2-Chlorotrityl resins for the synthesis of peptide hydrazides and hydroxamic acids

Chemfiles Volume 3 Article 4



Peptide hydroxamic acids have been made available from TFA-labile aminooxy-resins. The 2-chlorotrityl resin preloaded with N-Fmoc hydroxylamine proved to be an excellent and most convenient support for this purpose. Due to the poor nucleophilicity of the aminooxy group efficient coupling procedures employing HATU/diisopropylethylamine (DIEA) are highly recommended.



Protected peptide hydrazides are convenient intermediates, because they are easily converted into the corresponding azides. Peptide azides play an important role in the convergent synthesis of larger peptides. 2-Chlorotrityhydrazine resins are cleaved with dilute TFA.

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Materials

     

References

  1. Mellor S. L. et al., Tetrahedron Lett., 1997, 38, 3311.
  2. Stavropoulos, G. et al. Lett. Pept. Sci. 1995, 2, 315.

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