880489-96-3

Upstream product

• 246158-11-2 tert-butyl [(1S,2S)-2-azido-3-(4-tert-butoxyphenyl)-1-(2-oxoethyl)propoxy]acetate 
• 880489-95-2 methyl N-((2S)-2-{(7S)-7-[(1S)-1-azido-2-(4-hydroxyphenyl)-ethyl]-3-oxo-1,4-oxazepan-4-yl}-3-phenylpropanoyl)-L-leucinate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of leucine enkephalin turn mimetics

A cyclic Leu-enkephalin mimetic containing a 7-membered ring, and two linear analogues, has been prepared on solid phase. In the cyclic mimetic the intramolecular (1-4) hydrogen bond found in crystalline Leu-enkephalin has been replaced by an ethylene bridge. In addition, the amide bond between Tyr1 and Gly2 has been replaced by a methylene ether isostere and Gly3 has been deleted. The two linear analogues both contain the methylene ether isostere instead of the Tyr1-Gly2 amide bond and the shorter of the two lacks Gly3. The three compounds, and a β-turn mimetic analogous to the 7-membered turn mimetic but with Gly3 included, were evaluated for specific binding to μ- and δ-opioid receptors in rat brain membranes. With the exception of the β-turn mimetic the three other Leu-enkephalin analogues all bound with varying affinity to the μ- and δ-opioid receptors. From the results it could be concluded that Leu-enkephalin binds in a turn conformation to the opiate receptors, but that this conformation is not a (1-4) β-turn. The Royal Society of Chemistry 2006.