Beilstein J. Org. Chem.2014,10, 1557–1563, doi:10.3762/bjoc.10.160
binary combinations of α-D-Man or β-D-GlcNAc, thus providing rapid access to attractive heteroglycosylated platforms for diverse biological applications.
Keywords: chemoselective ligation; heteroglycocluster; multivalency; multivalent glycosystems; one-pot synthesis; Introduction
Multivalent
was irradiated at 365 nm for 45 min. Compound 4 (6.9 mg, 46%) was obtained as a white foam. Analytical RP-HPLC: tR = 9.71 min (gradient: 5 to 100% B in 20 min); ESIMS+ (m/z): [M + H]+calcd for C94Cl2H158N16O40S4, 2351.9; found, 2352.0.
Heteroglycocluster 5. Route A: Compounds 4 (6.9 mg, 0.029 mmol
% B in 20 min); ESIMS+ (m/z): [M + H]+ calcd for C110H187N18O60S6, 2753.1; found, 2753.2.
Heteroglycocluster 5. Route B (one-pot assembly). Compounds 2 (3.6 mg, 0.015 mmol) and 3 (10 mg, 0.0064 mmol) were dissolved in dry DMF (300 µL) and NaH (0.5 mg, 0.015 mmol) was added. After stirring 1 h at room
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Graphical Abstract
Figure 1:
Chemical strategy for the construction of heteroglycoclusters.
Beilstein J. Org. Chem.2012,8, 421–427, doi:10.3762/bjoc.8.47
: chemoselective ligation; click chemistry; cyclopeptide; heteroglycocluster; oxime; Introduction
Multivalent interactions between carbohydrates and proteins play key roles in diverse biological events, including fertilization, cell–cell communication, host–pathogen interactions, immune response and cancer
different sugar units instead of a single motif, namely heteroglycocluster, reflects the presence of sugars found in native biological systems more closely than homoglycocluster does. Although recognition mechanisms are not fully understood, these studies suggest that heteroglycoclusters should interact
heteroglycoclusters by using a protocol based on orthogonal chemoselective ligations. Two series of compounds containing different combinations of two different sugars have been designed (Figure 1). In one series (heteroglycocluster 2:2), two αMan, αFuc and/or βLac are conjugated at alternate positions into the
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Graphical Abstract
Figure 1:
(a) Schematic representation of a heteroglycocluster of the 2:2 series containing Man and Fuc. (b) ...