6533b7d9fe1ef96bd126c09f
RESEARCH PRODUCT
Convenient High Yielding Gram Scale Solution Synthesis of Methionine-Enkephalin.
Barbara RzeszotarskaElzbieta Masiukiewiczsubject
chemistry.chemical_classificationanimal structuresintegumentary systemChemistryHydantoinPeptideGeneral ChemistryGeneral MedicinePentapeptide repeatHigh-performance liquid chromatographyChemical synthesisAmino acidchemistry.chemical_compoundDrug DiscoveryPeptide synthesisOrganic chemistrySaponificationdescription
A simple, large-scale synthesis of a cytokine, methionine-enkephalin, Tyr-Gly-Gly-Phe-Met, has been elaborated. Classical solution peptide chemistry methods without protection of amino acid side-chain functions and 1+(2+2) segment condensation were used. A nine-step synthesis from commercial amino acid derivatives was developed with yields ranging from 86% to 99%, averaging 92%. The purity of all intermediates was found to be 99.0-100% by HPLC. The process has been used to prepare greater than 150 g quantities of the pentapeptide as a monohydrate of 100% purity. Hydantoin formation was observed during saponification of Boc-Tyr-Gly-Gly-Phe-Met-OMe and minimised.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1998-01-01 | Chemical and Pharmaceutical Bulletin |