| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348435 | Tetrahedron: Asymmetry | 2007 | 9 Pages |
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.
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2,3:5,6-Di-O-isopropylidene-2-C-trifluoromethanesulfonyloxymethyl-d-mannono-1,4-lactoneC14H19F3O9SEe = 100%[α]D21=+22.2 (c 1.0, CHCl3)Source of chirality: d-fructose as starting material
2,3:5,6-Di-O-isopropylidene-2-C-iodomethyl-d-mannono-1,4-lactoneC13H19IO6Ee = 100%[α]D22=+31.8 (c 1.1, CHCl3)Source of chirality: d-fructose as starting material
2,3:5,6-Di-O-isopropylidene-2-C-methyl-d-mannono-1,4-lactoneC13H20O6Ee = 100%[α]D22=+48.8 (c 0.9, CHCl3)Source of chirality: d-fructose as starting material
2-C-Azidomethyl-2,3:5,6-di-O-isopropylidene-d-mannono-1,4-lactoneC13H19N3O6Ee = 100%[α]D22=-130 (c 0.7, CHCl3)Source of chirality: d-fructose as starting material
2-C-Azidomethyl-2,3:5,6-di-O-isopropylidene-d-mannofuranoseC13H21N3O6Ee = 100%[α]D21=-39 (c 1.0, CHCl3)Source of chirality: d-fructose as starting material
2,3:5,6-Di-O-isopropylidene-2-C-hydroxymethyl-d-mannofuranoseC13H22O6Ee = 100%[α]D21=+11.5 (c 1.0, MeOH)Source of chirality:d-fructose as starting material
2-C-Methyl-d-mannopyranoseC7H14O6Ee = 100%[α]D22=+15.1 (c 1.0, H2O)Source of chirality: d-fructose as starting material
2-C-Hydroxymethyl-d-mannopyranoseC7H14O7Ee = 100%[α]D22=+27.4 (c 1.0, H2O)Source of chirality: d-fructose as starting material
2-C-Azidomethyl-d-mannopyranoseC7H13N3O6Ee = 100%[α]D23=+41.0 (c 1.0, H2O)Source of chirality: d-fructose as starting material
2-C-Aminomethyl-d-mannopyranoseC7H15NO6Ee = 100%[α]D22=+3.7 (c 1.0, H2O)Source of chirality: d-fructose as starting material
2-C-Azidomethyl-d-mannono-1,4-lactoneC7H11N3O6Ee = 100%[α]D25=+14.2 (c 0.85, MeOH)Source of chirality: d-fructose as starting material
2-C-Hydroxymethyl-d-mannono-1,4-lactoneC7H12O7Ee = 100%[α]D21=+10.0 (c 0.65, MeOH)Source of chirality: d-fructose as starting material
