Microbial transformation of (+)- and (-)-dehydrogriseofulvin by Streptomyces species analyzed by 2H nuclear magnetic resonance spectroscopy.

• 佐藤 良博

• 小田 泰子

• 斉藤 肇

抄録

To elueidate the stereochemical course of the microbial transformation of (+)-dehydrogriseofulvin (DGF) by Streptomyces species, (+)-[5'-²H] DGF, which was obtained by dehydrogenation of (+)-[5'α, 5'β-²H] epigriseofulvin, was incubated with S. cinereo-crocatus. The structure of the product was identified as (+)-[5'α-²H] griseofulvin (GF) by ²H nuclear magnetic resonance spectroscopy. The results of incubations of (-)-and (+)-DGF with eight Streptomyces species (S. cinereocrocatus, S. roseochromogenus, S. bikiniensis, S. griseinus, S. durhamensis, S. californicus, S. fimbriatus, and S. cinereoruber) showed that (-)-and (+)-DGF were isomerized to each other and converted to (+)-GF as the main product, although some (-)-GF was also formed depending on the microorganisms used. In particular, incubation of (+)-DGF with S. cinereoruber yielded (-)-GF as the main product. In addition, (±)-DGF was transformed by S. cinereocrocatus to the naturally occurring (+)-GF in 48% yield. The enantiomer ratios of DGF and GF obtained by microbial transformation were calculated from the [α]_D values of corresponding enantiomer mixtures.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 29 (8), 2313-2321, 1981

  公益社団法人 日本薬学会

キーワード

• Streptomyces species

詳細情報

• CRID: 1390001204164318080
• NII論文ID: 110003633980
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.29.2313
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/29/8/29_8_2313/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1982209933
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可