Synthesis of Fluorine-Containing Peptides. Analogues of Angiotensin II Containing Hexafluorovaline.

Article abstract of DOI:10.1021/jm00141a005

γ,γ,γ,γ',γ',γ'-Hexafluorovaline and derivatives have been prepared and incorporated into angiotensin II by fragment condensation and solid-phase peptide synthesis.Hexafluorovaline derivatives showed general resistance toward various enzymatic digestions and the tendency to racemize extensively upon carboxyl activation.When the angiotensin II analogues were assayed on rat uterus, 5>AII had 133percent activity, 5>AII was inactive, and 1,DL-Hfv⁸>AII was a potent inhibitor of angiotensin II in vitro and in vivo.