Synthesis of Fluorine-Containing,b Analogues of Angiotensin II Containing Hexafluorovaline

William H. Vine, Kun Hwa Hsieh, Garland R. Marshall

Research output: Contribution to journalArticlepeer-review

28 Scopus citations


γ,γγγ'γ'γ'-Hexafluorovaline and derivatives have been prepared and incorporated into angiotensin 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, [Hfv5]All had 133% activity, [d-Hfv5]All was inactive, and [Ac- Asn1,DL-Hfv8]AII was a potent inhibitor of angiotensin II in vitro and in vivo.

Original languageEnglish
Pages (from-to)1043-1047
Number of pages5
JournalJournal of Medicinal Chemistry
Issue number9
StatePublished - Sep 1981


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