Congrats!

Congratulations to my sister Emily for being a published researcher! Last year she worked in a chemistry lab and now the paper has been published and she's the third author. Pretty cool stuff, especially considering she's working in investment banking now.

CHED 000 - Synthesis of a histidine analog: (2-Imidazolyl)alanine
Grace Logan, Kathryn A. Lipford, Emily Oxford, and David R. Haines, Department of Chemistry, Wellesley College, 106 Central St., Wellesley, MA 02481, Fax: 781-283-3642, glogan@wellesley.edu

Glucagon-like peptide-1 (GLP-1) is an endogenous peptide released in the insulin induction pathway when food is ingested. GLP-1 binds to the glucagon-like peptide-1 receptor (GLP-1R) in pancreatic b-cells, initiating a second messenger cascade resulting in the release of insulin into the bloodstream. As part of an SAR study of the N-terminal histidine (1) of GLP-1, which is essential to the activation of GLP-1R, we have prepared (2-imidazolyl)alanine (2) as a histidine analog. Hydroxymethylation of a protected imidazole occurs preferentially at the 2 position. Reaction of the protected hydroxymethylimidazole with thionyl chloride, followed by reaction with a chirally protected glycine anion gave protected 2 as a single diastereomer. Removal of the protecting groups gave 2 enantiomerically pure and in excellent yield. BOC protection of 2 followed by incorporation, by solid phase synthesis, into GLP-1 in place of histidine gave a GLP-1 analog which was screened for activation of GLP-1R.