NMR determination of the absolute configuration of a macrophomate synthaseinhibitor by using an axial chiral reagent

Authors
Fukui, H Fukushi, Y Ohashi, S Tahara, S
Citation
H. Fukui et al., NMR determination of the absolute configuration of a macrophomate synthaseinhibitor by using an axial chiral reagent, BIOS BIOT B, 65(8), 2001, pp. 1920-1923
Citations number
6
Categorie Soggetti
Agricultural Chemistry","Biochemistry & Biophysics
Journal title
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
ISSN journal
09168451 → ACNP
Volume
65
Issue
8
Year of publication
2001
Pages
1920 - 1923
Database
ISI
SICI code
0916-8451(200108)65:8<1920:NDOTAC>2.0.ZU;2-G
Abstract
Macrophomate synthase catalyzes an extraordinary four-step transformation f rom oxalacetate and 2-pyrone to macrophomic acid by an intermolecular Diels -Alder reaction. The absolute configuration of the most potent macrophomate synthase inhibitor; (-)-2-carboxylmethyl-1-methoxybicyclo[2.2.2]oct-5-ene- 2-carboxylic acid, was determined to be (1S, 2R, 4R) by using an axial chir al reagent.