Cyclodextrin-mediated deacylation of amino acid esters with marked stereoselectivity.
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.
Goto
Koichi
K
Division of Applied Chemistry, Graduate School of Sojo University (former name: Kumamoto Institute of Technology), Japan.
Nakashima
Kentaro
K
Tanoue
Osamu
O
Nukushina
Satoshi
S
Toudo
Isao
I
Imamura
Chikara
C
Ihara
Yasuji
Y
Matsumoto
Yoko
Y
Ueoka
Ryuichi
R
D000215:Acylation; D000596:Amino Acids / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry*; D006868:Hydrolysis; D007202:Indicators and Reagents; D007700:Kinetics; D008958:Models, Molecular; D013237:Stereoisomerism
D000596:Amino Acids; D003505:Cyclodextrins; D007202:Indicators and Reagents