Synthesis of biosynthetic precursors of chromophores of red fluorescent proteins

  • P. E. Ivashkin
  • K. A. Lukyanov
  • I. V. Yampolsky
Article

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 condensa-tion 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.

Keywords

chromophore imidazolone green fluorescent protein GFP DsRed 

Abbreviations

AIBN

asobisisobutyronitrile

Bn

benzyl

DsRed

the red fluorescent protein of the coral polyp Discosoma

ESI

electrospray ionization

GFP

green fluorescent protein

HOBt

N-hydroxybezotriazole

MALDI

matrix-assisted laser desorption ionization

NBS

N-bromosuccinimide

PMB

p-methoxybenzyl

TBS

tert-butyldimethylsilyl

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Copyright information

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • P. E. Ivashkin
    • 1
  • K. A. Lukyanov
    • 1
  • I. V. Yampolsky
    • 1
  1. 1.Shemyakin-Ovchinnikov Institute of Bioorganic ChemistryRussian Academy of SciencesMoscowRussia

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