Synthesis of the Chromophores of Fluorescent
Proteins and Their Analogs

M. S. Baranov, K. A. Lukyanov, and I. V. Yampolsky¹

Institute of Bioorganic Chemistry, Russian Academy of Sciences,
ul. Miklukho-Makalya 16/10, Moscow, 117997 Russia

Received September 19, 2012; in final form, November 2, 2012

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-imidazol-4-ones, sub-
stituted at different positions. General, as well as specific methods, represented by single examples are consid-
ered. 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 het-
erocycles. 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 cycliza-
tions of N-acyldehydroamino acids, as well as all other approaches to 3,5-dihydro-4H-imidazol-4-ones.

Keywords: fluorescent protein, chromophore, GFP, azlactone, imidazolone

DOI: 10.1134/S1068162013030047

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