TY - JOUR
T1 - Gelozymes in organic synthesis. Part IV
T2 - Resolution of glycidate esters with crude Mung bean (Phaseolus radiatus) epoxide hydrolase immobilized in gelatin matrix
AU - Devi, Avala Vedamayee
AU - Lahari, Challa
AU - Swarnalatha, Lakshmi
AU - Fadnavis, N. W.
N1 - Funding Information:
We thank the Indo-French Center for the Promotion of Advanced Research and CSIR, New Delhi, for financial support.
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2008/5/16
Y1 - 2008/5/16
N2 - A crude extract of Mung bean meal (Phaseolus radiatus) possessing epoxide hydrolase activity immobilized in gelatin gel (gelozyme) is employed in the stereoselective epoxide ring opening of glycidate esters. Thus, ethyl trans-(±)-3-phenyl glycidate 1a and methyl trans-(±)-3-(4-methoxyphenyl) glycidate 1b gave (2S,3R)-glycidate esters (ee >99% and 45% yield) with gelatin immobilized enzyme in diisopropyl ether. The corresponding (2R,3S)-enantiomer of 1a was hydrolyzed by an epoxide hydrolase to predominantly give the anti-product, ethyl (2R,3R)-2,3-dihydroxy-3-phenylpropanoate, with a diastereomeric excess of 78% and ee 94% (40%). A small amount (5%) of racemic syn-product was also obtained as a result of the spontaneous hydrolysis. In the case of 1b, the hydrolysis product was racemic due to high reactivity of the glycidate toward water.
AB - A crude extract of Mung bean meal (Phaseolus radiatus) possessing epoxide hydrolase activity immobilized in gelatin gel (gelozyme) is employed in the stereoselective epoxide ring opening of glycidate esters. Thus, ethyl trans-(±)-3-phenyl glycidate 1a and methyl trans-(±)-3-(4-methoxyphenyl) glycidate 1b gave (2S,3R)-glycidate esters (ee >99% and 45% yield) with gelatin immobilized enzyme in diisopropyl ether. The corresponding (2R,3S)-enantiomer of 1a was hydrolyzed by an epoxide hydrolase to predominantly give the anti-product, ethyl (2R,3R)-2,3-dihydroxy-3-phenylpropanoate, with a diastereomeric excess of 78% and ee 94% (40%). A small amount (5%) of racemic syn-product was also obtained as a result of the spontaneous hydrolysis. In the case of 1b, the hydrolysis product was racemic due to high reactivity of the glycidate toward water.
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U2 - 10.1016/j.tetasy.2008.01.036
DO - 10.1016/j.tetasy.2008.01.036
M3 - Article
AN - SCOPUS:43649097567
SN - 0957-4166
VL - 19
SP - 1139
EP - 1144
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 9
ER -