Zhao Kake, Lim Dong Sung, Funaki Takashi, Welch John T
Department of Chemistry, University at Albany, Albany, NY 12222, USA.
Bioorg Med Chem. 2003 Jan 17;11(2):207-15. doi: 10.1016/s0968-0896(02)00384-x.
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.
