A molecular modelling approach to rationalize the stereochemical outcome of the Burkholderia cepacia lipase-catalyzed transesterification of aromatic primary alcohols with vinyl esters with different chain lengths in chloroform

Enzo Santaniello, Silvana Casati, Pierangela Ciuffreda, Giuseppe Meroni, Alessandro Pedretti, Giulio Vistoli

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The Burkholderia cepacia lipase-catalyzed transesterification of 2-methyl-3-phenyl-1-propanol with vinyl esters proceeds with high enantioselectivity independently of the acyl chain length and the low enantioselectivity of the same reaction with 2-phenyl-1-propanol is not affected by chain length of the vinyl esters. A molecular modelling approach has been developed in order to rationalize the enzymatic results.

Original languageEnglish
Pages (from-to)1833-1836
Number of pages4
JournalTetrahedron: Asymmetry
Volume20
Issue number16
DOIs
Publication statusPublished - Aug 26 2009

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Molecular modeling
Enantioselectivity
Transesterification
Lipases
Propanol
Chloroform
Chlorine compounds
chloroform
Lipase
Chain length
esters
Esters
alcohols
Alcohols
1-phenyl-2-propanol
2-methyl-3-phenyl-1-propanol

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

A molecular modelling approach to rationalize the stereochemical outcome of the Burkholderia cepacia lipase-catalyzed transesterification of aromatic primary alcohols with vinyl esters with different chain lengths in chloroform. / Santaniello, Enzo; Casati, Silvana; Ciuffreda, Pierangela; Meroni, Giuseppe; Pedretti, Alessandro; Vistoli, Giulio.

In: Tetrahedron: Asymmetry, Vol. 20, No. 16, 26.08.2009, p. 1833-1836.

Research output: Contribution to journalArticle

Santaniello, Enzo ; Casati, Silvana ; Ciuffreda, Pierangela ; Meroni, Giuseppe ; Pedretti, Alessandro ; Vistoli, Giulio. / A molecular modelling approach to rationalize the stereochemical outcome of the Burkholderia cepacia lipase-catalyzed transesterification of aromatic primary alcohols with vinyl esters with different chain lengths in chloroform. In: Tetrahedron: Asymmetry. 2009 ; Vol. 20, No. 16. pp. 1833-1836.
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