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Synfacts 2007(6): 0660-0660  
DOI: 10.1055/s-2007-968524
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of C-Terminal Variation of Peptide Carboxylic Acid

Contributor(s): Yasuhiro Uozumi, Yutaka Matsuura
A. El-Dahshan, S. Weik, J. Rademann*
Leibniz Institute for Molecular Pharmacology (FMP), Berlin and Free University Berlin, Germany
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Publication History

Publication Date:
22 May 2007 (online)

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Significance

The solid-phase synthesis of C-terminal variation of peptide carboxylic acid was demonstrated. The polymer-supported linear phosphoranylidene acetates 2a,b were prepared from triphenylphosphine resin 1 in three steps. Then, oxidative treatment of 2a with dimethyldi­oxirane (DMD) in acetone afforded peptidyl-2,3-diketoesters 3. Desilylation of 2b using TAS-F afforded 4. Peptidyl vinyl aldehyde 5 and 1,3-diamino-2-hydroxypropane 6 were obtained from 4 via DMD oxidation and Wittig olefination, respectively.