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Titolo:
Novel route for the resolution of both enantiomers of dropropizine by using oxime esters and supported lipases of Pseudomonas cepacia
Autore:
Salunkhe, MM; Nair, RV;
Indirizzi:
Inst Sci, Dept Chem, Bombay 400032, Maharashtra, India Inst Sci Bombay Maharashtra India 400032 ombay 400032, Maharashtra, India
Titolo Testata:
ENZYME AND MICROBIAL TECHNOLOGY
fascicolo: 4-5, volume: 28, anno: 2001,
pagine: 333 - 338
SICI:
0141-0229(20010308)28:4-5<333:NRFTRO>2.0.ZU;2-U
Fonte:
ISI
Lingua:
ENG
Soggetto:
QUANTITATIVE-ANALYSES; ENZYMATIC RESOLUTION; KINETIC RESOLUTION; ORGANIC-SOLVENT; ACYLATION; ALCOHOLS; ESTERIFICATIONS; HYDROLYSIS; VERSATILE;
Keywords:
lipase PS-C; lipase PS-D; resolution; oxime esters; regioselectivity; enantioselectivity;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Agriculture,Biology & Environmental Sciences
Life Sciences
Citazioni:
24
Recensione:
Indirizzi per estratti:
Indirizzo: Salunkhe, MM Inst Sci, Dept Chem, 15 Madam Cama Rd, Bombay 400032, Maharashtra, India Inst Sci 15 Madam Cama Rd Bombay Maharashtra India 400032 dia
Citazione:
M.M. Salunkhe e R.V. Nair, "Novel route for the resolution of both enantiomers of dropropizine by using oxime esters and supported lipases of Pseudomonas cepacia", ENZYME MICR, 28(4-5), 2001, pp. 333-338

Abstract

Resolution of (R)- and (S)-dropropizine which is an antitussive and central sedative therapeutic agent in high optical and chemical yields was achieved by lipases of Pseudomonas cepacia supported on ceramic particles (lipasePS-C) and on diatomite (lipase PS-D) with oxime esters in organic solvents. The influence of several factors (lipase source, structural variations inoxime esters, the amount of lipase and its recyclability) on the enantioselectivity have been investigated. Different properties were used to describe the solvents, namely the hydrophobicity (quantified by log P) and the dielectic constant (epsilon). This enzymatic acylation using oxime esters was significant as only (S)-dropropizine and (R)-dropropizine monoacetate was obtained. (R)-Dropropizine monoacetate was chemically hydrolyzed to obtain (R)-dropropizine. The highest enantioselectivity was observed when O-acetyl benzophenone oxime was used. This enzymatic resolution provides a versatilemethod for getting the pure enantiomers of dropropizine by effectively optimizing the various reaction parameters. (C) 2001 Elsevier Science Inc. Allrights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 27/11/20 alle ore 01:55:41