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Blue Fluorescent Amino Acid for Biological Spectroscopy and Microscopy

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Specialty Science
Date 2017 May 24
PMID 28533371
Citations 37
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Abstract

Many fluorescent proteins are currently available for biological spectroscopy and imaging measurements, allowing a wide range of biochemical and biophysical processes and interactions to be studied at various length scales. However, in applications where a small fluorescence reporter is required or desirable, the choice of fluorophores is rather limited. As such, continued effort has been devoted to the development of amino acid-based fluorophores that do not require a specific environment and additional time to mature and have a large fluorescence quantum yield, long fluorescence lifetime, good photostability, and an emission spectrum in the visible region. Herein, we show that a tryptophan analog, 4-cyanotryptophan, which differs from tryptophan by only two atoms, is the smallest fluorescent amino acid that meets these requirements and has great potential to enable in vitro and in vivo spectroscopic and microscopic measurements of proteins.

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References
1.
Wakamatsu K, Okada A, Miyazawa T, Ohya M, Higashijima T . Membrane-bound conformation of mastoparan-X, a G-protein-activating peptide. Biochemistry. 1992; 31(24):5654-60. DOI: 10.1021/bi00139a032. View

2.
Berezin M, Achilefu S . Fluorescence lifetime measurements and biological imaging. Chem Rev. 2010; 110(5):2641-84. PMC: 2924670. DOI: 10.1021/cr900343z. View

3.
Lepthien S, Hoesl M, Merkel L, Budisa N . Azatryptophans endow proteins with intrinsic blue fluorescence. Proc Natl Acad Sci U S A. 2008; 105(42):16095-100. PMC: 2571030. DOI: 10.1073/pnas.0802804105. View

4.
Ross J, Szabo A, Hogue C . Enhancement of protein spectra with tryptophan analogs: fluorescence spectroscopy of protein-protein and protein-nucleic acid interactions. Methods Enzymol. 1997; 278:151-90. DOI: 10.1016/s0076-6879(97)78010-8. View

5.
Shai Y . Mechanism of the binding, insertion and destabilization of phospholipid bilayer membranes by alpha-helical antimicrobial and cell non-selective membrane-lytic peptides. Biochim Biophys Acta. 1999; 1462(1-2):55-70. DOI: 10.1016/s0005-2736(99)00200-x. View