Photo-Click Immobilization of Carbohydrates on Polymeric Surfaces—A Quick Method to Functionalize Surfaces for Biomolecular Recognition Studies

Abstract

Methods to rapidly functionalize specific polymeric surfaces with alkynes, which can subsequently be linked to azide-containing carbohydrates, are presented. The methods are comprised of two main concepts: azide photoligation and Cu-catalyzed azide-alkyne cycloaddition. 2-Azidoethyl functionalized α-D-mannopyranoside was synthesized, and covalently attached to alkynefunctionalized polymeric surfaces using the techniques. The protein recognition properties of the carbohydrate-presenting surfaces were evaluated using quartz crystal microbalance biosensor instrumentation.

Stereoselective synthesis of light-activatable perfluorophenylazide-conjugated carbohydrates for glycoarray fabrication and evaluation of structural effects on protein binding by SPR imaging

“…This manipulation enabled the subsequent reduction of azide 10 without formation of any side products. Final conjugation using NHS-PFPA 11 15 instead of EDCI coupling resulted in good product yields.…”

“…In addition to evaluating the OEG type of linker structures with three, six and nine ethylene glycol units, the fourth synthetic pathway was developed in which an alternative linker structure 15 was designed and synthesized (compound 5 , Fig. 1).…”

“…10–19 In the latter case, PFPA-based photochemistry, 20,21 has been utilized in our laboratories to enable rapid, covalent and nondestructive immobilization of carbohydrates onto solid supports, resulting in the development of new methodologies in microarray and QCM biosensor systems. 15–17 …”

Stereocontrolled 1-S-glycosylation and comparative binding studies of photoprobe-thiosaccharide conjugates with their O-linked analogs

“…Several methods to study carbohydrate–protein interactions can be employed to address this difference, e.g., isothermal titration calorimetry (ITC) [44], hemagglutination inhibition [40], precipitation inhibition [45], equilibrium dialysis [46], spectrophotometry [47], enzyme-linked immunosorbent assay (ELISA) [48], fluorescence assay [49,50], nuclear magnetic resonance (NMR) [51], surface plasmon resonance (SPR) [41,52], quartz-crystal microbalance (QCM) [53,54], carbohydrate microarrays [55], and scanning probe microscopy (SPM) [56]. Of these, two major methods are especially advantageous: ITC and solid-phase binding techniques, the combination of which results in elucidation of overall binding performances.…”

Carbohydrate, Biomaterials, and Tissue Engineering Applications

“…Moreover, carbohydrates have very strategic locations on the cell surface [17]. Despite their importance, glycans have not been given as much attention as signaling molecules in biomaterial design for tissue engineering and regenerative medicine applications [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. One of the main successful exploitations of carbohydrates in biomaterial design is the creation of galactose-grafted scaffolds to support hepatocyte (liver cell) growth (Sections 16.2.4) [36,37].…”