Influences of reaction conditions on the enantioselective transesterification using Pseudomonas cepacia lipase

verfasst von: Uwe Bornscheuer, Stefan Schapöhler, Thomas Scheper, Karl Schügerl
Abstract: The influences of different reaction conditions on Pseudomonas cepacia lipase (PCL) catalyzed esterification of several chiral allylic alcohols (2-(1-hydroxyethyl)acrylonitrile and some closely related compounds) have been investigated. These compounds are possible precursors in the synthesis of the antibiotic Nyccomycin. An increase in the reaction temperature led to an increased final conversion, decreased enantioselectivity of the reaction, and a reduction of the residual activity of the lipase. PCL is thermostable and catalytically active for more than 100 hours at 100 °C. Variation of the chain length of the acyl group of the esters used as cosubstrates had only a small influence on the conversion. As expected, the alcohol generated during the synthesis had a strong negative influence on the progress of the reaction. PCL showed strong substrate selectivity for some of the tested allylic alcohols. The enantioselectivity changed from substrate to substrate.
Organisationseinheit(en): Institut für Technische Chemie
Typ: Artikel
Journal: Tetrahedron: Asymmetry
Band: 2
Seiten: 1011-1014
Anzahl der Seiten: 4
ISSN: 0957-4166
Publikationsdatum: 1991
Publikationsstatus: Veröffentlicht
Peer-reviewed: Ja
ASJC Scopus Sachgebiete: Katalyse, Physikalische und Theoretische Chemie, Organische Chemie, Anorganische Chemie
Elektronische Version(en): https://doi.org/10.1016/S0957-4166(00)86150-9 (Zugang: Unbekannt)

BibTeX

@article{f77894ccc4644cd8a5f3ad4570291f74,
title = "Influences of reaction conditions on the enantioselective transesterification using Pseudomonas cepacia lipase",
abstract = "The influences of different reaction conditions on Pseudomonas cepacia lipase (PCL) catalyzed esterification of several chiral allylic alcohols (2-(1-hydroxyethyl)acrylonitrile and some closely related compounds) have been investigated. These compounds are possible precursors in the synthesis of the antibiotic Nyccomycin. An increase in the reaction temperature led to an increased final conversion, decreased enantioselectivity of the reaction, and a reduction of the residual activity of the lipase. PCL is thermostable and catalytically active for more than 100 hours at 100 °C. Variation of the chain length of the acyl group of the esters used as cosubstrates had only a small influence on the conversion. As expected, the alcohol generated during the synthesis had a strong negative influence on the progress of the reaction. PCL showed strong substrate selectivity for some of the tested allylic alcohols. The enantioselectivity changed from substrate to substrate.",
author = "Uwe Bornscheuer and Stefan Schap{\"o}hler and Thomas Scheper and Karl Sch{\"u}gerl",
year = "1991",
doi = "10.1016/S0957-4166(00)86150-9",
language = "English",
volume = "2",
pages = "1011--1014",
journal = "Tetrahedron: Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Ltd.",
number = "10",
}