Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates
- 1 January 2000
- journal article
- Published by Oxford University Press (OUP) in Bioscience, Biotechnology, and Biochemistry
- Vol. 64 (3) , 530-538
- https://doi.org/10.1271/bbb.64.530
Abstract
Macrophomate synthase, which we have recently purified, catalyzes an unusual multistep transformation from 5-acetyl-4-methoxy-6-methyl-2-pyrone to 4-acetyl-3-methoxy-5-methyl-benzoic acid (macrophomic acid). To investigate the substrate diversity of the enzyme, 40 analogs of 2-pyrone were prepared and their relative efficiency was examined in the enzymatic conversions. The experimental results reveal the structural requirements of the substrates and the rough size of the enzyme active site, and eliminate the ambiguity caused by contamination by other enzymes in the whole-cell experiments.Keywords
This publication has 27 references indexed in Scilit:
- Substrate Specificity of 2-Deoxy-scyllo-inosose Synthase, the Starter Enzyme for 2-Deoxystreptamine Biosynthesis, toward Deoxyglucose-6-phosphates and Proposed MechanismBioscience, Biotechnology, and Biochemistry, 1998
- Biosynthesis of macrophomic acid: plausible involvement of intermolecular Diels–Alder reactionChemical Communications, 1997
- Dehydroquinate synthase: a sheep in wolf's clothing?Journal of the American Chemical Society, 1989
- Studies on metabolites of macrophoma commelinae. IV. Substrate specificity in the biotransformation of 2-pyrones to substituted benzoic acids.CHEMICAL & PHARMACEUTICAL BULLETIN, 1988
- Studies on metabolites of Macrophoma commelinae. III. Isolation of new metabolites and biosynthesis of macommelin group.CHEMICAL & PHARMACEUTICAL BULLETIN, 1988
- Stereochemical course of the cryptic elimination and cyclization steps in the reaction catalyzed by dehydroquinate synthaseJournal of the American Chemical Society, 1987
- Novel biotransformation of a 2-pyrone to a substituted benzoic acid.CHEMICAL & PHARMACEUTICAL BULLETIN, 1985
- X-ray crystal structure of pyrenocine A, a phytotoxin from Pyrenochaeta terrestris.Agricultural and Biological Chemistry, 1981
- Three new phytotoxins produced by Pyrenochaeta terrestris: Pyrenochaetic acids A,B and C.Agricultural and Biological Chemistry, 1981
- Phytotoxins produced by onion pink root fungus, Pyrenochaeta terrestris.Agricultural and Biological Chemistry, 1979