Enantiospecific synthesis of genetically encodable fluorescent unnatural amino acid L-3-(6-acetylnaphthalen-2-ylamino)-2-aminopropanoic acid

J Org Chem. 2011 Aug 5;76(15):6367-71. doi: 10.1021/jo2007626. Epub 2011 Jul 6.

Abstract

Fluorescent unnatural amino acids (UAAs), when genetically incorporated into proteins, can provide unique advantages for imaging biological processes in vivo. Synthesis of optically pure L-enantiomer of fluorescent UAAs is crucial for their effective application in live cells. An efficient six-step synthesis of L-3-(6-acetylnaphthalen-2-ylamino)-2-aminopropanoic acid (L-Anap), a genetically encodable and polarity-sensitive fluorescent UAA, has been developed. The synthesis takes advantage of a high-yield and enantiospecific Fukuyama-Mitsunobu reaction as the key transformation.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Amino Acids / genetics
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Protein Engineering / methods*
  • Stereoisomerism
  • beta-Alanine / analogs & derivatives*
  • beta-Alanine / chemical synthesis
  • beta-Alanine / chemistry

Substances

  • 3-(6-acetylnaphthalen-2-ylamino)-2-aminopropanoic acid
  • Amino Acids
  • Fluorescent Dyes
  • beta-Alanine