Structural relationships between senfolomycins and paulomycins

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 bombardmen...

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Bibliographic Details
Published in:	Journal of antibiotics Vol. 41; no. 9; p. 1212
Main Authors:	Argoudelis, A D, Baczynskyj, L, Mizsak, S A, Shilliday, F B, Wiley, P F
Format:	Journal Article
Language:	English
Published:	Japan 1988
Subjects:	Anti-Bacterial Agents Benzoquinones Chemical Phenomena Chemistry Chromatography, High Pressure Liquid Cyclohexenes Disaccharides - isolation & purification Disaccharides - pharmacology Enterococcus faecalis - drug effects Isothiocyanates Molecular Structure Staphylococcus aureus - drug effects Staphylococcus epidermidis - drug effects Streptococcus pneumoniae - drug effects Structure-Activity Relationship
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Summary:	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.
ISSN:	0021-8820
DOI:	10.7164/antibiotics.41.1212