The synthesis and biological activity of [Hyp4]morphiceptin and two glycosyl derivatives are reported. Glycopeptide amides were obtained using Fmoc solid-phase chemistry and mild conditions for cleavage from a tris(alkoxy)benzylamide (PAL) resin. Analogues were evaluated in the guinea pig ileum in vitro assay and in in vivo tail-flick and paw-pressure antinociceptive tests after intrathecal administration in rats. Substitution of Pro4 by Hyp4, and further derivatization of Hyp with glucose or galactose, resulted in an unexpected decrease in biological activity with respect to morphiceptin.
|Original language||English (US)|
|Number of pages||5|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|State||Published - 1991|