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