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Control of Crystallinity and Stereocomplexation of Synthetic Carbohydrate Polymers from d ‐ and l ‐Xylose
Author(s) -
McGuire Thomas M.,
Bowles Jessica,
Deane Edward,
Farrar Elliot H. E.,
Grayson Matthew N.,
Buchard Antoine
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202013562
Subject(s) - enantiopure drug , polymer , crystallinity , chirality (physics) , monosaccharide , monomer , xylose , chemistry , carbohydrate , polysaccharide , organic chemistry , polymerization , amorphous solid , carbohydrate chemistry , polymer chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , crystallography , chiral symmetry breaking , physics , quantum mechanics , quark , fermentation , nambu–jona lasinio model
Manipulating the stereochemistry of polymers is a powerful method to alter their physical properties. Despite the chirality of monosaccharides, reports on the impact of stereochemistry in natural polysaccharides and synthetic carbohydrate polymers remain absent. Herein, we report the cocrystallisation of regio‐ and stereoregular polyethers derived from d ‐ and l ‐xylose, leading to enhanced thermal properties compared to the enantiopure polymers. To the best of our knowledge, this is the first example of a stereocomplex between carbohydrate polymers of opposite chirality. In contrast, atactic polymers obtained from a racemic mixture of monomers are amorphous. We also show that the polymer hydroxyl groups are amenable to post‐polymerisation functionalization. These strategies afford a family of carbohydrate polyethers, the physical and chemical properties of which can both be controlled, and which opens new possibilities for polysaccharide mimics in biomedical applications or as advanced materials.