Premium
Antibiotics from Gliding Bacteria, LIV. Isolation and Structure Elucidation of Soraphen A 1α , a Novel Antifungal Macrolide from Sorangium cellulosum
Author(s) -
Bedorf Norbert,
Schomburg Dietmar,
Gerth Klaus,
Reichenbach Hans,
Höfle Gerhard
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301161
Subject(s) - chemistry , antifungal , absolute configuration , bacteria , fermentation , stereochemistry , crystal structure , crystallization , antibiotics , strain (injury) , combinatorial chemistry , microbiology and biotechnology , crystallography , biochemistry , organic chemistry , biology , genetics , anatomy
From the myxobacterium Sorangium cellulosum , strain So ce26, a novel group of highly active antifungal metabolites was isolated. Large‐scale production of the basic compound soraphen A 1α ( 1 ) was achieved by fermentation in the presence of the adsorber resin XAD‐16, extraction and crystallization. The 18‐membered macrolide structure of 1 was determined by spectroscopic methods. X‐ray crystal structure analysis revealed the absolute configuration of the ten asymmetric centers. According to proton coupling constants and difference NOE measurements the solution conformation in CDCl 3 and [D 6 ]DMSO is very similar to that in the crystal structure.