Azidoproline containing helices:: Stabilization of the polyproline II structure by a functionalizable group

被引：128

作者：

Kuemin, Michael ^{[1
]}

Sonntag, Louis-Sebastian ^{[1
]}

Wennemers, Helma ^{[1
]}

机构：

[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 03期

关键词：

D O I：

10.1021/ja067148o

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The conformation and functionalizability of 4-azidoproline containing polyprolines was studied. The conformational analyses demonstrate that the PPII helix is stabilized by (4R)Azp and destabilized by (4S)Azp. Functionalization of Azp containing polyprolines was accomplished efficiently in a differential fashion by "click chemistry", rendering Azp containing polyprolines attractive molecular scaffolds.

引用

收藏

页码：466 / 467

页数：2

相关论文

共 32 条

[1]

[Anonymous], 1992, Adv. Biophys. Chem

[2] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[3] Conformational stability of collagen relies on a stereoelectronic effect [J].

Bretscher, LE ;

Jenkins, CL ;

Taylor, KM ;

DeRider, ML ;

Raines, RT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :777-778

[4] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[5] The design and evaluation of heparin-binding foldamers [J].

Choi, S ;

Clements, DJ ;

Pophristic, V ;

Ivanov, I ;

Vemparala, S ;

Bennett, JS ;

Klein, ML ;

Winkler, JD ;

DeGrado, WE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (41) :6685-6689

[6] Collagen stability: Insights from NMR spectroscopic and hybrid density functional computational investigations of the effect of electronegative substituents on prolyl ring conformations [J].

DeRider, ML ;

Wilkens, SJ ;

Waddell, MJ ;

Bretscher, LE ;

Weinhold, F ;

Raines, RT ;

Markley, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) :2497-2505

[7] COOPERATIVE CONFORMATIONAL TRANSITIONS OF LINEAR BIOPOLYMERS [J].

ENGEL, J ;

SCHWARZ, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (06) :389-+

[8] Cell-penetrating cis-γ-amino-L-proline-derived peptides [J].

Farrera-Sinfreu, J ;

Giralt, E ;

Castel, S ;

Albericio, F ;

Royo, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (26) :9459-9468

[9] Cell penetrating agents based on a polyproline helix scaffold [J].

Fillon, YA ;

Anderson, JP ;

Chmielewski, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11798-11803

[10] Protein surface recognition and proteomimetics: mimics of protein surface structure and function [J].

Fletcher, S ;

Hamilton, AD .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2005, 9 (06) :632-638

← 1 2 3 4 →