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Titolo:
OPTICALLY-ACTIVE CYANOHYDRINS AND ENZYME CATALYSIS
Autore:
KANERVA LT; RAHIALA K; SUNDHOLM O;
Indirizzi:
UNIV TURKU,DEPT CHEM SF-20500 TURKU FINLAND UNIV TURKU,DEPT BIOMED SF-20500 TURKU FINLAND
Titolo Testata:
Biocatalysis
fascicolo: 1-4, volume: 10, anno: 1994,
pagine: 169 - 180
SICI:
0886-4454(1994)10:1-4<169:OCAEC>2.0.ZU;2-S
Fonte:
ISI
Lingua:
ENG
Soggetto:
ORGANIC-SOLVENTS; RESOLUTION; (S)-CYANOHYDRINS; LIPASE; ESTERIFICATION; HYDROLYSIS; ACETATES; ESTERS; ALMOND; ACIDS;
Keywords:
PORCINE PANCREATIC LIPASE; CANDIDA CYLINDRACEA LIPASE; PSEUDOMONAS CEPACIA LIPASE; ENZYMATIC TRANSESTERIFICATION; CYANOHYDRIN;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
24
Recensione:
Indirizzi per estratti:
Citazione:
L.T. Kanerva et al., "OPTICALLY-ACTIVE CYANOHYDRINS AND ENZYME CATALYSIS", Biocatalysis, 10(1-4), 1994, pp. 169-180

Abstract

The possibilities for the preparation of optically active aliphatic and para-substituted aromatic cyanohydrins (X-C6H4-CH(OH)CN) by lipase catalysis in organic solvents has been studied. Pseudomonas cepacia lipase catalyzed deacylation and acylation result in acylated aromatic (R)- and (S)-cyanohydrins, respectively, with high optical purity (mostly e.e. >95 %). A convenient access to increase the chemical yield of acylated (S)-cyanohydrins is to combine the base-catalyzed in situ racemization of the less reactive (R)-counterpart with a kinetic resolution. The nature of the para-substituent has not an effect on the enantioselectivity of lipase PS catalysis. In the Candida cylindracea lipasecatalyzed deacylation, the optical purity of the less reactive (S)-enantiomer is high (e.e. >95 %) in the case of the aromatic compounds with electron-donating substituents X. PPL catalysis can be used to acylate aliphatic cyanohydrins, but it is not possible to use the in situ racemization of the less reactive (R)-cyanohydrin owing to the enantiomeric stability of most aliphatic compounds studied.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/11/20 alle ore 00:58:56