Recognition of the remote chiral center in lipase-catalyzed kinetic resolution of [2-methyl-2-(2′-naphthyl)-1,3-benzodioxol-4-yl]methyl acetate, the precursor of 2-methyl-2-(2′-naphthyl)-1,3-benzodioxole-4-carboxylic acid (MNB carboxylic acid)

Naoki Natori, Kaoruko Nakagawara, Mitsuru Shoji, Takeshi Sugai, Kengo Hanaya

研究成果: Article査読

1 被引用数 (Scopus)

抄録

To access the enantiomers of 2-methyl-2-(2′-naphthyl)-1,3-benzodioxole-4-carboxylic acid (MNB carboxylic acid), lipase-catalyzed kinetic resolution of racemic [2-methyl-2-(2′-naphthyl)-1,3-benzodioxol-4-yl]methyl acetate was examined with Burkholderia cepacia lipase (Amano PS-IM) and Candida antarctica lipase B (Novozym 435) under transesterification conditions. Enantioselectivity of B. cepacia lipase (E = 72) was higher than that of C. antarctica lipase B (E = 1.7), and these lipases showed a reversal of enantiopreference in the recognition of a remote chiral center. The computational study showed that the tetrahedral intermediate complex of B. cepacia lipase with (R)-4a, the fast isomer, was more stable than that with (S)-4a, the slow isomer. The repetitive use of B. cepacia lipase and further chemical transformation provided both enantiomers [(R)-: 99.4% ee and (S)-: 99.4% ee] of MNB carboxylic acid as methyl esters.

本文言語English
ページ(範囲)130-135
ページ数6
ジャーナルJournal of Molecular Catalysis B: Enzymatic
109
DOI
出版ステータスPublished - 2014 11

ASJC Scopus subject areas

  • 触媒
  • バイオエンジニアリング
  • 生化学
  • プロセス化学およびプロセス工学

フィンガープリント

「Recognition of the remote chiral center in lipase-catalyzed kinetic resolution of [2-methyl-2-(2′-naphthyl)-1,3-benzodioxol-4-yl]methyl acetate, the precursor of 2-methyl-2-(2′-naphthyl)-1,3-benzodioxole-4-carboxylic acid (MNB carboxylic acid)」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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