Elsevier

Tetrahedron Letters

Volume 45, Issue 40, 27 September 2004, Pages 7519-7523
Tetrahedron Letters

Synthesis of ‘difficult’ peptide sequences: application of a depsipeptide technique to the Jung–Redemann 10- and 26-mers and the amyloid peptide Aβ(1–42)

https://doi.org/10.1016/j.tetlet.2004.07.162Get rights and content

Abstract

Recently a 26-mer peptide 1 incorporating Ser and Thr was described as a ‘difficult’ sequence that could not be synthesized by standard methods. If the first Ser residue was used to incorporate a depsipeptide unit, the resulting hybrid was readily assembled. The 26-mer ester was then converted to the native peptide by an O→N acyl shift. The technique may be general for other systems containing appropriate Ser and Thr units and was demonstrated here for the case of the amyloid peptide Aβ(1–42).

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Acknowledgements

We are indebted to the National Institutes of Health (GM-09706) and the National Science Foundation (NSF CHE-0078971) for support of the work in Amherst.

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