Plantazolicin

Plantazolicin
Names
Other names
plantazolicin A, PZN
Identifiers
3D model (JSmol)
ChemSpider
  • 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
    Key: SKALCVOFYPVXLA-UCYFTIMGSA-N
  • CC[C@H](C)[C@@H](c1nc(co1)c2nc(co2)c3nc(co3)c4nc(co4)C5=N[C@@H](C(O5)C)C(=O)N[C@@H](Cc6ccccc6)C(=O)O)NC(=O)C([C@@H](C)CC)NC(=O)c7c(oc(n7)c8c(oc(n8)c9csc(n9)c1c(oc(n1)c1csc(n1)[C@H](CCCNC(=N)N)N(C)C)C)C)C
Properties
C63H69N17O13S2
Molar mass 1336.47 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Plantazolicin (PZN) is a natural antibiotic produced by the gram-positive soil bacterium Bacillus velezensis FZB42[1] (previously Bacillus amyloliquefaciens FZB42).[2] PZN has specifically been identified as a selective bactericidal agent active against Bacillus anthracis, the causative agent of anthrax. This natural product is a ribosomally synthesized and post-translationally modified peptide (RiPP); it can be classified further as a thiazole/oxazole-modified microcin (TOMM) or a linear azole-containing peptide (LAP).[3]

The significance of PZN stems from its narrow-spectrum antibiotic activity. Most antibiotics in clinical use are broad-spectrum, acting against a wide variety of bacteria, and antibiotic resistance to these drugs is common. In contrast, PZN is antibacterial against only a small number of species, including Bacillus anthracis.[citation needed]

  1. ^ Proteomes - Bacillus velezensis (strain DSM 23117 / BGSC 10A6 / FZB42) (Bacillus amyloliquefaciens subsp. plantarum)
  2. ^ Fan, Ben; Wang, Cong; Song, Xiaofeng; Ding, Xiaolei; Wu, Liming; Wu, Huijun; Gao, Xuewen; Borriss, Rainer (2018-10-16). "Bacillus velezensis FZB42 in 2018: The Gram-Positive Model Strain for Plant Growth Promotion and Biocontrol". Frontiers in Microbiology. 9: 2491. doi:10.3389/fmicb.2018.02491. ISSN 1664-302X. PMC 6198173. PMID 30386322.
  3. ^ 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, 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). "Ribosomally synthesized and post-translationally modified peptide natural products: Overview and recommendations for a universal nomenclature". Nat. Prod. Rep. 30 (1): 108–160. doi:10.1039/c2np20085f. PMC 3954855. PMID 23165928.