KINETICS AND MECHANISM OF THE BAMBERGER CLEAVAGE OF IMIDAZOLE AND OF HISTIDINE DERIVATIVES BY DIETHYL PYROCARBONATE IN AQUEOUS-SOLUTION

被引：31

作者：

GRACE, ME ^{[1
]}

LOOSEMORE, MJ ^{[1
]}

SEMMEL, ML ^{[1
]}

PRATT, RF ^{[1
]}

机构：

[1] WESLEYAN UNIV,DEPT CHEM,MIDDLETOWN,CT 06457

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1980年 / 102卷 / 22期

关键词：

D O I：

10.1021/ja00542a020

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

引用

页码：6784 / 6789

页数：6

共 19 条

[1] ORTHO-ESTER HYDROLYSIS - DIRECT EVIDENCE FOR A 3-STAGE REACTION-MECHANISM [J].

AHMAD, M ;

BERGSTROM, RG ;

CASHEN, MJ ;

CHIANG, Y ;

KRESGE, AJ ;

MCCLELLAND, RA ;

POWELL, MF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (10) :2669-2677

[2] COVALENT HYDRATION IN NITROGEN-HETEROCYCLES [J].

ALBERT, A .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1976, 20 :117-143

[3]

Albert A, 1965, Adv Heterocycl Chem, V4, P1, DOI 10.1016/S0065-2725(08)60873-9

[4]

AVAEVA SM, 1975, BIOORG KHIM+, V1, P1600

[5] MECHANISM OF GENERAL ACID-BASE CATALYSIS OF BREAKDOWN AND FORMATION OF TETRAHEDRAL ADDITION-COMPOUNDS FROM ALCOHOLS AND A PHTHALIMIDIUM CATION - DEPENDENCE OF BRONSTED SLOPES ON ALCOHOL ACIDITY [J].

GRAVITZ, N ;

JENCKS, WP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (02) :507-515

[6] MECHANISM OF HYDROLYSIS OF A PHTHALIMIDIUM CATION - DIRECT OBSERVATION AND TRAPPING OF TETRAHEDRAL ADDITION INTERMEDIATE AND EFFECT OF STRONG ACID ON RATE AND EQUILIBRIUM-CONSTANTS OF REVERSIBLE-REACTION [J].

GRAVITZ, N ;

JENCKS, WP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (02) :489-499

[7]

KHOURI F, 1979, J AM CHEM SOC, V101, P2248

[8] IRREVERSIBLE CLEAVAGE OF HISTIDINE RESIDUES BY DIETHYLPYROCARBONATE (ETHOXYFORMIC ANHYDRIDE) [J].

LOOSEMORE, MJ ;

PRATT, RF .

FEBS LETTERS, 1976, 72 (01) :155-158

[9] KINETICS AND MECHANISM OF AMIDE ACETAL HYDROLYSIS - CARBON-OXYGEN VS CARBON-NITROGEN BOND-CLEAVAGE IN ACID-SOLUTIONS [J].

MCCLELLAND, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (06) :1844-1849

[10] ETHOXYFORMYLATION OF PROTEINS . REACTION OF ETHOXYFORMIC ANHYDRIDE WITH ALPHA-CHYMOTRYPSIN, PEPSIN, AND PANCREATIC RIBONUCLEASE AT PH 4 [J].

MELCHIOR, WB ;

FAHRNEY, D .

BIOCHEMISTRY, 1970, 9 (02) :251-&

← 1 2 →