6533b85bfe1ef96bd12ba92e

RESEARCH PRODUCT

ChemInform Abstract: Convenient High Yielding Gram Scale Solution Synthesis of Methionine-Enkephalin.

Barbara RzeszotarskaElzbieta Masiukiewicz

subject

chemistry.chemical_classificationanimal structuresChromatographyintegumentary systemChemistryCondensationHydantoinGeneral MedicineSolution synthesisPentapeptide repeatHigh-performance liquid chromatographyAmino acidchemistry.chemical_compoundSaponificationGram

description

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.

yearjournalcountryeditionlanguage
2010-06-16ChemInform
https://doi.org/10.1002/chin.199919219