Chemoenzymatic synthesis of narrow-polydispersity glycopolymers: poly(6-O-vinyladipoyl-D-glucopyranose).
The glycomonomer 6-O-vinyladipoyl-D-glucopyranose was prepared via lipase catalyzed transesterification of divinyladipate with alpha-D-glucopyranose in dry acetonitrile and acetone. The desired 6-O regioisomer was obtained in good yield, and its structure was confirmed by correlation NMR spectroscopy. Controlled radical polymerization of the unprotected monomer was performed in protic media using both xanthate and dithiocarbamate as chain transfer agents to give poly(6-O-vinyladipoyl-D-glucopyranose) with Mn of 17 and 19 kDa (SEC) respectively and a polydispersity as low as 1.10. To the best of our knowledge, this is the first example of a narrow-polydispersity, poly(vinyl ester)-like glycopolymer.
Albertin
Luca
L
Centre for Advanced Macromolecular Design, School of Chemical Engineering and Industrial Chemistry, School of Biotechnology and Biomolecular Sciences, The University of New South Wales, NSW 2052 Sydney, Australia.
Kohlert
Claudia
C
Stenzel
Martina
M
Foster
L John R
LJ
Davis
Thomas P
TP
D002384:Catalysis; D004800:Enzymes, Immobilized / Q000737:chemistry*; D005656:Fungal Proteins; D005947:Glucose / Q000032:analysis / Q000138:chemical synthesis*; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D011108:Polymers / Q000032:analysis / Q000138:chemical synthesis*
D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D011108:Polymers; C093667:Novozyme 435; D008049:Lipase; D005947:Glucose