Facile synthesis of (s)-5,5-difluoronorleucine and its incorporation in biologically active peptides as an methionine mimetic

Article abstract of DOI:10.3987/COM-05-S(T)44

Both Boc and Fmoc protected 5,5-difluoronorleucines (F₂Nle) were easily prepared from commercially available amino acid derivatives. F₂Nle can be viewed as a mimic of methionine in which the sulfur atom is replaced by the CF₂ moiety. Two analogues of methionine-containing biologically active peptides (fMLP and Met-enkephalin) were prepared. The validity of CF₂-substituted methionine analogues was confirmed in their biological assay.