Fechter_2007_Chemistry_13_3369

Reference

Title : Stereoselective biocatalytic synthesis of (S)-2-hydroxy-2-methylbutyric acid via substrate engineering by using thio-disguised precursors and oxynitrilase catalysis - Fechter_2007_Chemistry_13_3369
Author(s) : Fechter MH , Gruber K , Avi M , Skranc W , Schuster C , Pochlauer P , Klepp KO , Griengl H
Ref : Chemistry , 13 :3369 , 2007
Abstract :

3-Tetrahydrothiophenone (4) and 4-phenylthiobutan-2-one (7) were used as masked 2-butanone equivalents to give the corresponding cyanohydrins 5 (79 % yield, 91 % ee) and 8 (95 % yield, 96 % ee) in an enzymatic cyanohydrin reaction applying the hydroxynitrile lyase (HNL) from Hevea brasiliensis. After hydrolysis and desulphurisation the desired intermediate (S)-2-hydroxy-2-methylbutyric acid (10) was obtained with 99 % ee. Interestingly, when applying (R)-selective HNL from Prunus amygdalus again the (S)-cyanohydrin 5 was formed (62 % ee). The absolute configuration of 5 was verified by crystal structure determination of the corresponding hydrolysis derived carboxylate. The fact that both enzymes yield the same enantiomer was analysed and interpreted by molecular modelling calculations.

PubMedSearch : Fechter_2007_Chemistry_13_3369
PubMedID: 17226866

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Citations formats

Fechter MH, Gruber K, Avi M, Skranc W, Schuster C, Pochlauer P, Klepp KO, Griengl H (2007)
Stereoselective biocatalytic synthesis of (S)-2-hydroxy-2-methylbutyric acid via substrate engineering by using thio-disguised precursors and oxynitrilase catalysis
Chemistry 13 :3369

Fechter MH, Gruber K, Avi M, Skranc W, Schuster C, Pochlauer P, Klepp KO, Griengl H (2007)
Chemistry 13 :3369