Synthesis of 2-azaspiro[3.3]heptane-derived amino acids: ornitine and GABA analogues

Amino Acids. 2010 Jul;39(2):515-21. doi: 10.1007/s00726-009-0467-9. Epub 2010 Jan 27.

Abstract

Synthesis of 6-amino-2-azaspiro[3.3]heptane-6-carboxylic acid and 2-azaspiro[3.3]heptane-6-carboxylic acid was performed. Both four-membered rings in the spirocyclic scaffold were constructed by subsequent ring closure of corresponding 1,3-bis-electrophiles at 1,1-C- or 1,1-N-bis-nucleophiles. The two novel amino acids were added to the family of the sterically constrained amino acids for the use in chemistry, biochemistry, and drug design.

MeSH terms

  • Aza Compounds / chemical synthesis*
  • Ornithine / analogs & derivatives*
  • Ornithine / chemical synthesis
  • Spiro Compounds / chemical synthesis*
  • gamma-Aminobutyric Acid / analogs & derivatives*
  • gamma-Aminobutyric Acid / chemical synthesis

Substances

  • Aza Compounds
  • Spiro Compounds
  • gamma-Aminobutyric Acid
  • Ornithine