Synthesis and Characterization of Model Compounds for the Neutral Green Fluorescent Protein Chromophore

Michael Åxman Petersen; Peter Riber; Lars H. Andersen; Mogens Brøndsted Nielsen

doi:10.1055/s-2007-990852

PAPER

Synthesis and Characterization of Model Compounds for the Neutral Green Fluorescent Protein Chromophore

Michael Åxman Petersen^a, Peter Riber^a, Lars H. Andersen^b, Mogens Brøndsted Nielsen*^a
^a Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen Ø, Denmark
Fax: +4535320212; e-Mail: mbn@kiku.dk;
^b Department of Physics and Astronomy, University of Aarhus, 8000 Aarhus C, Denmark

Abstract

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Abstract

Two new derivatives of the green fluorescent protein (GFP) chromophore each containing a charged substituent (CH₂CH₂NH₃ ⁺ and CH₂CH₂NMe₃ ⁺, respectively) on the imidazolone ring have been prepared. These compounds are model systems for the neutral GFP chromophore with an unprotonated phenol moiety. The ammonium groups allow for electrospray ionization and the possibility to study the optical properties of the isolated chromophores in the gas phase. A derivative containing a CH₂CH₂OH substituent arm was also prepared.

Key words

amides - amines - chromophores - heterocycles - phenols

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References

1a Gerdes H.-H. Kaether C. FEBS Lett. 1996, 389: 44

1b Phillips GNJ. Curr. Opin. Struct. Biol. 1997, 7: 821

1c Tsien RY. Annu. Rev. Biochem. 1998, 67: 509

1d Zimmer M. Chem. Rev. 2002, 102: 759

2 Bizzarri R. Nifosì R. Abbruzzetti S. Rocchia W. Guidi S. Arosio D. Garau G. Campanini B. Grandi E. Ricci F. Viappiani C. Beltram F. Biochemistry 2007, 46: 5494

3 Lammich L. Petersen MÅ. Nielsen MB. Andersen LH. Biophys. J. 2007, 92: 201

4a Andersen LH. Nielsen IB. Kristensen MB. El Ghazaly MOA. Haacke S. Nielsen MB. Petersen MÅ. J. Am. Chem. Soc. 2005, 127: 12347

4b Nielsen IB. Petersen MÅ. Lammich L. Nielsen MB. Andersen LH. J. Phys. Chem. A 2006, 110: 12592

5a Dakin HD. J. Biol. Chem. 1929, 82: 439

5b Wong HNC. Xu ZL. Chang HM. Lee CM. Synthesis 1992, 8: 793

5c Hager B. Schwarzinger B. Falk H. Monatsh. Chem. 2006, 137: 163

5d Stafforst T. Diederichsen U. Eur. J. Org. Chem. 2007, 899

6a Kojima S. Ohkawa H. Maki S. Niwa H. Ohashi M. Inouye S. Tsuji FI. Tetrahedron Lett. 1998, 39: 5239

6b He X. Bell AF. Tonge PJ. Org. Lett. 2002, 4: 1523

6c Prüger B. Bach T. Synthesis 2007, 1103

7a Kojima S. Hirano T. Niwa H. Ohashi M. Inouye S. Tsuji FI. Tetrahedron Lett. 1997, 38: 2875

7b He X. Bell AF. Tonge PJ. J. Phys. Chem. B 2002, 106: 6056

7c Vengris M. van Stokkum IHM. He X. Bell AF. Tonge PJ. van Grondelle R. Larsen DS. J. Phys. Chem. A 2004, 108: 4587

7d Dong J. Solntsev KM. Tolbert LM. J. Am. Chem. Soc. 2006, 128: 12038

8 Andersen LH. Lapierre A. Nielsen SB. Nielsen IB. Pedersen SU. Pedersen UV. Tomita S. Eur. Phys. J., D: Atom. Mol. Opt. Phys. 2002, 20: 597