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Invited Article

Phosphorylation status of peptide monolayers modulates hydrogen bonding and orientations of nematic liquid crystals

ORCID Icon, , &
Pages 2253-2268 | Received 08 Jun 2018, Published online: 23 Aug 2018

References

  • Carlton R, Hunter J, Miller D, et al. Chemical and biological sensing using liquid crystals. Liq Cryst Rev. 2013;1(1):29–51.
  • Bai Y, Abbott N. Enantiomeric interactions between liquid crystals and organized monolayers of tyrosine-containing dipeptides. J Am Chem Soc. 2012;134(1):548–558.
  • Bai Y, Abbasi R, Wang C, et al. Liquid crystals anchored on mixed monolayers of chiral versus achiral molecules: continuous change in orientation as a function of enantiomeric excess. Angew Chem -Int Edit. 2014;53(31):8079–8083.
  • Chen C, Yang K. Detection and quantification of DNA adsorbed on solid surfaces by using liquid crystals. Langmuir. 2010;26(3):1427–1430.
  • Price A, Schwartz D. DNA hybridization-induced reorientation of liquid crystal anchoring at the nematic liquid crystal/aqueous interface. J Am Chem Soc. 2008;130(26):8188–8194.
  • Bera T, Fang J. Optical detection of lithocholic acid with liquid crystal emulsions. Langmuir. 2013;29(1):387–392.
  • Malone S, Schwartz D. Macroscopic liquid crystal response to isolated DNA helices. Langmuir. 2011;27(19):11767–11772.
  • Setia S, Sidiq S, De J, et al. Applications of liquid crystals in biosensing and organic light-emitting devices: future aspects. Liq Cryst. 2016;43(13–15):2009–2050.
  • Govindaraju T, Bertics P, Raines R, et al. Using measurements of anchoring energies of liquid crystals on surfaces to quantify proteins captured by immobilized ligands. J Am Chem Soc. 2007;129(36):11223–11231.
  • Nelson D. Lehninger principles of biochemistry. 6th ed. New york (NY): W. H. Freeman and Co.; 2012.
  • Wade L Jr. Organic chemistry. 5th ed. Upper Saddle River (NJ): Prentice Hall; 2003.
  • Lodish H, Berk A, Kaiser C, et al. Molecular cell biology. 7th. New York (NY): W. H. Freeman; 2007.
  • Petoral R Jr, Uvdal K. Arg–cys and Arg–cysteamine adsorbed on gold and the G-protein–adsorbate interaction. Colloids Surf B Biointerfaces. 2002;25(4):335–346.
  • Uvdal K, Vikinge T. Chemisorption of the dipeptide Arg-Cys on a gold surface and the selectivity of G-protein adsorption. Langmuir. 2001;17(6):2008–2012.
  • Hernández B, Pflüger F, Adenier A, et al. Vibrational analysis of amino acids and short peptides in hydrated media. VIII. amino acids with aromatic side chains: L-phenylalanine, L-tyrosine, and L-tryptophan. J Phys Chem B. 2010;114(46):15319–15330.
  • Nucci N, Scott J, Vanderkooi J. Coupling of complex aromatic ring vibrations to solvent through hydrogen bonds: effect of varied on-ring and off-ring hydrogen-bonding substitutions. J Phys Chem B. 2008;112(13):4022–4035.
  • Hostetler M, Stokes J, Murray R. Infrared spectroscopy of three-dimensional self-assembled monolayers: N-alkanethiolate monolayers on gold cluster compounds. Langmuir. 1996;12(15):3604–3612.
  • Papastavrou G, Akari S. Interaction forces between OH-groups in different solvents as observed by scanning force microscopy. Colloids Surf A Physicochem Eng Asp. 2000;164(2–3):175–181.
  • Johnson K, Kendall K, Roberts A. Surface energy and the contact of elastic solids. Proc Math Phys Eng Sci. 1971;324(1558):301–313.
  • Widrig C, Chung C, Porter M. The electrochemical desorption of n-alkanethiol monolayers from polycrystalline Au and Ag electrodes. J Electroanal Chem Interfacial Electrochem. 1991;310(1):335–359.
  • Luo M, Frechette J. Electrochemical stability of low-density carboxylic acid terminated monolayers. J Phys Chem C. 2010;114(47):20167–20172.
  • Arnett E, Mitchell E, Murty T. Basicity. Comparison of hydrogen bonding and proton transfer to some Lewis bases. J Am Chem Soc. 1974;96(12):3875–3891.
  • Forster M, Dyer M, Persson M, et al. 2D Random organization of racemic amino acid monolayers driven by nanoscale adsorption footprints: proline on Cu(110). Angew Chem. 2010;122(13):2394–2398.
  • Barlow S, Raval R. Nanoscale insights in the creation and transfer of chirality in amino acid monolayers at defined metal surfaces. Curr Opin Colloid Interface Sci. 2008;13(1–2):65–73.
  • Eralp T, Shavorskiy A, Zheleva Z, et al. Hydrogen bond-induced pair formation of glycine on the chiral Cu{531} surface. Langmuir. 2010;26(13):10918–10923.
  • Raval R. Chiral expression from molecular assemblies at metal surfaces: insights from surface science techniques. Chem Soc Rev. 2009;38(3):707–721.
  • Seljamäe-Green R, Simpson G, Grillo F, et al. Assembly of a chiral amino acid on an unreactive surface: (S)-proline on Au(111). Langmuir. 2014;30(12):3495–3501.
  • Tranca I, Smerieri M, Savio L, et al. Unraveling the self-assembly of the (S)-glutamic acid “flower” structure on Ag(100). Langmuir. 2013;29(25):7876–7884.
  • Trudeau T, Hore D. Hydrophobic amino acid adsorption on surfaces of varying wettability. Langmuir. 2010;26(13):11095–11102.
  • Feyer V, Plekan O, Tsud N, et al. Adsorption of histidine and histidine-containing peptides on Au(111). Langmuir. 2010;26(11):8606–8613.
  • Lingenfelder M, Tomba G, Costantini G, et al. Tracking the chiral recognition of adsorbed dipeptides at the single-molecule level. Angew Chem. 2007;119(24):4576–4579.
  • Monti S, Carravetta V, Battocchio C, et al. Peptide/TiO2 surface interaction: a theoretical and experimental study on the structure of adsorbed ALA-GLU and ALA-LYS. Langmuir. 2008;24(7):3205–3214.
  • Nuzzo R, Dubois L, Allara D. Fundamental studies of microscopic wetting on organic surfaces. 1. formation and structural characterization of a self-consistent series of polyfunctional organic monolayers. J Am Chem Soc. 1990;112(2):558–569.
  • Sun L, Kepley L, Crooks R. Molecular interactions between organized, surface-confined monolayers and vapor-phase probe molecules: hydrogen-bonding interactions. Langmuir. 1992;8(9):2101–2103.
  • Sun L, Crooks R, Ricco A. Molecular interactions between organized, surface-confined monolayers and vapor-phase probe molecules. 5. acid-base interactions. Langmuir. 1993;9(7):1775–1780.
  • Crooks R, Yang H, McEllistrem L, et al. Interactions between self-assembled monolayers and an organophosphonate detailed study using surface acoustic wave-based mass analysis, polarization modulation-FTIR spectroscopy and ellipsometry. Faraday Discuss. 1997;107:285–305.
  • Luk Y, Yang K, Cadwell K, et al. Deciphering the interactions between liquid crystals and chemically functionalized surfaces: role of hydrogen bonding on orientations of liquid crystals. Surf Sci. 2004;570(1–2):43–56.

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