:
1157:
1153:
1149:
1142:
1140:
1131:
1127:
1123:
1119:
1115:
1111:
1103:
1088:
1087:
1082:
1075:
1071:
1061:
1058:
1055:
1052:
1050:
1049:Hachimoji DNA
1047:
1045:
1042:
1040:
1037:
1035:
1032:
1030:
1027:
1025:
1022:
1020:
1017:
1015:
1012:
1010:
1007:
1005:
1002:
1000:
997:
995:
992:
990:
987:
985:
982:
980:
979:Deoxyribozyme
977:
975:
974:Dark quencher
972:
970:
967:
966:
956:
952:
949:
945:
941:
938:
934:
931:
928:
927:
926:
917:
915:
910:
906:
901:
899:
895:
891:
887:
883:
878:
876:
872:
868:
864:
860:
856:
852:
848:
844:
840:
836:
832:
828:
822:
812:
808:
805:
801:
796:
794:
793:square planar
790:
786:
782:
771:
763:
760:
756:
753:
749:
748:
744:
740:
737:
733:
730:
726:
725:
720:
713:
709:
705:
702:
699:
698:
697:
694:
692:
682:
678:
675:
671:
668:
664:
663:
659:
655:
652:
648:
645:
641:
640:
635:
629:
625:
624:
623:
621:
620:diaminopurine
611:
607:
604:
600:
599:
595:
591:
588:
584:
583:
578:
575:
573:
563:
561:
557:
546:
538:
529:
527:
519:
515:
512:
509:
506:
502:
498:
494:
493:
492:
490:
486:
482:
473:
468:
458:
456:
450:
448:
445:
441:
437:
433:
429:
428:5-bromouracil
419:
417:
415:
410:
408:
404:(UBPs) named
403:
395:
392:
389:
386:
385:
384:
379:
373:
363:
357:
349:
343:
324:
322:
318:
314:
310:
304:
294:
292:
288:
284:
280:
276:
272:
263:
261:
257:
253:
249:
245:
241:
237:
229:
212:
209:
206:
202:
199:
195:
191:
187:
184:
180:
179:
178:
171:
162:
159:
153:
143:
140:
135:
133:
129:
125:
121:
117:
113:
108:
106:
102:
98:
94:
90:
86:
82:
78:
74:
73:Nucleic acids
70:
66:
62:
58:
52:to the right.
51:
47:
43:
39:
33:
19:
3773:Bacterial
3748:Lambda phage
3679:
3412:Constituents
3339:
3335:
3329:
3302:
3298:
3288:
3255:
3251:
3245:
3237:
3229:
3196:
3192:
3186:
3151:
3147:
3137:
3102:
3098:
3088:
3055:
3051:
3044:
3011:
3007:
3000:
2992:
2984:
2941:
2937:
2927:
2915:. Retrieved
2911:
2901:
2889:. Retrieved
2886:The Guardian
2885:
2875:
2863:. Retrieved
2859:
2834:. Retrieved
2829:
2819:
2774:
2770:
2760:
2719:
2715:
2709:
2684:
2680:
2674:
2657:
2653:
2647:
2622:
2618:
2612:
2595:
2591:
2584:
2559:
2555:
2549:
2519:(1): 93–98.
2516:
2512:
2506:
2481:
2477:
2471:
2446:
2442:
2436:
2395:
2391:
2385:
2352:
2348:
2338:
2303:
2299:
2289:
2254:
2250:
2240:
2215:
2211:
2205:
2170:
2166:
2156:
2115:
2111:
2105:
2070:
2066:
2028:
2024:
2014:
1979:
1975:
1965:
1930:
1926:
1916:
1891:
1887:
1881:
1846:
1842:
1832:
1799:
1795:
1785:
1766:
1760:
1735:
1731:
1725:
1708:
1704:
1698:
1673:
1669:
1663:
1638:
1634:
1627:
1610:
1606:
1599:
1566:
1562:
1552:
1525:
1521:
1511:
1468:
1464:
1420:
1414:
1402:. Retrieved
1396:
1386:
1343:
1339:
1329:
1304:
1300:
1294:
1261:
1257:
1251:
1216:
1213:Theranostics
1212:
1202:
1159:
1155:
1113:
1109:
1102:
1090:. Retrieved
1084:
1074:
1004:Nucleic acid
923:
913:
908:
902:
893:
879:
870:
862:
824:
809:
797:
789:dodecahedral
777:
769:
695:
688:
617:
569:
566:Base-pairing
552:
539:
535:
523:
481:fluorophores
478:
461:Fluorophores
455:hypoxanthine
451:
425:
412:
405:
401:
399:
382:
306:
273:are used in
269:
234:
176:
155:
136:
109:
97:triple helix
56:
55:
3768:P1-derived
3536:Antisense
3429:Nucleotides
3424:Nucleosides
3419:Nucleobases
3233:Schmidt M.
2830:Nature News
1039:Xenobiology
989:Fluorophore
898:nucleobases
882:amino acids
851:nucleobases
847:nucleotides
800:nucleobases
785:tetrahedral
505:Alexa Fluor
489:fluorescein
467:Fluorophore
388:Pyrimidines
139:nucleotides
105:xenobiology
89:nucleobases
85:deoxyribose
46:nucleobases
18:Base analog
3818:Categories
3720:Morpholino
3633:Organellar
3541:Processual
3506:Regulatory
3450:non-coding
3105:(2): e14.
1148:Holliger P
1067:References
1019:Nucleotide
1014:Nucleoside
1009:Nucleobase
827:nucleobase
518:Affymetrix
444:transition
436:nucleobase
372:Nucleobase
362:Pyrimidine
291:tubercidin
283:cordycepin
281:is called
275:sequencing
248:morpholino
116:Morpholino
3680:Analogues
3665:Hachimoji
3448:(coding,
3403:Types of
3238:Bioessays
2598:: 61–73.
2369:0002-7863
1360:1943-0264
781:bidentate
691:isosteres
572:base pair
520:DNAchips.
485:rhodamine
483:(such as
479:Commonly
309:RNA world
279:adenosine
242:(LNA) or
198:ribozymes
77:phosphate
61:analogous
44:with its
3803:Category
3738:Phagemid
3589:Ribozyme
3364:37181098
3356:16408021
3321:11278911
3272:19554563
3221:23329867
3213:23563318
3178:22121213
3129:19073696
3072:16929319
3036:22055476
3028:11821864
2993:BBC News
2976:29189780
2811:22773812
2752:22413126
2744:12595687
2639:15368377
2541:41568646
2533:12144356
2498:16852946
2463:12620678
2428:37244007
2420:14593180
2377:11734038
2330:17693436
2281:18847263
2232:17592846
2197:15051811
2097:23727144
2045:19317504
2006:18003656
1957:16147985
1908:11456897
1873:20205430
1824:10783202
1816:20478079
1752:17102869
1690:16076156
1655:18761442
1591:12134698
1583:11898867
1503:24805238
1439:86967999
1378:20739415
1321:10807004
1286:19372403
1243:23781286
1194:25470036
1130:15686374
1092:July 20,
1029:Ribozyme
994:Genetics
962:See also
914:in vitro
909:in vitro
886:proteins
560:TΨC loop
447:mutation
422:Mutagens
146:Medicine
3743:Plasmid
3280:8572188
3169:3315302
3120:2632903
3080:6494156
2967:5796663
2946:Bibcode
2802:3409741
2779:Bibcode
2724:Bibcode
2716:Science
2701:8398074
2564:Bibcode
2400:Bibcode
2392:Science
2321:2018647
2272:2675700
2148:4177449
2120:Bibcode
2088:4521407
1997:2248743
1948:1201328
1864:2868948
1544:5767305
1494:4058825
1473:Bibcode
1369:3331698
1278:9212909
1234:3677410
1185:4336857
1164:Bibcode
1056:(AEGIS)
894:E. coli
875:plasmid
871:E. coli
863:E. coli
859:plasmid
804:thymine
556:inosine
501:cyanine
440:guanine
394:Purines
246:(BNA),
182:chance;
126:(GNA),
114:(PNA),
3758:Fosmid
3753:Cosmid
3703:Hexose
3625:acids
3577:Others
3362:
3354:
3319:
3278:
3270:
3219:
3211:
3176:
3166:
3127:
3117:
3078:
3070:
3034:
3026:
2974:
2964:
2938:Nature
2809:
2799:
2750:
2742:
2699:
2637:
2539:
2531:
2496:
2461:
2426:
2418:
2375:
2367:
2328:
2318:
2279:
2269:
2230:
2195:
2188:390373
2185:
2146:
2140:413053
2138:
2112:Nature
2095:
2085:
2043:
2004:
1994:
1955:
1945:
1906:
1871:
1861:
1822:
1814:
1773:
1750:
1688:
1653:
1589:
1581:
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