Cyclic peptide synthesis with thioacids.

Abstract

C-Terminal amino acid 9-fluorenylmethylthioesters may be carried through Boc chemistry solution phase peptide synthesis sequences. After insertion of the final residue in the form of an Fmoc carbamate, treatment with piperidine releases a seco-peptide as a C-terminal thioacid that on treatment with Sanger's reagent undergoes cyclization to a cyclic peptide. Cyclic penta- and hexapeptides have been synthesized in this manner, as has a cyclic glycopeptide. Functional group compatibility with alcohols and carboxylic acids is demonstrated.

DOI: 10.1021/ol101201w

Cite this paper

@article{Sasaki2010CyclicPS, title={Cyclic peptide synthesis with thioacids.}, author={Kaname Sasaki and David Crich}, journal={Organic letters}, year={2010}, volume={12 14}, pages={3254-7} }