Tetrahedron letters

Synthesis and structure of a small macrocyclic hexapeptide model for antiparallel β-sheet containing two restrained 2-(3′-aminopropynyl)-aniline reverse-turn …

N Pitt, D Gani

Index: Pitt, Nigel; Gani, David Tetrahedron Letters, 1999 , vol. 40, # 19 p. 3811 - 3814

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Citation Number: 13

Abstract

A new reverse-turn mimetic containing a 2-(3′-aminopropynyl)-phenyl moiety in place of the natural i+ 1 and i+ 2 turn residues is described in which the key C C bond was formed from an N-protected propargylamine and 2-iodoaniline using Heck chemistry. Nucleophilic displacement of triflate from activated (2S)-2-hydroxyalkanoate esters by the anilino N-atom, with inversion at C-2, gave homochiral tripeptide mimetics. Two variants of these were ...