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

[1] Glycoconjugated peptide dendrimers-based nanoparticulate system for the delivery of chloroquine phosphate [J].

Agrawal, Payal ;

Gupta, Umesh ;

Jain, N. K. .

BIOMATERIALS, 2007, 28 (22) :3349-3359

[2] 'Click' chemistry in polymer and material science: An update [J].

Binder, Wolfgang H. ;

Sachsenhofer, Robert .

MACROMOLECULAR RAPID COMMUNICATIONS, 2008, 29 (12-13) :952-981

[3] Development of thermal and photochemical strategies for thiol-ene click polymer functionalization [J].

Campos, Luis M. ;

Killops, Kato L. ;

Sakai, Ryosuke ;

Paulusse, Jos M. J. ;

Damiron, Denis ;

Drockenmuller, Eric ;

Messmore, Benjamin W. ;

Hawker, Craig J. .

MACROMOLECULES, 2008, 41 (19) :7063-7070

[4]

DeForest CA, 2009, NAT MATER, V8, P659, DOI [10.1038/NMAT2473, 10.1038/nmat2473]

[5] Azobenzene-Containing Linear-Dendritic Diblock Copolymers by Click Chemistry: Synthesis, Characterization, Morphological Study, and Photoinduction of Optical Anisotropy [J].

del Barrio, Jesus ;

Oriol, Luis ;

Alcala, Rafael ;

Sanchez, Carlos .

MACROMOLECULES, 2009, 42 (15) :5752-5760

[6] Designed dendrimer syntheses by self-assembly of single-site, ssDNA functionalized dendrons [J].

DeMattei, CR ;

Huang, BH ;

Tomalia, DA .

NANO LETTERS, 2004, 4 (05) :771-777

[7] Stimuli-responsive supramolecular assemblies of linear-dendritic copolymers [J].

Gillies, ER ;

Jonsson, TB ;

Fréchet, JMJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11936-11943

[8] Hybrid linear dendritic macromolecules: From synthesis to applications [J].

Gitsov, Ivan .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (16) :5295-5314

[9] Dendronized linear polymers via "click chemistry" [J].

Helms, B ;

Mynar, JL ;

Hawker, CJ ;

Fréchet, JMJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15020-15021

[10] Synthesis of star-shaped poly(ε-caprolactone) via 'click' chemistry and 'supramolecular click' chemistry [J].

Hoogenboom, Richard ;

Moore, Brian C. ;

Schubert, Ulrich S. .

CHEMICAL COMMUNICATIONS, 2006, (38) :4010-4012

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