ISSN:
0947-3440
Keywords:
Antibiotics
;
Sorangium cellulosum
;
Macrolides
;
Chivosazole
;
Biosynthesis
;
Natural products
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The myxobacterial metabolites chivosazole A (1) and its variants (2-6) were discovered in Sorangium cellulosum, strain So ce12, which simultaneously provides the broad spectrum antibiotic sorangicin as well as the sorangiolides and disorazoles. The antifungal and cytotoxic chivosazoles (1-6) are novel glycosides of 6-deoxyglucopyranose derivatives and an aglycon that includes an oxazole in its 31-membered macrolide ring. The aglycon itself, chivosazole F (7), was formed by strain So ce885 and showed similar activity antibiotic and cytotoxic.The biogenetic origin of the structural elements in chivosazole F (7) was studied by feeding experiments with [1-13C]-, [1,2-13C]acetate, [methyl-13C]methionine and [1-13C]serine. Accordingly, the aglycon 7 is a polyketide assembled by condensation of nine acetate units, one serine unit and a further seven acetate units. While C-1 of serine is part of the macrolide ring, the amido to hydroxyl part of the serine together with C-1 of the adjacent N-acetyl unit form the 1,3-oxazole ring. C- and O-methyl groups are derived from methionine.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970814
