Title

Development of a hypusine reagent for peptide synthesis

Authors

Authors

R. J. Bergeron; C. Ludin; R. Muller; R. E. Smith;O. Phanstiel

Comments

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Abbreviated Journal Title

J. Org. Chem.

Keywords

ESTERS CAM-ESTERS; PROTEIN-SYNTHESIS; INITIATION; DEPROTECTION; TRANSLATION; DERIVATIVES; ACIDS; ANION; Chemistry, Organic

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,SR)-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.

Journal Title

Journal of Organic Chemistry

Volume

62

Issue/Number

10

Publication Date

1-1-1997

Document Type

Article

Language

English

First Page

3285

Last Page

3290

WOS Identifier

WOS:A1997XG22100060

ISSN

0022-3263

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