Cyclodextrin-mediated deacylation of amino acid esters with marked stereoselectivity.
Chem Pharm Bull (Tokyo)
; 50(9): 1283-5, 2002 Sep.
Article
in En
| MEDLINE
| ID: mdl-12237555
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.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Cyclodextrins
/
Amino Acids
Language:
En
Journal:
Chem Pharm Bull (Tokyo)
Year:
2002
Document type:
Article
Affiliation country:
Japan