Chemoenzymatic synthesis of narrow-polydispersity glycopolymers: Poly(6-O-vinyladipolyl-D-glucopyranose)

Luca Albertin; Claudia Kohlert; Martina Stenzel; John R. Foster; Thomas P. Davis

doi:10.1021/bm034199u

Chemoenzymatic synthesis of narrow-polydispersity glycopolymers: Poly(6-O-vinyladipolyl-D-glucopyranose)

Luca Albertin, Claudia Kohlert, Martina Stenzel, John R. Foster, Thomas P. Davis

Research output: Contribution to journal › Article › Research › peer-review

103 Citations (Scopus)

Abstract

The glycomonomer 6-O-vinyladipoyl-D-glucopyranose was prepared via lipase catalyzed transesterification of divinyladipate with α-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 M_n 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.

Original language	English
Pages (from-to)	255-260
Number of pages	6
Journal	Biomacromolecules
Volume	5
Issue number	2
DOIs	https://doi.org/10.1021/bm034199u
Publication status	Published - 1 Mar 2004
Externally published	Yes

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abstract = "The glycomonomer 6-O-vinyladipoyl-D-glucopyranose was prepared via lipase catalyzed transesterification of divinyladipate with α-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.",

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T2 - Poly(6-O-vinyladipolyl-D-glucopyranose)

AU - Albertin, Luca

AU - Kohlert, Claudia

AU - Stenzel, Martina

AU - Foster, John R.

AU - Davis, Thomas P.

PY - 2004/3/1

Y1 - 2004/3/1

N2 - The glycomonomer 6-O-vinyladipoyl-D-glucopyranose was prepared via lipase catalyzed transesterification of divinyladipate with α-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.

AB - The glycomonomer 6-O-vinyladipoyl-D-glucopyranose was prepared via lipase catalyzed transesterification of divinyladipate with α-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.

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Chemoenzymatic synthesis of narrow-polydispersity glycopolymers: Poly(6-O-vinyladipolyl-D-glucopyranose)

Abstract

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