Stereospecific Incorporation of Hydrogen from Reduced Nicotinamide Adenine Dinucleotide Phosphate in Hydrogenation of (—)-Dehydrogriseofulvin to (+)-Griseofulvin by a Partially Purified Enzyme System of Streptomyces cinereocrocatus

Taiko Oda; Yoshihiro Sato

doi:10.1248/cpb.34.4635

Stereospecific Incorporation of Hydrogen from Reduced Nicotinamide Adenine Dinucleotide Phosphate in Hydrogenation of (—)-Dehydrogriseofulvin to (+)-Griseofulvin by a Partially Purified Enzyme System of Streptomyces cinereocrocatus

Taiko Oda, Yoshihiro Sato

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

The stereochemistry of reduced nicotinamide adenine dinucleotide phosphate (NADPH)-dependent hydrogenation was investigated by the conversion of (—)-dehydrogriseofulvin (1) to (+)-griseofulvin (2a) by the use of a partially purified enzyme system of Streptomyces cinereocrocatus in the presence of (4R)- or (4S)-[4-²H₁]NADPH. The results of 270 MHz proton nuclear magnetic resonance spectroscopy indicated that the origin of the 6’α-hydrogen of 2a is a hydride ion donated by pro-4R-hydrogen of NADPH.

Original language	English
Pages (from-to)	4635-4640
Number of pages	6
Journal	Chemical and Pharmaceutical Bulletin
Volume	34
Issue number	11
DOIs	https://doi.org/10.1248/cpb.34.4635
Publication status	Published - 1986 Jan 1

Keywords

(4R)-[4-2H1]NADPH
(4S)-[4-2H1]-NADPH
NADPH
Streptomyces cinereocrocatus
dehydrogriseofulvin
enzyme system
griseofulvin
hydrogenation

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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Stereospecific Incorporation of Hydrogen from Reduced Nicotinamide Adenine Dinucleotide Phosphate in Hydrogenation of (—)-Dehydrogriseofulvin to (+)-Griseofulvin by a Partially Purified Enzyme System of Streptomyces cinereocrocatus. / Oda, Taiko; Sato, Yoshihiro.
In: Chemical and Pharmaceutical Bulletin, Vol. 34, No. 11, 01.01.1986, p. 4635-4640.

Research output: Contribution to journal › Article › peer-review

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title = "Stereospecific Incorporation of Hydrogen from Reduced Nicotinamide Adenine Dinucleotide Phosphate in Hydrogenation of (—)-Dehydrogriseofulvin to (+)-Griseofulvin by a Partially Purified Enzyme System of Streptomyces cinereocrocatus",

abstract = "The stereochemistry of reduced nicotinamide adenine dinucleotide phosphate (NADPH)-dependent hydrogenation was investigated by the conversion of (—)-dehydrogriseofulvin (1) to (+)-griseofulvin (2a) by the use of a partially purified enzyme system of Streptomyces cinereocrocatus in the presence of (4R)- or (4S)-[4-2H1]NADPH. The results of 270 MHz proton nuclear magnetic resonance spectroscopy indicated that the origin of the 6{\textquoteright}α-hydrogen of 2a is a hydride ion donated by pro-4R-hydrogen of NADPH.",

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AU - Sato, Yoshihiro

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N2 - The stereochemistry of reduced nicotinamide adenine dinucleotide phosphate (NADPH)-dependent hydrogenation was investigated by the conversion of (—)-dehydrogriseofulvin (1) to (+)-griseofulvin (2a) by the use of a partially purified enzyme system of Streptomyces cinereocrocatus in the presence of (4R)- or (4S)-[4-2H1]NADPH. The results of 270 MHz proton nuclear magnetic resonance spectroscopy indicated that the origin of the 6’α-hydrogen of 2a is a hydride ion donated by pro-4R-hydrogen of NADPH.

AB - The stereochemistry of reduced nicotinamide adenine dinucleotide phosphate (NADPH)-dependent hydrogenation was investigated by the conversion of (—)-dehydrogriseofulvin (1) to (+)-griseofulvin (2a) by the use of a partially purified enzyme system of Streptomyces cinereocrocatus in the presence of (4R)- or (4S)-[4-2H1]NADPH. The results of 270 MHz proton nuclear magnetic resonance spectroscopy indicated that the origin of the 6’α-hydrogen of 2a is a hydride ion donated by pro-4R-hydrogen of NADPH.

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KW - (4S)-[4-2H1]-NADPH

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KW - Streptomyces cinereocrocatus

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KW - enzyme system

KW - griseofulvin

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Stereospecific Incorporation of Hydrogen from Reduced Nicotinamide Adenine Dinucleotide Phosphate in Hydrogenation of (—)-Dehydrogriseofulvin to (+)-Griseofulvin by a Partially Purified Enzyme System of Streptomyces cinereocrocatus

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