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Binding of 9-N-Butyladenine by Carboxylic Acids:  Evidence that Hoogsteen Binding Can Dominate in Solution

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Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India
Cite this: J. Phys. Chem. B 1999, 103, 21, 4528–4533
Publication Date (Web):May 5, 1999
https://doi.org/10.1021/jp984235x
Copyright © 1999 American Chemical Society

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    Abstract

    1H NMR titration of 9-N-butyladenine (1) with a series of 11 representative carboxylic acids has been carried out in CDCl3 by following the chemical shifts of δH-2 and δH-8 of 1 to determine the association constants for the Watson−Crick and the Hoogsteen modes of binding. Compound 1 has been found to bind carboxylic acids through the Watson−Crick (WC) site or the Hoogsteen (HG) site. The binding of carboxylic acids from the WC site shifts the δH-2 signal upfield, whereas the binding from the HG site shifts the δH-8 signal downfield. Analyses of binding-induced shifts of δH-2 and δH-8 of 1 in the presence of the carboxylic acids have indicated a distinct preference for the HG site by aromatic carboxylic acids, such as benzoic acid and monobenzyl isophthalate. On the other hand, aliphatic acids such as 4-nitrophenylacetic acid and propanoic acid are found to prefer the WC site for complexing 1. Binding affinities of a few alkenoic and alkynoic acids were also determined. In addition to the complexes (1/acid) of 1:1 stoichiometry, the possibility of a 1:2 complexation between 1 and the carboxylic acids is addressed. A possible rationale for the upfield shift of H-2 (of 1) upon binding by a carboxylic acid is discussed. The Ka's were found to increase in general with enhanced acidity of the carboxylic acids. However, the pKa values of the acids do not appear to determine the site-specificity of the binding of 1.

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    Cited By

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    1. Yagang Zhang, Di Song, Laura M. Lanni and Ken D. Shimizu. Importance of Functional Monomer Dimerization in the Molecular Imprinting Process. Macromolecules 2010, 43 (15) , 6284-6294. https://doi.org/10.1021/ma101013c
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    3. Dominique M. S. Buyens, Lynne A. Pilcher, Emil Roduner. Towards a Molecular Understanding of Cation‐Anion Interactions and Self‐aggregation of Adeninate Salts in DMSO by NMR and UV Spectroscopy and Crystallography. ChemPhysChem 2021, 22 (19) , 2025-2033. https://doi.org/10.1002/cphc.202100098
    4. Michael G. Crisp, Poya Kavianpour, Louis M. Rendina. Molecular recognition of an adenine derivative by organoplatinum(II) complexes with hydrogen-bonding functionality. Journal of Organometallic Chemistry 2019, 883 , 86-89. https://doi.org/10.1016/j.jorganchem.2018.12.005
    5. Samson Jegan Jennifer, Packianathan Thomas Muthiah, Duraiswamy Tamilselvi. Importance of halide involving interactions at Hoogsteen sites in supramolecular architectures of some coordination metal complexes of N6-benzyl/furfuryl adenine. Chemistry Central Journal 2014, 8 (1) https://doi.org/10.1186/s13065-014-0058-z
    6. Nagarjun Narayanaswamy, M. B. Avinash, T. Govindaraju. Exploring hydrogen bonding and weak aromatic interactions induced assembly of adenine and thymine functionalised naphthalenediimides. New Journal of Chemistry 2013, 37 (5) , 1302. https://doi.org/10.1039/c3nj00060e
    7. Bassam Lamale, William P. Henry, Lee M. Daniels, Cungen Zhang, Suzane M. Klein, Yu Lin Jiang. Synthesis and crystal structures of fluorescent receptors for 9-butyladenine. Tetrahedron 2009, 65 (1) , 62-69. https://doi.org/10.1016/j.tet.2008.10.041
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    9. Kumaresh Ghosh, Tanushree Sen, Roland Fröhlich. Adenine-based receptor for dicarboxylic acids. Tetrahedron Letters 2007, 48 (39) , 7022-7026. https://doi.org/10.1016/j.tetlet.2007.07.110
    10. Ronald K. Castellano, Volker Gramlich, François Diederich. Rebek Imides and Their Adenine Complexes: Preferences for Hoogsteen Binding in the Solid State and in Solution. Chemistry - A European Journal 2002, 8 (1) , 118-129. https://doi.org/10.1002/1521-3765(20020104)8:1<118::AID-CHEM118>3.0.CO;2-0

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