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AssigneesZaidan Hojin Biseibutsu Kagaku Kenkyu Kai, Banyu Pharmaceutical Co., Ltd.
InventorsHamao Umezawa, Tomio Takeuchi, Toshiharu Nagatsu, Masa Hamada, Shuichi Iwadare, Ikuo Matsumoto, Hajime Morishima
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N-acyl-DL-3-(3,4-dihydroxyphenyl)serine or a catecholic hydroxyl-protected derivative thereof is stereospecifically de-acylated by reaction with a microorganism of the genus Streptomyces or Streptoverticillium having an acylase or with an extract of said microorganism containing said acylase, to produce L-3-(3,4-dihydroxyphenyl)serine or the hydroxyl-protected derivative thereof, with the N-acyl-D-3-(3,4-dihydroxyphenyl)serine compound remaining unaltered. The L-3-(3,4-dihydroxyphenyl)serine compound so produced can be separated from the N-acyl-D-3-(3,4-dihydroxyphenyl)serine compound owing to the difference in the properties of them.
A process for producing an optically active L-3-(3,4-dihydroxyphenyl)serine compound of the formula (II) ##STR10## wherein R.sup.1 and R.sup.2 each are a hydrogen atom such that --OR.sup.1 and --OR.sup.2 are catecholic 3- and 4-hydroxyl groups, or R.sup.1 and R.sup.2 each are a hydroxyl-protecting group for the catecholic 3- and 4-hydroxyl groups, and an optically active N-acyl-D-3-(3,4-dihydroxyphenyl)serine compound of the formula (III) ##STR11## wherein R.sup.1 and R.sup.2 are as defined above and R.sup.3 is an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group, which process comprises reacting an N-acyl-DL-3-(3,4-dihydroxyphenyl)serine compound of the general formula (I) ##STR12## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above, with a microorganism having an acylase or with an extract of said microorganism containing said acylase capable of removing hydrolytically the N-acyl group (--CO--R.sup.3) from the L-isomer of the DL-serine compound of the formula (I), and thereby to produce the L-3-(3,4-dihydroxyphenyl)serine compound of the formula (II), and separating this L-serine compound (II) from the N-acyl-D-3-(3,4-dihydroxyphenyl)serine compound of the formula (III) which remains unaltered without being de-acylated, said microorganism being selected from the group consisting of Actinomyces aureoverticillatus ATCC 19726;
Dependencies are inferred from the claim text.