Microwave-Enhanced Solid-Phase Synthesis of N,N′-Linked Aliphatic Oligoureas and Related Hybrids

被引:46
作者
Douat-Casassus, Celine [1 ]
Pulka, Karolina [1 ]
Claudon, Paul [1 ]
Guichard, Gilles [1 ]
机构
[1] Univ Bordeaux, Inst Europeen Chim & Biol, CNRS, UMR 5248, F-33607 Pessac, France
关键词
PEPTIDE-SYNTHESIS; DERIVATIVES; FOLDAMERS; DESIGN; ACID; AZIDES; HELIX;
D O I
10.1021/ol3012106
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient microwave-assisted solid-phase method for the synthesis of N,N'-linked oligoureas and related amide/urea hybrid oligomers, featuring the use of succinimidyl (2-azido-2-substituted ethyl) carbamate monomers, is reported. The rate enhancement of urea formation under microwave irradiation combined with the mild conditions of the phosphine-based azide reduction makes this approach very effective for routine synthesis of oligoureas and possibly for library production.
引用
收藏
页码:3130 / 3133
页数:4
相关论文
共 41 条
[1]   Metal catalyzed diazo transfer for the synthesis of azides from amines [J].
Alper, PB ;
Hung, SC ;
Wong, CH .
TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032
[2]   Solid-phase synthesis of difficult peptide sequences at elevated temperatures:: A critical comparison of microwave and conventional heating technologies [J].
Bacsa, Bernadett ;
Horvati, Kata ;
Bosze, Szilvia ;
Andreae, Fritz ;
Kappe, C. Oliver .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7532-7542
[3]   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
[4]   A FAST PROCEDURE FOR THE REDUCTION OF AZIDES AND NITRO-COMPOUNDS BASED ON THE REDUCING ABILITY OF SN(SR)3-SPECIES [J].
BARTRA, M ;
ROMEA, P ;
URPI, F ;
VILARRASA, J .
TETRAHEDRON, 1990, 46 (02) :587-594
[5]   Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy [J].
Boeijen, A ;
van Ameijde, J ;
Liskamp, RMJ .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8454-8462
[6]   SOLID-PHASE SYNTHESES OF UNNATURAL BIOPOLYMERS CONTAINING REPEATING UREA UNITS [J].
BURGESS, K ;
LINTHICUM, DS ;
SHIN, HW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (08) :907-909
[7]   Solid phase syntheses of oligoureas [J].
Burgess, K ;
Ibarzo, J ;
Linthicum, DS ;
Russell, DH ;
Shin, H ;
Shitangkoon, A ;
Totani, R ;
Zhang, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (07) :1556-1564
[8]   Consequences of Isostructural Main-Chain Modifications for the Design of Antimicrobial Foldamers: Helical Mimics of Host-Defense Peptides Based on a Heterogeneous Amide/Urea Backbone [J].
Claudon, Paul ;
Violette, Aude ;
Lamour, Karen ;
Decossas, Marion ;
Fournel, Sylvie ;
Heurtault, Beatrice ;
Godet, Julien ;
Mely, Yves ;
Jamart-Gregoire, Brigitte ;
Averlant-Petit, Marie-Christine ;
Briand, Jean-Paul ;
Duportail, Guy ;
Monteil, Henri ;
Guichard, Gilles .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (02) :333-336
[9]   Azidopeptide nucleic acid. An alternative strategy for solid-phase peptide nucleic acid (PNA) synthesis [J].
Debaene, F ;
Winssinger, N .
ORGANIC LETTERS, 2003, 5 (23) :4445-4447
[10]   Folding and self-assembly of aromatic and aliphatic urea oligomers: Towards connecting structure and function [J].
Fischer, Lucile ;
Guichard, Gilles .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (14) :3101-3117