Process for producing optically active n-substituted azetidine-2 carboxylic acid compound

A process for producing an optically active N-substituted azetidine-2-carboxylic acid compound represented by the formula (1):

• ##STR5## wherein R.sup.2 represents:
• an aralkyl group, which may be substituted on its aromatic ring with at least one group selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, or
• an alkylcarbonyl group having 1 to 8 carbon atoms, which may be substituted with at least one group selected from an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, or
• an arylcarbonyl group, which may be substituted on its aromatic ring with at least one group selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, a phenyl group and a nitro group, or
• an alkyloxycarbonyl group having 1 to 8 carbon atoms, which may be substituted with at least one group selected from a halogen atom, a sulfonyl group and an aryl group, which aryl group may be substituted on its aromatic ring with at least one group selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, or
• an allyloxycarbonyl group, or
• an aryloxycarbonyl group, which may be substituted on its aromatic ring with at least one group selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, or
• an alkyl group having 1 to 8 carbon atoms, which may be substituted with at least one group selected from an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, or
• an allyl group, or
• an aryl group, which may be substituted on its aromatic ring with at least one group selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, or
• an arylsulfonyl group, which may be substituted on its aromatic ring with at least one group selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, and
• * represents an asymmetric carbon atom,
• the process comprising asymmetrically hydrolyzing an N-substituted azetidine-2-carboxylic acid ester compound represented by the following formula (2):
• ##STR6## wherein R.sup.1 represents:
• an alkyl group having 1 to 8 carbon atoms, which may be substituted with at least one group selected from an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, or
• an allyl group, or
• an aralkyl group, which may be substituted, on its aromatic ring with at least one group selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, or
• an aryl group, which may be substituted on its aromatic ring with at least one group selected from an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom and a nitro group, and
• R.sup.2 has the same meaning as defined above,
• by contacting the same 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.