Pseudo-Prolines in Peptide Synthesis: Direct Insertion of Serine and Threonine Derived Oxazolidines in Dipeptides

Article abstract of DOI:10.1016/0040-4039(95)00667-2

Dipeptides containing serine and threonine derived oxazolidines are prepared by reacting side chain unprotected dipeptides containing C-terminal Thr or Ser with dimethoxypropane.The resulting building blocks can be coupled in Fmoc-based solid phase peptide synthesis enhancing peptide solvation by its secondary structure disrupting potential.The present procedure may be considered as a first step towards a reversible modification of structural and functional properties of bioactive peptides and proteins.