Source:http://linkedlifedata.com/resource/pubmed/id/11937360
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
6
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pubmed:dateCreated |
2002-4-8
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pubmed:abstractText |
Glycamino acids, a family of sugar amino acids, are derivatives of C-glycosides that possesses a carboxyl group at the C-1 position and an amino group replacing one of the hydroxyl groups at either the C-2, 3, 4, or 6 position. We have prepared a series of glucose-type glycamino acids as monomeric building blocks: these are derivatives of 2-NH(2)-Glc-beta-CO(2)H 1, 3-NH(2)-Glc-beta-CO(2)H 2, 4-NH(2)-Glc-beta-CO(2)H 3, and 6-NH(2)-Glc-beta-CO(2)H 4 and constructed four types of homo-oligomers, beta(1-->2)-linked I, beta(1-->3)-linked II, beta(1-->4)-linked III, and beta(1-->6)-linked IV, employing the well-established N-Boc and BOP strategy. CD and NMR spectral studies of these oligomers suggested that only the beta(1-->2)-linked homo-oligomer possessed a helical structure that seems to be predetermined by the linkage position. Homo-oligomers with beta(1-->2)-linkages I and beta(1-->6)-linkages IV were also subjected to O-sulfation, and these O-sulfated oligomers were found to be able, in a linkage-specific manner, to effectively inhibit L-selectin-mediated cell adhesion, HIV infection, and heparanase activity without the anticoagulant activity associated with naturally occurring sulfated polysaccharides such as heparin.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Amino Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Anti-HIV Agents,
http://linkedlifedata.com/resource/pubmed/chemical/Glucuronidase,
http://linkedlifedata.com/resource/pubmed/chemical/Glycosides,
http://linkedlifedata.com/resource/pubmed/chemical/Oligosaccharides,
http://linkedlifedata.com/resource/pubmed/chemical/Selectins,
http://linkedlifedata.com/resource/pubmed/chemical/heparanase
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pubmed:status |
MEDLINE
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pubmed:month |
Jun
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pubmed:issn |
0968-0896
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
10
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1999-2013
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:11937360-Amino Acids,
pubmed-meshheading:11937360-Anti-HIV Agents,
pubmed-meshheading:11937360-Carbohydrate Conformation,
pubmed-meshheading:11937360-Cell Adhesion,
pubmed-meshheading:11937360-Circular Dichroism,
pubmed-meshheading:11937360-Glucuronidase,
pubmed-meshheading:11937360-Glycosides,
pubmed-meshheading:11937360-HIV,
pubmed-meshheading:11937360-Magnetic Resonance Spectroscopy,
pubmed-meshheading:11937360-Oligosaccharides,
pubmed-meshheading:11937360-Selectins
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pubmed:year |
2002
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pubmed:articleTitle |
Oligomers of glycamino acid.
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pubmed:affiliation |
Department of Pharmacology and Molecular Sciences, Johns Hopkins University School of Medicine, 725North Wolfe Street, Baltimore, MD 21205, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, Non-U.S. Gov't
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