Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
LIPASE-CATALYZED ENANTIOMERIC RESOLUTION OF CERAMIDES
Autore:
BAKKE M; TAKIZAWA M; SUGAI T; OHTA H;
Indirizzi:
KEIO UNIV,DEPT CHEM,3-14-1 HIYOSHI YOKOHAMA KANAGAWA 223852 JAPAN KEIO UNIV,DEPT CHEM YOKOHAMA KANAGAWA 223852 JAPAN
Titolo Testata:
Journal of organic chemistry
fascicolo: 20, volume: 63, anno: 1998,
pagine: 6929 - 6938
SICI:
0022-3263(1998)63:20<6929:LEROC>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
D-ERYTHRO-SPHINGOSINE; D-THREO-SPHINGOSINE; BASIDIOMYCETE SCHIZOPHYLLUM-COMMUNE; FRUITING-INDUCING CEREBROSIDE; TRI-O-ACYLGLYCEROLS; STEREOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; L-SERINE;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
132
Recensione:
Indirizzi per estratti:
Citazione:
M. Bakke et al., "LIPASE-CATALYZED ENANTIOMERIC RESOLUTION OF CERAMIDES", Journal of organic chemistry, 63(20), 1998, pp. 6929-6938

Abstract

Lipase-catalyzed enantiomeric kinetic resolution of ceramides relatedto C-16-sphinganine and C-18-sphingenine is described. Two hydroxy groups in readily available racemic N-stearoyl-erythro-C-16-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 weregreatly affected by some additives. Especially, the combined use of adetergent, 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-C-18-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.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/09/20 alle ore 16:06:54