Soluble, Clickable Polypeptides from Azide-Containing N-Carboxyanhydride Monomers

被引：36

作者：

Rhodes, Allison J. ^{[1
]}

Deming, Timothy J. ^{[1
,2
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] Univ Calif Los Angeles, Dept Bioengn, Los Angeles, CA 90095 USA

来源：

ACS MACRO LETTERS | 2013年 / 2卷 / 05期

基金：

美国国家科学基金会;

关键词：

SOLID-PHASE; EFFICIENT; POLYMERIZATION; CYCLOADDITION; FUNCTIONALITY;

D O I：

10.1021/mz4001089

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

We report a method for the synthesis of soluble, well-defined, azide-functionalized polypeptides via living polymerization of new azide-containing amino acid N-carboxyanhydride (NCA) monomers. Homo and diblock azidopolypeptides were prepared with controlled segment lengths using (PMe3)(4)Co initiator and were subsequently modified by reaction with functional alkyne reagents. The azide groups were found to be quantitatively converted to the corresponding triazole derivatives, and the functionalized polymers were obtained in high yield. This methodology provides a facile and straightforward method for preparation of functional and side chain reactive, high molecular weight polypeptides.

引用

页码：351 / 354

页数：4

共 41 条

[1] A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].

Agard, NJ ;

Prescher, JA ;

Bertozzi, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047

[2] "Clicking" Polymers or Just Efficient Linking: What Is the Difference? [J].

Barner-Kowollik, Christopher ;

Du Prez, Filip E. ;

Espeel, Pieter ;

Hawker, Craig J. ;

Junkers, Tanja ;

Schlaad, Helmut ;

Van Camp, Wim .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (01) :60-62

[3] Synthesis and self-assembly of "tree-like" amphiphilic glycopolypeptides [J].

Bonduelle, Colin ;

Huang, Jin ;

Ibarboure, Emmanuel ;

Heise, Andreas ;

Lecommandoux, Sebastien .

CHEMICAL COMMUNICATIONS, 2012, 48 (67) :8353-8355

[4] Polypeptide end-capping using functionalized isocyanates: Preparation of pentablock copolymers [J].

Brzezinska, KR ;

Curtin, SA ;

Deming, TJ .

MACROMOLECULES, 2002, 35 (08) :2970-2976

[5] Clickable Enzyme-Linked Immunosorbent Assay [J].

Canalle, Luiz A. ;

Vong, TuHa ;

Adams, P. Hans H. M. ;

van Delft, Floris L. ;

Raats, Jos M. H. ;

Chirivi, Renato G. S. ;

van Hest, Jan C. M. .

BIOMACROMOLECULES, 2011, 12 (10) :3692-3697

[6] Versatile synthesis of temperature-sensitive polypeptides by click grafting of oligo(ethylene glycol) [J].

Cheng, Yilong ;

He, Chaoliang ;

Xiao, Chunsheng ;

Ding, Jianxun ;

Zhuang, Xiuli ;

Chen, Xuesi .

POLYMER CHEMISTRY, 2011, 2 (11) :2627-2634

[7] Dual Responsiveness of a Tunable Thermosensitive Polypeptide [J].

Chopko, Caroline M. ;

Lowden, Erika L. ;

Engler, Amanda C. ;

Griffith, Linda G. ;

Hammond, Paula T. .

ACS MACRO LETTERS, 2012, 1 (06) :727-731

[8] Synthetic polypeptides for biomedical applications [J].

Deming, Timothy J. .

PROGRESS IN POLYMER SCIENCE, 2007, 32 (8-9) :858-875

[9] Cobalt and iron initiators for the controlled polymerization of α-amino acid-N-carboxyanhydrides [J].

Deming, TJ .

MACROMOLECULES, 1999, 32 (13) :4500-4502

[10] The synthetic tuning of clickable pH responsive cationic polypeptides and block copolypeptides [J].

Engler, Amanda C. ;

Bonner, Daniel K. ;

Buss, Hilda G. ;

Cheung, Eva Y. ;

Hammond, Paula T. .

SOFT MATTER, 2011, 7 (12) :5627-5637

← 1 2 3 4 5 →