Strategies for the synthesis of sequence-controlled glycopolymers and their potential for advanced applications

https://doi.org/10.1016/j.progpolymsci.2021.101393Get rights and content
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Abstract

Natural and largely abundant macromolecules such as carbohydrates have become a center point of interest for the polymer community, mostly due to their more environment-friendly nature and excellent capacity to bind to proteins found in the plant and animal reigns alike. The binding between saccharide units and proteins is key to plethora of biological events, therefore a fundamental understanding of this mechanism could open doors towards a new age of biomedical advances. Synthetic macromolecules bearing saccharide units (i.e. glycopolymers) are of particular interest because they can be produced on a controlled fashion with tailored molecular weight, structure, functionality and even sequencing. Vast improvements have been made for the fabrication of sequence-controlled glycopolymers, thanks in part to new monomer synthesis routes and to the recent developments in controlled polymerization techniques. This review article aims at providing the reader with a comprehensive guide on the synthesis of glycomonomers as well as on polymerization techniques for the production of block-type glycopolymers.

Keywords

Block copolymers
Nanostructures
Self-assembly
Polysaccharides
Controlled polymerization

Abbreviations

AROP
anionic ring-opening polymerization
ATRP
atom transfer radical polymerization
BCP
block copolymer
CDSA
crystallization-driven self-assembly
CROP
cationic ring-opening polymerization
CTA
chain-transfer agent
CuAAC
copper-catalyzed azide-alkyne cycloaddition
DEGA
di(ethylene glycol) methyl ether acrylate
DEGMA
di(ethylene glycol) methyl ether methacrylate
DMAEMA
2-(dimethylamino)ethyl methacrylate
DMF
N,N-dimethylformamide
FRP
free radical polymerization
HEA
2-hydroxyethyl acrylate
HEMA
2-hydroxyethyl methacrylate
LAP
living anionic polymerization
LCP
living cationic polymerization
MAA
methacrylic acid
nBA
n-butyl acrylate
nBMA
n-butyl methacrylate
NCA
N-carboxyanhydride
NiPAAm
N-isopropyl acrylamide
NMP
nitroxide-mediated polymerization
P3HT
poly(3-hexylthiophene)
PBLG
poly(benzyl-L-glutamate)
PCL
poly(ε-caprolactone)
PDEGA
poly(di(ethylene glycol) methyl ether acrylate)
PDEGMA
poly(di(ethylene glycol) methyl ether methacrylate)
pDNA
plasmid DNA
PEO
poly(ethylene oxide)
PHEA
poly(2-hydroxyethyl acrylate)
PHEMA
poly(2-hydroxyethyl methacrylate)
PISA
polymerization-induced self-assembly
PLA
poly(lactic acid)
PMAA
poly(methacrylic acid)
PMMA
poly(methyl methacrylate)
PnBA
poly(n-butyl acrylate)
PnBMA
poly(n-butyl methacrylate)
PS
polystyrene
RAFT
reversible addition-fragmentation chain-transfer
ROMP
ring-opening metathesis polymerization
ROP
ring-opening polymerization
rROP
radical ring-opening polymerization
SET-LRP
single electron transfer ‘living’ radical polymerization
TEMPO
(2,2,6,6-tetramethylpiperidin-1-yl)oxyl)

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