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
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-aminomethyl-d-mannose bind to the C-type lectin DC-SIGN (CD209) with sig...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2007
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| _version_ | 1797065459776880640 |
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| author | Mitchell, D Jones, N Hunter, S Cook, J Jenkinson, S Wormald, M Dwek, R Fleet, G |
| author_facet | Mitchell, D Jones, N Hunter, S Cook, J Jenkinson, S Wormald, M Dwek, R Fleet, G |
| author_sort | Mitchell, D |
| collection | OXFORD |
| description | 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-aminomethyl-d-mannose 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. |
| first_indexed | 2024-03-06T21:28:58Z |
| format | Journal article |
| id | oxford-uuid:4404ed36-fa34-4937-a602-4852d2c90ca6 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:28:58Z |
| publishDate | 2007 |
| record_format | dspace |
| spelling | oxford-uuid:4404ed36-fa34-4937-a602-4852d2c90ca62022-03-26T14:59:09ZSynthesis 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-mannoseJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:4404ed36-fa34-4937-a602-4852d2c90ca6EnglishSymplectic Elements at Oxford2007Mitchell, DJones, NHunter, SCook, JJenkinson, SWormald, MDwek, RFleet, G2-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-aminomethyl-d-mannose 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. |
| spellingShingle | Mitchell, D Jones, N Hunter, S Cook, J Jenkinson, S Wormald, M Dwek, R Fleet, G 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 |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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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