Development of a Hypusine Reagent for Peptide Synthesis

Raymond J. Bergeron; Christian Ludin; Ralf Müller; Richard E. Smith; Otto Phanstiel IV

doi:10.1021/jo970119z

Development of a Hypusine Reagent for Peptide Synthesis

J Org Chem. 1997 May 16;62(10):3285-3290. doi: 10.1021/jo970119z.

Authors

Raymond J. Bergeron¹, Christian Ludin, Ralf Müller, Richard E. Smith, Otto Phanstiel IV

Affiliation

¹ 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.

PMID: 11671715
DOI: 10.1021/jo970119z

Abstract

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.