title: Cyclodextrin-mediated deacylation of amino acid esters with marked stereoselectivity.
abstract: With respect to the hydrolysis (deacylation) of Z-D(L)-amino acid esters (N-(benzyloxycarbonyl)-D(L)-amino acid p-nitrophenyl esters) mediated by alpha-, beta- and gamma-cyclodextrins (CyDs), a remarkably high enantioselectivity (L/D=9.0) was observed for the deacylation of Ala substrate with gamma-CyD. The kinetic results on the basis of the Michaelis-Menten principle indicate that the enantioselectivity should be mainly originated in the deacylation process of substrates following the formation of gamma-CyD-substrate (1 : 1) complexes. The computer modeling (molecular mechanics) studies on the inclusion complexes are also described.
authors.affiliation: Division of Applied Chemistry, Graduate School of Sojo University (former name: Kumamoto Institute of Technology), Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Goto
authors.forename: Kentaro
authors.initials: K
authors.lastname: Nakashima
authors.forename: Osamu
authors.initials: O
authors.lastname: Tanoue
authors.forename: Satoshi
authors.initials: S
authors.lastname: Nukushina
authors.forename: Isao
authors.initials: I
authors.lastname: Toudo
authors.forename: Chikara
authors.initials: C
authors.lastname: Imamura
authors.forename: Yasuji
authors.initials: Y
authors.lastname: Ihara
authors.forename: Yoko
authors.initials: Y
authors.lastname: Matsumoto
authors.forename: Ryuichi
authors.initials: R
authors.lastname: Ueoka
mesh_terms: D000215:Acylation; D000596:Amino Acids / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry*; D006868:Hydrolysis; D007202:Indicators and Reagents; D007700:Kinetics; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D003505:Cyclodextrins; D007202:Indicators and Reagents