Record number :
1173424
Title of article :
Biochemical approaches to the synthesis of ethyl 5-(s)-hydroxyhexanoate and 5-(s)-hydroxyhexanenitrile
Author/Authors :
Venkata B Nanduri، نويسنده , , Ronald L Hanson، نويسنده , , Animesh Goswami، نويسنده , , John M Wasylyk، نويسنده , , Thomas L. LaPorte، نويسنده , , Kishta Katipally، نويسنده , , Hyei-Jha Chung، نويسنده , , Ramesh N Patel، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2001
Pages :
5
From page :
632
To page :
636
Abstract :
Three different biochemical approaches were used for the synthesis of ethyl 5-(S)-hydroxyhexanoate 1 and 5-(S)-hydroxyhexanenitrile 2. In the first approach, ethyl 5-oxo-hexanoate 3 and 5-oxo-hexanenitrile 4 were reduced by Pichia methanolica (SC 16116) to the corresponding (S)-alcohols, ethyl (S)-5-hydroxyhexanoate 1 and 5-(S)-hydroxyhexanenitrile 2, with an 80–90% yield and >95% enantiomeric excess (e.e). In the second approach, racemic 5-hydroxyhexanenitrile 5 was resolved by enzymatic succinylation, leading to the formation of (R)-5-hydroxyhexanenitrile hemisuccinate and leaving the desired alcohol 5-(S)-hydroxyhexanenitrile 2 with a yield of 34% (50% maximum yield) and >99% e.e. In the third approach, enzymatic hydrolysis of racemic 5-acetoxy hexanenitrile 6 resulted in the hydrolysis of the R-isomer to provide 5-(R)-hydroxyhexanenitrile, leaving 5-(S)-acetoxyhexanenitrile 7 with a 42% yield (50% maximum yield) and >99% e.e.
Keywords :
Keto-reduction , Pichia methanolica , Enzymatic acetylation/hydrolysis
Journal title :
Enzyme and Microbial Technology
Link To Document :