378185-86-5Relevant academic research and scientific papers
Stereospecific synthesis of (2S)-2-methyl-3-(2′,6′-dimethyl-4′-hydroxyphenyl)-propionic acid (Mdp) and its incorporation into an opioid peptide
Lu, Yixin,Weltrowska, Grazyna,Lemieux, Carole,Chung, Nga N.,Schiller, Peter W.
, p. 323 - 325 (2007/10/03)
To examine the effect of replacing the N-terminal amino group in opioid peptides with a methyl group on biological activity, a stereospecific synthesis of the tyrosine analogue (2S)-2-methyl-3-(2′,6′-dimethyl-4′-hydroxyphenyl)-propionic acid (Mdp) was performed. The enkephalin analogue (2S)-Mdp-D-Ala-Gly-Phe-Leu-NH2 turned out to be a quite potent δ opioid antagonist and a somewhat less potent μ antagonist, indicating that a positively charged N-terminal amino group is not a conditio sine qua non for the binding of opioid peptides to δ and μ receptors but may be required for signal transduction.
Stereospecific syntheses of 2-alkyl and 2-phenyl substituted 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acids
Lu,Schiller
, p. 1639 - 1644 (2007/10/03)
Stereospecific syntheses of 2-methyl-, 2-ethyl-, 2-cyclohexyland 2-phenyl- substituted 3-(2,6-dimethyl-4-hydroxyphenyl)propanoic acids were developed. The key steps for the formation of the stereogenic centers involved the utilization of Evans' 4-benzyl-2-oxazolidinone chiral auxiliary. These compounds were designed to replace the N-terminal tyrosine residue in opioid peptides.
