| Stereoselective synthesis of conformationally constrained glycosylated amino acids using an enzyme-catalyzed desymmetrization. | |
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MedLine Citation:
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PMID: 12585874 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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As part of an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, constrained glycopeptides, compounds 2 and 3, based on the alpha-N-acetylgalactosaminyl serine substructure 1, were designed. In this paper we describe a stereoselective preparation of protected versions of these compounds. A pig liver esterase-catalyzed enzymatic desymmetrization of a diacetate substrate, 10, was employed as a key component in the synthesis. |
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Authors:
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Jonathan W Lane; Randall L Halcomb |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 68 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2003 Feb |
Date Detail:
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Created Date: 2003-02-14 Completed Date: 2003-10-20 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 1348-57 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemical synthesis* Catalysis Glycopeptides / chemical synthesis* Glycosylation Glycosyltransferases / metabolism* Indicators and Reagents Molecular Structure Nuclear Magnetic Resonance, Biomolecular Oligosaccharides / chemistry* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Glycopeptides; 0/Indicators and Reagents; 0/Oligosaccharides; EC 2.4.-/Glycosyltransferases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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