Process of producing optically active cephalosporin analogs by enzyme selective deacylation

DETAILED DESCRIPTION OF THE INVENTION Optically active compounds of the cephalosporin analogs represented by the general formula (I) or compounds represented by the assumed absolute structural formula (I-1) are produced by optically selective deacylation of a compound represented by the general formula (V) ##STR8## wherein R represents a substituted or unsubstituted unsaturated six-membered carbocycle, or a substituted or unsubstituted five- or six-membered heterocycle wherein the substituent represents a hydroxy group, a halo group, a nitro group or a methansulfonamide group, X represents a hydrogen, an amino group, a hydroxy group or a lower alkyl group, R.
sub.
1 and R.
sub.
2 have the same significance as defined above, and the hydrogens at the 6- and 7-positions have cis configuration (referred to as Compound [V] hereinafter).
As the unsaturated six-membered carbocycle and five- or six-membered heterocycle, a phenyl group, a cyclohexenyl group, a cyclohexadienyl group, a thienyl group, a furyl group, a pyrrolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an iso-oxazolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, a pyridinyl group, and a pyrazinyl group are exemplified.
As the substituent, a hydroxy group, a halo group, a nitro group, a methansulfonamide group, and the like are mentioned.
As the lower alkyl group, a straight-chain or branched alkyl group having 1 to 5 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl and the like are mentioned.
The optically selective deacylation of Compound [V] to obtain optically active Compound [I-1] is carried out in the presence of an enzyme obtained from a microorganism capable of producing optically active Compound [I-1] by optically selective deacylation of Compound [V].
As the microorganism having the ability of optically selective deacylation, microorganisms belonging to the genus Aeromonas, Achromobacter, Arthrobacter, Acetobacter, Alcaligenes, Escherichia, Xanthomonas, Kluyvera, Gluconobacter, Clostridium, Comamonas, Corynebacterium, Sarcina, Staphylococcus, Spirillum, Bacillus, Pseudomonas, Flavobacterium, Brevibacterium, Protaminobacter, Proteus, Beneckea, Micrococcus, Mycoplana or Rhodopseudomonas are used