HYDROLYSIS OF PEPTIDE BONDS BY INTRAMOLECULAR PARTICIPATION OF BENZIMIDAZOLIUM IONS

被引：8

作者：

KIRK, KL

COHEN, LA

机构：

[1] Laboratory of Chemistry, National Institute of Arthritis and Metabolic Diseases, National Institutes of Health, Maryland 20014, Bethesda

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 02期

关键词：

D O I：

10.1021/jo01254a028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 5,7-dinitrobenzimidazolyl-4 peptides have been prepared and the rates of hydrolysis of the peptide bond determined as a function of acidity and temperature. It is demonstrated that the rate of hydrolysis is dependent on the degree of protonation of a benzimidazole nitrogen atom. The effectiveness of the intramolecular participation varies with the nature of the peptide side chain and with the degree of alkylation of the imidazole ring. No correlation is observed between pKa and specific rate constant for the various substrates. Heats of ionization and activation parameters are reported for two cases. The compound, 1,2-dimethyl-5,7-dinitrobenzimidazolyl-4-alanylglycine, was found to hydrolyze 65,000 times as rapidly as 2,4-dinitrophenylalanylglycine. © 1969, American Chemical Society. All rights reserved.

引用

页码：390 / &

共 57 条

[11] BRUICE TC, 1966, BIOORG MECH, V1, pCH1
[12] BRUICE TC, 1966, J AMER CHEM SOC, V84, P365
[13] BUNTON CA, 1967, CHEM IND-LONDON, P1835
[14] ACID-CATALYZED AMIDE HYDROLYSIS ASSISTED BY NEIGHBORING AMIDE GROUP
COHEN, T
LIPOWITZ, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) : 5611 - &
[15] CROOY P, 1964, B SOC CHIM BELG, V73, P44
[16] HYDROXYL GROUP PARTICIPATION IN AMIDE HYDROLYSIS . INFLUENCE OF CATALYSTS ON PARTITIONING OF A TETRAHEDRAL INTERMEDIATE
CUNNINGHAM, BA
SCHMIR, GL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (04) : 917 - +
[17] DELALLOSA P, 1960, B SOC CHIM FR, P1624
[18] ON THE MECHANISM OF THE PHENYL ISOTHIOCYANATE DEGRADATION OF PEPTIDES
EDMAN, P
[J]. ACTA CHEMICA SCANDINAVICA, 1956, 10 (05): : 761 - 768
[19] ELIEL EL, 1956, STERIC EFFECTS ORGAN, P119
[20] DEGRADATIVE STUDIES ON PEPTIDES AND PROTEINS .1. A NEW METHOD OF STEPWISE DEGRADATION OF PEPTIDES FROM THE END BEARING A FREE AMINO-GROUP, EMPLOYING N-ACYLDITHIOCARBAMATES
ELMORE, DT
TOSELAND, PA
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1954, (DEC): : 4533 - 4537

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