227288-19-9

Upstream product

• 99208-98-7 methyl (S)-2-[(trifluoromethanesulfonyl)oxy]propionate 
• 227288-15-5 tert-butyl [3-(2-aminophenyl)prop-2-yn-1-yl]carbamate 
• 92136-39-5 N-tert-Butoxycarbonyl-1-amino-3-propyne 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 744185-23-7 (R)-2-[2-(3-{(R)-2-[2-(3-Amino-prop-1-ynyl)-phenylamino]-propionylamino}-prop-1-ynyl)-phenylamino]-4-methyl-pentanoic acid 
• 227288-25-7 (R)-2-[2-(3-{(R)-2-[2-(3-tert-Butoxycarbonylamino-prop-1-ynyl)-phenylamino]-propionylamino}-prop-1-ynyl)-phenylamino]-4-methyl-pentanoic acid methyl ester 
• 227288-28-0 (R)-2-[2-(3-{(R)-2-[2-(3-tert-Butoxycarbonylamino-prop-1-ynyl)-phenylamino]-propionylamino}-prop-1-ynyl)-phenylamino]-4-methyl-pentanoic acid 
• 227288-23-5 2-[2-(3-tert-butoxycarbonylamino-prop-1-ynyl)-phenylamino]-propionic acid 

Relevant academic research and scientific papers

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

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 coupled and the product was deprotected and then cyclised to give a stable cyclo-hexapeptide analogue that possessed an anti-parallel β-sheet structure as determined by NMR spectroscopy.