A Novel Approach to Unzipped Tubes Synthesis Using Sulfanilic Acid as the Backbone Amino Acid

Abstract:

In this research, unzipped sulfanilic acid inspired hydrophobic peptide tube was synthesis by increasing the polarity of sulfanilic acid through nucleophilic attachment of aniline which then provided two reactive sites at the S-terminus. These two sites were then attached with the N-terminal of valine and alanine respectively at an intensity of 1000-1600 of 11 2θ (°). Through π- π stacking at the side chains, the opened ended peptide was linearly arranged to form the unzipped tube. Fourier transform infrared spectroscopy (FTIR) confirm the amine bond formation whiles X-ray diffraction test results confirmed D-spacing 7.36 and 4.44 corresponding 2θ (°)12 and 19.97 respectively whiles the torsion angles (Ø₂₎ conformations was between-150.5°and-169.2° and-2 between-129.0° and-150.6°. The Thermogravimetric analysis result showed an increase in the rigidity of the bond with an increasing intensity. Finally, Differential scanning calorimetry (DSC) test was carried out to confirm the crystallinity of the structure. Keywords: Sulfanilic acid, hydrophobic Peptide, Unzipped tubes, Nanomaterial

• Periodical: Journal of Nano Research (Volume 57)
• Pages: 17-30
• DOI: https://doi.org/10.4028/www.scientific.net/JNanoR.57.17
• Online since: April 2019
• Authors: Christopher Narh, Charles Frimpong, Qu Fu Wei*
• Keywords: Hydrophobic Peptide, Nanomaterial, Sulfanilic Acid, Unzipped Tubes

References

[1] Cheng, S.-S., et al., Synthesis, crystal structure, spectroscopic properties and potential anti-cancerous activities of four unsaturated bis-norcantharimides. Journal of Molecular Structure, 2016. 1115: pp.228-240.

DOI: 10.1016/j.molstruc.2016.02.093

[2] Rossetti, I. and M. Compagnoni, Chemical reaction engineering, process design and scale-up issues at the frontier of synthesis: Flow chemistry. Chemical Engineering Journal, 2016. 296: pp.56-70.

DOI: 10.1016/j.cej.2016.02.119

[3] Seth, S.K., et al., Exploring contribution of intermolecular interactions in supramolecular layered assembly of naphthyridine co-crystals: Insights from Hirshfeld surface analysis of their crystalline states. Journal of Molecular Structure, 2013. 1048: pp.157-165.

DOI: 10.1016/j.molstruc.2013.05.048

[4] Weiss Iv, W.F., T.M. Young, and C.J. Roberts, Principles, approaches, and challenges for predicting protein aggregation rates and shelf life. Journal of Pharmaceutical Sciences, 2009. 98(4): pp.1246-1277.

DOI: 10.1002/jps.21521

[5] Görbitz, C.H., Peptide structures. Current Opinion in Solid State and Materials Science, 2002. 6(2): pp.109-116.

DOI: 10.1016/s1359-0286(02)00044-x

[6] Piela, L., Chapter 13 - Intermolecular Interactions, in Ideas of Quantum Chemistry (Second Edition). 2014, Elsevier: Oxford. pp.793-882.

DOI: 10.1016/b978-0-444-59436-5.00013-1

[7] Banik, R., et al., Supramolecular interactions through lone pair(lp)–π and hydrogen bonding in cobalt(III) and manganese(II) derivatives of N,N'-dimethylvioluric acid: A combined experimental and theoretical study. Inorganica Chimica Acta, 2015. 435: pp.178-186.

DOI: 10.1016/j.ica.2015.06.018

[8] Brewer, G., et al., Synthesis, structure and supramolecular features of homonuclear iron(III) and heteronuclear iron(III)–cobalt(III) complexes, [FeH3L][ML](ClO4)3 (M = Fe(III) or Co(III). 2D sheet and tetrahedral arrays. Inorganica Chimica Acta, 2014. 421: pp.100-109.

DOI: 10.1016/j.ica.2014.05.034

[9] Brewer, G., et al., Synthesis, structure and supramolecular features of cobalt(III) and cobalt(II) complexes, [CoHxL](ClO4)y (x = y = 3, 2, 1.50, 1.45, 1 and 0 and x = 3, y = 2) of a triprotic imidazole containing Schiff base ligand. Effect of protonation state on supramolecular structure. Inorganica Chimica Acta, 2014. 410: pp.94-105.

DOI: 10.1016/j.ica.2013.10.017

[10] Liu, W., et al., Helix Packing Moments Reveal Diversity and Conservation in Membrane Protein Structure. Journal of Molecular Biology, 2004. 337(3): pp.713-729.

DOI: 10.1016/j.jmb.2004.02.001

[11] Zong, C., Packing, covering and tiling in two-dimensional spaces. Expositiones Mathematicae, 2014. 32(4): pp.297-364.

DOI: 10.1016/j.exmath.2013.12.002

[12] Zhao, N., et al., Syntheses, structures and third-order nonlinear optical properties of three coordination polymers based on bis(imidazol-l-yl-methyl)benzene and aromatic dicarboxylic ligands. Polyhedron, 2015. 85: pp.607-614.

DOI: 10.1016/j.poly.2014.09.021

[13] Mumbaraddi, D., S. Sarkar, and S.C. Peter, A review on the synthesis, crystal growth, structure and physical properties of rare earth based quaternary intermetallic compounds. Journal of Solid State Chemistry, 2016. 236: pp.94-115.

DOI: 10.1016/j.jssc.2015.10.032

[14] An, B., Y.-S. Lin, and B. Brodsky, Collagen interactions: Drug design and delivery. Advanced Drug Delivery Reviews, 2016. 97: pp.69-84.

DOI: 10.1016/j.addr.2015.11.013

[15] Dass, C., 9.12 - Mass Spectrometry: Structure Determination of Proteins and Peptides, in Comprehensive Natural Products II. 2010, Elsevier: Oxford. pp.457-496.

DOI: 10.1016/b978-008045382-8.00685-7

[16] Narh, C., et al., Sulfanilic acid inspired self-assembled fibrous materials. Colloid and Polymer Science, 2016. 294(9): pp.1483-1494.

DOI: 10.1007/s00396-016-3911-x

[17] Armstrong, A., J.E.K. Hildreth, and L.M. Amzel, Structural and Thermodynamic Insights into the Recognition of Native Proteins by Anti-Peptide Antibodies. Journal of Molecular Biology, 2013. 425(11): pp.2027-2038.

DOI: 10.1016/j.jmb.2013.02.031

[18] Hedwig, G.R. and H. Høiland, Thermodynamic properties of peptide solutions 20. Partial molar volumes and isothermal compressions for some tripeptides of sequence gly-X-gly (X = gly, ala, leu, asn, thr, and tyr) in aqueous solution at T = 298.15 K and p = (10–120) MPa. The Journal of Chemical Thermodynamics, 2016. 99: pp.30-39.

DOI: 10.1016/j.jct.2016.03.032

[19] Charaschanya, M., et al., Nucleophilic aromatic substitution of heterocycles using a high-temperature and high-pressure flow reactor. Tetrahedron Letters, 2016. 57(9): pp.1035-1039.

DOI: 10.1016/j.tetlet.2016.01.080

[20] Leushina, E., et al., SNAr nucleophilic substitution of 1,9-dihalodipyrrins by S- and N- nucleophiles. Synthesis of new dipyrrins bearing pendant substituents. Dyes and Pigments, 2016. 129: pp.149-155.

DOI: 10.1016/j.dyepig.2016.02.018

[21] Ren, Y., J. Yang, and S. Chen, The fate of a nitrobenzene-degrading bacterium in pharmaceutical wastewater treatment sludge. Chemosphere, 2015. 141: pp.13-18.

DOI: 10.1016/j.chemosphere.2015.05.098

[22] Pereira, R., et al., Fate of aniline and sulfanilic acid in UASB bioreactors under denitrifying conditions. Water Research, 2011. 45(1): pp.191-200.

DOI: 10.1016/j.watres.2010.08.027

[23] Gonzalez-Silva, B.M., et al., Nitrification at different salinities: Biofilm community composition and physiological plasticity. Water Research, 2016. 95: pp.48-58.

DOI: 10.1016/j.watres.2016.02.050

[24] Kim, Y.M., H. Park, and K. Chandran, Nitrification inhibition by hexavalent chromium Cr(VI) – Microbial ecology, gene expression and off-gas emissions. Water Research, 2016. 92: pp.254-261.

DOI: 10.1016/j.watres.2016.01.042

[25] Baran, J., A.J. Barnes, and H. Ratajczak, The polarized IR and Raman spectra of the diglycine hydrochloride crystal. Journal of Molecular Structure, 2012. 1009: pp.55-68.

DOI: 10.1016/j.molstruc.2011.09.016

[26] Baran, J.A., M.A. Drozd, and H. Ratajczak, Polarised IR and Raman spectra of monoglycine nitrate single crystal. Journal of Molecular Structure, 2010. 976(1–3): pp.226-242.

DOI: 10.1016/j.molstruc.2010.03.055

[27] Canè, E., et al., Infrared spectroscopy of 15ND3: The ν2 and ν4 bending fundamental bands. Journal of Quantitative Spectroscopy and Radiative Transfer, 2013. 119: pp.1-11.

DOI: 10.1016/j.jqsrt.2013.01.019

[28] Cao, C.-T., Y. Bi, and C. Cao, Effects of single bond-ion and single bond-diradical form on the stretching vibration of CN bridging bond in 4,4'-disubstituted benzylidene anilines. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2016. 163: pp.96-101.

DOI: 10.1016/j.saa.2016.03.021

[29] Tursun, M. and C. Parlak, Conformation stability, halogen and solvent effects on CO stretching of 4-chloro-3-halogenobenzaldehydes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015. 141: pp.58-63.

DOI: 10.1016/j.saa.2015.01.023

[30] Gorbitz, C.H., Nanotube formation by hydrophobic dipeptides. Chemistry-a European Journal, 2001. 7(23): pp.5153-5159.

[31] Yeap, G.-Y., et al., Molecular structure–thermal behaviour relationship of dimers consisting of different terminal substituents and sulphur–sulphur linking group. Journal of Molecular Structure, 2014. 1074: pp.666-672.

DOI: 10.1016/j.molstruc.2014.03.071