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Intercalation of basic amino acids into layered zirconium proline-N-methylphosphonate phosphate

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Abstract

Intercalation of basic amino acids into layered zirconium proline-N-methylphosphonate phosphate (α-ZPMP) was investigated at room temperature. Three kinds of host-guest compounds were prepared and characterised by elemental analysis, inductively coupled plasma analysis (ICP), Fourier transform infrared spectrum (FT-IR), Raman spectrum, X-ray powder diffraction (XRD) and thermoanalysis. The interaction of amino acid guests with P-OH of α-ZPMP host was documented by FT-IR and Raman spectra. In addition, the XRD patterns indicated that l-arginine or l-lysine were intercalated into the interlayer galleries of α-ZPMP host; the interlayer distances of the Larginine and l-lysine intercalation compounds were expanded from 1.520 nm to 2.218 nm and 2.207 nm, respectively. l-arginine and l-lysine would be arranged as a mono-molecule layer in different orientations. The interlayer distance of l-histidine (d = 1.522 nm) was similar to that of α-ZPMP host (d = 1.520 nm), l-histidine might be adsorbed on the outer surface of the α-ZPMP host. Thermoanalysis showed that the intercalated l-arginine and l-lysine were removed at 110–305°C or 150–250°C, respectively, the adsorbed l-histidine was released at a temperature of up to 320°C.

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References

  • Alberti, G., Casciola, M., Costantino, U., & Vivani, R. (1996). Layered and pillered metal(IV) phosphates and phosphonate. Advanced Materials, 8, 291–303. DOI: 10.1002/adma.199600 80405.

    Article  CAS  Google Scholar 

  • Alberti, G., Costantino, U., Alluilli, S., & Tomassini, N. (1978). Crystalline Zr(R-PO3)2 and Zr(R-OPO3)2 compounds (R = organic radical): A new class of materials having layered structure of the zirconium phosphate type. Journal of Inorganic and Nuclear Chemistry, 40, 1113–1117. DOI: 10.1016/0022-1902(78)80520-X.

    Article  CAS  Google Scholar 

  • Behrendt, D., Beneke, K., & Lagaly, G. (1976). Intercalation compounds of zirconium phosphate. Angewandte Chemie International Edition, 15, 544–545. DOI: 10.1002/anie.197605 441.

    Article  Google Scholar 

  • Beneš, L., Melánová, K., Svoboda, J., Zima, V., & Kincl, M. (2007). Intercalation of aminonaphthalenes into α-zirconium hydrogenphosphate. Journal of Physics and Chemistry of Solids, 68, 803–807. DOI: 10.1016/j.jpcs.2006.12.017.

    Article  Google Scholar 

  • Beneš, L., Melánová, K., Zima, V., Patrono, P., & Galli, P (2003). Intercalation of amino alcohols into α-Zr(HPO4)2· H2O. European Journal of Inorganic Chemistry, 2003, 1577–1580. DOI: 10.1002/ejic.200390206.

    Article  Google Scholar 

  • Bhambhani, A., & Kumar, C. V. (2006). Protein/DNA/inorganic materials: DNA binding to layered α-zirconium phosphate enhances bound protein structure and activity. Advanced Materials, 18, 939–942. DOI: 10.1002/adma.200502 230.

    Article  CAS  Google Scholar 

  • Casciola, M., Capitani, D., Donnadio, A., Frittella, V., Pica, M., & Sganappa, M. (2009). Preparation, proton conductivity and mechanical properties of nafion 117-zirconium phosphate sulphophenylphosphonate composite membranes. Fuel Cells, 9, 381–386. DOI: 10.1002/fuce.200800128.

    Article  CAS  Google Scholar 

  • Clearfield, A. (1988). Role of ion exchange in solid-state chemistry. Chemical Reviews, 88, 125–148. DOI: 10.1021/cr00083 a007.

    Article  CAS  Google Scholar 

  • Clearfield, A., & Smith, G. D. (1969). The crystallography and structure of α-zirconium bis(monohydrogen orthophosphate) monohydrate. Inorganic Chemisitry, 8, 431–436. DOI: 10.1021/ic50073a005.

    Article  CAS  Google Scholar 

  • Clearfield, A., & Stynes, J. A. (1964). The preparation of crystalline zirconium phosphate and some observation on its exchange behaviour. Journal of Inorganic and Nuclear Chemistry, 26, 117–119. DOI: 10.1016/0022-1902(64)80238-4.

    Article  CAS  Google Scholar 

  • Costantino, U. (1979). Intercalation of alkanols and glycols into zirconium(IV) hydrogenphosphate monohydrate. Journal of the Chemical Society, Dalton Transactions, 1979, 402–405. DOI: 10.1039/dt9790000402.

    Article  Google Scholar 

  • Costantino, U., Fringuelli, F., Orrù, M., Nocchetti, M., Piermatti, O., & Pizzo, F. (2009). Direct aza-Diels-Alder reaction in water catalyzed by layered α-zirconium hydrogen phosphate and sodium dodecyl sulfate. European Journal of Organic Chemistry, 2009, 1214–1220. DOI: 10.1002/ejoc.200801132.

  • Costantino, U., Nocchetti, M., & Vivani, R. (2002). Preparation, characterization, and structure of zirconium fluoride alkylamino-N,N-bis methylphosphonates: A new design for layered zirconium diphosphonates with a poorly hindered interlayer region. Journal of the American Chemical Society, 124, 8428–8434. DOI: 10.1021/ja026124o.

    Article  CAS  Google Scholar 

  • Díaz, A, David, A., Pérez, R., González, M. L., Báez, A., Wark, S. E., Zhang, P., Clearfield, A., & Colón, J. L. (2010). Nanoencapsulation of insulin into for oral delivery applications. Biomacromolecules, 11, 2465–2470. DOI: 10.1021/bm100659p.

    Article  Google Scholar 

  • Dines, M. B., & DiGiacomo, P. M. (1981). Derivetized lameller phosphates and phosphonetes of M(IV) ions. Inorganic Chemistry, 20, 92–97. DOI: 10.1021/ic50215a022.

    Article  CAS  Google Scholar 

  • Dragone, R., Galli, P., Massucci, M. A., & Trombetta, M. (2003). Preparation and characterization of histidine- and iron-histidine-α-zirconium phosphate intercalation compounds. Catalytic behaviour of the iron derivatives in oxidation reactions with H2O2. Journal of Materials Chemistry, 13, 834–840. DOI: 10.1039/b207687j.

    Article  CAS  Google Scholar 

  • Gentili, P. L., Costantino, U., Vivani, R., Latterini, L., Nocchetti, M., & Aloisi, G. G. (2004). Preparation and characterization of zirconium phosphonate-azobenzene intercalation compounds. A structural, photophysical and photochemical study. Journal of Materials Chemistry, 14, 1656–1662. DOI: 10.1039/b313828c.

    Article  CAS  Google Scholar 

  • Hix, G. B., Kitchin, S. J., & Harris, K. D. M. (1998). Topotactic synthesis of α-zirconium phenylphosphonate from α-zirconium phosphate. Journal of the Chemical Society, Dalton Transactions, 1998, 2315–2320. DOI: 10.1039/a802673D.

    Article  Google Scholar 

  • Kijima, T., Ohe, K., Sasaki, F., Yada, M., & Machida, M. (1998). Intercalation of dendritic polyamines by α- and γ-zirconium phosphate. Bulletin of the Chemical Society of Japan, 71, 141–148. DOI: 10.1246/bcsj.71.141.

    Article  CAS  Google Scholar 

  • Kijima, T., Ueno, S., & Goto, M. (1982). Uptake of amino-acids by zirconium phosphates. Part 2. Intercalation of l-histidine, l-lysine, and l-arginine by α-zirconium phosphate. Journal of the Chemical Society, Dalton Transactions, 1982, 2499–2503. DOI: 10.1039/DT9820002499.

  • Kumar, C. V., & Chaudhari, A. (2000). Proteins immobilized at the galleries of layered α-zirconium phosphate: Structure and activity studies. Journal of the American Chemical Society, 122, 830–837. DOI: 10.1021/ja993310u.

    Article  CAS  Google Scholar 

  • Martí, A. A., & Colón, J. L. (2010). Photophysical characterization of the interactions among tris(2,2′-bipyridyl)ruthenium (II) complexes ion-exchanged within zirconium phosphate. Inorganic Chemistry, 49, 7298–7303. DOI: 10.1021/ic9024 19z.

    Article  Google Scholar 

  • Martí, A. A., & Colón, J. L. (2003). Direct ion exchange of tris(2,2’-bipyridine)ruthenium into an α-zirconium phosphate framework. Inorganic Chemistry, 42, 2830–2832. DOI: 10.1021/ic025548g.

    Article  Google Scholar 

  • Martí, A. A., Rivera, N., Soto, K., Maldonado, L., & Colón, J. L. (2007). Intercalation of Re(phen)(CO)3Cl into zirconium phosphate: a water insoluble inorganic complex immobilized in a highly polar rigid matrix. Dalton Transactions, 2007, 1713–1718. DOI: 10.1039/b618802h.

    Article  Google Scholar 

  • Rao, X.-P., Fu, X.-K., & Rao, K. (2004). Synthesis and intercalation behavior of layered zirconium (proline-N-methylphosphonate-phosphate). Chemical Journal of Chinese Universities, 25, 1209–1212.

    CAS  Google Scholar 

  • Sebti, S., Zahouily, M., Lazrek, H. B., Mayoral, J. A., & Macquarrie, D. J. (2008). Phosphates: new generation of liquid-phase heterogeneous catalysts in organic chemistry. Current Organic Chemistry, 12, 203–232. DOI: 10.2174/138527208783497484.

    Article  CAS  Google Scholar 

  • Sui, Y., Fu, X., Zeng, R., & Ma, X. (2004). Preparation, characterization and application of a new type of ion exchanger and solid acid zirconium sulfonated oligopolystyrenylphosphonate-phosphate supported on ZrO2. Journal of Molecular Catalysis A: Chemical, 217, 133–138. DOI: 10.1016/j.molcata.2004.03.003.

    Article  Google Scholar 

  • Vermeulen, L. A., & Thompson, M. E. (1992). Stable photoinduced charge separation in layered viologen compounds. Nature, 358, 656–658. DOI: 10.1038/358656a0.

    Article  CAS  Google Scholar 

  • Yang, X.-B., Fu, X.-K., & Zeng, R.-Q. (2010). Intercalation of non-aromatic heterocyclic amines into layered zirconium glycine-N,N-dimethylphosphonate. Chemical Papers, 64, 118–122. DOI: 10.2478/s11696-009-0091-x.

    Article  CAS  Google Scholar 

  • Zeng, R., Fu, X., Gong, C., Sui, Y., Ma, X., & Yang, X. (2005). Preparation and catalytic property of the solid base supported on the mixed zirconium phosphate phosphonate for Knoevenagel condensation. Journal of Molecular Catalysis A: Chemical, 229, 1–5. DOI: 10.1016/j.molcata.2004.11.002.

    Article  CAS  Google Scholar 

  • Zeng, R., Fu, X., Sui, Y., Yang, X., Sun, M., & Chen, J. (2008). Synthesis, characterization and intercalation property of layered zirconium benzylamino-N,N-dimethylphosphonate phosphate materials. Journal of Organometallic Chemistry, 693, 2666–2672. DOI: 10.1016/j.jorganchem.2008.04.009.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Rongchang Campus, Southwest University, Chongqing, 402460, China

    Ren-Quan Zeng & Xin-Bin Yang

  2. College of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China

    Xiang-Kai Fu

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  1. Ren-Quan Zeng
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Correspondence to Ren-Quan Zeng.

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Zeng, RQ., Fu, XK. & Yang, XB. Intercalation of basic amino acids into layered zirconium proline-N-methylphosphonate phosphate. Chem. Pap. 65, 676–681 (2011). https://doi.org/10.2478/s11696-011-0049-7

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