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Berninamycin D

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Berninamycin D
Category Bioactive by-products
Catalog number BBF-00573
CAS 161263-50-9
Molecular Weight 1007.98
Molecular Formula C45H45N13O13S
Purity >99% by HPLC

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Berninamycin D is a peptide antibiotic produced by Streptomyces bernensis NRRL 3572.

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Storage -20°C
IUPAC Name (17Z)-17-ethylidene-14-(1-hydroxyethyl)-27-(2-hydroxypropan-2-yl)-20,33-dimethyl-24,30,37,40-tetramethylidene-12,15,22,25,28,35,38-heptaoxo-19,32,42-trioxa-9-thia-3,13,16,23,26,29,36,39,44,45,46,47-dodecazahexacyclo[39.2.1.18,11.118,21.131,34.02,7]heptatetraconta-1(43),2(7),3,5,8(47),10,18(46),20,31(45),33,41(44)-undecaene-4-carboxamide
Canonical SMILES CC=C1C2=NC(=C(O2)C)C(=O)NC(=C)C(=O)NC(C(=O)NC(=C)C3=NC(=C(O3)C)C(=O)NC(=C)C(=O)NC(=C)C4=NC(=CO4)C5=C(C=CC(=N5)C(=O)N)C6=NC(=CS6)C(=O)NC(C(=O)N1)C(C)O)C(C)(C)O
InChI InChI=1S/C45H45N13O13S/c1-11-24-43-57-30(22(8)71-43)39(66)48-17(3)35(62)58-32(45(9,10)68)40(67)50-19(5)42-56-29(21(7)70-42)38(65)47-16(2)34(61)49-18(4)41-53-26(14-69-41)31-23(12-13-25(51-31)33(46)60)44-54-27(15-72-44)36(63)55-28(20(6)59)37(64)52-24/h11-15,20,28,32,59,68H,2-5H2,1,6-10H3,(H2,46,60)(H,47,65)(H,48,66)(H,49,61)(H,50,67)(H,52,64)(H,55,63)(H,58,62)/b24-11-
InChI Key ACYFBJUVNSGWDG-MYKKPKGFSA-N
Source Streptomyces sp.
Appearance White solid
Solubility Soluble in DMF or DMSO. Moderately soluble in methanol or ethanol. Poor water solubility.
1. Berninamycins B, C, and D, minor metabolites from Streptomyces bernensis
K L Rinehart, R C Lau J Antibiot (Tokyo) . 1994 Dec;47(12):1466-72. doi: 10.7164/antibiotics.47.1466.
Berninamycins B, C, and D were isolated from fermentation of Streptomyces bernensis and their structures were studied with 13C NMR and FAB mass spectrometry. Berninamycin B has a valine unit in its cyclic peptide loop instead of the beta-hydroxyvaline unit found in berninamycin A. Berninamycin D has two fewer dehydroalanine units attached to the carboxyl carbon of the pyridine ring. Based on FAB-MS results, berninamycin C is postulated to have only one dehydroalanine unit attached to the carboxyl carbon of pyridine. The biogenesis of berninamycins B, C, and D is discussed.

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