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

Ashraf Brik; Jerry Alexandratos; Ying Chuan Lin; John H. Elder; Arthur J. Olson; Alexander Wlodawer; David S. Goodsell; Chi Huey Wong

doi:10.1002/cbic.200500101

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

Ashraf Brik, Jerry Alexandratos, Ying Chuan Lin, John H. Elder, Arthur J. Olson, Alexander Wlodawer, David S. Goodsell, Chi Huey Wong

Research output: Contribution to journal › Article › peer-review

274 Scopus citations

Abstract

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).

Original language	English (US)
Pages (from-to)	1167-1169
Number of pages	3
Journal	ChemBioChem
Volume	6
Issue number	7
DOIs	https://doi.org/10.1002/cbic.200500101
State	Published - Jul 2005
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Organic Chemistry

Keywords

Click chemistry
Inhibitors
Peptidomimetics
Triazole

Access to Document

10.1002/cbic.200500101

Cite this

@article{86f18191907f4c769c63fe7107d39fbd,

title = "1,2,3-Triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors",

abstract = "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).",

keywords = "Click chemistry, Inhibitors, Peptidomimetics, Triazole",

author = "Ashraf Brik and Jerry Alexandratos and Lin, {Ying Chuan} and Elder, {John H.} and Olson, {Arthur J.} and Alexander Wlodawer and Goodsell, {David S.} and Wong, {Chi Huey}",

year = "2005",

month = jul,

doi = "10.1002/cbic.200500101",

language = "English (US)",

volume = "6",

pages = "1167--1169",

journal = "ChemBioChem",

issn = "1439-4227",

publisher = "Wiley-VCH Verlag",

number = "7",

}

TY - JOUR

T1 - 1,2,3-Triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors

AU - Brik, Ashraf

AU - Alexandratos, Jerry

AU - Lin, Ying Chuan

AU - Elder, John H.

AU - Olson, Arthur J.

AU - Wlodawer, Alexander

AU - Goodsell, David S.

AU - Wong, Chi Huey

PY - 2005/7

Y1 - 2005/7

N2 - 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).

AB - 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).

KW - Click chemistry

KW - Inhibitors

KW - Peptidomimetics

KW - Triazole

UR - http://www.scopus.com/inward/record.url?scp=22144498399&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=22144498399&partnerID=8YFLogxK

U2 - 10.1002/cbic.200500101

DO - 10.1002/cbic.200500101

M3 - Article

C2 - 15934050

AN - SCOPUS:22144498399

SN - 1439-4227

VL - 6

SP - 1167

EP - 1169

JO - ChemBioChem

JF - ChemBioChem

IS - 7

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Access to Document

Other files and links

Fingerprint

Cite this