Glycoconjugations of Biomolecules by Chemical Methods

Abstract

Bioconjugations under benign aqueous conditions have the most promise to covalently link carbohydrates onto chosen molecular and macromolecular scaffolds. Chemical methodologies relying on C-C and C-heteroatom bond formations are the methods of choice, coupled with the reaction conditions being under aqueous milieu. A number of methods, including metal-mediated, as well as metal-free azide-alkyne cyclo-addition, photocatalyzed thiol-ene reaction, amidation, reductive amination, disulfide bond formation, conjugate addition, nucleophilic addition to vinyl sulfones and vinyl sulfoxides, native chemical ligation, Staudinger ligation, olefin metathesis, and Suzuki-Miyaura cross coupling reactions have been developed, in efforts to conduct glycoconjugation of chosen molecular and biomolecular structures. Within these, many methods require pre-functionalization of the scaffolds, whereas methods that do not require such pre-functionalization continue to be few and far between. The compilation covers synthetic methodology development for carbohydrate conjugation onto biomolecular and biomacromolecular scaffolds. The importance of such glycoconjugations on the functional properties is also covered.

Exploring Glycan Binding Specificity of Odorranalectin by Alanine Scanning Library

“…Fluorescein‐labelled lectins (AAL and SBA), SBA‐Alexa Fluor (488 conjugate), and BSA‐conjugated monosaccharides (L‐fucose, D‐galactose, and N ‐acetyl‐D‐galactosamine) were purchased from Vector Labs (Burlingame, CA). The monosaccharides were modified by vinyl sulfone at the anomeric carbon and subsequently conjugated to BSA [51,52] …”

“…The monosaccharides were modified by vinyl sulfone at the anomeric carbon and subsequently conjugated to BSA. [51,52] Synthesis of cyclic Ala scan analogues. The linear peptidyl-resin precursors for naturally occurring OL peptide 1 and its Ala scan analogues (2-17) were synthesized using TentaGel XV RAM resin (substitution 0.27 mmol/g, 0.1 mmol scale) and standard Fmoc-SPPS on a PS3 automated peptide synthesizer (Protein Technologies Inc., Tucson, AZ).…”

A universal concept for area‐selective assembly of metal oxide core‐shell nanoparticles, nanorods, and organic molecules via amide coupling reactions

“…[ 57 ] The N‐hydroxysuccinimide (NHS) was used in order to form the stable NHS ester in situ as one of the three ways by adding EDC, otherwise, o‐acylisourea by contact with H 2 O results into regenerated carboxyl group by hydrolysis. [ 50 ] As a result, the EDC‐HCl as the 1 st increment and NHS as the 2 nd (with ratio for Ia as 63.789:95.750 mg, Ib as 60.410:90.680 mg, Ic as 49.622:74.484 mg, respectively) were added into aMES/NMs solution (20 ml) for incubation (20 minutes, 25°C). The dispersed IIa , IIc in H 2 O (10 ml) by sonication were added into aMES (10 ml).…”

Display of Rich Reactivities of Endo‐ and Exocyclic Unsaturated Sugars that Parallel the Native Sugars

“…The biochemical studies showed further that the glycoconjugated protein retained the antimicrobial activities as that of the native lysozyme. [63] In a plethora methods known for glycoconjugations of biomolecules, [64,65] the benign nature of the newly developed methodology lies in the reaction being reagent-less, pending to only a basic pH of the solution.…”