Biosynthesis of acaterin: mechanism of the reaction catalyzed by dehydroacaterin reductase.
Dehydroacaterin reductase is an enzyme which catalyzes the final step of acaterin biosynthesis, that is, the reduction of the C-4/C-5 double bond of dehydroacaterin. The mechanism of the reduction was investigated with a cell-free preparation obtained from the acaterin-producing microorganism, Pseudomonas sp. A 92. Incubation of dehydroacaterin in the presence of [4,4- 2H2]NADPH or D2O followed by 2H NMR analysis of the resulting acaterin revealed that the deuterium atom from NADPH was incorporated into the C-5 position of acaterin, while the deuterium atom from D2O was introduced into the C-4 position. It was further demonstrated that the pro-R hydrogen at C-4 of NADPH was stereospecifically utilized in this reduction.
Nakano
Sayaka
S
Department of Chemistry and Materials Science, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.
Sakane
Wataru
W
Oinaka
Hiroshi
H
Fujimoto
Yoshinori
Y
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D017666:Deuterium Oxide / Q000737:chemistry; D005663:Furans / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure; D009249:NADP / Q000737:chemistry; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000737:chemistry*; D011549:Pseudomonas / Q000737:chemistry / Q000201:enzymology
D005663:Furans; C514598:dehydroacaterin; C077326:acaterin; D009249:NADP; D010088:Oxidoreductases; D017666:Deuterium Oxide; D015107:4-Butyrolactone