Document Detail

Cyclodextrin-mediated deacylation of amino acid esters with marked stereoselectivity.
MedLine Citation:
PMID:  12237555     Owner:  NLM     Status:  MEDLINE    
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.
Koichi Goto; Kentaro Nakashima; Osamu Tanoue; Satoshi Nukushina; Isao Toudo; Chikara Imamura; Yasuji Ihara; Yoko Matsumoto; Ryuichi Ueoka
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  50     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  2002 Sep 
Date Detail:
Created Date:  2002-09-18     Completed Date:  2003-03-04     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  1283-5     Citation Subset:  IM    
Division of Applied Chemistry, Graduate School of Sojo University (former name: Kumamoto Institute of Technology), Japan.
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MeSH Terms
Amino Acids / chemistry*
Cyclodextrins / chemistry*
Indicators and Reagents
Models, Molecular
Reg. No./Substance:
0/Amino Acids; 0/Cyclodextrins; 0/Indicators and Reagents

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