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 journalArticlepeer-review

285 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 languageEnglish
Pages (from-to)1167-1169
Number of pages3
JournalChemBioChem
Volume6
Issue number7
DOIs
StatePublished - 1 Jul 2005
Externally publishedYes

Keywords

  • Click chemistry
  • Inhibitors
  • Peptidomimetics
  • Triazole

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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