Synthesis of a 6,6-spiroketal amino acid and its incorporation into a peptide turn sequence using solid-phase peptide synthesis

Chemistry. 2013 Mar 18;19(12):3807-11. doi: 10.1002/chem.201204546. Epub 2013 Feb 19.


Spiropins for SPPS: The rigid structure of an anomerically stabilised spiroketal motif enables the appendage of substituents in a fixed conformation. To assess the ability of a spiroketal motif to induce a turn structure and participate in solid-phase peptide synthesis (SPPS), an Fmoc-spiroketal amino acid was synthesised and incorporated into a spiroketal-containing cyclic peptide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Models, Molecular
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides / chemical synthesis*
  • Solid-Phase Synthesis Techniques / methods*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry


  • Amino Acids
  • Furans
  • Peptides
  • Spiro Compounds
  • spiroketal