Method for optically resolving a racemic alpha-substituted...

Details Method for optically resolving a racemic alpha-substituted... Method for optically resolving a racemic alpha-substituted...

C - Chemistry, Metallurgy

12

P

C12P 7/40 (2006.01) C12P 17/04 (2006.01) C12P 41/00 (2006.01)

Patent

CA 2410438

Disclosed is a method for optically resolving a racemic alpha-substituted heterocyclic carboxylic acid (alpha-HCCA) by taking advantage of enantioselectivity of enzymes. alpha-HCCA is reacted with alcohol to give a racemic alpha-HCCA ester, which is then reacted with an enzyme with enantioselectivity, whereby either R-form or S-form of the racemate is hydrolyzed. Extraction with an organic solvent can obtain enantiomers of the alpha-HCCA ester. The extracted enantiomeric alpha-HCCA ester is converted to enantiomeric alpha-HCCA by catalytic hydrogenation in an organic solution or by enzymatic hydrolysis in an aqueous solution. Thus, a racemic mixture of alpha-HCCA can be optically resolved with high optical purity at high yields as well as at low cost.

L'invention concerne un procédé de résolution optique d'un acide carboxylique hétérocyclique alpha-substitué (alpha-HCCA) racémique dans lequel on utilise de manière avantageuse l'énantiosélectivité des enzymes. Alpha-HCCA est mis en réaction avec de l'alcool afin d'obtenir un ester alpha-HCCA racémique, qui est alors mis en réaction avec une enzyme à énantiosélectivité, la forme R ou la forme S du racémate étant hydrolysée. L'extraction avec un solvant organique peut permettre d'obtenir des énantiomères de l'ester alpha-HCCA. L'ester alpha-HCCA énantiomérique extrait est converti en alpha-HCCA énantiomérique par hydrogénation catalytique dans une solution organique ou par hydrolyse enzymatique dans une solution aqueuse. Un mélange racémique d'alpha-HCCA peut ainsi faire l'objet d'une résolution optique de grande pureté optique à haut rendement et à faible coût.

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