Homocysteine thiolactone and protein homocysteinylation: mechanistic studies with model peptides and proteins.
In vitro incubations were performed to show that homocysteine thiolactone could generate covalent adducts with model peptides and proteins. MS and MS/MS data suggest that the thiolactone reacts with the side-chain amino group of lysine residues as well as with the N-terminal amino group or C-terminal carboxy group. For larger peptides and proteins, the contribution from the in-amino groups of lysine residues should be predominant. These data could help explain the detrimental effects of elevated levels of homocysteine and homocysteine thiolactone.
Hop
Cornelis E C A
CE
Department of Drug Metabolism, Merck Research Laboratories, Rahway, NJ 07065, USA. cornelis_hop@merck.com
Bakhtiar
Ray
R
D006710:Homocysteine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008239:Lysine / Q000737:chemistry; D013058:Mass Spectrometry; D010455:Peptides / Q000737:chemistry*; D011485:Protein Binding
D010455:Peptides; D006710:Homocysteine; C007957:homocysteine thiolactone; D008239:Lysine