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Hydroxynitrile Lyase-catalyzed Synthesis of Cyanohydrins in Organic Solvents by David Costes; Ernst Wehtje; Patrick Adlercreutz is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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S)-Hydroxynitrile lyases from Hevea brasiliensis, Manihot esculenta, and Sorghum bicolor and (R)-hydroxynitrile lyase from Prunus amygdalus have been used as biocatalyst for the enantiospecific addition of hydrogen cyanide to aldehydes in organic solvents. The effects of the reaction parameters on the enzymatic reaction rate and product enantiomeric excess (e.e.) are presented. The reaction rate increased with the solvent hydrophobicity but highly hydrophobic solvents were not adapted to high hydrogen cyanide concentrations and provoked loss of activity and product e.e. In the synthesis of 3-phenylpropionaldehyde cyanohydrin catalyzed by (S)-hydroxynitrile lyases from H. brasiliensis, an e.e. value of 88 Ϯ 1% was obtained under optimized reaction conditions. Lower enantiomeric excess values were obtained under conditions where the enzyme was inactivated: high hydrogen cyanide concentration, high solvent log P, low enzyme loading. At lower temperature (down to Ϫ5°C) the e.e. was increased for all four enzymes used. Enzymes from different sources used under identical optimized reaction conditions were found to yield cyanohydrins with very different enantiopurities. This intrinsic ena

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Author

David Costes; Ernst Wehtje; Patrick Adlercreutz

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0141-0229)

Published

1999

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)