Development of a Hypusine Reagent for Peptide Synthesis.
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.
Bergeron
Raymond J.
RJ
Department of Medicinal Chemistry, University of Florida, Gainesville, Florida 32610-0485, Institut für Organische Chemie, Freiest. 3, Bern, CH-3012, Switzerland, and Chemistry Department, University of Central Florida, Orlando, Florida 32816-2366.
Ludin
Christian
C
Müller
Ralf
R
Smith
Richard E.
RE
Phanstiel
Otto
O