The Enzyme-catalysed Stereoselective Transesterification of Phenylalanine Derivatives in Supercritical Carbon Dioxide

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Smallridge, Andrew John, Trewhella, Maurice Arthur and Wang, Z (2002) The Enzyme-catalysed Stereoselective Transesterification of Phenylalanine Derivatives in Supercritical Carbon Dioxide. Australian Journal of Chemistry, 55 (4). pp. 259-262. ISSN 0004-9425

Abstract

The subtilisin Carlsberg catalysed transesterification of N-acetyl phenylalanine methyl ester (1), N-acetyl phenylalanine ethyl ester (2), N-trifluoroacetyl phenylalanine methyl ester (3) and N-trifluoroacetyl phenylalanine ethyl ester (4) was studied in supercritical carbon dioxide. The water content of the reaction affects the reactivity of the system; for the transesterification of the methyl esters with ethanol the optimum concentration of water was determined to be about 0.74 M, while for the transesterification of the ethyl esters with methanol the optimum concentration of water was about 1.3 M. The conversion is also dependent upon the concentration of alcohol; for ethanol, 2% v/v gives the maximum conversion, whilst for methanol, only 0.8-1.2% v/v is required. This is probably due to a difference in the solubility of the substrates in the two alcohol/supercritical carbon dioxide mixtures. The reaction is highly stereoselective, in all cases no evidence for reaction of the D-isomer could be detected by chiral gas chromatography.

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Item type Article
URI https://vuir.vu.edu.au/id/eprint/2362
DOI https://doi.org/10.1071/CH01018
Official URL http://dx.doi.org/10.1071/CH01018
Subjects Historical > Faculty/School/Research Centre/Department > School of Engineering and Science
Historical > FOR Classification > 0305 Organic Chemistry
Keywords ResPubID16375, Phenylalanine Derivatives, transesterification, stereoselectivity
Citations in Scopus 5 - View on Scopus
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