Modification of arginine and lysine in proteins with 2,4-pentanedione

Biochemistry
H F Gilbert, M H O'Leary

Abstract

Primary amines react with 2,4-pentanedione at pH 6-9 to form enamines, N-alkyl-4-amino-3-penten-2-ones. The latter compounds readily regenerate the primary amine at low pH or on treatment with hydroxylamine. Guanidine and substituted guanidines react with 2,4-pentanedione to form N-substituted 2-amino-4,6-dimethylpyrimidines at a rate which is lower by at least a factor of 20 than the rate of reaction of 2,4-pentanedione with primary amines. Selective modification of lysine and arginine side chains in proteins can readily be achieved with 2,4-pentanedione. Modification of lysine is favored by reaction at pH 7 or for short reaction times at pH 9. Selective modification of arginine is achieved by reaction with 2,4-pentanedione for long times at pH 9, followed by treatment of the protein with hydroxylamine. The extent of modification of lysine and arginine side chains can readily be measured spectrophotometrically. Modification of lysozyme with 2,4-pentanedione at pH 7 results in modification of 3.8 lysine residues and less than 0.4 arginine residue in 24 hr. Modification of lysozyme with 2,4-pentanedione at pH 9 results in modification of 4 lysine residues and 4.5 arginine residues in 100 hr. Treatment of this modified protein wi...Continue Reading

Citations

Feb 1, 1991·Journal of Protein Chemistry·T Sejlitz, H Y Neujahr
Jun 6, 1979·Biochimica Et Biophysica Acta·H B OtwellR B Dunlap
Aug 13, 1981·Biochimica Et Biophysica Acta·S K Lambiris, P F Leadlay
Jan 1, 1989·Toxicon : Official Journal of the International Society on Toxinology·V M MahnirG B Elyakov
Mar 1, 1988·Molecular and Cellular Endocrinology·E Michel, J A Parsons
Jul 3, 2007·Bioconjugate Chemistry·Fujie TanakaC F Barbas
Jul 17, 1999·The Journal of Peptide Research : Official Journal of the American Peptide Society·O Kinzel, H Budzikiewicz
May 15, 1981·European Journal of Biochemistry·E A FleerG H de Haas
Dec 18, 2014·ACS Medicinal Chemistry Letters·Verena Grundler, Karl Gademann
Aug 13, 1981·Biochimica Et Biophysica Acta·G G Chang, T M Huang
Jun 15, 1977·FEBS Letters·J P Kabayo, D W Hutchinson
Jan 1, 1986·Drug and Chemical Toxicology·B BallantyneD J Nachreiner
Sep 10, 1991·Biochemistry·P F Guidinger, T Nowak
Oct 1, 1986·Journal of Muscle Research and Cell Motility·S C el-SalehJ D Potter
Jul 1, 2020·The Journal of Clinical Investigation·Elena PacheraOliver Distler

Related Concepts

Arginine hydrochloride
Hydrogen-Ion Concentration
Ketones
Enisyl
Micrococcus
Leftose
Pentanones
Plasma Protein Binding Capacity
Protein Conformation
Gene Products, Protein

Related Feeds

Bacterial Cell Wall Structure

Bacterial cell walls are made of peptidoglycan (also called murein), which is made from polysaccharide chains cross-linked by unusual peptides containing D-amino acids. Here is the latest research on bacterial cell wall structures.

Bacterial Cell Wall Structure (ASM)

Bacterial cell walls are made of peptidoglycan (also called murein), which is made from polysaccharide chains cross-linked by unusual peptides containing D-amino acids. Here is the latest research on bacterial cell wall structures.