248:
173:
512:
35:
648:
409:
535:(T) as it is identical to adenine (A) but has an amine group at position 2 forming 3 intermolecular hydrogen bonds, eliminating the major difference between the two types of basepairs (weak:A-T and strong:C-G). This improved stability affects protein-binding interactions that rely on those differences.
1482:
Trzaska, C; Amand, S; Bailly, C; Leroy, C; Marchand, V; Duvernois-Berthet, E; Saliou, JM; Benhabiles, H; Werkmeister, E; Chassat, T; Guilbert, R; Hannebique, D; Mouray, A; Copin, MC; Moreau, PA; Adriaenssens, E; Kulozik, A; Westhof, E; Tulasne, D; Motorin, Y; Rebuffat, S; Lejeune, F (20 March 2020).
1089:
Pezo, Valerie; Jaziri, Faten; Bourguignon, Pierre-Yves; Louis, Dominique; Jacobs-Sera, Deborah; Rozenski, Jef; Pochet, Sylvie; Herdewijn, Piet; Hatfull, Graham F.; Kaminski, Pierre-Alexandre; Marliere, Philippe (30 April 2021). "Noncanonical DNA polymerization by aminoadenine-based siphoviruses".
1446:
Zouharova, D; Lipenska, I; Fojtikova, M; Kulich, P; Neca, J; Slany, M; Kovarcik, K; Turanek-Knotigova, P; Hubatka, F; Celechovska, H; Masek, J; Koudelka, S; Prochazka, L; Eyer, L; Plockova, J; Bartheldyova, E; Miller, AD; Ruzek, D; Raska, M; Janeba, Z; Turanek, J (29 February 2016). "Antiviral
1037:
Sleiman, Dona; Garcia, Pierre Simon; Lagune, Marion; Loc’h, Jerome; Haouz, Ahmed; Taib, Najwa; Röthlisberger, Pascal; Gribaldo, Simonetta; Marlière, Philippe; Kaminski, Pierre
Alexandre (30 April 2021). "A third purine biosynthetic pathway encoded by aminoadenine-based viral DNA genomes".
1141:
Zhou, Yan; Su, Xuexia; Wei, Yifeng; Cheng, Yu; Guo, Yu; Khudyakov, Ivan; Liu, Fuli; He, Ping; Song, Zhangyue; Li, Zhi; Gao, Yan; Ang, Ee Lui; Zhao, Huimin; Zhang, Yan; Zhao, Suwen (30 April 2021).
1540:
Kamiya, Y; Donoshita, Y; Kamimoto, H; Murayama, K; Ariyoshi, J; Asanuma, H (5 October 2017). "Introduction of 2,6-Diaminopurines into
Serinol Nucleic Acid Improves Anti-miRNA Performance".
903:
Kirnos, MD; Khudyakov, IY; Alexandrushkina, NI; Vanyushin, BF (November 1977). "2-aminoadenine is an adenine substituting for a base in S-2L cyanophage DNA".
1447:
activities of 2,6-diaminopurine-based acyclic nucleoside phosphonates against herpesviruses: In vitro study results with pseudorabies virus (PrV, SuHV-1)".
576:; expression of this system is toxic to the cell. The structures of MazZ (subtype 2) and PurZ are also determined, showing a possible link between PurZ and
416:
520:
947:
294:
1325:
Weckbecker, G; Cory, JG (1989). "Metabolic activation of 2,6-diaminopurine and 2,6-diaminopurine-2'-deoxyriboside to antitumor agents".
1276:
Burchenal, JH; Karnofsky, DA; Kingsley-Pillers, EM; Southam, CM; Myers, WP; Escher, GC; Craver, LF; Dargeon, HW; Rhoads, CP (May 1951).
570:
In August 2021, it was shown that DatZ, MazZ and PurZ are sufficient to replace some occurrence of A by Z in the bacterial genome of
1294:
1277:
967:
Czernecki, Dariusz; Legrand, Pierre; Tekpinar, Mustafa; Rosario, Sandrine; Kaminski, Pierre-Alexandre; Delarue, Marc (2021-04-23).
1585:"The use of diaminopurine to investigate structural properties of nucleic acids and molecular recognition between ligands and DNA"
1278:"The effects of the folic acid antagonists and 2,6-diaminopurine on neoplastic disease, with special reference to acute leukemia"
790:
Callahan, M.P.; Smith, K.E.; Cleaves, H.J.; Ruzica, J.; Stern, J.C.; Glavin, D.P.; House, C.H.; Dworkin, J.P. (11 August 2011).
776:
1201:"Characterization of a triad of genes in cyanophage S-2L sufficient to replace adenine by 2-aminoadenine in bacterial DNA"
762:
691:
262:
17:
423:
745:
DAP is used similarly to other nuclear acid analogues in the investigation of enzyme structures and mechanisms.
538:
Four papers published April 2021 further describes the use and production of the Z-base. It is now known that:
109:
969:"How cyanophage S-2L rejects adenine and incorporates 2-aminoadenine to saturate hydrogen bonding in its DNA"
205:
168:
735:
226:
129:
555:
responsible for handling the Z base occurs in the same gene cluster as the three aforementioned enzymes;
714:
virus, a economically important livestock disease. This base, in its free form, is able to correct UGA
528:
854:
545:
The Z base is produced by a pathway involving DUF550 (MazZ) and PurZ in S-2L and Vibrio phage PhiVC8;
690:
in mouse leukemia cells by 1989. Cancer cells are known to become resistant to DAP by losing their
243:
879:
1199:
Czernecki, Dariusz; Bonhomme, Frédéric; Kaminski, Pierre-Alexandre; Delarue, Marc (2021-08-05).
662:
506:
47:
542:
The S-2L phage avoids incorporating A bases in the genome by hydrolyzing dATP (DatZ enzyme);
1643:
1496:
1373:
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807:
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8:
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Shao, C; Deng, L; Henegariu, O; Liang, L; Stambrook, PJ; Tischfield, JA (20 June 2000).
1216:
1158:
1103:
1051:
984:
916:
811:
661:
Please expand the article to include this information. Further details may exist on the
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1016:
998:
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835:
715:
474:
1569:
1311:
1143:"A widespread pathway for substitution of adenine by diaminopurine in phage genomes"
742:
nucleic acid type) incorporating base Z instead of A show enhanced binding to RNA.
1638:
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387:
317:
1362:"Chromosome instability contributes to loss of heterozygosity in mice lacking p53"
194:
1460:
1508:
1366:
Proceedings of the
National Academy of Sciences of the United States of America
1235:
993:
552:
400:
1225:
948:"Some Viruses Have a Completely Different Genome to The Rest of Life on Earth"
792:"Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases"
588:
2-aminoadenine is produced in two steps. The enzyme MazZ (homologous to MazG,
1632:
1600:
1244:
1002:
455:
376:
161:
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1111:
1059:
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10.1002/1097-0142(195105)4:3<549::aid-cncr2820040308>3.0.co;2-j
1262:
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952:
883:
839:
711:
559:
524:
1618:
1485:"2,6-Diaminopurine as a highly potent corrector of UGA nonsense mutations"
1346:
1432:
1275:
932:
563:
494:
902:
777:"Some viruses thwart bacterial defenses with a unique genetic alphabet"
719:
687:
612:
589:
466:
345:
141:
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707:
399:
Except where otherwise noted, data are given for materials in their
271:
InChI=1S/C5H6N6/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H5,6,7,8,9,10,11)=
34:
683:
577:
447:
281:
InChI=1S/C5H6N6/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H5,6,7,8,9,10,11)
880:"DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests"
108:
739:
696:
572:
532:
490:
486:
451:
366:
181:
1445:
1198:
647:
1539:
966:
630:
The resulting dSMP is processed by host enzymes analogously to
120:
1418:
723:
686:
since as early as 1951. It is known to arrest progression of
470:
98:
855:"NASA Researchers: DNA Building Blocks Can Be Made in Space"
659:
about results of the altered H-bond strength in DNA and RNA.
231:
1419:
Kocharian, ShM; Chukanova, TI; Sukhodolets, VV (1977). "".
858:
803:
462:
381:
117 to 122 °C (243 to 252 °F; 390 to 395 K)
1088:
789:
482:
478:
473:, was published suggesting 2,6-diaminopurine and related
1036:
1481:
1359:
566:, based on the occurrence of the said gene cluster.
877:
1630:
193:
796:Proceedings of the National Academy of Sciences
531:). Diaminopurine base (Z) pairs perfectly with
84:
1324:
1140:
446:) is a compound once used in the treatment of
527:), diaminopurine is used instead of adenine (
493:, may have been formed extraterrestrially in
852:
846:
246:
171:
149:
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992:
829:
819:
213:
510:
450:. As the Z base, it is found instead of
783:
694:(APRT) function, a process shared with
558:The Z base is quite widespread in both
242:
14:
1631:
1582:
1027:
945:
274:Key: MSSXOMSJDRHRMC-UHFFFAOYSA-N=
162:
1194:
1192:
623:+ L-aspartate = (d)ADP + phosphate +
611:The enzyme PurZ (homologous to PurA,
128:
1134:
1082:
878:ScienceDaily Staff (9 August 2011).
755:
641:
454:(A) in the genetic material of some
853:Steigerwald, John (8 August 2011).
637:
625:2-aminodeoxyadenylosuccinate (dSMP)
461:In August 2011, a report, based on
361:White to yellow crystalline powder
184:
24:
1189:
871:
25:
1655:
729:
692:adenine phosphoribosyltransferase
646:
407:
335:
329:
33:
1576:
1533:
1475:
1439:
1412:
1353:
1318:
1269:
583:
403:(at 25 °C , 100 kPa).
960:
946:Bowler, Jacinta (4 May 2021).
939:
896:
769:
323:
13:
1:
1327:Advances in Enzyme Regulation
748:
500:
1583:Bailly, C (1 October 1998).
1461:10.1016/j.vetmic.2016.01.010
1339:10.1016/0065-2571(89)90068-x
722:, through the inhibition of
7:
736:anti-miRNA oligonucleotides
10:
1660:
1509:10.1038/s41467-020-15140-z
1236:10.1038/s41467-021-25064-x
994:10.1038/s41467-021-22626-x
682:2,6-DAP was used to treat
504:
1226:10.1101/2021.04.30.442174
720:translational readthrough
515:DiampurineT DNA base pair
397:
310:
290:
258:
68:
60:
46:
41:
32:
1449:Veterinary Microbiology
1387:10.1073/pnas.97.13.7405
1167:10.1126/science.abe4882
1112:10.1126/science.abe6542
1060:10.1126/science.abe6494
821:10.1073/pnas.1106493108
63:2-aminoadenine; 2,6-DAP
1601:10.1093/nar/26.19.4309
1589:Nucleic Acids Research
1554:10.1002/cbic.201700272
657:is missing information
516:
507:nucleic acid analogues
1489:Nature Communications
1205:Nature Communications
973:Nature Communications
763:"George H. Hitchings"
514:
703:DAP derivatives are
1501:2020NatCo..11.1509T
1378:2000PNAS...97.7405S
1217:2021NatCo..12.4710C
1159:2021Sci...372..512Z
1104:2021Sci...372..520P
1052:2021Sci...372..516S
985:2021NatCo..12.2420C
917:1977Natur.270..369K
812:2011PNAS..10813995C
738:(specifically, the
734:In bioengineering,
388:Solubility in water
353: g·mol
55:-purine-2,6-diamine
29:
716:nonsense mutations
592:) first performs:
580:versions of PurA.
517:
424:Infobox references
393:2.38 g/L at 20 °C
28:2,6-Diaminopurine
27:
1595:(19): 4309–4314.
1548:(19): 1917–1922.
1153:(6541): 512–516.
1098:(6541): 520–524.
1046:(6541): 516–520.
765:. nobelprize.org.
680:
679:
634:to produce dZTP.
615:) then performs:
475:organic molecules
436:2,6-diaminopurine
432:Chemical compound
430:
429:
227:CompTox Dashboard
110:Interactive image
18:2,6-diaminopurine
16:(Redirected from
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911:(5635): 369–70.
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638:In cellular life
632:adenylosuccinate
477:, including the
442:, also known as
414:
411:
410:
352:
337:
331:
325:
318:Chemical formula
302:Nc1nc(N)nc2c1nc2
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1427:(10): 1821–30.
1417:
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1372:(13): 7405–10.
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806:: 13995–13998.
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718:by encouraging
710:useful against
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521:cyanophage S-2L
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553:DNA polymerase
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505:Main article:
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444:2-aminoadenine
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401:standard state
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1288:(3): 549–69.
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779:. 5 May 2021.
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655:This article
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584:Biosynthesis
571:
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560:Siphoviridae
537:
529:host evasion
525:Siphoviridae
518:
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130:ChEMBL388596
69:Identifiers
61:Other names
52:
1644:Nucleobases
1542:ChemBioChem
1495:(1): 1509.
1211:(1): 4710.
979:(1): 2420.
564:Podoviridae
550:PrimPol/AEP
495:outer space
485:components
371:1.743 g/cm
358:Appearance
311:Properties
169:100.016.006
1633:Categories
1333:: 125–44.
889:2011-08-09
864:2011-08-10
749:References
708:antivirals
688:cell cycle
613:EC 6.3.4.4
590:EC 3.6.1.8
501:In viruses
467:meteorites
346:Molar mass
215:49P95BAU4Z
142:ChemSpider
97:3D model (
76:CAS Number
48:IUPAC name
1455:: 84–93.
1245:2041-1723
1183:233448821
1128:233448788
1076:233448787
1003:2041-1723
663:talk page
619:(d)ATP +
469:found on
458:viruses.
86:1904-98-9
1570:35619213
1562:28748559
1527:32198346
1469:26854349
1421:Genetika
1406:10861008
1312:31262125
1304:14839611
1263:34354070
1175:33926954
1120:33926956
1068:33926955
1021:33893297
840:21836052
705:in vitro
684:leukemia
578:archaeal
448:leukemia
1639:Purines
1619:9742229
1518:7083880
1497:Bibcode
1374:Bibcode
1347:2624171
1254:8342488
1221:bioRxiv
1213:Bibcode
1155:Bibcode
1147:Science
1100:Bibcode
1092:Science
1048:Bibcode
1040:Science
1012:8065100
981:Bibcode
913:Bibcode
831:3161613
808:Bibcode
740:serinol
697:E. coli
573:E. coli
533:thymine
491:guanine
487:adenine
452:adenine
440:2,6-DAP
417:what is
415: (
367:Density
351:150.145
182:PubChem
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905:Nature
838:
828:
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295:SMILES
121:ChEMBL
42:Names
1566:S2CID
1397:16558
1308:S2CID
1179:S2CID
1124:S2CID
1072:S2CID
724:FTSJ1
471:Earth
263:InChI
195:30976
151:28738
99:JSmol
1615:PMID
1558:PMID
1523:PMID
1465:PMID
1429:PMID
1402:PMID
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1300:PMID
1259:PMID
1241:ISSN
1171:PMID
1116:PMID
1064:PMID
1017:PMID
999:ISSN
929:PMID
859:NASA
836:PMID
804:PNAS
621:dGMP
605:dGMP
603:O =
597:dGTP
562:and
548:The
489:and
481:and
463:NASA
206:UNII
1605:PMC
1597:doi
1550:doi
1513:PMC
1505:doi
1457:doi
1453:184
1392:PMC
1382:doi
1335:doi
1290:doi
1249:PMC
1231:doi
1163:doi
1151:372
1108:doi
1096:372
1056:doi
1044:372
1007:PMC
989:doi
921:doi
909:270
826:PMC
816:doi
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599:+ H
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483:RNA
479:DNA
232:EPA
185:CID
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