title: Inhibition of dipeptidyl peptidase IV (DPP IV) by 2-(2-amino-1-fluoro-propylidene)-cyclopentanecarbonitrile, a fluoroolefin containing peptidomimetic.
abstract: Novel, potent inhibitors of dipeptidyl peptidase IV (DPP IV, EC 3.4.14.5, CD26), containing the fluoroolefin peptide isostere psi [CFz.dbnd6;C], have been prepared via the intermediacy of the Peterson fluoroolefination reaction. The nitrile containing inhibitors were found to inhibit dipeptidyl peptidase IV competitively with K(i) values for the l-3 and u-3 inhibitors of 7.69 and 6.03 microM, respectively. In contrast to earlier reported fluoroolefin containing inhibitors, the nitriles underwent no detectable degradation at pH 7.6 under buffered conditions.
authors.affiliation: Department of Chemistry, University at Albany, Albany, NY 12222, USA.
authors.forename: Kake
authors.initials: K
authors.lastname: Zhao
authors.forename: Dong Sung
authors.initials: DS
authors.lastname: Lim
authors.forename: Takashi
authors.initials: T
authors.lastname: Funaki
authors.forename: John T
authors.initials: JT
authors.lastname: Welch
mesh_terms: D001667:Binding, Competitive; D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000494:pharmacology; D018819:Dipeptidyl Peptidase 4 / Q000378:metabolism*; D004355:Drug Stability; D005260:Female; D006801:Humans; D006863:Hydrogen-Ion Concentration; D009570:Nitriles / Q000737:chemistry* / Q000494:pharmacology*; D010455:Peptides / Q000737:chemistry* / Q000494:pharmacology*; D010920:Placenta / Q000201:enzymology; D011247:Pregnancy; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D009570:Nitriles; D010455:Peptides; D011480:Protease Inhibitors; D018819:Dipeptidyl Peptidase 4