Solid phase synthesis of peptidotriazoles with multiple cycles of triazole formation

被引：49

作者：

Zhang, ZS ^{[1
]}

Fan, E ^{[1
]}

机构：

[1] Univ Washington, Dept Biochem, Biomol Struct Ctr, Seattle, WA 98195 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 05期

关键词：

peptidotriazole; peptidomimetics; unnatural oligomer; solid phase;

D O I：

10.1016/j.tetlet.2005.11.111

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Peptidotriazoles, unnatural oligomers with alternating amide and triazole linkages, are synthesized efficiently on solid support. The key transformations involve multiple cycles of 1,2,3-triazolc formation, using soluble Cu(I) catalyst and conditions that do not generate precipitate on solid support nor require exclusion of oxygen. Our synthetic protocol will enable the preparation of other unnatural oligomers with multiple triazoles using solid phase methodologies. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：665 / 669

页数：5

共 51 条

[1] A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction
Appukkuttan, P
Dehaen, W
Fokin, VV
Van der Eycken, E
[J]. ORGANIC LETTERS, 2004, 6 (23) : 4223 - 4225
[2] Parallel synthesis and biological screening of dopamine receptor ligands taking advantage of a click chemistry based BAL linker
Bettinetti, L
Löber, S
Hübner, H
Gmeiner, P
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (02): : 309 - 316
[3] C2-symmetric macrocyclic carbohydrate/amino acid hybrids through copper(I)-catalyzed formation of 1,2,3-triazoles
Billing, JF
Nilsson, UJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) : 4847 - 4850
[4] Highly convergent synthesis of C3- or C2-symmetric carbohydrate macrocycles
Bodine, KD
Gin, DY
Gin, MS
[J]. ORGANIC LETTERS, 2005, 7 (20) : 4479 - 4482
[5] Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide
Bodine, KD
Gin, DY
Gin, MS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) : 1638 - 1639
[6] Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy
Boeijen, A
van Ameijde, J
Liskamp, RMJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) : 8454 - 8462
[7] 1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors
Brik, A
Alexandratos, J
Lin, YC
Elder, JH
Olson, AJ
Wlodawer, A
Goodsell, DS
Wong, CH
[J]. CHEMBIOCHEM, 2005, 6 (07) : 1167 - +
[8] SOLID-PHASE SYNTHESES OF UNNATURAL BIOPOLYMERS CONTAINING REPEATING UREA UNITS
BURGESS, K
LINTHICUM, DS
SHIN, HW
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (08): : 907 - 909
[9] Solid phase syntheses of oligoureas
Burgess, K
Ibarzo, J
Linthicum, DS
Russell, DH
Shin, H
Shitangkoon, A
Totani, R
Zhang, AJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (07) : 1556 - 1564
[10] Polytriazoles as copper(I)-stabilizing ligands in catalysis
Chan, TR
Hilgraf, R
Sharpless, KB
Fokin, VV
[J]. ORGANIC LETTERS, 2004, 6 (17) : 2853 - 2855

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