Solid-phase synthesis of linear and cyclic peptides containing a calix[4]arene amino acid

被引：8

作者：

Baldini, Laura ^{[1
]}

Sansone, Francesco ^{[1
]}

Scaravelli, Federico ^{[1
]}

Massera, Chiara ^{[2
]}

Casnati, Alessandro ^{[1
]}

Ungaro, Rocco ^{[1
]}

机构：

[1] Dipartimento Chim Organ & Ind, I-43100 Parma, Italy

[2] Univ Parma, Dipartimento Chim Gen & Inorgan, I-43100 Parma, Italy

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 26期

关键词：

RGD PEPTIDES; INTEGRIN ANTAGONISTS; DRUG DESIGN; UPPER RIM; RECOGNITION; LIBRARY;

D O I：

10.1016/j.tetlet.2009.02.198

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Solid-phase synthesis is used to obtain new linear and cyclic N,C-linked peptidocalixarenes. The synthetic strategy allows, for the first time, the condensation of a calix[4]arene amino acid during the stepwise elongation sequence of the peptide. An important role is played by the lower rim functionalization of the calixarene since it modulates the flexibility of the calixarene scaffold and the conformational properties of the resulting non-natural peptide. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3450 / 3453

页数：4

共 50 条

[1] Solid-phase synthesis of a novel peptide substituted calix[4]arene
Shuker, SB
Esterbrook, J
Gonzalez, J
SYNLETT, 2001, (02) : 210 - 213
[2] Solid-phase synthesis of cyclic homodetic peptides
Blackburn, C
Kates, SA
SOLID-PHASE PEPTIDE SYNTHESIS, 1997, 289 : 175 - 198
[3] Solid-phase synthesis of cyclic RGD-furanoid sugar amino acid peptides as integrin inhibitors
van Well, RM
Overkleeft, HS
van der Marel, GA
Bruss, D
Thibault, G
de Groot, PG
van Boom, JH
Overhand, M
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (03) : 331 - 334
[4] Solid-Phase Synthesis of Biaryl Cyclic Peptides Containing a 3-Aryltyrosine
Afonso, Ana
Cusso, Olaf
Feliu, Lidia
Planas, Marta
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (31) : 6204 - 6211
[5] Studies on the solid-phase synthesis of cyclic peptides using arene chromium "traceless" linker.
Rigby, JH
Kondratenko, M
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U124 - U124
[6] Solid phase synthesis of α-amino squaric acid-containing peptides
Maeda, Kentaro
Kiniwa, Yu-ichi
Ohfune, Yasufumi
Ishiguro, Shinichi
Suzuki, Koichi
Murata, Kazuya
Matsuda, Hideaki
Shinada, Tetsuro
RSC ADVANCES, 2014, 4 (92) : 50639 - 50643
[7] Synthesis and amino acid extraction abilities of chiral calix[4]arene triamides containing amino alcohol units
Erdemir, Serkan
Tabakci, Mustafa
Yilmaz, Mustafa
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2007, 59 (3-4) : 197 - 202
[8] Synthesis and amino acid extraction abilities of chiral calix[4]arene triamides containing amino alcohol units
Serkan Erdemir
Mustafa Tabakci
Mustafa Yilmaz
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2007, 59 : 197 - 202
[9] SYNTHESIS OF CYCLIC-PEPTIDES BY SOLID-PHASE METHODOLOGY
LEBL, M
HRUBY, VJ
TETRAHEDRON LETTERS, 1984, 25 (20) : 2067 - 2068
[10] Solid-phase synthesis of biaryl cyclic peptides containing a histidine-tyrosine linkage
Ng-Choi, Iteng
Oliveras, Angel
Planas, Marta
Feliu, Lidia
TETRAHEDRON, 2019, 75 (18) : 2625 - 2636

← 1 2 3 4 5 →