A comparison of four methods for the solution-state synthesis of N-acyl dipeptide and tripeptide esters will be presented. The methods include carbodiimide-based couplings using DCC (N,N’-dicyclohexylcarbodiimide) and DIC (N,N’-diisopropylcarbodiimide), Mukaiyama’s method using TPP/DPDS (triphenylphosphine/2,2’-dipyridyldisulfide), and the simple modification of commercial dipeptides. Specific problems include the known allergenic character of DCC, evident residue epimerization under DIC conditions, and the difficulty of removing by-products in the TPP/DPDS method. An update on the impact of long-range structure on the rates of base-promoted methanolysis of the products will also be provided.

Comparing methods for the solution-state synthesis of dipeptide and tripeptide esters

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.