Lipase-catalyzed enantiomeric resolution of ceramides 1

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

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)6929-6938
Number of pages10
JournalJournal of Organic Chemistry
Volume63
Issue number20
Publication statusPublished - 1998

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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.

In: Journal of Organic Chemistry, Vol. 63, No. 20, 1998, p. 6929-6938.

Research output: Contribution to journalArticle

Bakke, M, Takizawa, M, Sugai, T, Ohta, H & Herold, P 1998, 'Lipase-catalyzed enantiomeric resolution of ceramides 1', Journal of Organic Chemistry, vol. 63, no. 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. In: Journal of Organic Chemistry. 1998 ; Vol. 63, No. 20. pp. 6929-6938.
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