6533b7dafe1ef96bd126e9e7

RESEARCH PRODUCT

Large Scale Synthesis of Mono- and Di-urethane Derivatives of Lysine.

Stanislaw WiejakElzbieta MasiukiewiczBarbara Rzeszotarska

subject

chemistry.chemical_classificationCopper complexStereochemistryLysinechemistry.chemical_elementPeptideGeneral ChemistryGeneral MedicineCopperChemical synthesisDerivative (finance)chemistryDrug DiscoveryAliphatic compoundProtecting group

description

Orthogonally protected diurethane derivatives of lysine are valuable materials for peptide syntheses. An example is ZLys(Boc), which is exploited in the industrial production of certain well-established peptide drugs. 3,4) Another derivative is Fmoc-Lys(Boc), which is in common use in the laboratory synthesis of peptides. 5) The simplest route to these lysine derivatives seems to be using the copper complex for simultaneous protection of the a-amino and a-carboxyl function, N e -tert-butoxycarbonylation and then copper detachment. The obtained Lys(Boc) might be then subjected to N a -benzyloxycarbonylation.

https://doi.org/10.1248/cpb.47.1489