CHED 436 |
| Type II diabetes mellitus is characterized by the body's decreased sensitivity to and/or inefficient production of insulin. Normal regulation of insulin levels is maintained via the interaction of glucogon-like peptide-1 with its receptor, GLP-1R. Past studies have proven that the N-terminal histidine of GLP-1 is crucial to the binding and activation of the receptor. The literature asserts that GLP-1 requires a protonated N-terminal amino acid for activity. We have tested this assertion through the replacement of this N-terminal histidine with analogs possessing a range of pKa's and hydrogen bonding capabilities. Our current study includes the synthesis of the 4-(beta-alanyl)-2-methyl-imidazole (1) and 2-(beta-alanyl)-pyrrole (2). The synthesis of 1 requires the hydroxymethylation of a benzyl-protected methyl-imidazole while the synthesis of 2 requires the addition of a methyl-trimethylammonium group to a benzyl-protected pyrrole. Further elaboration including addition of a chirally protected glycine anion results in the stereospecific amino acid synthesis.
|
|
Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster
Division of Chemical Education |
