Solid-Phase Methodology for Synthesis of O-Alkylated Aromatic Oligoamide Inhibitors of α-Helix-Mediated ProteinProtein Interactions

被引：39

作者：

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

Prabhakaran, Panchami ^{[1
,2
]}

Azzarito, Valeria ^{[1
,2
]}

Plante, Jeffrey P. ^{[1
]}

Hardie, Michaele J. ^{[1
]}

Kilner, Colin A. ^{[1
]}

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

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

机构：

[1] Univ Leeds, Sch Chem, Leeds LS29 JT, W Yorkshire, England

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 18期

基金：

欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

amides; foldamers; helical structures; proteinprotein interactions; solid-phase synthesis; BETA-PEPTIDES; FOLDAMERS; MIMETICS; ANTAGONISTS; SCAFFOLD; MIMICRY; FAMILY;

D O I：

10.1002/chem.201204098

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rapid access to rigid rods: A method is described for the synthesis of 3-O-alkylated aromatic oligobenzamide foldamers that could be used for assembly of libraries of α-helix mimetic inhibitors of protein-protein interactions (see scheme; Fmoc=9-fluorenylmethoxycarbonyl). © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5546 / 5550

页数：5

共 44 条

[1] 2-O-Alkylated para-benzamide α-helix mimetics: the role of scaffold curvature [J].

Azzarito, Valeria ;

Prabhakaran, Panchami ;

Bartlett, Alice I. ;

Murphy, Natasha S. ;

Hardie, Michaele J. ;

Kilner, Colin A. ;

Edwards, Thomas A. ;

Warriner, Stuart L. ;

Wilson, Andrew J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (32) :6469-6472

[2] Solid Phase Synthesis of Aromatic Oligoamides: Application to Helical Water-Soluble Foldamers [J].

Baptiste, Benoit ;

Douat-Casassus, Celine ;

Laxmi-Reddy, Katta ;

Godde, Frederic ;

Huc, Ivan .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) :7175-7185

[3] Evaluation of Diverse α/β-Backbone Patterns for Functional α-Helix Mimicry: Analogues of the Bim BH3 Domain [J].

Boersma, Melissa D. ;

Haase, Holly S. ;

Peterson-Kaufman, Kimberly J. ;

Lee, Erinna F. ;

Clarke, Oliver B. ;

Colman, Peter M. ;

Smith, Brian J. ;

Horne, W. Seth ;

Fairlie, W. Douglas ;

Gellman, Samuel H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :315-323

[4] 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

[5] 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

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

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

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

[7] 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

[8]

Delsuc N., 2007, ANGEW CHEM, V119, P218, DOI DOI 10.1002/ZAAC.201600313

[9] Proteomorphous objects from abiotic backbones [J].

Delsuc, Nicolas ;

Leger, Jean-Michel ;

Massip, Stephane ;

Huc, Ivan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (1-2) :214-217

[10] Microwave-Enhanced Solid-Phase Synthesis of N,N′-Linked Aliphatic Oligoureas and Related Hybrids [J].

Douat-Casassus, Celine ;

Pulka, Karolina ;

Claudon, Paul ;

Guichard, Gilles .

ORGANIC LETTERS, 2012, 14 (12) :3130-3133

← 1 2 3 4 5 →