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Synfacts 2010(8): 0958-0958  
DOI: 10.1055/s-0030-1257793
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Solid-Phase Synthesis of Peptides Using Cysteine Orthoesters

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
Z. Huang, D. J. Derksen, J. C. Vederas*
University of Alberta, Edmonton, Canada
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Chiral cysteine derivatives 2a,b bearing an acid-labile 4-methyl-2,6,7-trioxabi­cyclo[2.2.2]octyl (OBO) orthoester were prepared and applied to the solid-phase synthesis of peptides having C-terminal cysteine (Cys) residues. Thus, hexanedithiol was used as a linker to immobilize the OBO cysteine derivative 3 onto trityl polystyrene resin 4, affording the polymer-supported orthoesters 5a,b. Fmoc-based solid-­supported peptide synthesis (SSPS) led to the tripeptides Gly-Phe-Cys 8a,b with both 94% de.