Expanding the accessible chemical space by solid phase synthesis of bicyclic homodetic peptides

被引：20

作者：

Bartoloni, Marco ^{[1
]}

Kadam, Rameshwar U. ^{[1
]}

Schwartz, Julian ^{[1
]}

Furrer, Julien ^{[1
]}

Darbre, Tamis ^{[1
]}

Reymond, Jean-Louis ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 47期

基金：

瑞士国家科学基金会;

关键词：

COMBINATORIAL LIBRARIES; RIBOSOMAL SYNTHESIS; DESIGN; RECEPTORS; ANTAGONIST; STRATEGIES; MIMETICS; PROGRESS; SYSTEM; DRUGS;

D O I：

10.1039/c1cc15704c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Norbornapeptides (bicyclo[2.2.1]heptapeptides) and related bicyclic homodetic peptides were prepared by solid-phase peptide synthesis using an orthogonal protection scheme. These conformationally rigid peptides cover an almost pristine area of peptide topological space and adopt globular shapes similar to those of short alpha-helical peptides.

引用

页码：12634 / 12636

页数：3

共 38 条

[1] On-resin peptide macrocyclization using thiol-ene click chemistry [J].

Aimetti, Alex A. ;

Shoemaker, Richard K. ;

Lin, Chien-Chi ;

Anseth, Kristi S. .

CHEMICAL COMMUNICATIONS, 2010, 46 (23) :4061-4063

[2] Conformationally Homogeneous Heterocyclic Pseudotetrapeptides as Three-Dimensional Scaffolds for Rational Drug Design: Receptor-Selective Somatostatin Analogues [J].

Beierle, John M. ;

Horne, W. Seth ;

van Maarseveen, Jan H. ;

Waser, Beatrice ;

Reubi, Jean Claude ;

Ghadiri, M. Reza .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (26) :4725-4729

[3]

Blackburn C, 1997, METHOD ENZYMOL, V289, P175

[4] Hit and lead generation:: Beyond high-throughput screening [J].

Bleicher, KH ;

Böhm, HJ ;

Müller, K ;

Alanine, AI .

NATURE REVIEWS DRUG DISCOVERY, 2003, 2 (05) :369-378

[5] 970 Million Druglike Small Molecules for Virtual Screening in the Chemical Universe Database GDB-13 [J].

Blum, Lorenz C. ;

Reymond, Jean-Louis .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8732-+

[6] SYNTHESIS AND NUCLEAR-MAGNETIC-RESONANCE STRUCTURE DETERMINATION OF AN ALPHA-HELICAL, BICYCLIC, LACTAM-BRIDGED HEXAPEPTIDE [J].

BRACKEN, C ;

GULYAS, J ;

TAYLOR, JW ;

BAUM, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6431-6432

[7] Naturally occurring circular proteins: distribution, biosynthesis and evolution [J].

Cascales, Laura ;

Craik, David J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (22) :5035-5047

[8] The Amber biomolecular simulation programs [J].

Case, DA ;

Cheatham, TE ;

Darden, T ;

Gohlke, H ;

Luo, R ;

Merz, KM ;

Onufriev, A ;

Simmerling, C ;

Wang, B ;

Woods, RJ .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 2005, 26 (16) :1668-1688

[9] MEN 11420 (Nepadutant), a novel glycosylated bicyclic peptide tachykinin NK2 receptor antagonist [J].

Catalioto, RM ;

Criscuoli, M ;

Cucchi, P ;

Giachetti, A ;

Giannotti, D ;

Giuliani, S ;

Lecci, A ;

Lippi, A ;

Patacchini, R ;

Quartara, L ;

Renzetti, AR ;

Tramontana, M ;

Arcamone, F ;

Maggi, CA .

BRITISH JOURNAL OF PHARMACOLOGY, 1998, 123 (01) :81-91

[10] Biosynthesis and mode of action of lantibiotics [J].

Chatterjee, C ;

Paul, M ;

Xie, LL ;

van der Donk, WA .

CHEMICAL REVIEWS, 2005, 105 (02) :633-683

← 1 2 3 4 →