155:
InChI=1S/C63H69N17O13S2/c1-11-28(3)43(74-51(83)46-31(6)93-59(77-46)47-32(7)91-56(78-47)41-27-95-61(73-41)48-33(8)92-57(79-48)40-26-94-60(72-40)42(80(9)10)19-16-20-66-63(64)65)49(81)75-44(29(4)12-2)58-71-38(24-89-58)54-69-36(22-87-54)52-68-37(23-86-52)53-70-39(25-88-53)55-76-45(30(5)90-55)50(82)67-35(62(84)85)21-34-17-14-13-15-18-34/h13-15,17-18,22-30,35,42-45H,11-12,16,19-21H2,1-10H3,(H,67,82)(H,74,83)(H,75,81)(H,84,85)(H4,64,65,66)/t28-,29-,30+,35-,42-,43-,44-,45-/m0/s1
87:
416:
262:
27:
594:
Arnison, Paul G.; Bibb, Mervyn J.; Bierbaum, Gabriele; Bowers, Albert A.; Bugni, Tim S.; Bulaj, Grzegorz; Camarero, Julio A.; Campopiano, Dominic J.; Challis, Gregory L.; Clardy, Jon; Cotter, Paul D.; Craik, David J.; Dawson, Michael; Dittmann, Elke; Donadio, Stefano; Dorrestein, Pieter C.; Entian,
595:
Karl-Dieter; Fischbach, Michael A.; Garavelli, John S.; Göransson, Ulf; Gruber, Christian W.; Haft, Daniel H.; Hemscheidt, Thomas K.; Hertweck, Christian; Hill, Colin; Horswill, Alexander R.; Jaspars, Marcel; Kelly, Wendy L.; Klinman, Judith P.; et al. (2013).
744:
Kalyon, Bahar; Helaly, Soleiman E.; Scholz, Romy; Nachtigall, Jonny; Vater, Joachim; Borriss, Rainer; SüSsmuth, Roderich D. (2011). "Plantazolicin a and B: Structure
Elucidation of Ribosomally Synthesized Thiazole/Oxazole Peptides from
468:
The exact mechanism of the association of the trimeric enzyme complex with the N-terminal leader peptide region is not yet understood; however, it is thought that the leader peptide is cleaved from the core peptide putatively by the
453:, a ribosomally-synthesized precursor peptide undergoes extensive post-translational modification, including cyclodehydrations and dehydrogenations, catalyzed by a trimeric enzyme complex. This process converts
179:
CC(C)(c1nc(co1)c2nc(co2)c3nc(co3)c4nc(co4)C5=N(C(O5)C)C(=O)N(Cc6ccccc6)C(=O)O)NC(=O)C((C)CC)NC(=O)c7c(oc(n7)c8c(oc(n8)c9csc(n9)c1c(oc(n1)c1csc(n1)(CCCNC(=N)N)N(C)C)C)C)C
838:
Banala, Srinivas; Ensle, Paul; Süssmuth, Roderich D. (2013). "Total
Synthesis of the Ribosomally Synthesized Linear Azole-Containing Peptide Plantazolicin a from
789:
Molohon, Katie J.; Melby, Joel O.; Lee, Jaeheon; Evans, Bradley S.; Dunbar, Kyle L.; Bumpus, Stefanie B.; Kelleher, Neil L.; Mitchell, Douglas A. (2011).
275:
597:"Ribosomally synthesized and post-translationally modified peptide natural products: Overview and recommendations for a universal nomenclature"
644:
Lee, S. W.; Mitchell, D. A.; Markley, A. L.; Hensler, M. E.; Gonzalez, D.; Wohlrab, A.; Dorrestein, P. C.; Nizet, V.; Dixon, J. E. (2008).
171:
791:"Structure Determination and Interception of Biosynthetic Intermediates for the Plantazolicin Class of Highly Discriminating Antibiotics"
695:
Scholz, R.; Molohon, K. J.; Nachtigall, J.; Vater, J.; Markley, A. L.; Sussmuth, R. D.; Mitchell, D. A.; Borriss, R. (2011).
270:
535:
Fan, Ben; Wang, Cong; Song, Xiaofeng; Ding, Xiaolei; Wu, Liming; Wu, Huijun; Gao, Xuewen; Borriss, Rainer (2018-10-16).
391:. The structure of PZN was solved later that year by two independent research groups, primarily through high-resolution
146:
524:
Proteomes - Bacillus velezensis (strain DSM 23117 / BGSC 10A6 / FZB42) (Bacillus amyloliquefaciens subsp. plantarum)
282:
355:
The significance of PZN stems from its narrow-spectrum antibiotic activity. Most antibiotics in clinical use are
697:"Plantazolicin, a Novel Microcin B17/Streptolysin S-Like Natural Product from Bacillus amyloliquefaciens FZB42"
363:
to these drugs is common. In contrast, PZN is antibacterial against only a small number of species, including
537:"Bacillus velezensis FZB42 in 2018: The Gram-Positive Model Strain for Plant Growth Promotion and Biocontrol"
507:
have been identified with similar gene clusters that have the potential to produce PZN-like molecules.
477:. Following leader peptide removal, the newly formed N-terminus undergoes methylation to yield an Nα,Nα
419:
The biosynthesis of plantazolicin (PZN) entails modification of a precursor peptide by several enzymes.
396:
387:
315:
491:
435:
then chemically alter the peptide to install its post-translational modifications, including several
356:
344:(RiPP); it can be classified further as a thiazole/oxazole-modified microcin (TOMM) or a linear
306:
107:
932:
424:
360:
63:
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400:
8:
947:
53:
879:"Thiazole/Oxazole-modified microcins: Complex natural products from ribosomal templates"
957:
903:
878:
815:
790:
721:
696:
672:
645:
621:
596:
571:
536:
385:
of PZN were first reported in 2008. The natural product was then isolated in 2011 from
365:
325:
132:
952:
942:
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423:
In bacteria, plantazolicin (PZN) is synthesized first as an unmodified peptide via
194:
497:
404:
334:
523:
465:
residues into thiazole and (methyl)oxazole heterocycles (as seen to the right).
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Except where otherwise noted, data are given for materials in their
646:"Discovery of a widely distributed toxin biosynthetic gene cluster"
470:
454:
428:
415:
86:
479:-dimethylarginine. This final modification results in mature PZN.
432:
349:
341:
330:
119:
458:
877:
Melby, Joel O.; Nard, Nathan J.; Mitchell, Douglas A. (2011).
443:
436:
378:
345:
338:
76:
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694:
319:
FZB42). PZN has specifically been identified as a selective
26:
643:
593:
339:
ribosomally synthesized and post-translationally modified
788:
837:
876:
359:, acting against a wide variety of bacteria, and
924:
449:Specifically, during the biosynthesis of PZN in
131:
650:Proceedings of the National Academy of Sciences
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62:
784:
782:
780:
492:Clavibacter michiganensis subsp. sepedonicus
403:studies of PZN were reported, including a
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902:
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671:
661:
620:
570:
552:
414:
844:Angewandte Chemie International Edition
925:
158:Key: SKALCVOFYPVXLA-UCYFTIMGSA-N
883:Current Opinion in Chemical Biology
122:
13:
14:
969:
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212:
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25:
410:
256:(at 25 °C , 100 kPa).
870:
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688:
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587:
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473:contained in the biosynthetic
224:
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200:
1:
510:
401:biomimetic chemical synthesis
7:
498:Corynebacterium urealyticum
10:
974:
895:10.1016/j.cbpa.2011.02.027
388:Bacillus amyloliquefaciens
372:
316:Bacillus amyloliquefaciens
749:amyloliquefaciensFZB42".
541:Frontiers in Microbiology
329:, the causative agent of
250:
187:
167:
142:
46:
38:
33:
24:
554:10.3389/fmicb.2018.02491
483:Other organisms such as
701:Journal of Bacteriology
663:10.1073/pnas.0801338105
856:10.1002/anie.201302266
420:
504:Brevibacterium linens
418:
361:antibiotic resistance
842:amyloliquefaciens".
795:ACS Chemical Biology
41:plantazolicin A, PZN
713:10.1128/JB.00784-10
399:. In 2013, various
311:Bacillus velezensis
246: g·mol
21:
613:10.1039/c2np20085f
442:and an N-terminal
421:
366:Bacillus anthracis
326:Bacillus anthracis
321:bactericidal agent
313:FZB42 (previously
283:Infobox references
19:
850:(36): 9518–9523.
807:10.1021/cb200339d
801:(12): 1307–1313.
763:10.1021/ol200809m
757:(12): 2996–2999.
656:(15): 5879–5884.
393:mass spectrometry
291:Chemical compound
289:
288:
88:Interactive image
16:Chemical compound
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486:Bacillus pumilus
397:NMR spectroscopy
305:produced by the
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195:Chemical formula
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446:dimethylation.
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323:active against
309:soil bacterium
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889:(3): 369–378.
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607:(1): 108–160.
601:Nat. Prod. Rep
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431:. A series of
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20:Plantazolicin
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451:B. velezensis
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295:Plantazolicin
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933:Bactericides
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475:gene cluster
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440:heterocycles
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411:Biosynthesis
386:
383:biosynthesis
376:
364:
354:
348:-containing
324:
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310:
298:
294:
293:
64:1354655-37-0
47:Identifiers
39:Other names
938:Antibiotics
425:translation
188:Properties
948:Oxazolines
927:Categories
511:References
303:antibiotic
235:Molar mass
99:ChemSpider
75:3D model (
54:CAS Number
958:Thiazoles
563:1664-302X
471:peptidase
463:threonine
133:139031015
953:Oxazoles
943:Peptides
913:21429787
864:23761292
840:Bacillus
825:21950656
771:21568297
747:Bacillus
731:20971906
682:18375757
631:23165928
581:30386322
547:: 2491.
455:cysteine
429:ribosome
381:for the
108:57643663
904:3947797
816:3241860
722:3019963
673:2311365
622:3954855
572:6198173
433:enzymes
427:at the
373:History
352:(LAP).
350:peptide
342:peptide
333:. This
331:anthrax
276:what is
274: (
120:PubChem
911:
901:
862:
823:
813:
769:
729:
719:
680:
670:
629:
619:
579:
569:
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459:serine
271:verify
268:
172:SMILES
34:Names
501:, and
444:amine
437:azole
379:genes
346:azole
337:is a
147:InChI
77:JSmol
909:PMID
860:PMID
821:PMID
767:PMID
727:PMID
678:PMID
627:PMID
577:PMID
559:ISSN
457:and
395:and
377:The
899:PMC
891:doi
852:doi
811:PMC
803:doi
759:doi
717:PMC
709:doi
705:193
668:PMC
658:doi
654:105
617:PMC
609:doi
567:PMC
549:doi
299:PZN
244:.47
242:336
123:CID
929::
907:.
897:.
887:15
885:.
881:.
858:.
848:52
846:.
819:.
809:.
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779:^
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222:13
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210:69
204:63
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660::
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611::
583:.
551::
545:9
461:/
297:(
266:N
240:1
228:2
225:S
219:O
213:N
207:H
201:C
79:)
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