The acetone-dried powder and bacterial suspension of the soil bacteria KT 84 (
Pseudomonas sp.) did not hydrolyze the N-benzoyl derivative of
threo-β-phenyl-DL-serine but did effect asymmetric hydrolysis of its N-dichloroacetyl derivatives to produce
threo-β-phenyl-L-serine (II) and N-dichloroacetyl-
threo-β-phenyl-D-serine (III). The N-dichloroacetyl and N-benzoyl derivatives of
erythro-β-phenyl-DL-serine were asymmetrically hydrolyzed by KT 84 and respectively formed N-dichloroacetyl- (VI) and N-benzoyl-
erythro-β-phenyl-D-serine, besides
erythro-β-phenyl-L-serine (V).
The acetone-dried powder and bacterial suspension of KT 83 hydrolyzed (III) and (VI), respectively forming
threo- and
erythro-β-phenyl-D-serines, and also hydrolyzed N-dichloroacetyl-
threo- and -
erythro-β-phenyl-L-serines.
Both KT 84 and 83 hydrolyzed the
erythro-type of N-dichloroacetyl-β-phenylserine more easily than its
threo type. The dichloroacetyl derivatives of β-phenylserine were prepared by the chloral hydrate method.
The acetone-dried powder and bacterial suspension of KT 84 effected asymmetric hydrolysis of N-dichloroacetyl-
threo- (XIII) and -
erythro-β-
p-nitrophenyl-DL-serine (XVI) to form, respectively,
threo-β-
p-nitrophenyl-L-serine (XIV) and N-dichloroacetyl-
threo-β-
p-nitrophenyl-D-serine (XV), and
erythro-β-
p-nitrophenyl-L-serine (XVII) and N-dichloroacetyl-
erythro-β-
p-nitrophenyl-D-serine (XVIII).
The acetone-dried powder of KT 83 hydrolyzed (XV) and (XVIII) to respectively form
threo- (XIX) and
erythro-β-
p-nitrophenyl-D-serine (XX), and also hydrolyzed N-dichloroacetyl-
threo- and -
erythro-β-
p-nitrophenyl-L-serines.
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