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Mixed Acetate‐Glycerol Biosynthesis and Formation of Benzoate Directly from Shikimate in Streptomyces sp.
Author(s) -
Hoffmann Luise,
Grond Stephanie
Publication year - 2004
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/ejoc.200400367
Subject(s) - shikimic acid , chemistry , biosynthesis , shikimate pathway , streptomyces , stereochemistry , glycerol , benzoic acid , streptomycetaceae , strain (injury) , biochemistry , actinomycetales , bacteria , enzyme , biology , anatomy , genetics
Biosynthetic studies of γ‐butyrolactones and 3‐furanylcarbonyl α‐ L ‐rhamnopyranosides reveal a new mixed biosynthetic pathway which provides different types of secondary metabolites. The new γ‐butyrolactone 1 is produced by Streptomyces sp. (strain GT 61150) together with (propenyl‐3‐furanyl)carbonyl α‐ L ‐rhamnopyranoside ( 2 ). Their structures were elucidated by chemical and spectroscopic methods. The biosynthesis of 1 and 2 was established by feeding 13 C‐labelled acetate and glycerol to Streptomyces sp. and resulted in a complete labelling pattern of 1 and 2 . Benzoyl α‐ L ‐rhamnopyranoside ( 3 ) is a rare compound of the rhamnoside family and is produced by Streptomyces griseoviridis (strain Tü 3634). [1,7‐ 13 C 2 ]Shikimic acid was fed to prove the hypothesis that the benzoyl unit is derived directly from shikimate and not from the plant‐like pathway with phenylalanine as an intermediate. The results exemplify a novel bacterial benzoate biosynthesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)