Bottromycin B2
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| Category | Antibiotics |
| Catalog number | BBF-00166 |
| CAS | |
| Molecular Weight | 809.03 |
| Molecular Formula | C41H60N8O7S |
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Description
Bottromycin B2 is a peptide antibiotic produced by Streptomyces bottropensis. It has anti-gram-positive bacteria, mycobacteria, gram-negative bacteria (individually) and mycoplasma activity.
Specification
| IUPAC Name | methyl (3R)-3-[[(2S,3S)-2-[[(2S)-2-[[(6S,9S,12S)-6-tert-butyl-2,8,11-trioxo-9-propan-2-yl-1,4,7,10-tetrazabicyclo[10.3.0]pentadec-4-en-5-yl]amino]-3,3-dimethylbutanoyl]amino]-3-phenylbutanoyl]amino]-3-(1,3-thiazol-2-yl)propanoate |
| Canonical SMILES | CC(C)C1C(=O)NC(C(=NCC(=O)N2CCCC2C(=O)N1)NC(C(=O)NC(C(C)C3=CC=CC=C3)C(=O)NC(CC(=O)OC)C4=NC=CS4)C(C)(C)C)C(C)(C)C |
| InChI | InChI=1S/C41H60N8O7S/c1-23(2)30-36(53)48-32(40(4,5)6)34(43-22-28(50)49-19-14-17-27(49)35(52)45-30)47-33(41(7,8)9)38(55)46-31(24(3)25-15-12-11-13-16-25)37(54)44-26(21-29(51)56-10)39-42-18-20-57-39/h11-13,15-16,18,20,23-24,26-27,30-33H,14,17,19,21-22H2,1-10H3,(H,43,47)(H,44,54)(H,45,52)(H,46,55)(H,48,53)/t24-,26+,27-,30-,31-,32+,33+/m0/s1 |
| InChI Key | UVHKHTJWCYXSLC-PPZIYWBKSA-N |
Reference Reading
1. Characterization of the Stereoselective P450 Enzyme BotCYP Enables the In Vitro Biosynthesis of the Bottromycin Core Scaffold
Sebastian Adam, Laura Franz, Mohammed Milhim, Rita Bernhardt, Olga V Kalinina, Jesko Koehnke J Am Chem Soc. 2020 Dec 9;142(49):20560-20565. doi: 10.1021/jacs.0c10361. Epub 2020 Nov 28.
Bottromycins are ribosomally synthesized and post-translationally modified peptide natural product antibiotics that are effective against high-priority human pathogens such as methicillin-resistant Staphylococcus aureus. The total synthesis of bottromycins involves at least 17 steps, with a poor overall yield. Here, we report the characterization of the cytochrome P450 enzyme BotCYP from a bottromycin biosynthetic gene cluster. We determined the structure of a close BotCYP homolog and used our data to conduct the first large-scale survey of P450 enzymes associated with RiPP biosynthetic gene clusters. We demonstrate that BotCYP converts a C-terminal thiazoline to a thiazole via an oxidative decarboxylation reaction and provides stereochemical resolution for the pathway. Our data enable the two-pot in vitro production of the bottromycin core scaffold and may allow the rapid generation of bottromycin analogues for compound development.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
