Shortcut access to peptidosteroid conjugates: building blocks for solid-phase bile acid scaffold decoration by convergent ligation

Molecules. 2011 Dec 7;16(12):10168-86. doi: 10.3390/molecules161210168.

Abstract

We present three versatile solid-supported scaffold building blocks based on the (deoxy)cholic acid framework and decorated with handles for further derivatization by modern ligation techniques such as click chemistry, Staudinger ligation or native chemical ligation. Straightforward procedures are presented for the synthesis and analysis of the steroid constructs. These building blocks offer a new, facile and shorter access route to bile acid-peptide conjugates on solid-phase with emphasis on heterodipodal conjugates with defined spatial arrangements. As such, we provide versatile new synthons to the toolbox for bile acid decoration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Bile Acids and Salts / chemical synthesis*
  • Bile Acids and Salts / chemistry
  • Click Chemistry / methods*
  • Cysteine / metabolism
  • Endocrine Disruptors / metabolism
  • Macromolecular Substances / chemistry
  • Molecular Sequence Data
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Receptors, Cell Surface / metabolism
  • Steroids / chemical synthesis*
  • Steroids / chemistry
  • Sulfhydryl Compounds / metabolism

Substances

  • Bile Acids and Salts
  • Endocrine Disruptors
  • Macromolecular Substances
  • Peptides
  • Receptors, Cell Surface
  • Steroids
  • Sulfhydryl Compounds
  • Cysteine