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Large Scale Synthesis of Mono- and Di-urethane Derivatives of Lysine.
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1999
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Peptide EngineeringOrganic ChemistryPeptide ScienceChemistryChemical DerivativeLarge Scale SynthesisDerivativesBiochemistryPharmacologyNatural Product SynthesisNε-tert-butoxycarbonyl-l-lysine CopperBiomolecular EngineeringNatural SciencesNα-benzyloxycarbonyl-nε-tert-butoxycarbonyl-l-lysine Dicyclohexylamine SaltPeptide SynthesisDiurethane DerivativesMedicineDerivative (Chemistry)Synthetic Chemistry
In the search for a practical route to lysine diurethane derivatives useful for peptide synthesis, we elaborated the synthesis of Nε-tert-butoxycarbonyl-L-lysine copper(II) complex (1). This served as substrate for obtaining Nε-tert-butoxycarbonyl-L-lysine (2), Nα-benzyloxycarbonyl-Nε-tert-butoxycarbonyl-L-lysine dicyclohexylamine salt (3) and Nα-(9-fluorenyl)methoxycarbonyl-Nε-tert-butoxycarbonyl-L-lysine (4).