Synthesis of Functionalized Amphiphilic Glycoconjugates and Glycoclusters

Abstract

Glycolipids are involved in many cellular recognition processes, so there is a need for their synthesis as well as for the design and preparation of glycolipid mimetics. In addition to the application of glycolipid mimetics in a glycobiological context, they are also of interest in many other fields of research, due to their amphiphilic characters. Our goal was to elaborate a series of known orthogonally functionalized glycomimetics and cluster glycosides into glycomimetics of a glycolipid type, so monosaccharide building blocks such as 3, glycodendrons such as 19, and branched cluster glycosides of the type 24 were ligated with lipophilic molecules by peptide coupling, this conjugation providing a new class of complex amphiphilic glycoconjugates with high molecular diversity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Dendrimers Designed for Functions: From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine

“…The cores of glycodendrimers are mostly based on classic ones (most frequently PAMAM, – ,,,, but also PPI, – ,,,– polypropylamine, – ,, carbosilane, silsesquioxane, polyphenylene, etc – ,– cyclodextrins, – cycloveratrylene, calixarene, ,– calix(4)resorcarene (Figure ), – carbopeptides ,, ), porphyrin, fullerene, transition metal (Cu 2+ ) bipyridyl, – and cyclic decapeptide template. – …”

Carbohydrates as potentially versatile core subcarriers for multivalent immunogens

“…Using carbohydrates as core molecules for creating clusters as probes for many purposes in the life sciences, also as chiral scaffolds, 15 is quite common 16–32 but to our knowledge making carbohydrate clusters by attaching fragments of O-SPs to cores by click chemistry and attaching the resulting cluster of antigens to carrier proteins by squaric acid chemistry to make neoglycoconjugate vaccines for bacterial diseases has not been explored. Here, we propose carbohydrates as convenient starting materials to form tailor-made core subcarriers for making clustered immunogens/vaccines.…”

Synthesis, self-assembly, and immunological activity of α-galactose-functionalized dendron–lipid amphiphiles

“…The carbohydrate moiety selected for the functionalization of the lipid-dendron hybrids was α-galactose (α-Gal). 30 There are currently very few examples of multivalent assemblies presenting α-galactose. 23,38 Although terminal α-galactose moieties are found in other mammals, they are not normally found in humans.…”

“…[24][25][26][27] In addition, the step-wise synthesis of dendrons affords well-defined products, allowing the number of peripheral groups to be carefully controlled. Carbohydratefunctionalized dendrons have been conjugated to the hydrophilic blocks of polymer vesicles, 28,29 and have also served as the hydrophilic blocks of amphiphiles where linear or dendritic hydrocarbons [30][31][32][33][34][35][36][37] or polypeptides 38 have served as the hydrophobic blocks. Percec et al reported that amphiphilic Janus glycodendrimers could self-assemble into a wide range of hard and soft assemblies including spherical and tubular vesicles, rod-like micelles, cubosomes, and solid lamellae depending on the chemical structures of their hydrophobic and carbohydratefunctionalized hydrophilic dendrons.…”