Abstract
The green fluorescent protein (GFP) chromophore is a heterocyclic compound containing a p-hydroxybenzylidine attached to an imidazol-5(4H)-one ring. This review covers the synthesis of a variety of model systems for elucidating the intrinsic optical properties of the chromophore in the gas phase and its response in particular to hydrogen bond interactions. The overall goal is to understand how the protein binding pocket influences the absorption behavior, and the current status of our ongoing efforts is presented.
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Möglich A, Yang X, Ayers RA, Moffat K (2010) Annu Rev Plant Biol 61:21
Henry AA, Jimenez R, Hanway D, Romesberg FE (2004) Chem Bio Chem 5:1088
Nielsen MB (2009) Chem Soc Rev 38:913
Shimomura FH, Johnson FH, Saiga Y (1962) J Cell Comp Physiol 59:223
Griffin BA, Adams SR, Tsien RY (1998) Science 281:269
Tsien RY (1998) Annu Rev Biochem 67:509
Zimmer M (2002) Chem Rev 102:759
Pakhomov AA, Martynov VI (2008) Chem Biol 15:755
Sanders JM, Jackson SE (2009) Chem Soc Rev 38:2821
Seward HE, Bagshaw CR (2009) Chem Soc Rev 38:2842
Craggs TD (2009) Chem Soc Rev 38:2865
Brejc K, Sixma TK, Kitts PA, Kain SR, Tsien RY, Ormö M, Remington SJ (1997) Proc Natl Acad Sci U S A 94:2306
Sniegowski JA, Phail ME, Wachter RM (2005) Biochem Biophys Res Commun 332:657
Jung G, Wiehler J, Zumbusch A (2005) Biophys J 88:1932
Wood TI, Barondeau DP, Hitomi C, Kassmann CJ, Tainer JA, Getzoff ED (2005) Biochemistry 44:16211
Møller SP (1997) Nucl Instrum Methods Phys Res A 394:281
Andersen JU, Hvelplund P, Nielsen SB, Tomita S, Wahlgreen H, Møller SP, Pedersen UV, Forster JS, Jørgensen TJD (2002) Rev Sci Instrum 73:1284
Andersen LH, Heber O, Zajfman D (2004) J Phys B At Mol Opt Phys 37:R59
Nielsen SB, Andersen JU, Hvelplund P, Liu B, Tomita S (2004) J Phys B At Mol Opt Phys 37:R25
Petersen MÅ, Riber P, Andersen LH, Nielsen MB (2007) Synthesis 3635
Lincke K, Sølling T, Andersen LH, Klærke B, Rahbek DB, Rajput J, Oehlenschlæger CB, Petersen MÅ, Nielsen MB (2010) Chem Commun 46:734
Nielsen SB, Lapierre, Andersen JU, Pedersen UV, Tomita S, Andersen LH (2001) Phys Rev Lett 87:2281021
Dong J, Solntsev KM, Tolbert LM (2006) J Am Chem Soc 128:12038
Rajput J, Rahbek DB, Andersen LH, Rocha-Rinza T, Christiansen O, Bravaya KB, Erokhin AV, Bochenkova AV, Solntsev KM, Dong J, Kowalik J, Tolbert LM, Petersen MÅ, Nielsen MB (2009) Phys Chem Chem Phys 11:9996
Lammich L, Petersen MÅ, Nielsen MB, Andersen LH (2007) Biophys J 92:201
Acknowledgments
We are grateful to all co-workers whose names appear in the publications cited below. The Danish Research Agency (FNU) is gratefully acknowledged for financial support.
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Nielsen, M.B., Andersen, L.H. & Rocha-Rinza, T. Absorption tuning of the green fluorescent protein chromophore: synthesis and studies of model compounds. Monatsh Chem 142, 709–715 (2011). https://doi.org/10.1007/s00706-010-0430-1
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DOI: https://doi.org/10.1007/s00706-010-0430-1