Process for producing optically active n-substituted azetidine-2

Details Process for producing optically active n-substituted azetidine-2 Process for producing optically active n-substituted azetidine-2

1999-07-13

2000-11-07

Lambkin, Deborah C.

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

548953, C07C 104, C07D20504

Patent

active

061435546

ABSTRACT:
There is provided a process for producing an optically active N-substituted azetidine-2-carboxylic acid compound represented by the formula (2): ##STR1## by contacting a corresponding N-substituted azetidine-2-carboxylic acid ester of formula (2) with an enzyme derived from a microorganism selected from Arthrobacter SC-6-98-28 strain, Arthrobacter sp. ATCC21908 strain, Chromobacterium SC-YM-1 strain, and a mutant thereof. A process is also provided for preparing an optically active azetidine-2-carboxylic acid by eliminating the N-substituent of a N-substituted azetidine-2-carboxylic acid ester of formula (2).

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Wim A. J. Starmans et al., "Enzymatic resolution of methyl N-alkyl-azetidine-2-carboxylates by Candida antarCtica lipase-mediated ammoniolysis", Tetrehedron: Asymmetry, vol. 9, 1998, pp. 429-435.
A. Kozikowski et al., "Synthesis and Metabotropic Receptor Activity of the Novel Rigidified Glutamate Analogues (+)-and (-)-trans-Azetidine-2,4-dicarboxylic Acid and Their N-Methyl Derivatives, " J. Med Chem. (1993), 36, pp. 2706-2708.

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