METHIONINE ENKEPHALIN AND ISOSTERIC ANALOGUES I. Synthesis on a Phenolic Resin Support†
- 1 September 1979
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 14 (3) , 177-185
- https://doi.org/10.1111/j.1399-3011.1979.tb01923.x
Abstract
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 the peptide backbone plays in receptor interaction. Free hexapeptide phenyl ester resins underwent intramolecular aminolysis liberating the corresponding cyclic peptides.Keywords
This publication has 17 references indexed in Scilit:
- The Bakerian Lecture Towards synthesis of proteinsProceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences, 1977
- Conformational analysis of Methionine-Enkephalin and some analogsBiochemical and Biophysical Research Communications, 1977
- Biosynthetic origin and receptor conformation of methionine enkephalinNature, 1976
- Phenolic resins for solid‐phase peptide synthesis: Copolymerization of styrene and p‐acetoxystyreneJournal of Polymer Science: Polymer Chemistry Edition, 1974
- Solid-Phase Synthesis of Selectively Protected Peptides: Use of Thallous Alkoxide as Catalyst in the Transesterification StepCanadian Journal of Chemistry, 1974
- Solid-phase synthesis of selectively protected peptides for use as building units in the solid-phase synthesis of large moleculesJournal of the American Chemical Society, 1973
- Rapid solid-phase synthesis of bradykininBiochemical and Biophysical Research Communications, 1972
- Phenyl esters for C-terminal protection in peptide synthesisJournal of the American Chemical Society, 1972
- Synthesis of peptides containing N-2-aminoethylglycine—‘reduction analogues’Journal of the Chemical Society C: Organic, 1971
- A Synthesis of Cyclic Peptides Utilizing High Molecular Weight CarriersJournal of the American Chemical Society, 1965