Synthesis of Orthogonally Protected Thioamide Dipeptides for Use in Solid-Phase Peptide Synthesis

Authors

Fintan Kelleher, Technological University DublinFollow
Kim Manzor, Institute of Technology Tallaght

Document Type

Article

Rights

Available under a Creative Commons Attribution Non-Commercial Share Alike 4.0 International Licence

Disciplines

1.4 CHEMICAL SCIENCES, Organic Chemistry

Publication Details

Tetrahedron Letters

Abstract

Orthogonally protected thioamide-containing dipeptides were efficiently and cleanly prepared from the precursor dipeptides using Curphey’s method (P₄S₁₀, hexamethyldisiloxane (HMDO), reflux, DCM) in 67-96% isolated yield. This was in contrast to the use of Lawesson’s or Berzelius’ reagents where significant issues with reaction non-completion, decomposition and purification were observed. Subsequent clean removal of the dipeptides’ t-butyl ester protecting groups gave thioamide dipeptide acids which were suitable for use in solid-phase peptide synthesis (SPPS).

DOI

https://doi.org/10.1016/j.tetlet.2016.10.036

Recommended Citation

Kelleher, F. & Manzor, K. (2016) Synthesis of Orthogonally Protected Thioamide Dipeptides for Use in Solid-Phase Peptide Synthesis, Tetrahedron Letters Vol. 57, Issue 47,pp.5237–5239. DOI: 10.1016/j.tetlet.2016.10.036

Funder

Science Foundation Ireland