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Modification of arginine and lysine in proteins with 2,4-pentanedione.
Metadata
Journalbiochemistry2.865Date
1975-Nov-18
Publication Type
Research Support, U.S. Gov't, P.H.S.
Journal Article
Volume
1975-Nov-18 / 14 : 5194-9
Author
Gilbert HF , O'Leary MH
DoiPMIDMESH
Arginine
Binding Sites
Hydrogen-Ion Concentration
Ketones
Kinetics
Lysine
Micrococcus
Muramidase
Pentanones
Protein Binding
Protein Conformation
Proteins
Spectrophotometry, Ultraviolet
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 with hydroxylamine regenerated the modified lysine residues but caused no change in the modified arginine residues. One arginine residue seems to be essential for the catalytic activity of the enzyme.
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2.9
Biochemistrybiochemistry
Metadata
LocationUnited States
FromAMER CHEMICAL SOC

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