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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Silyl linker-based approach to the solid-phase synthesis of Fmoc glycopeptide thioesters.

An efficient solid-phase synthesis of Fmoc (glyco)peptide thioesters is described. Fmoc x Ser x OAll and Fmoc x Thr x OAll bound to resin with a silyl ether linker were deallylated by Pd(0) catalysis and condensed with thiophenol, benzyl mercaptane, and ethyl 3-mercaptopropionate by activation with DCC/HOBt. The thioesters were released from the resin either by treatment with CsF-AcOH or by acidic hydrolysis. The effectiveness of this silyl linker strategy is further demonstrated by the synthesis of more complex (glyco)peptide thioesters 25, 26 and 27 involving N-->C and C-->N peptide elongation.[1]

References

  1. Silyl linker-based approach to the solid-phase synthesis of Fmoc glycopeptide thioesters. Ishii, A., Hojo, H., Nakahara, Y., Ito, Y., Nakahara, Y. Biosci. Biotechnol. Biochem. (2002) [Pubmed]
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