Beilstein J. Org. Chem.2014,10, 1603–1612, doi:10.3762/bjoc.10.166
building blocks. The obtained glycoligands are monodisperse and present azobenzene moieties as well as sugar ligands at defined positions within the oligomeric backbone and side chains, respectively. We show that the combination of molecular precision together with the photoswitchable properties of the
azobenzene unit allows for the photosensitive control of glycoligand binding to protein receptors. These stimuli-sensitive glycoligands promote the understanding of multivalent binding and will be further developed as novel biosensors.
Keywords: azobenzene; glycopolymer; lectin binding; multivalency
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Graphical Abstract
Figure 1:
Synthesis of photoswitchable precision glycooligomers via stepwise addition of building blocks on s...
Beilstein J. Org. Chem.2013,9, 2395–2403, doi:10.3762/bjoc.9.276
the straightforward synthesis of multivalent glycoligands with full control over monomer sequence and functionalization pattern. We demonstrate the potential of this building-block approach by synthesizing oligomers with different numbers and spacing of carbohydrates and also show the feasibility of
heteromultivalent glycosylation patterns by combining building blocks presenting different mono- and disaccharides.
Keywords: continuous flow; flow chemistry: flow synthesis; glycoligands; multivalency; photochemistry; solid-phase synthesis; thiol–ene; thioglycosides; Introduction
Multivalent carbohydrate ligand
; RP-HPLC analysis 5% to 50% MeCN in 30 min, retention time = 7.8 min.
Versatile synthetic strategy for access to multivalent glycoligands: First, the building block DDS 1 is functionalized with different acetyl-protected thioglycosides 2–7 via thiol–ene addition in flow at >275 nm, resulting in a
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Graphical Abstract
Figure 1:
Versatile synthetic strategy for access to multivalent glycoligands: First, the building block DDS 1...