1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors

被引：262

作者：

Brik, A

Alexandratos, J

Lin, YC

Elder, JH

Olson, AJ

Wlodawer, A

Goodsell, DS

Wong, CH

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[3] NCI, Macromol Crystallog Lab, Frederick, MD 21702 USA

[4] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

来源：

CHEMBIOCHEM | 2005年 / 6卷 / 07期

关键词：

click chemistry; inhibitors; peptidomimetics; triazole;

D O I：

10.1002/cbic.200500101

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Substitute for another bond. Docking simulations of two potent inhibitors that bear the 1,2,3-triazole moiety produced two conformations of approximately equal energy. Further analysis of the protease by X-ray crystallography solved the ambiguity of the binding mode and revealed that the triazole ring is an effective amide surrogate and retains all the hydrogen bonds in the active site (see figure).

引用

页码：1167 / +

页数：4

共 17 条

[11] Rostovtsev V. V., 2002, ANGEW CHEM, V114, P2708, DOI DOI 10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO
[12] 2-0
[13] Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO
[14] 2-4
[15] Sheldrick G. M., 1997, SHELXS 97 PROGRAM CR
[16] Spatola A. F., 1983, CHEM BIOCH AMINO ACI, V7, P267
[17] Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
Tornoe, CW
Christensen, C
Meldal, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) : 3057 - 3064

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