Mixed Acetate‐Glycerol Biosynthesis and Formation of Benzoate Directly from Shikimate in Streptomyces sp.

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 13C-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 Tu 3634). [1,7-13C2]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)

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