NMR determination of the absolute configuration of a macrophomate synthase inhibitor by using an axial chiral reagent.
Macrophomate synthase catalyzes an extraordinary four-step transformation from 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 chiral reagent.
Fukui
H
H
Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.
Fukushi
Y
Y
Ohashi
S
S
Oikawa
H
H
Tahara
S
S
D002264:Carboxylic Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009097:Multienzyme Complexes / Q000037:antagonists & inhibitors*; D011487:Protein Conformation; D013237:Stereoisomerism
C448766:2-carboxylmethyl-1-methoxybicyclo(2.2.2)oct-5-ene-2-carboxylic acid; D002264:Carboxylic Acids; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D009097:Multienzyme Complexes; C408144:macrophomate synthase