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  • Title: Enhancement of enantioselectivity in the Bacillus subtilis protease-catalyzed hydrolysis of N-free amino acid esters using the ester grouping-modification approach.
    Author: Miyazawa T, Minowa H, Yamada T.
    Journal: Biotechnol Lett; 2006 Mar; 28(5):295-9. PubMed ID: 16614915.
    Abstract:
    The generality of enantioselectivity enhancement through the modification of the alcohol moiety of a substrate ester was ascertained, for in the Bacillus subtilis protease-catalyzed hydrolysis of N-unprotected amino acid esters the enantioselectivity was enhanced largely by switching the conventional methyl ester to esters with a longer alkyl chain such as the isobutyl ester (from E = 3 to E = 130-170 in the case of 4-fluorophenylalanine esters) as in the enzymatic hydrolysis mediated by Aspergillus oryzae protease. There was indeed a profound dependence of E on the nature of the ester grouping.
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