Complete Protection and Glycosylation of Hydroxylysine

Complete Protection and Glycosylation of Hydroxylysine

One of the most common types of cardiovascular disease is the coronary heart disease, atherosclerosis. Adiponectin, a protein hormone, has been shown to play a role in preventing the development of atherosclerosis. Modification of this compound could help to produce more beneficial effects. One of the amino acids in adiponectin, Hydroxylysine (HYL), can often undergo posttranslational modifications, such as glycosylation.

The aim of the intended research is to protect specific functional groups of the amino acid to make it suitable for peptide synthesis. Total synthetic route will entail a differential protection of the amino acid, and addition of specific sugar molecules to the hydroxyl group. Galactose and glucose are the sugars that will be used for attachment, by processes galactosylation and glycosylation respectively. First, galactose will each be attached to hydroxylysine alone, and later it will be attempted to attach both galactose and glucose, as a dimer to the same molecule of hydroxylysine. Infrared spectroscopy (IR), gas chromatography-mass spectrometry (GC-MS), and thin layer chromatography (TLC) will be used for characterization.

The organic molecules synthesized in the laboratory will be sent to a collaborator, Dr. Mare Cudic, at Torrey Pines Institute for Molecular Studies, in Port St. Lucie, FL, for incorporation into the larger peptide, adiponectin. The peptides will be used to investigate the effects of tobacco use in the cardiovascular disease, atherosclerosis.