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Andrastins A-C, New Protein Farnesyltransferase Inhibitors Produced by Penicillium Sp. FO-3929. II. Structure Elucidation and Biosynthesis

Andrastins A-C, New Protein Farnesyltransferase Inhibitors Produced by Penicillium Sp. FO-3929. II. Structure Elucidation and Biosynthesis

R Uchida, K Shiomi, J Inokoshi, T Sunazuka, H Tanaka, Y Iwai, H Takayanagi, S Omura

J Antibiot (Tokyo). 1996 May;49(5):418-24.

PMID: 8682717

Abstract:

The structures of new protein farnesyltransferase inhibitors, andrastins A-C, were elucidated. The cyclopentane ring of andrastins exhibited keto-enol tautomerism, which made the structure hard to elucidate. Therefore, the structure of andrastin A was elucidated by INADEQUATE and 13C-13C couplings using 13C-labeled andrastin A. The absolute configuration of the p-bromobenzoyl derivative of andrastin A was elucidated by X-ray crystallographic analysis and its skeleton was shown to be ent-5 alpha,14 beta-androstane. The biosynthesis of andrastin A was also studied by the incorporation of 13C-labeled acetates. Though the andrastins had a common androstane skeleton, they were biosynthesized from a sesquiterpene and a tetraketide.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP174232429	Andrastin A		174232-42-9	Price

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