Synthesis of model chromophores related to the gold fluorescent protein (GdFP)

Birgit Prüger, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

The two model chromophores 2 and 3 for the core 1 of the gold fluorescent protein (GdFP) were synthesized from commercially available 2-methyl-3- nitroaniline (4) in six synthetic steps and overall yields of 13% and 8%, respectively. The key step of the sequence is the chemoselective, reductive introduction of the amino group after assembly of the Z-configured 5-(indol-3-ylmethylene)imidazolin-4-one skeleton of the chromophore. Compound (Z)-2 was shown to undergo a light-initiated E/Z-isomerization, which allows access also to its E-isomer.

Original languageEnglish
Pages (from-to)1103-1106
Number of pages4
JournalSynthesis
Issue number7
DOIs
StatePublished - 3 Apr 2007

Keywords

  • Aldol reactions
  • Bioorganic chemistry
  • Heterocycles
  • Indoles
  • Photochemistry

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