Title
Synthesis of Orthogonally Protected Thioamide Dipeptides for Use in Solid-Phase Peptide Synthesis
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
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).
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
DOI
https://doi.org/10.1016/j.tetlet.2016.10.036
Funder
Science Foundation Ireland
Publication Details
Tetrahedron Letters