Syn and anti-oriented imidazole carboxylates as models for the histidine-aspartate couple in serine proteases and other enzymes

Steven C. Zimmerman, Jean S. Korthals, Katherine D. Gramer

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

Several compounds containing an imidazole and a carboxylic acid group have been synthesized and studied as models for the His-Asp couple found in serine proteases and other enzymes. The ability of the carboxylic acid group to increase the basicity of the imidazole and its role in nucleophilic and general base catalysis by the imidazole is described.

Original languageEnglish
Pages (from-to)2649-2660
Number of pages12
JournalTetrahedron
Volume47
Issue number14-15
DOIs
StatePublished - 1 Jan 1991
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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