Unexpected Ring Transformations on Functionalization of 2-(omega-Alken-1-yl)-3,3,3-trifluoroalanine Derivatives

摘要

2-(omega-Alken-1-yl)-3,3,3-trifluoroalanine derivatives are transformed into trifluoromethyl substituted heterocycles via epoxidation reactions. Incorporation of alpha-trifluoromethyl amino acids (alpha-Tfm amino acids) into strategical positions of peptides retards proteolytic degradation, induces secondary structure motifs, and improves lipophilicity [1] enhancing in vivo absorption, thus improving permeability through certain body barriers.