Biotin α-end-functionalized gradient glycopolymers synthesized by RAFT copolymerization

被引：37

作者：

Gody, Guillaume ^{[1
,2
]}

Boullanger, Paul ^{[2
]}

Ladaviere, Catherine ^{[1
]}

Charreyre, Marie-Therese ^{[1
]}

Delair, Thierry ^{[1
]}

机构：

[1] Ecole Normale Super Lyon, Unite Mixte CNRS Biomerieux, F-69364 Lyon 7, France

[2] UCBL, CNRS, Lab Chim Organ 2, UMR 5622, F-69616 Villeurbanne, France

来源：

MACROMOLECULAR RAPID COMMUNICATIONS | 2008年 / 29卷 / 06期

关键词：

biotin; copolymerization; glycopolymer; matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS); reversible addition fragmentation chain transfer (RAFT);

D O I：

10.1002/marc.200700768

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Biotinylated gradient glycopolymers have been synthesized via RAFT copolymerization of an acrylamide derivative of galactose with N-acryloylmorpholine in the presence of a biotin CTA. The polymerization was controlled with a linear increase in molecular weights up to 80% conversion. Copolymer chains have a gradient microstructure with an increasing proportion of galactose units towards the omega chain end. The presence of the biotin ligand at the a end of the chains was confirmed by H-1 NMR and MALDI-ToF MS. This strategy based on the use of a biotin-CTA instead of a post-polymerization labelling of the chains resulted in a high percentage of alpha-functionalized chains (92-95%). Such alpha-end-functionalized glycopolymer chains may interact with streptavidin-modified surfaces.

引用

页码：511 / 519

页数：9

共 59 条

[1] Well-defined diblock glycopolymers from RAFT polymerization in homogeneous aqueous medium [J].

Albertin, L ;

Stenzel, MH ;

Barner-Kowollik, C ;

Foster, LJR ;

Davis, TP .

MACROMOLECULES, 2005, 38 (22) :9075-9084

[2] Well-defined glycopolymers from RAFT polymerization:: Poly(methyl 6-O-methacryloyl-α-D-glucoside) and its block copolymer with 2-hydroxyethyl methacrylate [J].

Albertin, L ;

Stenzel, M ;

Barner-Kowollik, C ;

Foster, LJR ;

Davis, TP .

MACROMOLECULES, 2004, 37 (20) :7530-7537

[3] Chemoenzymatic synthesis of narrow-polydispersity glycopolymers:: Poly(6-O-vinyladipoly-D-glucopyranose) [J].

Albertin, L ;

Kohlert, C ;

Stenzel, M ;

Foster, LJR ;

Davis, TP .

BIOMACROMOLECULES, 2004, 5 (02) :255-260

[4] Versatile precursors of functional RAFT agents. Application to the synthesis of bio-related end-functionalized polymers [J].

Bathfield, M ;

D'Agosto, F ;

Spitz, R ;

Charreyre, MT ;

Delair, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2546-2547

[5] Synthesis of various glycopolymer architectures via RAFT polymerization: From block copolymers to stars [J].

Bernard, J ;

Hao, XJ ;

Davis, TP ;

Barner-Kowollik, C ;

Stenzel, MH .

BIOMACROMOLECULES, 2006, 7 (01) :232-238

[6] Synthesis of light harvesting polymers by RAFT methods [J].

Chen, M ;

Ghiggino, KP ;

Mau, AWH ;

Rizzardo, E ;

Thang, SH ;

Wilson, GJ .

CHEMICAL COMMUNICATIONS, 2002, (19) :2276-2277

[7]

CORPART P, 1998, Patent No. 9858974

[8] Kinetic study of the "living" cationic polymerization of a galactose carrying vinyl ether. MALDI-TOF MS analysis of the resulting glycopolymers [J].

D'Agosto, F ;

Charreyre, MT ;

Delolme, F ;

Dessalces, G ;

Cramail, H ;

Deffieux, A ;

Pichot, C .

MACROMOLECULES, 2002, 35 (21) :7911-7918

[9]

D'Agosto F, 2001, MACROMOL CHEM PHYSIC, V202, P1689, DOI 10.1002/1521-3935(20010601)202:9<1689::AID-MACP1689>3.0.CO

[10]

2-P

← 1 2 3 4 5 6 →