Facile synthesis of linear-dendritic cholesteryl-poly(ε-caprolactone)-b-(L-lysine)G2 by thiol-ene and azide-alkyne "click" reactions

被引：30

作者：

Javakhishvili, Irakli ^{[1
]}

Binder, Wolfgang H. ^{[2
]}

Tanner, Susanne ^{[2
]}

Hvilsted, Soren ^{[1
]}

机构：

[1] Tech Univ Denmark, Dept Chem & Biochem Engn, Danish Polymer Ctr, DK-2800 Lyngby, Denmark

[2] Univ Halle Wittenberg, Fac Nat Sci 2, Inst Chem, Lehrstuhl Makromol Chem, D-06120 Halle, Germany

来源：

POLYMER CHEMISTRY | 2010年 / 1卷 / 04期

关键词：

RING-OPENING POLYMERIZATION; BLOCK-COPOLYMERS; TERMINAL ALKYNES; CHEMISTRY; DENDRIMERS; FUNCTIONALIZATION; COMBINATION; INITIATORS;

D O I：

10.1039/b9py00303g

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

The construction of a linear-dendritic block copolymer consisting of terminal cholesteryl moiety, poly(epsilon-caprolactone), and a second generation L-lysine dendron has been accomplished by the combination of copper(I) catalyzed azide-alkyne and UV-triggered thiol-ene "click" reactions. Ring-opening polymerization of E-caprolactone initiated by 5-hexyn-1-ol and Mitsunobu coupling with 4-pentenoic acid provide hetero-telechelic poly(epsilon-caprolactone) bearing terminal alkyne and alkene groups. It is then employed in the sequential "click" reactions with the azide-functionalized dendritic wedge and thiocholesterol. Near to quantitative functionalization of the intermediate and final products has been attained as confirmed by NMR spectroscopy and MALDI-TOF spectrometry.

引用

页码：506 / 513

页数：8

共 27 条

[21]

2-4

[22] Thiol-Ene Modification of 1,2-Polybutadiene Using UV Light or Sunlight [J].

ten Brummelhuis, Niels ;

Diehl, Christina ;

Schlaad, Helmut .

MACROMOLECULES, 2008, 41 (24) :9946-9947

[23] Comb-dendritic block copolymers as tree-shaped macromolecular amphiphiles for nanoparticle self-assembly [J].

Tian, Lu ;

Hammond, Paula T. .

CHEMISTRY OF MATERIALS, 2006, 18 (17) :3976-3984

[24] Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides [J].

Tornoe, CW ;

Christensen, C ;

Meldal, M .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3057-3064

[25] Multivalent, bifunctional dendrimers prepared by click chemistry [J].

Wu, P ;

Malkoch, M ;

Hunt, JN ;

Vestberg, R ;

Kaltgrad, E ;

Finn, MG ;

Fokin, VV ;

Sharpless, KB ;

Hawker, CJ .

CHEMICAL COMMUNICATIONS, 2005, (46) :5775-5777

[26] Dendritic-linear AxBx block copolymers prepared via controlled ring-opening polymerization of lactones from orthogonally protected multifunctional initiators [J].

Würsch, A ;

Möller, M ;

Glauser, T ;

Lim, LS ;

Voytek, SB ;

Hedrick, JL ;

Frank, CW ;

Hilborn, JG .

MACROMOLECULES, 2001, 34 (19) :6601-6615

[27] Dendron rodcoils: Synthesis of novel organic hybrid structures [J].

Zubarev, ER ;

Stupp, SI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5762-5773

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