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

doi:10.1016/S0040-4020(01)81797-X

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 journal › Article › peer-review

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 language	English (US)
Pages (from-to)	2649-2660
Number of pages	12
Journal	Tetrahedron
Volume	47
Issue number	14-15
DOIs	https://doi.org/10.1016/S0040-4020(01)81797-X
State	Published - 1991

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/S0040-4020(01)81797-X

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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.",

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AU - Korthals, Jean S.

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AB - 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.

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

Abstract

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