Orthogonal protection of peptides and peptoids for cyclization by the thiol-ene reaction and conjugation

J Org Chem. 2014 Apr 4;79(7):2843-53. doi: 10.1021/jo500427c. Epub 2014 Mar 21.

Abstract

Cyclic peptides and peptoids were prepared using the thiol-ene Michael-type reaction. The linear precursors were provided with additional functional groups allowing for subsequent conjugation: an orthogonally protected thiol, a protected maleimide, or an alkyne. The functional group for conjugation was placed either within the cycle or in an external position. The click reactions employed for conjugation with suitably derivatized nucleoside or oligonucleotides were either cycloadditions (Diels-Alder, Cu(I)-catalyzed azide-alkyne) or the same Michael-type reaction as for cyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Click Chemistry
  • Copper / chemistry
  • Cycloaddition Reaction
  • Maleimides / chemistry*
  • Molecular Structure
  • Oligonucleotides / chemistry*
  • Peptides, Cyclic / chemistry*
  • Peptoids / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Alkynes
  • Maleimides
  • Oligonucleotides
  • Peptides, Cyclic
  • Peptoids
  • Sulfhydryl Compounds
  • maleimide
  • Copper