Chemoenzymatic approach to optically active phenylglycidates: resolution of bromo- and iodohydrins
IR@IIIM: CSIR-Indian Institute of Integrative Medicine, Jammu
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| Title |
Chemoenzymatic approach to optically active phenylglycidates: resolution of bromo- and iodohydrins
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| Creator |
Anand, Naveen
Kapoor, Munish Koul, Surrinder Taneja, Subhash C. Sharma, Rattan L. Qazi, Ghulam N. |
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| Subject |
Chemical Sciences
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| Description |
Enantiomerically enriched phenylglycidates, precursors of the taxol C-13 phenylisoserine side chain and diltiazem, were prepared by kinetic resolution of anti-2-bromo-3-hydroxy- and anti-3-hydroxy-2-iodophenylpropanoates to provide enantioriched(2R,3R)- and (2S,3S)-halohydrins. The bulkiness and inflexibility of bromo and iodo groups in halohydrins have made them inaccessible to the active site of most of the lipases utilized for the hydrolysis of their acyloxy derivatives. In a set of 22 hydrolases screened herein,including native as well as commercial enzymes, only Aspergillus niger (Lipase AS, AMANO) could catalyze the hydrolysis with high enantioselectivity (E = 176). The resolved halohydrins easily underwent transformation to the corresponding (2S,3R)- and (2R,3S)-phenylglycidates.
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| Date |
2004
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://iiim.csircentral.net/229/1/10.1016j.tetasy.2004.08.026.pdf
Anand, Naveen and Kapoor, Munish and Koul, Surrinder and Taneja, Subhash C. and Sharma, Rattan L. and Qazi, Ghulam N. (2004) Chemoenzymatic approach to optically active phenylglycidates: resolution of bromo- and iodohydrins. Tetrahedron: Asymmetry, 15 (19). pp. 3131-3138. ISSN 09574166 |
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| Relation |
http://dx.doi.org/10.1016/j.tetasy.2004.08.026
http://iiim.csircentral.net/229/ |
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