Examination of spacer effects on stereochemical recognition of a remote sterically hindered chiral center in lipase-catalyzed acylation

Ryohei Kobayashi, Hanghang Huang, Manabu Hamada, Toshinori Higashi, Mitsuru Shoji, Takeshi Sugai

研究成果: Article査読

1 被引用数 (Scopus)

抄録

To date, the enzyme-catalyzed kinetic resolution of the secondary alcohol [Ar-C*H(CH 3)OH, Ar = 2′,4′,6′- triisopropylphenyl] has not been available, due to high steric hindrance around the hydroxy group. To achieve resolution, the reaction site was extended by the introduction of two kinds of spacers, [-C(=O)CH 2] and [-C(=O)C**HCN]. In the first substrate, the recognition of remote chirality [Ar-C*H(CH 3)O-C(=O)CH 2OH] by acylation with Burkholderia cepacia lipase was examined by changing reaction conditions and acyl donors. An E = 22 in the preference of (1′R)-isomer, was recorded with vinyl acetate as an acyl donor at 25 °C. In the second substrate, there was a matched enantiomeric pair [stereoselective ratio at C-1′ = 15, in the preference of (1′R)-isomer] and a mismatched pair [stereoselective ratio at C-1′ = 2.5, in the preference of (1′S)-isomer] based on the relative stereochemistry between the two chiral centers [Ar- C*H(CH 3)O-C(=O)C**HCN-OH].

本文言語English
ページ(範囲)52-57
ページ数6
ジャーナルJournal of Molecular Catalysis B: Enzymatic
81
DOI
出版ステータスPublished - 2012 9月

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

「Examination of spacer effects on stereochemical recognition of a remote sterically hindered chiral center in lipase-catalyzed acylation」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。

引用スタイル