Acid-labile Cys-protecting groups for the Fmoc/tBu strategy: filling the gap

Org Lett. 2012 Nov 2;14(21):5472-5. doi: 10.1021/ol302550p. Epub 2012 Oct 17.

Abstract

To address the existing gap in the current set of acid-labile Cys-protecting groups for the Fmoc/tBu strategy, diverse Fmoc-Cys(PG)-OH derivatives were prepared and incorporated into a model tripeptide to study their stability against TFA. S-Dpm proved to be compatible with the commonly used S-Trt group and was applied for the regioselecive construction of disulfide bonds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Combinatorial Chemistry Techniques
  • Cysteine / analogs & derivatives
  • Cysteine / chemistry*
  • Fluorenes / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Peptides / chemistry

Substances

  • Amino Acids
  • Fluorenes
  • Peptides
  • Cysteine