Chemical modification of hydroxyl groups of poly(vinyl alcohol) by a glycosidation reaction

Abstract

A new procedure for chemical modification of poly(vinyl alcohol) (PVA) was established by a glycosidation reaction of hydroxyl groups in PVA with triacetylated sugar oxazoline 1. 1H and 13C NMR analyses indicated that triacetylated N‐acetyl‐D‐glucosamine (GlcNAc) was introduced onto a PVA backbone selectively via a β‐O‐glycoside linkage. Deacetylation of triacetylated GlcNAc‐substituted PVA 2 resulted in GlcNAc‐substituted PVA 3 in good yield. These modified PVAs 2 and 3 exhibited solubilities and thermal properties different from the original PVA.

Poly(Vinyl Alcohol) Physical Hydrogels: New Vista on a Long Serving Biomaterial

“…In another report, chemical modification of PVA by glycosylation was achieved using oxazoline derivatives of triacetylated sugar, e.g. N ‐acetyl‐ D ‐glucosamine (GlcNAc) or chitobiose,71, 72 with subsequent deacetylation to yield GlcNAc and chitobiose‐PVA conjugates.…”

Glycopolymers obtained by chemical modification of well‐defined block copolymers

“…There are mainly two approaches to prepare glycopolymers;20 by either polymerization of carbohydrate‐containing monomers25–36 or by the postpolymerization chemical modification of synthetic polymers 37–51. The first one includes the synthesis of glycomonomers protected or unprotected by using standard chemical modification15, 16, 19, 52 or click chemistry approaches20, 53–56 and posterior polymerization using different methodologies; that is, conventional and controlled radical polymerization, living anionic polymerization, cyanoxyl mediated polymerization, ring opening polymerization or combination of different techniques 25–36.…”

“…The first one includes the synthesis of glycomonomers protected or unprotected by using standard chemical modification15, 16, 19, 52 or click chemistry approaches20, 53–56 and posterior polymerization using different methodologies; that is, conventional and controlled radical polymerization, living anionic polymerization, cyanoxyl mediated polymerization, ring opening polymerization or combination of different techniques 25–36. In the case of postpolymerization chemical modification, different polymer matrices have been applied to obtain glycopolymers, being hydroxylated polymers that possess weak reactive groups such as poly(vinyl alcohol)37, 39, 41 and copolymers of ethylene‐vinyl alcohol43, 44, 46, 47, 49, 50, 57, 58 the most utilized. These weak groups have to be previously activated with others highly reactive moieties, such as phthalic anhydride, chloroacetyl chloride and p ‐nitrophenyl chloroformate, to incorporate the saccharide into macromolecular structure.…”

“…[37][38][39][40][41][42][43][44][45][46][47][48][49][50][51] The first one includes the synthesis of glycomonomers protected or unprotected by using standard chemical modification 15,16,19,52 or click chemistry approaches 20,[53][54][55][56] and posterior polymerization using different methodologies; that is, conventional and controlled radical polymerization, living anionic polymerization, cyanoxyl mediated polymerization, ring opening polymerization or combination of different techniques. [25][26][27][28][29][30][31][32][33][34][35][36] In the case of postpolymerization chemical modification, different polymer matrices have been applied to obtain glycopolymers, being hydroxylated polymers that possess weak reactive groups such as poly(vinyl alcohol) 37,39,41 and copolymers of ethylene-vinyl alcohol 43,44,46,47,49,50,…”

Free‐radical copolymerization of ethyl α‐hydroxymethylacrylate with methyl methacrylate by reversible addition–fragmentation chain transfer

“…On the other hand, carbohydrate science is a developing area because saccharides are involved in a great number of important biological processes, such as cell–cell recognition phenomena 52. One of the approaches to developing glycopolymers is the introduction of saccharide units into natural or synthetic polymers 53–60. Some possible applications for these types of polymers are drug delivery systems, dental medicine, bioimplants, contact lenses, and tissue engineering 60–62.…”