Inactivation of serine protease, α-chymotrypsin by fluorinated phenylalanine analogues

Synthesis of α,α‐Difluoro‐β‐amino Esters or gem‐Difluoro‐β‐lactams as Potential Metallocarboxypeptidase Inhibitors

“…Replacement of various functional groups by a gem ‐difluoromethylene group has generated potent transition‐state‐type inhibitors 16. Several α,α‐difluoro‐β‐amino acids17 or gem ‐difluorinated peptides18 have been synthesized and tested as potent competitive serine protease inhibitors or [ 18 F]‐radiolabeled markers 19. The gem ‐difluoromethylene/methylene transposition in the “western” β‐amino acid moiety of the naturally occurring antifungal cyclic tetrapeptide rhodopeptin results in improved activity and novel physical properties (Scheme ) 20.…”

New enantiomerically enriched amino allyl- and allenylsilanes derived from naturally occurring amino acids

“…20 To the best of our knowledge, the procedure reported here is the most expeditious route to these compounds. 21 Unfortunately, the mixture of diastereoisomers 8a-c could not be separated using standard chromatographic techniques. Recent studies with fluorinated amino acids have shown that these compounds are useful tools in proteins and peptidomimetics design.…”

New gem-difluoromethylene-containing isocyanide as a useful building block for the synthesis of difluorinated pseudopeptides via Ugi reaction

“…1). 3 The replacement of the methylene group with the difluoromethylene in b-amino acids has been recognized as an important method in the blockage of metabolic processes. The combination of fluorinated b-amino acid moieties with naturally occurring pharmacophores can alter both molecule metabolism and enzyme substrate recognition.…”