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Synfacts 2006(7): 0741-0741  
DOI: 10.1055/s-2006-941892
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Synthesis of CD40L Mimetics

Contributor(s): Yasuhiro Uozumi, Masahiro Kimura
A. Bianco*, S. Fournel, S. Wieckowski, J. Hoebeke, G. Guichard*
Université de Strasbourg, France
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

A solid-phase synthesis of CD40L mimetics was described. Coupling of resin-supported amine 1 with Fmoc-l-Lys(Mtt)-OH followed by deprotection of the allyl group gave carboxylic acid 2. H-l-Lys(Mtt)-OAll was coupled with 2 followed by removal of the Fmoc group to afford tri­peptide 3. After elongation by solid-phase peptide synthesis (SPPS), cyclization of hexapeptide 4 by DIC/HOAt and removal of the Mtt groups under mild acidic conditions gave cyclized peptide 5. The standard SPPS followed by cleavage of the resulting cyclic peptide from the resin with TFA gave CD40L mimetic, macrocyclic peptide 6 in 16% yield.