Topological Defects in Hyperbranched Glycopolymers Enhance Binding to Lectins

Abstract

Central scaffold topology and carbohydrate density are important features in determining the binding mechanism and potency of synthetic multivalent of poly- versus monodisperse carbohydrate systems against a model plant toxin (Ricinus communis agglutinin (RCA )). Lower densities of protein receptors favour the use of heterogeneous, polydisperse glycoconjugate presentations, as determined by surface plasmon resonance and dynamic light scattering.

Probing Site‐Selective Conjugation Chemistries for the Construction of Homogeneous Synthetic Glycodendriproteins

“…[16] These structures possess significant rigidity and useful distances between their β‐D‐Gal tip sugars, features that can prove favourable for multivalent ligand display [17,18] . Indeed, it has been noted that glycodendrimers can mimic the non‐reducing termini as well as some secondary interactions using only imperfect structural analogues [19] of the branched carbohydrates found in glycoproteins, without the necessity of presenting the whole, synthetically‐challenging, natural complex oligosaccharide [20] . In addition, we selected thioglycosides as the glycan motifs in these glycodendrons as these typically confer greater stability under both basic and acidic aqueous conditions, as well as resistance to enzymatic hydrolysis [21] .…”

“…1 H NMR (500 MHz, CDCl 3 ,): δ 7.47 (bs, 1H, NH), 7.32 (bs, 2H, NH), 7.29 (s, 2H, Ar), 5.41 (d, J 3',4' = 3 Hz, 3H, H-4'), 5.20 (appt, J 1',2' = 10 Hz, J 2',3' = 9.5 Hz, 3H, H-2'), 5.10 (dd, J 2',3' = 9.5 Hz, J 3',4' = 3.5 Hz, 3H, H-3'), 4.74 (d, J 1',2' = 10 Hz, 1H, H-1'), 4.70 (d, J 1',2' = 10 Hz, 2H, H-1'), 4.15-4.07 (m, 12H, H-6'ab, OCH 2 ), 3.97 (m, 3H, H-5'), 3.90 (s, 3H, OCH 3 ), 3.73-3.52 (m, 6H, CH 2 NH), 3.37-3.29 (m, 6H, CH 2 S), 2.14-1.98 (bs, 36H, CH 3 ). 13 (19), 1552.38 (7).…”

Bioresponsive Functional Phenylboronic Acid-Based Delivery System as an Emerging Platform for Diabetic Therapy

“…In recent years, functional biomaterials have been widely studied in the drug delivery system because of their low price and good biocompatibility in human body, and have been found to have great application prospects. 12,[74][75][76] Sugar polymer is a functional polymer material synthesized by different biological reactions and chemical reactions. It not only retains the special properties of sugar, but also has new functions such as good hydrophilicity, biocompatibility, and biodegradability.…”

Hyperbranched Glycopolymers of 2-(α-d-Mannopyranose) Ethyl Methacrylate and N,N’-Methylenebisacrylamide: Synthesis, Characterization and Multivalent Recognitions with Concanavalin A

“…Carbohydrates and their corresponding conjugated glycoproteins are key participants in a measureless array of biological functions, and can also be used as the carrier or drug in the treatment of diseases, such as cancer, cytotoxic chemotherapy or radiotherapy [1,2,3,4,5,6,7,8]. However, the monovalent interaction between the monosaccharide units and proteins is relatively weak due to their low affinity [9,10,11,12,13,14]. Compared with monosaccharide, polysaccharides being of high molecular weight show strong affinity due to the “cluster glycoside effect” [15,16,17,18].…”