Lipase-catalyzed enantiomeric resolution of ceramides 1

Mikio Bakke, Masahiro Takizawa, Takeshi Sugai, Hiromichi Ohta, P. Herold

研究成果: Article

27 引用 (Scopus)

抄録

Lipase-catalyzed enantiomeric kinetic resolution of ceramides related to C16-sphinganine and C18-sphingenine is described. Two hydroxy groups in readily available racemic N-stearoyl-erythroC16-sphinganine were acetylated, and several kinds of lipases were screened for the hydrolysis of this substrate. Among them, a Burkholderia cepacia lipase (SC lipase A, Sumitomo Chemical Co., Ltd.) showed the highest reactivity and enantioselectivity. The rate of hydrolysis and selectivity were greatly affected by some additives. Especially, the combined use of a detergent, Triton X-100, and the solid support, Florisil, for immobilization showed the highest enantioselectivity (E = ca. 170), although the reaction rate turned low. Introduction of a double bond into the substrate (N-stearoyl-erythro-Cis-sphingenine) also retarded the hydrolysis. By utilizing the preferential hydrolysis of the acetate on the primary hydroxy group, another advantageous feature of this enzyme-catalyzed reaction, the resulting product could directly be used as the glycosyl acceptor for cerebroside synthesis.

元の言語English
ページ(範囲)6929-6938
ページ数10
ジャーナルJournal of Organic Chemistry
63
発行部数20
出版物ステータスPublished - 1998

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Ceramides
Lipase
Hydrolysis
Enantioselectivity
Cerebrosides
Octoxynol
Substrates
Detergents
Reaction rates
Acetates
Kinetics
Enzymes

ASJC Scopus subject areas

  • Organic Chemistry

これを引用

Bakke, M., Takizawa, M., Sugai, T., Ohta, H., & Herold, P. (1998). Lipase-catalyzed enantiomeric resolution of ceramides 1. Journal of Organic Chemistry, 63(20), 6929-6938.

Lipase-catalyzed enantiomeric resolution of ceramides 1. / Bakke, Mikio; Takizawa, Masahiro; Sugai, Takeshi; Ohta, Hiromichi; Herold, P.

:: Journal of Organic Chemistry, 巻 63, 番号 20, 1998, p. 6929-6938.

研究成果: Article

Bakke, M, Takizawa, M, Sugai, T, Ohta, H & Herold, P 1998, 'Lipase-catalyzed enantiomeric resolution of ceramides 1', Journal of Organic Chemistry, 巻. 63, 番号 20, pp. 6929-6938.
Bakke M, Takizawa M, Sugai T, Ohta H, Herold P. Lipase-catalyzed enantiomeric resolution of ceramides 1. Journal of Organic Chemistry. 1998;63(20):6929-6938.
Bakke, Mikio ; Takizawa, Masahiro ; Sugai, Takeshi ; Ohta, Hiromichi ; Herold, P. / Lipase-catalyzed enantiomeric resolution of ceramides 1. :: Journal of Organic Chemistry. 1998 ; 巻 63, 番号 20. pp. 6929-6938.
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