Reactions of proteins with ethyl vinyl sulfone.
Ethly vinyl sulfone (EVS) alkylates xi-amino groups of lysine side chains and imidazole groups of histidine residues in proteins. Amino acid analysis of hydrolyzates of EVS-treated polylysine shows that lysine forms two derivatives, presumably xi-N-(ethylsulfonylethyl)lysine and xi, xi, N,N-bis(ethylsulfonylethyl)lysine that are eluted as well-resolved peaks on the (long basic) physiological column of our amino acid analyzer at about 118 and 60 min, respectively. Peaks with identical elution times were also observed after EVS-treatment of BSA and wool. The postulated histidine derivative, presumably N3-im-(ethylsulfonylethyl)histidine is also eluted as a well-resolved peak on the same column at about 90 min. A peak with an identical elution time was observed in a hydrolyzate of EVS-treated polyhistidine. The described alkylation has potential utility for modifying proteins.
D000478:Alkylation; D000596:Amino Acids / Q000032:analysis; D000818:Animals; D002364:Caseins; D055598:Chemical Phenomena; D002621:Chemistry; D002852:Chromatography, Ion Exchange; D006639:Histidine; D006868:Hydrolysis; D008239:Lysine; D010455:Peptides; D011506:Proteins; D012710:Serum Albumin, Bovine; D013450:Sulfones; D014753:Vinyl Compounds; D014935:Wool
D000596:Amino Acids; D002364:Caseins; D010455:Peptides; D011506:Proteins; D013450:Sulfones; D014753:Vinyl Compounds; D012710:Serum Albumin, Bovine; D006639:Histidine; D008239:Lysine