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 |
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