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5-Cyanotryptophan As an Infrared Probe of Local Hydration Status of Proteins

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Journal Chem Phys Lett
Date 2010 Feb 18
PMID 20161057
Citations 40
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Abstract

The nitrile (C≡N) stretching vibration is sensitive to environment, making nitrile-derivatized amino acids an increasingly utilized tool to study various biological processes. Herein, we show that the bandwidth of the C≡N stretching vibration of 5-cyanotryptophan is particularly sensitive to water, rendering it an attractive infrared probe of local hydration status. We confirm the utility of this probe in biological applications by using it to examine how the hydration status of individual tryptophan sidechains of an antimicrobial peptide, indolicidin, changes upon peptide binding to model membranes. Furthermore, we show that p-cyanophenylalanine and 5-cyanotryptophan constitute a useful fluorescence energy transfer pair.

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References
1.
Cho M . Vibrational solvatochromism and electrochromism: coarse-grained models and their relationships. J Chem Phys. 2009; 130(9):094505. DOI: 10.1063/1.3079609. View

2.
Li T, Hassanali A, Kao Y, Zhong D, Singer S . Hydration dynamics and time scales of coupled water-protein fluctuations. J Am Chem Soc. 2007; 129(11):3376-82. DOI: 10.1021/ja0685957. View

3.
Webb L, Boxer S . Electrostatic fields near the active site of human aldose reductase: 1. New inhibitors and vibrational stark effect measurements. Biochemistry. 2008; 47(6):1588-98. DOI: 10.1021/bi701708u. View

4.
Khandelia H, Kaznessis Y . Cation-pi interactions stabilize the structure of the antimicrobial peptide indolicidin near membranes: molecular dynamics simulations. J Phys Chem B. 2007; 111(1):242-50. PMC: 2440664. DOI: 10.1021/jp064776j. View

5.
Tucker M, Oyola R, Gai F . Conformational distribution of a 14-residue peptide in solution: a fluorescence resonance energy transfer study. J Phys Chem B. 2006; 109(10):4788-95. DOI: 10.1021/jp044347q. View