Design of an inversion center between two helical segments

被引：68

作者：

Maurizot, V

Dolain, C

Leydet, Y

Léger, JM

Guionneau, P

Huc, I

机构：

[1] Inst Europeen Chim & Biol, F-33607 Pessac, France

[2] Lab Pharmacochim, F-33076 Bordeaux, France

[3] Inst Chim Mat Condensee Bordeaux, F-33608 Pessac, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 32期

关键词：

D O I：

10.1021/ja0481981

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new strategy is proposed to control the relative orientation of two folded helical oligomers in such a way that they diverge from an aromatic linker and have opposite helical handedness. Mutual steric exclusion between the two helices results from the fact that they cannot be at the same time folded and on the same side of the linker. The concept is validated using the helical conformations of oligoamides of 8-amino-2-quinolinecarboxylic acid, but it should be applicable to many families of oligomers and leads to the first designed meso-helices.

引用

收藏

页码：10049 / 10052

页数：4

相关论文

共 30 条

[1] TETRAPHILIN - A 4-HELIX PROTON CHANNEL BUILT ON A TETRAPHENYLPORPHYRIN FRAMEWORK [J].

AKERFELDT, KS ;

KIM, RM ;

CAMAC, D ;

GROVES, JT ;

LEAR, JD ;

DEGRADO, WF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9656-9657

[2] A hydrogen-bonded supramolecular meso-helix [J].

Blay, G ;

Fernández, I ;

Pedro, JR ;

Ruiz-García, R ;

Muñoz, MC ;

Cano, J ;

Carrasco, R .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (09) :1627-1630

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

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

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

[4] Surprisingly stable helical conformations in α/β-peptides by incorporation of cis-β-aminocyclopropane carboxylic acids [J].

De Pol, S ;

Zorn, C ;

Klein, CD ;

Zerbe, O ;

Reiser, O .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (04) :511-514

[5] A DIBENZOFURAN-BASED AMINO-ACID DESIGNED TO NUCLEATE ANTIPARALLEL BETA-SHEET STRUCTURE - EVIDENCE FOR INTRAMOLECULAR HYDROGEN-BOND FORMATION [J].

DIAZ, H ;

ESPINA, JR ;

KELLY, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8316-8318

[6] Design and application of an α-helix-mimetic scaffold based on an oligoamide-foldamer strategy:: Antagonism of the bak BH3/Bcl-xL complex [J].

Ernst, JT ;

Becerril, J ;

Park, HS ;

Yin, H ;

Hamilton, AD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (05) :535-+

[7] DESIGN OF AN ARTIFICIAL 4-HELIX BUNDLE METALLOPROTEIN VIA A NOVEL RUTHENIUM(II)-ASSISTED SELF-ASSEMBLY PROCESS [J].

GHADIRI, MR ;

SOARES, C ;

CHOI, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (10) :4000-4002

[8] A template-induced incipient collagen-like triple-helical structure [J].

Goodman, M ;

Feng, YB ;

Melacini, G ;

Taulane, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5156-5157

[9]

Guichard G., 2004, PSEUDOPEPTIDES DRUG, P33

[10] De novo design of antibacterial β-peptides [J].

Hamuro, Y ;

Schneider, JP ;

DeGrado, WF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :12200-12201