Biomimetic models for cysteine proteases. 3. Acylation of imidazolium-thiolate zwitterions by p-nitrophenylacetate as a model for the acylation step and demonstration of intramolecular general-base-catalyzed delivery of water by imidazole to thiol esters as a model for the deacylation step

J. P. Street; K. I. Skorey; R. S. Brown; R. G. Ball

doi:10.1021/ja00311a074

Biomimetic models for cysteine proteases. 3. Acylation of imidazolium-thiolate zwitterions by p-nitrophenylacetate as a model for the acylation step and demonstration of intramolecular general-base-catalyzed delivery of water by imidazole to thiol esters as a model for the deacylation step

Journal of the American Chemical Society ◽

10.1021/ja00311a074 ◽

1985 ◽

Vol 107 (25) ◽

pp. 7669-7679 ◽

Cited By ~ 16

Author(s):

J. P. Street ◽

K. I. Skorey ◽

R. S. Brown ◽

R. G. Ball

Keyword(s):

Cysteine Proteases ◽

Biomimetic Models ◽

General Base ◽

Thiol Esters

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Correction. Biomimetic Models for Cysteine Proteases. 3. Acylation of Imidazolium-Thiolate Zwitterions byp-Nitrophenylacetates as a Model for the Acylation Step and Demonstration of Intramolecular General-Base-Catalyzed Delivery of H2O by Imidazole to Thiol Esters as a Model for the Deacylation Step

Journal of the American Chemical Society ◽

10.1021/ja00269a603 ◽

1986 ◽

Vol 108 (9) ◽

pp. 2492-2492

Author(s):

J P. Street ◽

K I. Skorey ◽

R S. Brown ◽

R G. Ball

Keyword(s):

Cysteine Proteases ◽

Biomimetic Models ◽

General Base ◽

Thiol Esters

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ChemInform Abstract: Biomimetic Models for Cysteine Proteases. Part 3. Acylation of Imidazolium-Thiolate Zwitterions by p-Nitrophenylacetate as a Model for the Acylation Step and Demonstration of Intramolecular General-Base-Catalyzed Delivery of H2O by Im

Chemischer Informationsdienst ◽

10.1002/chin.198613136 ◽

1986 ◽

Vol 17 (13) ◽

Author(s):

J. P. STREET ◽

K. I. SKOREY ◽

R. S. BROWN ◽

R. G. BALL

Keyword(s):

Cysteine Proteases ◽

Biomimetic Models ◽

General Base

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ChemInform Abstract: GENERAL-BASE-CATALYZED INTRAMOLECULAR AMINOLYSIS OF THIOL ESTERS. CYCLIZATION OF S-N-PROPYL O-(2-IMIDAZOLYL)THIOLBENZOATE. RELATIONSHIP OF THE UNCATALYZED AND BASE-CATALYZED NUCLEOPHILIC REACTIONS

Chemischer Informationsdienst ◽

10.1002/chin.198009103 ◽

1980 ◽

Vol 11 (9) ◽

Author(s):

T. H. FIFE ◽

B. R. DEMARK

Keyword(s):

General Base ◽

Nucleophilic Reactions ◽

Thiol Esters ◽

Relationship Of

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Ab Initio Evaluation of the Free Energy Surfaces for the General Base/Acid Catalyzed Thiolysis of Formamide and the Hydrolysis of Methyl Thiolformate: A Reference Solution Reaction for Studies of Cysteine Proteases

The Journal of Physical Chemistry B ◽

10.1021/jp010279l ◽

2001 ◽

Vol 105 (19) ◽

pp. 4471-4484 ◽

Cited By ~ 40

Author(s):

Marek Štrajbl ◽

Jan Florián ◽

Arieh Warshel

Keyword(s):

Free Energy ◽

Ab Initio ◽

Cysteine Proteases ◽

Reference Solution ◽

General Base ◽

Acid Catalyzed ◽

Solution Reaction ◽

Energy Surfaces ◽

Hydrolysis Of

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Biomimetic models for cysteine proteases. 1. Intramolecular imidazole catalysis of thiol ester solvolysis: a model for the deacylation step

Journal of the American Chemical Society ◽

10.1021/ja00307a043 ◽

1985 ◽

Vol 107 (21) ◽

pp. 6084-6089 ◽

Cited By ~ 5

Author(s):

J. P. Street ◽

R. S. Brown

Keyword(s):

Cysteine Proteases ◽

Thiol Ester ◽

Biomimetic Models ◽

Imidazole Catalysis

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Correction. Biomimetic Models for Cysteine Proteases. 2. Nucleophilic Thiolate-Containing Zwitterions Produced from Imidazole-Thiol Pairs. A Model for the Acylation Step in Papain-Mediated Hydrolyses

Journal of the American Chemical Society ◽

10.1021/ja00285a600 ◽

1986 ◽

Vol 108 (25) ◽

pp. 8119-8119

Author(s):

K I. Skorey ◽

R S. Brown

Keyword(s):

Cysteine Proteases ◽

Biomimetic Models

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Biomimetic models for cysteine proteases. 2. Nucleophilic thiolate-containing zwitterions produced from imidazole-thiol pairs. A model for the acylation step in papain

Journal of the American Chemical Society ◽

10.1021/ja00299a049 ◽

1985 ◽

Vol 107 (13) ◽

pp. 4070-4072 ◽

Cited By ~ 4

Author(s):

K. I. Skorey ◽

R. S. Brown

Keyword(s):

Cysteine Proteases ◽

Biomimetic Models

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General-base-catalyzed intramolecular aminolysis of thiol esters. Cyclization of S-n-propyl o-(2-imidazolyl)thiolbenzoate. Relationship of the uncatalyzed and base-catalyzed nucleophilic reactions

Journal of the American Chemical Society ◽

10.1021/ja00518a041 ◽

1979 ◽

Vol 101 (24) ◽

pp. 7379-7385 ◽

Cited By ~ 7

Author(s):

Thomas H. Fife ◽

B. R. DeMark

Keyword(s):

General Base ◽

Nucleophilic Reactions ◽

Thiol Esters ◽

Relationship Of

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ChemInform Abstract: REACTION OF THIOLS WITH PHENYLGLYOXAL TO GIVE THIOL ESTERS OF MANDELIC ACID. II. INTRAMOLECULAR GENERAL-BASE CATALYSIS AND CHANGE IN RATE-DETERMINING STEP

Chemischer Informationsdienst ◽

10.1002/chin.198233133 ◽

1982 ◽

Vol 13 (33) ◽

Author(s):

T. OKUYAMA ◽

S. KOMOGUCHI ◽

T. FUENO

Keyword(s):

Mandelic Acid ◽

Base Catalysis ◽

General Base ◽

Rate Determining Step ◽

Thiol Esters

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Reaction of thiols with phenylglyoxal to give thiol esters of mandelic acid. II. Intramolecular general-base catalysis and change in rate-determining step

Journal of the American Chemical Society ◽

10.1021/ja00373a041 ◽

1982 ◽

Vol 104 (9) ◽

pp. 2582-2587 ◽

Cited By ~ 13

Author(s):

Tadashi Okuyama ◽

Shinji Komoguchi ◽

Takayuki Fueno

Keyword(s):

Mandelic Acid ◽

Base Catalysis ◽

General Base ◽

Rate Determining Step ◽

Thiol Esters

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