Stereospecific synthesis of histidine analogs from an aziridine

CHED 861

Alissa D Agnello and David R. Haines. Department of Chemistry, Wellesley College, 106 Central St, Wellesley, MA 02481
Histidine analogs are important for structure activity studies of several known biologically active peptides. While 3-(1,2,4-triazol-1-yl)-L-alanine (1) is commercially available, via enzymatic synthesis, a high yield chemical synthetic method is desirable, and could possibly be generalized to other heterocyclic histidine analogs. Methyl-1R-phenylethyl-aziridine-2S-carboxylate (2) can be prepared stereospecifically, and provides a chemical entry into the stereospecific synthesis of such histidine analogs. Nucleophilic attack of 1,2,4-triazole on the chiral aziridine, catalyzed by a strong Lewis acid, opens the ring to give the N-phenethyl protected 1 as an ester. We are optimizing the catalyst and conditions for the activation of the aziridine, and will report our results and the general applicability of the methodology developed.

 

Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster

Division of Chemical Education

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004