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Deprotection of O-methyltyrosine by a ‘push–pull’ mechanism using the thioanisole–trifluoromethanesulphonic acid system. Application to the convenient synthesis of a potent N-methylenkephalin derivative
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1979
Year
Bioorganic ChemistryPhenolic OxygenOrganic ChemistryClick ChemistryChemistryChemical BiologyChemical DerivativeMedicinal ChemistryThioanisole–trifluoromethanesulphonic Acid SystemConvenient SynthesisStereoselective SynthesisNew Potent EnkephalinBiochemistryPotent N-methylenkephalin DerivativePharmacologyMethyl GroupNatural SciencesDerivative (Chemistry)Synthetic Chemistry
The methyl group attached at the phenolic oxygen of tyrosine can be smoothly cleaved by a thioanisole–trifluoromethanesulphonic acid system; this deblocking method was successfully applied to the synthesis of a new potent enkephalin derivative, MeTyr-Gly-Gly-Phe-Metol (Metol = L-methioninol residue).