Aromatic Amide Foldamers: Structures, Properties, and Functions

被引：570

作者：

Zhang, Dan-Wei ^{[1
]}

Zhao, Xin ^{[2
]}

Hou, Jun-Li ^{[1
]}

Li, Zhan-Ting ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL REVIEWS | 2012年 / 112卷 / 10期

基金：

中国国家自然科学基金;

关键词：

OLIGOPYRIDINE-DICARBOXAMIDE STRANDS; DE-NOVO DESIGN; VIBRATIONAL CIRCULAR-DICHROISM; PROTEIN-PROTEIN INTERACTIONS; ORTHO-SUBSTITUTED ARYLAMIDES; DYNAMIC COVALENT SYNTHESIS; HYDROGEN-BONDING PATTERNS; SINGLE HELICAL STRUCTURES; SOLID-PHASE SYNTHESIS; ONE-POT SYNTHESIS;

D O I：

10.1021/cr300116k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A study was conducted to demonstrate structures, properties, and functions of aromatic amide foldamers. The study covered those foldamers that comprised aromatic amide segments and were stabilized mainly by intramolecular hydrogen bonding. Aromatic amide foldamers folded to form cavities of varying sizes in comparison with other kinds of aromatic foldamers such as those based on m-phenylene ethynylene oligomers. The backbones of these foldamers gave rise to many different conformations such as extended or straight, zigzag, and V-styled structures, depending on the nature of the monomeric segments. Investigations also revealed that the stability of the secondary structure of an aromatic amide foldamer depended on the strength of the intramolecular hydrogen bonding formed by monomeric segments.

引用

页码：5271 / 5316

页数：46

共 363 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] Hydrogen-Bonded Synthetic Mimics of Protein Secondary Structure as Disruptors of Protein-Protein Interactions [J].

Adler, Marc J. ;

Jamieson, Andrew G. ;

Hamilton, Andrew D. .

SMALL-MOLECULE INHIBITORS OF PROTEIN-PROTEIN INTERACTIONS, 2011, 348 :1-23

[3] Facile synthesis of benzamides to mimic an α-helix [J].

Ahn, Jung-Mo ;

Han, Sun-Young .

TETRAHEDRON LETTERS, 2007, 48 (20) :3543-3547

[4] The crystal structure of glycine [J].

Albrecht, G ;

Corey, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1939, 61 :1087-1103

[5]

[Anonymous], 1960, The Nature of the Chemical Bond, 3rd ed

[6] Definition of the hydrogen bond (IUPAC Recommendations 2011) [J].

Arunan, Elangannan ;

Desiraju, Gautam R. ;

Klein, Roger A. ;

Sadlej, Joanna ;

Scheiner, Steve ;

Alkorta, Ibon ;

Clary, David C. ;

Crabtree, Robert H. ;

Dannenberg, Joseph J. ;

Hobza, Pavel ;

Kjaergaard, Henrik G. ;

Legon, Anthony C. ;

Mennucci, Benedetta ;

Nesbitt, David J. .

PURE AND APPLIED CHEMISTRY, 2011, 83 (08) :1637-1641

[7] Functionalized 2,5-dipyridinylpyrroles by electrochemical reduction of 3,6-dipyridinylpyridazine precursors [J].

Bakkali, Hicham ;

Marie, Cecile ;

Ly, Akarim ;

Thobie-Gautiera, Christine ;

Graton, Jerome ;

Pipelier, Muriel ;

Sengmany, Stephane ;

Leonel, Eric ;

Nedelec, Jean-Yves ;

Evain, Michel ;

Dubreuil, Didier .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (12) :2156-2166

[8] Converting sequences of aromatic amino acid monomers into functional three-dimensional structures: Second-generation helical capsules [J].

Bao, Chunyan ;

Kauffmann, Brice ;

Gan, Quan ;

Srinivas, Kolupula ;

Jiang, Hua ;

Huc, Ivan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4153-4156

[9] A Self-Assembled Foldamer Capsule: Combining Single and Double Helical Segments in One Aromatic Amide Sequence [J].

Bao, Chunyan ;

Gan, Quan ;

Kauffmann, Brice ;

Jiang, Hua ;

Huc, Ivan .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (43) :11530-11536

[10] 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

← 1 2 3 4 5 6 7 8 9 10 →