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

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)130-135
Number of pages6
JournalJournal of Molecular Catalysis B: Enzymatic
Volume109
DOIs
Publication statusPublished - 2014 Nov

Keywords

  • Kinetic resolution
  • Lipase
  • Molecular dynamics simulation
  • Remote chiral center
  • Transesterification

ASJC Scopus subject areas

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology

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