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DOI: 10.1055/s-2006-931982
SPOS of Olefin-Containing Peptides Using the Horner-Emmons Reaction
J. K. Bang, H. Naka, K. Teruya, S. Aimoto, H. Konno, K. Nosaka, T. Tatsumi, K. Akaji*
Osaka University and Kyoto Prefectural University of Medicine, Japan
Publikationsverlauf
Publikationsdatum:
21. Februar 2006 (online)
Significance
The syntheses of olefin-containing peptides by the solid-phase Horner-Emmons reaction were demonstrated. Thus, for example, the resin-supported peptide 2 prepared from cross-linked ethoxylate acrylate resin (CLEAR)-supported Fmoc-Glu-O-allyl (1) was treated with Dess-Martin periodinane followed by the Horner-Emmons reaction with allyl diethylphosphonoacetate/[Me3Si]2NLi to give (E)-olefin peptide 3. After cleavage of the allyl ester with Pd(PPh3)4, H-Pro-O-allyl was coupled with 3 using HATU/HOAt to give peptide 4. Removal of the protecting groups followed by cleavage from resin by TFA/H2O (95:5) afforded the desired (E)-olefin peptide 5 in 20% yield. For CLEAR support, see: M. Kempe, G. Barany J. Am. Chem. Soc. 1996, 118, 7083-7093.