Synthesis of biosynthetic precursors of chromophores of red fluorescent proteins

P. E. Ivashkin, K. A. Lukyanov, I. V. Yampolsky

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A method for the synthesis of 5-arylidene-3,5-dihydro-4H-imidazol-4-ones corresponding to the chromophore of the green fluorescent protein (GFP) with acylaminoalkyl substituents at position 2 of the imidazolone core has been developed. These biomimetic model compounds are the precursors of the chromophores of red fluorescent proteins. The method is based on the masking of the dehydrotyrosine fragment of target compounds by the β-hydroxytyrosine moiety. The key stages of the synthesis include the condensation of β-hydroxytyrosine with the appropriate N-acetylamino acid, the unmasking of dehydrotyrosine by O-acylation with subsequent elimination, and the cyclization of the resulting 3-acylaminocinnamic acid derivatives in basic medium.

Original languageEnglish
Pages (from-to)411-420
Number of pages10
JournalRussian Journal of Bioorganic Chemistry
Volume37
Issue number4
DOIs
Publication statusPublished - Jul 2011
Externally publishedYes

Keywords

  • Chromophore
  • DsRed
  • GFP
  • Green fluorescent protein
  • Imidazolone

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