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. 2014 Jul 25:10:1686-91.
doi: 10.3762/bjoc.10.177. eCollection 2014.

Bifunctional dendrons for multiple carbohydrate presentation via carbonyl chemistry

Davide Bini  1 , Francesco Nicotra  1 , Laura Cipolla  1
Affiliations

Bifunctional dendrons for multiple carbohydrate presentation via carbonyl chemistry

Davide Bini et al. Beilstein J Org Chem. .

Abstract

The synthesis of new dendrons of the generations 0, 1 and 2 with a double bond at the focal point and a carbonyl group at the termini has been carried out. The carbonyl group has been exploited for the multivalent conjugation to a sample saccharide by reductive amination and alkoxyamine conjugation.

Keywords: bis-MPA; carbohydrates; dendrons; levulinic acid; multivalency; multivalent glycosystems.

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Figures

Figure 1
Figure 1
Synthesized G0, G1 and G2 dendrons and functionalized saccharides used for carbonyl conjugation.
Scheme 1
Scheme 1
Schematic depiction of dendron conjugation to saccharides by carbonyl chemistry.
Scheme 2
Scheme 2
Synthesis of the dendrons.
Scheme 3
Scheme 3
Dendron conjugation to fucose moieties by reductive amination. Reagents and conditions: a) 4, 3 M Na2SO4, AcOH, NaCNBH3, EtOH, 80 °C, 6 h.
Scheme 4
Scheme 4
Dendron conjugation to fucose via oxime ligation (buffer = citrate buffer).
See this image and copyright information in PMC

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