[The synthesis of 4'-(2-carboxyethyl)phenyl trans-4-aminomethyl cyclohexane carboxylate hydrochloride (cetraxate hydrochloride) by means of enzymatic debenzylation].
Cetraxate hydrochloride (1) (antiulcer agent) has been industrially produced by the chemical protective method of p-hydroxy propionic acid derivatives. Screening of enzymes which quantitatively hydrolyzed cetraxate benzyl ester hydrochloride (2) into 1 was undertaken to establish a novel enzymatic method of production of 1. It was found that the enzyme activity for debenzylation of 2 is contained in cellulase enzymes originated from Aspergillus sp. Lower alkyl groups or phenyl groups of p-hydroxy propionic acid derivatives are likewise selectively hydrolyzed by the cellulase enzyme. This enzymatic synthetic method is very useful for the industrial preparation of 1.
Kuroda
H
H
Miyadera
A
A
Kaneuchi
T
T
Imura
A
A
D000897:Anti-Ulcer Agents / Q000138:chemical synthesis*; D001230:Aspergillus; D002480:Cellulase; D003509:Cyclohexanecarboxylic Acids / Q000138:chemical synthesis*; D008722:Methods; D014148:Tranexamic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D000897:Anti-Ulcer Agents; D003509:Cyclohexanecarboxylic Acids; C000665:cetraxate; D014148:Tranexamic Acid; D002480:Cellulase