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The Crocacins, Novel Antifungal and Cytotoxic Antibiotics from Chondromyces crocatus and Chondromyces pediculatus (Myxobacteria): Isolation and Structure Elucidation
Author(s) -
Jansen Rolf,
Washausen Peter,
Kunze Brigitte,
Reichenbach Hans,
Höfle Gerhard
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199905)1999:5<1085::aid-ejoc1085>3.0.co;2-g
Subject(s) - myxobacteria , chemistry , stereochemistry , polyketide , antifungal , residue (chemistry) , amide , antibiotics , combinatorial chemistry , bacteria , biochemistry , microbiology and biotechnology , biosynthesis , biology , enzyme , genetics
Four novel antifungal and highly cytotoxic metabolites, the crocacins A–D ( 1 – 4 ), were isolated in our screening of the myxobacterial genus Chondromyces from strains of C. crocatus and C. pediculatus . Crocacin A, B, and D ( 1 , 2 , and 4 ) are unusual dipeptides of glycine and a 6‐aminohexenoic or ‐hexadienoic acid, which is N ‐protected by a complex polyketide‐derived acyl residue. The latter is a multiply substituted phenylundecatrienoic acid, which is found as its primary amide crocacin C ( 3 ). Based on 1 H coupling constants, NOEs and MM + calculations the relative configuration of the asymmetric centers and their preferred conformation are proposed for the crocacins.