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Development of a Hypusine Reagent for Peptide Synthesis

1997; American Chemical Society; Volume: 62; Issue: 10 Linguagem: Inglês

10.1021/jo970119z

1520-6904

Raymond J. Bergeron, Christian Ludin, Ralf Müller, Richard E. Smith, Phanstiel,

Amino Acid Enzymes and Metabolism

The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)-hypusine (Hpu) into peptide sequences is described. The reagent, (2S,9R)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2-[(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.