1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics

被引：263

作者：

Bock, Victoria D.

Speijer, Dave

Hiemstra, Henk

van Maarseveen, Jan H.

机构：

[1] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1018 WS Amsterdam, Netherlands

[2] Univ Amsterdam, Acad Med Ctr, Dept Biochem Med, NL-1105 AZ Amsterdam, Netherlands

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2007年 / 5卷 / 06期

关键词：

D O I：

10.1039/b616751a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Since the discovery of Cu-I-catalysed click chemistry, the field of peptidomimetics has expanded to include 1,4-connected 1,2,3-triazoles as useful peptide bond isosteres. Here, we report the synthesis of triazole-containing analogues of the naturally occurring tyrosinase inhibitor cyclo-[Pro-Val-Pro-Tyr] and show that the analogues retain enzyme inhibitory activity, demonstrating the effectiveness of a 1,4-connected 1,2,3-triazole as a trans peptide bond isostere.

引用

页码：971 / 975

页数：5

共 43 条

[1] Ring closure to β-turn mimics via copper-catalyzed azide/alkyne cycloadditions [J].

Angell, Y ;

Burgess, K .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9595-9598

[2] Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers [J].

Angelo, NG ;

Arora, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17134-17135

[3] Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry [J].

Aucagne, Vincent ;

Leigh, David A. .

ORGANIC LETTERS, 2006, 8 (20) :4505-4507

[4] C2-symmetric macrocyclic carbohydrate/amino acid hybrids through copper(I)-catalyzed formation of 1,2,3-triazoles [J].

Billing, JF ;

Nilsson, UJ .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) :4847-4850

[5] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[6] Click chemistry as a route to cyclic tetrapeptide analogues:: Synthesis of cyclo-[Pro-Val-Ψ(triazole)-Pro-Tyr] [J].

Bock, VD ;

Perciaccante, R ;

Jansen, TP ;

Hiemstra, H ;

van Maarseveen, JH .

ORGANIC LETTERS, 2006, 8 (05) :919-922

[7] SYNTHESIS OF 1,2,4-OXADIAZOLE-DERIVED, 1,3,4-OXADIAZOLE-DERIVED, AND 1,2,4-TRIAZOLE-DERIVED DIPEPTIDOMIMETICS [J].

BORG, S ;

ESTENNEBOUHTOU, G ;

LUTHMAN, K ;

CSOREGH, I ;

HESSELINK, W ;

HACKSELL, U .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3112-3120

[8] Freeze-frame inhibitor captures acetylcholinesterase in a unique conformation [J].

Bourne, Y ;

Kolb, HC ;

Radic, Z ;

Sharpless, KB ;

Taylor, P ;

Marchot, P .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (06) :1449-1454

[9] 1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors [J].

Brik, A ;

Alexandratos, J ;

Lin, YC ;

Elder, JH ;

Olson, AJ ;

Wlodawer, A ;

Goodsell, DS ;

Wong, CH .

CHEMBIOCHEM, 2005, 6 (07) :1167-+

[10] Application of azide-alkyne cycloaddition 'click chemistry' for the synthesis of Grb2 SH2 domain-binding macrocycles [J].

Choi, Won Jun ;

Shi, Zhen-Dan ;

Worthy, Karen M. ;

Bindu, Lakshman ;

Karki, Raieshri G. ;

Nicklaus, Marc C. ;

Fisher, Robert J. ;

Burke, Terrence R., Jr. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (20) :5265-5269

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