Enzymatic process for the enantiomeric resolution of amino...

Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...

Reexamination Certificate

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C435S106000

Reexamination Certificate

active

06902927

ABSTRACT:
An enzymatic process permitting the enantiomeric resolution of amino acids is provided. More specifically, this process for separating the enantiomers of an amino acid comprises treating a racemic mixture of the amino acid with glutaric anhydride and then with the enzyme glutaryl-7-ACA acylase so as to recover one of the enantiomers of the amino acid, the other enantiomer remaining in the form of the corresponding glutarylamide derivative.

REFERENCES:
patent: WO 98/50575 (1998-11-01), None
Raimondi et al. “Kinetic resolutions of racemic amines and alcohols catalyzed by an industrial glutaryl-7-aminocephalosporanic acylase with unexpected broad substrate specificity,” Tetrahedron: Assymetry (2003) 14: 1091-1094.
Raimondi et al. “Glutaryl acylases : One-reaction enzymes or versatile enantioselective biocatalysts?” Adv. Synth. Cata. (2003) 345: 783-789.
Shibuya et al., “Isolation and Properties of 7β-(4-Carboxybutanamido)cephalosporanic Acid Acylase-producing Bacteria,” Agric. Biol. Chem., 45(7): 561-1567 (1981).
Soloshonok et al., “Biocatalytic Approach to Enantiomerically Pure β-Amino Acids,” Tetrahedron: Asymmetry, 6(7): 1601-1610 (1995).
Topgi et al., “Use of Enzyme Penicillin Acylase in Selective Amidation/Amide Hydrolysis to Resolve Ethyl 3-amino-4-pentynoate Isomers,” Bioorganic & Medicinal Chemistry 7:2221-2229 (1999).

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