Methionine enkephalin and isosteric analogues. I. Synthesis on a phenolic resin support.
An efficient synthesis of methionine enkephalin using a phenolic resin support is described. Analogues modified at their C-termini, such as peptide acids, amides, methyl esters and compounds formed by their reduction, were prepared conveniently from common peptide phenyl ester resins. The resin was used in the synthesis of complex isosterically modified analogues designed to investigate the role of peptide backbone plays in receptor interaction. Free hexapeptide phenyl ester resins underwent intramolecular aminolysis liberating the corresponding cyclic peptides.
D000595:Amino Acid Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D004723:Endorphins / Q000138:chemical synthesis*; D004745:Enkephalins / Q000138:chemical synthesis*; D005998:Glycine; D008715:Methionine / Q000138:chemical synthesis; D008722:Methods; D010636:Phenols; D012117:Resins, Synthetic
D004723:Endorphins; D004745:Enkephalins; D010636:Phenols; D012117:Resins, Synthetic; D008715:Methionine; D005998:Glycine