2-O-Alkylated para-benzamide α-helix mimetics: the role of scaffold curvature

被引：44

作者：

Azzarito, Valeria ^{[1
,2
]}

Prabhakaran, Panchami ^{[1
,2
]}

Bartlett, Alice I. ^{[1
,2
]}

Murphy, Natasha S. ^{[1
,2
]}

Hardie, Michaele J. ^{[1
]}

Kilner, Colin A. ^{[1
]}

Edwards, Thomas A. ^{[2
,3
]}

Warriner, Stuart L. ^{[1
,2
]}

Wilson, Andrew J. ^{[1
,2
]}

机构：

[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

[2] Univ Leeds, Astbury Ctr Struct Mol Biol, Leeds LS2 9JT, W Yorkshire, England

[3] Univ Leeds, Inst Mol & Cellular Biol, Leeds LS2 9JT, W Yorkshire, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 32期

基金：

欧洲研究理事会;

关键词：

PROTEIN-PROTEIN INTERACTIONS; ANTAGONISTS; INHIBITION; P53; RECOGNITION; ACTIVATION; FOLDAMERS; PEPTIDES; AFFINITY; DESIGN;

D O I：

10.1039/c2ob26262b

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

The design and synthesis of a new 2-O-alklyated benzamide alpha-helix mimetic is described. Comparison with regioisomeric 3-O-alkylated benzamides permits a preliminary evaluation of the role that mimetic curvature has in determining molecular recognition properties.

引用

收藏

页码：6469 / 6472

页数：4

相关论文

共 41 条

[1]

Oligophenylenaminones as Scaffolds for α-Helix Mimicry [J].

Adler, Marc J. ;

Hamilton, Andrew D. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (17) :7040-7047

[2]

Molecular recognition of protein-ligand complexes: Applications to drug design [J].

Babine, RE ;

Bender, SL .

CHEMICAL REVIEWS, 1997, 97 (05) :1359-1472

[3]

HELIX GEOMETRY IN PROTEINS [J].

BARLOW, DJ ;

THORNTON, JM .

JOURNAL OF MOLECULAR BIOLOGY, 1988, 201 (03) :601-619

[4]

Bridged β3-Peptide Inhibitors of p53-hDM2 Complexation: Correlation between Affinity and Cell Permeability [J].

Bautista, Arjel D. ;

Appelbaum, Jacob S. ;

Craig, Cody J. ;

Michel, Julien ;

Schepartz, Alanna .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2904-+

[5]

Hydrocarbon double-stapling remedies the proteolytic instability of a lengthy peptide therapeutic [J].

Bird, Gregory H. ;

Madani, Navid ;

Perry, Alisa F. ;

Princiotto, Amy M. ;

Supko, Jeffrey G. ;

He, Xiaoying ;

Gavathiotis, Evripidis ;

Sodroski, Joseph G. ;

Walensky, Loren D. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (32) :14093-14098

[6]

Heterocyclic α-helix mimetics for targeting protein-protein interactions [J].

Biros, Shannon M. ;

Moisan, Lionel ;

Mann, Enrique ;

Carella, Alexandre ;

Zhai, Dayong ;

Reed, John C. ;

Rebek, Julius, Jr. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (16) :4641-4645

[7]

Assessing Helical Protein Interfaces for Inhibitor Design [J].

Bullock, Brooke N. ;

Jochim, Andrea L. ;

Arora, Paramjit S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (36) :14220-14223

[8]

N-alkylated oligoamide α-helical proteomimetics [J].

Campbell, Frederick ;

Plante, Jeffrey P. ;

Edwards, Thomas A. ;

Warriner, Stuart L. ;

Wilson, Andrew J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (10) :2344-2351

[9]

Disrupting protein-protein interactions with non-peptidic, small molecule α-helix mimetics [J].

Cummings, Christopher G. ;

Hamilton, Andrew D. .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2010, 14 (03) :341-346

[10]

Synthetic non-peptide mimetics of α-helices [J].

Davis, Jessica M. ;

Tsou, Lun K. ;

Hamilton, Andrew D. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) :326-334

← 1 2 3 4 5 →