Synthesis of heteroaromatic thyrotropin-releasing hormone analogues

Abstract

Novel thyrotropin-releasing hormone (TRH) analogues containing the unnatural and heteroaromatic L-pyrrolylalanine, D-pyrrolylalanine, and L-furylalanine amno acids in position 2 have been synthesized. L-Furylalanine was obtained by the stereospecific hydrolysis of the N-acetyl-D,L-amino acid with acylase I. A protected derivative of D,L-pyrrolylalanine was prepared, the racemate was incorporated into the tripeptide and the LLL and LDL diastereoisomers were separated at the end of the synthesis.