Stereochemistry of Transformation of 5'-Formylgriseofulvin to 5'α-Hydroxymethylgriseofulvin with a Cell-Free System of Streptomyces cinereocrocatus
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概要
- 論文の詳細を見る
The enzymatic hydrogenation of 5'-formylgriseofulvin (3a) with a cell-free system of Streptomyces cinereocrocatus afforded 5'α-hydroxymethylgriseofulvin (4a). The structure of 4a was determined by comparison of the proton nuclear magnetic resonance (^1H-NMR) spectrum, mass spectrum (MS), circular dichroism (CD) and ultraciolet (UV) spectrum with those of 5'α-and 5'β-hydroxymethylgriseofulvin (4a and 5a) which were synthesized chemically. The stereochemistry of hydrogenation was unequivocally determined by 270 MHz ^1H-NMR analysis of the acetonide (10b) whith was derived from the product obtained by the enzymatic conversion of [7'-^2H]5'-formylgriseofulvin (3b) (Chart 3). The results clearly indicated that the 7'-pro-S-hydrogen of 4a originates from the 7'-hydrogen atom of the substrate(3a), and it was further proved that the 5'β-hydrogen of 4a originates from the medium by the use of deuterium oxide.
- 公益社団法人日本薬学会の論文
- 1988-10-25
著者
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佐藤 良博
共立薬科大学名誉
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小田 泰子
Kyoritsu College of Pharmacy
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佐藤 良博
Kyoritsu College of Pharmacy
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佐藤 良博
共立薬大
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末吉 裕美子
Kyoritsu College of Pharmacy
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広田 薫子
Kyoritsu College of Pharmacy
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