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Titolo:
Enantioselectivity of Pseudomonas cepacia lipase towards 2-methyl-3(or 4)-arylalkanols: An approach based on the stereoelectronic theory and molecular modeling
Autore:
Tomic, S; Dobovicnik, V; Sunjic, V; Kojic-Prodic, B;
Indirizzi:
Rudjer Boskovic Inst, HR-10002 Zagreb, Croatia Rudjer Boskovic Inst Zagreb Croatia HR-10002 t, HR-10002 Zagreb, Croatia
Titolo Testata:
CROATICA CHEMICA ACTA
fascicolo: 2, volume: 74, anno: 2001,
pagine: 343 - 357
SICI:
0011-1643(200104)74:2<343:EOPCLT>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
CANDIDA-RUGOSA LIPASE; SECONDARY ALCOHOLS; STRUCTURAL BASIS; CATALYZED TRANSESTERIFICATION; KINETIC RESOLUTION; RHIZOMUCOR-MIEHEI; SUBSTRATE-BINDING; MICROBIAL LIPASES; OPEN CONFORMATION; SEC-ALCOHOLS;
Keywords:
Pseudomonas cepacia lipase; kinetic resolution; primary alcohols; enantioselectivity; molecular modeling; stereoelectronic theory;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
39
Recensione:
Indirizzi per estratti:
Indirizzo: Tomic, S Rudjer Boskovic Inst, POB 180, HR-10002 Zagreb, Croatia Rudjer Boskovic Inst POB 180 Zagreb Croatia HR-10002 eb, Croatia
Citazione:
S. Tomic et al., "Enantioselectivity of Pseudomonas cepacia lipase towards 2-methyl-3(or 4)-arylalkanols: An approach based on the stereoelectronic theory and molecular modeling", CROAT CHEM, 74(2), 2001, pp. 343-357

Abstract

For a better understanding of the previously reported enantioselectivity of Pseudomonas cepacia lipase (PCL) in acylation of racemic primary alcohols, 2-methyl-3(or 4)-arylalkanols, molecular modeling of tetrahedral intermediates (TIs) at the active site was performed. The most probable conformers of TIs were elucidated and their interactions with the amino acid residues of the binding pockets at the enzyme active site were studied. The free energy difference between TIs of two enantiomers was approximated by the differences in potential energy and the solvent accesible surface area. Correlation between the HE(His286). . .O gamma (Ser87) hydrogen bond differences ofdiastereomeric, low energy gauche-TIs, and experimentally determined enantiomeric ratios was found. In agreement with the stereoelectronic theory, the gauche-TI precedes ester release.

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Documento generato il 25/11/20 alle ore 07:39:10