PMID: 42623Jan 1, 1979

A new arylating agent, 2-carboxy-4,6-dinitrochlorobenzene. Reaction with model compounds and bovine pancreatic ribonuclease

International Journal of Peptide and Protein Research
J BelloG Kartha

Abstract

The reagent 2-carboxy-4,6-dinitrochlorobenzene (CDNCB) reacts with the imino, amino and sulfhydryl groups of model compounds. At pH 8.2, sulfhydryl groups react much faster than do amines. N alpha-Acetylhistidine, N alpha-acetyltyrosine and N alpha-acetyltryptophan do not react. Poly(L-Lysine) and poly(DL-lysine) react about 50 times as fast as does N alpha-acetyllysine. A dichloroanalog, 6-carboxy-2,4-dinitro-1,3-dichlorobenzene, shows stepwise reactivity with amines. With bovine pancreatic ribonuclease, which contains no sulfhydryl, CDNCB reacts preferentially with the epsilon-amino of Lys-41 at 450 times the rate with the epsilon-amino of N alpha-acetyllysine. The preferential reactivity at Lys-41 is discussed in relation to the pK of Ly-41, the cationic character of the active site cleft, and the mechanism of RNAase action on substrates.

Citations

Mar 28, 1977·Biochimica Et Biophysica Acta·H IijimaJ Bello
May 1, 1975·European Journal of Biochemistry·L R Brown, J H Bradbury
Jan 1, 1975·International Journal of Peptide and Protein Research·P RiquelmeF Marcus
Aug 21, 1970·Biochimica Et Biophysica Acta·D M Glick, E A Barnard
Feb 1, 1969·Biochemistry·J Bello, E F Nowoswiat
May 1, 1969·European Journal of Biochemistry·H Rüterjans, H Witzel
Jul 1, 1965·Archives of Biochemistry and Biophysics·C H HirsJ H Kycia
Jul 1, 1965·Archives of Biochemistry and Biophysics·C H Hirs, J H Kycia

Related Concepts

Amines
Nitrobenzenes
Dinitrochlorobenzene
Pancreatitis
Bos taurus
Sulfhydryl Compounds
Lysine
Alkaline Ribonuclease
LY 41
X-Ray Diffraction

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