Resolution of DL-2-aminosuberic acid via protease-catalyzed ester hydrolysis.
Papain-catalyzed regioselective cleavage of alpha-methyl ester in Z-DL-Asu(OMe)-OMe leads to Z-L-Asu(OMe)-OH and Z-D-Asu(OMe)-OMe. Subsequent saponifications yield Z-L-Asu-OH and Z-D-Asu-OH. The enzymatic alpha-ester hydrolysis was also achieved by subtilisin BPN' in organic solvent with low water content.
Rivard
M
M
Laboratoires des Reactions Organiques Selectives, Université Paris-Sud, Orsay, France.
Malon
P
P
Cerovský
V
V
D000596:Amino Acids / Q000737:chemistry*; D000600:Amino Acids, Dicarboxylic / Q000032:analysis*; D002210:Caprylates; D003998:Dicarboxylic Acids / Q000737:chemistry*; D006868:Hydrolysis; D010206:Papain / Q000737:chemistry; D013381:Subtilisins / Q000737:chemistry
D000596:Amino Acids; D000600:Amino Acids, Dicarboxylic; D002210:Caprylates; D003998:Dicarboxylic Acids; C019146:2-aminosuberic acid; C005738:suberic acid; D013381:Subtilisins; D010206:Papain