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Synthesis of 2-C-branched derivatives of D-mannose: 2-C-aminomethyl-D-mannose binds to the human C-type lectin DC-SIGN with affinity greater than an order of magnitude compared to that of D-mannose
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Mitchell, Daniel A., Jones, Nigel A., Hunter, Stuart J., Cook, Joseph M. D., Jenkinson, Sarah F., Wormald, Mark R., Dwek, Raymond A. and Fleet, George W. J. (2007) Synthesis of 2-C-branched derivatives of D-mannose: 2-C-aminomethyl-D-mannose binds to the human C-type lectin DC-SIGN with affinity greater than an order of magnitude compared to that of D-mannose. Tetrahedron: Asymmetry, Vol.18 (No.12). pp. 1502-1510. doi:10.1016/j.tetasy.2007.06.003 ISSN 0957-4166.
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Official URL: http://dx.doi.org/10.1016/j.tetasy.2007.06.003
Abstract
2-C-Substituted branched D-mannose analogues are novel monosaccharides, readily obtained from a Kiliani-acetonation sequence on D-fructose, followed by subsequent functional group manipulation. 2-C-Azidomethyl-D-mannose and 2-C-aminomethylD-marmose bind to the C-type lectin DC-SIGN (CD209) with significantly greater affinity than mannose. In particular, 2-C-aminomethyl-D-mannose exhibits a comparative 48-fold increase in binding as determined using a surface plasmon resonance-based competition assay. DC-SIGN is an important cell-surface type II transmembrane protein that interacts with blood group antigens, endogenous glycoproteins such as ICAM-3, and also deadly pathogens such as the human immunodeficiency and hepatitis C viruses. The effective use of small compounds to block target binding by mannose-selective C-type lectins at sub-millimolar concentrations has not been shown previously; thus, these data represent a very attractive thoroughfare to novel antiviral and immunomodulatory drug development. @ 2007 Elsevier Ltd. All rights reserved.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Medicine > Warwick Medical School | ||||
Journal or Publication Title: | Tetrahedron: Asymmetry | ||||
Publisher: | Pergamon | ||||
ISSN: | 0957-4166 | ||||
Official Date: | 4 July 2007 | ||||
Dates: |
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Volume: | Vol.18 | ||||
Number: | No.12 | ||||
Number of Pages: | 9 | ||||
Page Range: | pp. 1502-1510 | ||||
DOI: | 10.1016/j.tetasy.2007.06.003 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access |
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