Synthesis and structural investigations of a a-hydroxylated b-hexapeptide

Abstract

(2S,3S)-a-Hydroxy-b3-Hleu, -b3-HAla and -b3-HVal-amino acids were prepd. and used for the synthesis of a b-hexapeptide. The resulting a-hydroxylated-b3-hexapeptide (terminally protected) and its fully deprotected form are insol. in most org. solvents including MeOH and fluorinated alcs., suggesting that they form aggregates or that they adopt a sheet-like conformation. Their phys. properties prevented any CD spectroscopic investigations and limited the possibilities of NMR spectroscopy. [on SciFinder (R)]