Synthesis of the chromophores of fluorescent proteins and their analogs

M. S. Baranov, K. A. Lukyanov, I. V. Yampolsky

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Members of the green fluorescent protein (GFP) family are widely used in experimental biology as genetically encoded fluorescent tags. Chromophores of GFP-like proteins share a common structural core: 3,5-dihydro-4H-imidazol-4-one. This review covers synthetic approaches to 3,5-dihydro-4H-imida-zol-4-ones, substituted at different positions. General, as well as specific methods, represented by single examples are considered. The most popular synthetic route to substituted 3,5-dihydro-4H-imidazol-4-ones includes synthesis of azlactones, followed by transformation into N-acyldehydroamino acids and, finally, cyclization into target heterocycles. Accordingly, the review is divided into three parts: the first part covers syntheses of azlactones, the second part covers main approaches to N-acyldehydroamino acids, and in the third part we summarize cyclizations of N-acyldehydroamino acids, as well as all other approaches to 3,5-dihydro-4H-imidazol-4-ones.

Original languageEnglish
Pages (from-to)223-244
Number of pages22
JournalRussian Journal of Bioorganic Chemistry
Volume39
Issue number3
DOIs
Publication statusPublished - May 2013
Externally publishedYes

Keywords

  • azlactone
  • chromophore
  • fluorescent protein
  • GFP
  • imidazolone

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