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Senfolomycin B

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Category Antibiotics
Catalog number BBF-02901
CAS 11031-56-4
Molecular Weight 702.68
Molecular Formula C29H38N2O16S

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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

It is produced by the strain of Str. ochrosporus NRRL 3146. It has the effect of anti-Gram-positive bacteria and mycobacterium, and also has the effect of anti-Staphylococcus aureus resistant to penicillin, streptomycin, neomycin, macrolide antibiotics. It also has weaker effect of anti-Gram-negative bacteria.

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Related CAS 114413-27-3
Synonyms Paulomycin F; 1-Cyclohexene-1-carboxylic acid, 5-[6-O-acetyl-3-O-[2,6-dideoxy-4-C-(1-hydroxyethyl)-3-O-methyl-α-L-xylo-hexopyranosyl]-4-O-[(2Z)-2-isothiocyanato-1-oxo-2-buten-1-yl]-β-D-allopyranosyl]-2-amino-5-hydroxy-3,6-dioxo-, (5S)-; Antibiotic LL RA 6950BB
IUPAC Name (3S)-3-[(2R,3R,4S,5R,6R)-6-(acetyloxymethyl)-3-hydroxy-4-[(2R,4S,5R,6S)-5-hydroxy-5-(1-hydroxyethyl)-4-methoxy-6-methyloxan-2-yl]oxy-5-[(Z)-2-isothiocyanatobut-2-enoyl]oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid
Canonical SMILES CC=C(C(=O)OC1C(OC(C(C1OC2CC(C(C(O2)C)(C(C)O)O)OC)O)C3(CC(=O)C(=N)C(=C3O)C(=O)O)O)COC(=O)C)N=C=S
InChI InChI=1S/C29H38N2O16S/c1-6-14(31-10-48)27(39)47-22-16(9-43-13(4)33)45-25(28(40)8-15(34)20(30)19(24(28)36)26(37)38)21(35)23(22)46-18-7-17(42-5)29(41,11(2)32)12(3)44-18/h6,11-12,16-18,21-23,25,30,32,35-36,40-41H,7-9H2,1-5H3,(H,37,38)/b14-6-,30-20?/t11?,12-,16+,17-,18-,21+,22+,23-,25+,28+,29+/m0/s1
InChI Key HPQDYNPAMCQCMI-AIBFWOTOSA-N
Appearance White Acicular Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Mycobacteria
Boiling Point 881.0±65.0°C (Predicted)
Density 1.59±0.1 g/cm3 (Predicted)
Solubility Soluble in Methanol, Dimethylformamide
1. Structural relationships between senfolomycins and paulomycins
A D Argoudelis, L Baczynskyj, S A Mizsak, F B Shilliday, P F Wiley J Antibiot (Tokyo). 1988 Sep;41(9):1212-22. doi: 10.7164/antibiotics.41.1212.
Senfolomycins A and B (Antimicrob. Agents Chemother.-1965: 828-831, 1966) are two antibacterial agents with physico-chemical and biological properties similar to those of paulomycin. Recent studies indicate that senfolomycin A (C29H36N2O16S, MW 700) has molecular composition and fast atom bombardment MS fragmentation pattern identical to those of paulomycin E. Extensive NMR work indicates that the two antibiotics, which have been separated by HPLC and TLC, differ only in the stereochemistry of the OCH3 group present in their respective sugar moieties. Indirect evident suggests that senfolomycin B is dihydrosenfolomycin A (C29H38N2O16S, MW 702) and in this respect it is related to paulomycin F. The proposed structures for senfolomycins A and B are discussed.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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