Method for preparing L-alpha-amino acids

Details Method for preparing L-alpha-amino acids Method for preparing L-alpha-amino acids

1993-05-28

1996-07-30

Gitomer, Ralph J.

Chemistry: molecular biology and microbiology

Measuring or testing process involving enzymes or...

Involving hydrolase

435 24, 548228, 548232, 564303, C12Q 134, C12Q 137, C07B 5700

Patent

active

055410804

ABSTRACT:
A process is provided for preparing an L-.alpha.-amino acid from a 5(4H)-oxazolone precursor. The precursor is subjected to a two-step process sequence in which the precursor is first contacted with a methanolytically active lipase in the presence of methanol in a non-polar solvent to enantioselectively solvolyze the precursor and produce an intermediate optically active methyl ester of the desired .alpha.-amino acid. This ester is then contacted with a protease in the presence of water to enantioselectively cleave the ester and accomplish an enzymatic kinetic resolution to prepare the product L-.alpha.-amino acid in high optical purity.

REFERENCES:
Sih et al., J. Indus. Micro., Suppl. 3, Develop. Ind. Micro.,29, 221-229 (1988).
Bevinakatti, H. S. et al., "Lipase-Catalyzed Enantioselective Ring-Opening of Oxagol-5(4H)-ones Coupled With Partial in Situ Rocemisation of the Less Reactive Isomer", J. Chem. Soc. Comm., 1990, pp. 1091-1092.
McGahren et al., Tetrahedron, 23, 2017 (1967).
Chibata et al., J. Appl. Microbiol., 13 638 (1965).
T. Fukumura, Agric. Biol. Chem., 41 1321 and 1327 (1977).
de Jersey et al., Biochemistry, 8 1967 (1969).
Bautista, F. M., Porcine Pancreatic Lipase-Catalized Amino Acids (1992) 2:87-95.
O'Donnell, M. J. et al., "Steroselective Synthesis . . . ", JACS v. III:6, pp. 2353-2355, 1989.
Daffe, V. et al. "Enantiomeric Enrichment . . . ", JACS v. 102:10, pp. 3601-3604, 1980.

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