75816-16-9Relevant academic research and scientific papers
Synthesis of tripeptides containing d-Trp substituted at the indole ring, assessment of opioid receptor binding and in vivo central antinociception
De Marco, Rossella,Bedini, Andrea,Spampinato, Santi,Gentilucci, Luca
supporting information, p. 6861 - 6866 (2014/10/15)
The noncationizable tripeptide Ac-d-Trp-Phe-GlyNH2 was recently proposed as a novel minimal recognition motif for μ-opioid receptor. The introduction of different substituents (methyl, halogens, nitro, etc.) at the indole of d-Trp significantly influenced receptor affinities and resulted in serum stability and in a measurable effect on central antinociception in mice after ip administration.
The facile synthesis of a series of tryptophan derivatives
Blaser, Georg,Sanderson, John M.,Batsanov, Andrei S.,Howard, Judith A.K.
, p. 2795 - 2798 (2008/09/19)
This study reports a facile method for the synthesis of a variety of 5- and 6-substituted tryptophan derivatives that are difficult to prepare using alternative enzymatic approaches. Acylation of an activated amino acid, derived from serine in situ, is coupled with an enzymatic resolution step to furnish enantiopure analogues bearing a range of electron withdrawing and releasing substituents. Isolation of a dehydroalanine derivative as a by-product from some reactions provides some insights into the likely mechanism of the reaction.
Synthesis of 5- and 7-Bromotryptophan and of 9>-β-corticotrophin-(1-24)-tetracosapeptide, a Highly Potent Corticotrophin Analogue
Allen, Mark C.,Brundish, Derek E.,Wade, Roy
, p. 1928 - 1932 (2007/10/02)
The synthesis of 5- and 7-bromo-L-tryptophans via Fischer cyclisation of the appropriate bromophenylhydrazone of 4-acetamido-4,4-bis(ethoxycarbonyl)butanal is described.The title tetracosapeptide was synthesised using standard methods of stepwise and fragment condensation.The product was pure as judged by amino-acid analysis after acidic or enzymic hydrolysis and by high pressure liquid chromatography.In an isolated adrenal cell bioassay, the peptide had a steroidogenic potency 2.4 times that of Synacthen.
