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Antibiotics from Gliding Bacteria, LXXVIII. Ripostatin A, B, and C: Isolation and Structure and Structure Elucidation of Novel Metabolites fromSorangium cellulosum

✍ Scribed by Augustiniak, Hermann ;Höfle, Gerhard ;Irschik, Herbert ;Reichenbach, Hans

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
657 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Three closely related new metabolites named ripostatins were isolated from the myxobacterium Sorangium cellulosum and their structures elucidated by spectroscopic methods. Two of them, ripostatin A (1a, b) and B (2a), are 14‐membered macrolides with an acetic acid and a phenylalkyl side chain, whereas the third metabolite ripostatin C (3a) is an acyclic derivative of ripostatin A. By application of the method of Helmchen the absolute stereochemistry could be determined as (11__R__,13__R__) for ripostatin A, 11__R__,13__S__,15__R__ for ripostatin B and 11__S__ for ripostatin C. The polyketide origin of A was revealed by feeding experiments with ^13^C‐labeled precursors demonstrating the incorporation of one molecule of phenylacetic acid derived from phenylalanine, one propionate unit, and ten acetate units.

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## Abstract For Abstract see ChemInform Abstract in Full Text.