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Chapter 9,610

The preparation of zaragozic acid A analogues by directed biosynthesis

Chen, T.S.; Petuch, B.; MacConnell, J.; White, R.; Dezeny, G.; Arison, B.; Bergstrom, J.D.; Colwell, L.; Huang, L.; Monaghan, R.L.

Journal of Antibiotics 47(11): 1290-1294

1994


ISSN/ISBN: 0021-8820
PMID: 8002393
DOI: 10.7164/antibiotics.47.1290
Accession: 009609442

Zaragozic acid A analogues are produced by an unidentified sterile fungus when it is exogenously supplied with 2-thiophenecarboxylic acid, 3-thiophenecarboxylic acid, 2-furoic acid, 2-fluorobenzoic acid, 3-fluorobenzoic acid, or 4-fluorobenzoic acid. The analogues carry 2-thiophenyl, 3-thiophenyl, 2-furyl, o-fluorophenyl, m-fluorophenyl, or p-fluorophenyl group, respectively, at C-6' of the C-1 alkyl side chain replacing the phenyl group of natural zaragozic acid A. All the new analogues of zaragozic acid A possess picomolar inhibitory activity against squalene synthase in vitro.

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