DL-5-置換ヒダントインを用いる D-アミノ酸の微生物的合成

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A new process for the production of D-amino acids was investigated using microbial transformation of DL-5-substituted hydantoins.Hydantoin-hydrolyzing activity was found in widely distributed microorganisms, particularly in bacteria and actinomycetes. The enzyme hydantoinase was purified and crystallized from a cell-free extract of Pseudomonas striata and its properties were established in some detail. This enzyme hydrolyzed D-isomers of various 5-substituted hydantoins to provide the corresponding N-carbamyl-D-amino acids. The advantage in using hydantoin was that enzymatic hydrolysis and chemical recemization of the substrate occurred simultaneously, so that DL-hydantoin could be completely transformed into N-carbamyl-D-amino acid.Based on these results, a new and convenient enzymatic process was developed for producing various D-amino acids.Step 1. Hydantoin synthesis Step 2. Asymmetric hydrolysis (microbial hydantoinase)Step 3. Chemical decarbamylation (nitrite oxidation)Furthemore, instead of using the Bucherer method (Step 1), a new method for 5-(p-hydroxyphenyl)hydantoin production was developed by employing amidoalkylation of phenol, in which glyoxylic acid, urea, and phenol were condensed under acidic conditions.
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