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

36 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 language	English
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 - 1 Jan 1991
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)81797-X

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

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 - Zimmerman, Steven C.

AU - Korthals, Jean S.

AU - Gramer, Katherine D.

PY - 1991/1/1

Y1 - 1991/1/1

N2 - 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.

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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U2 - 10.1016/S0040-4020(01)81797-X

DO - 10.1016/S0040-4020(01)81797-X

M3 - Article

AN - SCOPUS:0026027796

SN - 0040-4020

VL - 47

SP - 2649

EP - 2660

JO - Tetrahedron

JF - Tetrahedron

IS - 14-15

ER -

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

Abstract

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