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Benzyloxycarbonyl compounds (abbreviated as Cbz or Z) are organic compounds containing the carbonyl group attached to a benzyloxy group. Benzyloxylcarbonyl derivatives are used in peptide synthesis as nitrogen protecting groups (Green, T. W.; Wuts, P. G. M., Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, pp 531-537, 736-739). The amine group is protected by Benzyloxycarbonyl from attack by electrophiles and other reagents employed during organic transformations. The synthesis of many organic compounds is most conveniently performed by the route of an N-benzyloxycarbonyl-substituted compound as an intermediate and then elimination of the protecting group at the final stage by catalytic reduction with hydrogen or treatment with hydrobromic acid to liberate the desired compound.
N-(Benzyloxycarbonyloxy)succinimide is a reagent for selective protection of the amino with benzyloxycarbonyl in amino acids and in aminoglycoside antibiotics. Chlorinated benzyloxycarbonyl protecting groups are used to eliminate N(epsilon)-branching at lysine during solid-phase peptide synthesis. Benzyloxycarbonyl-amino acid prodrugs of phenytoin have anticonvulsant properties. Benzyloxycarbonyl compounds of morpholine derivatives are used in the treatment of Parkinson disease.