Navegar

Colección

Datos Estadísticas

Artículo

Rodríguez, S.D.; Bernik, D.L.; Méreau, R.; Castet, F.; Champagne, B.; Botek, E. "Amylose-vanillin complexation assessed by a joint experimental and theoretical analysis" (2011) Journal of Physical Chemistry C. 115(47):23315-23322
La versión final de este artículo es de uso interno. El editor solo permite incluir en el repositorio el artículo en su versión post-print. Por favor, si usted la posee enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

A joint experimental and theoretical study has been carried out on the amylose-vanillin complex, demonstrating its formation by X-ray diffraction as well as UV/visible and circular dichroism spectroscopic techniques. Theoretical simulations substantiate these experimental data and the variations of properties upon complexation by evidencing the stability of the inclusion of vanillin in the helical cavity as well as by explaining the related changes of the linear (chiro-)optical properties. In particular, the circular dichroism (CD) signature of the vanillin inclusion complex results from a geometrical distortion induced by the complexation with the surrounding amylose helix. The use of the ONIOM technique mixing B3LYP and PM6 levels of approximation to include the interactions between different layers (together with the IEFPCM model to describe the solvent) appears to be a satisfactory methodology to simulate both the UV and CD spectra for these compounds. © 2011 American Chemical Society.

Registro:

Documento: Artículo
Título:Amylose-vanillin complexation assessed by a joint experimental and theoretical analysis
Autor:Rodríguez, S.D.; Bernik, D.L.; Méreau, R.; Castet, F.; Champagne, B.; Botek, E.
Filiación:Instituto de Química-Física de Materiales, Medio Ambiente y Energía, Universidad de Buenos Aires, Pabellón II, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
Institut des Sciences Moléculaires, UMR 5255 CNRS, Université de Bordeaux, Cours de la Libération, 351, F-33405 Talence CEDEX, France
Laboratoire de Chimie Théorique, Facultés Universitaires Notre-Dame de la Paix, rue de Bruxelles, 61, B-5000 Namur, Belgium
Palabras clave:Dichroism; X ray diffraction; CD spectra; Different layers; Geometrical distortion; Inclusion complex; Spectroscopic technique; Theoretical simulation; Theoretical study; Cyclodextrins
Año:2011
Volumen:115
Número:47
Página de inicio:23315
Página de fin:23322
DOI: http://dx.doi.org/10.1021/jp208328n
Título revista:Journal of Physical Chemistry C
Título revista abreviado:J. Phys. Chem. C
ISSN:19327447
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_19327447_v115_n47_p23315_Rodriguez

Referencias:

  • Robyt, J.F., (1998) Essentials of Carbohydrate Chemistry, , Springer: New York, NY
  • Conde-Petit, B., Escher, F., Nuessli, J., (2006) Trends Food Sci. Technol., 17, pp. 227-235
  • Itthisoponkul, T., Mitchell, J.R., Taylor, A.J., Farhat, I.A., (2007) Carbohydr. Polym., 69, pp. 106-115
  • Clays, K., Olbrechts, G., Munters, T., Persoons, A., Kim, O.-K., Choi, L.-S., (1998) Chem. Phys. Lett., 293, pp. 337-342
  • Star, A., Steuerman, D.W., Heath, J.R., Stoddart, J.F., (2002) Angew. Chem., Int. Ed., 41, pp. 2508-2512
  • Xie, Y.H., Soh, A.K., (2005) Mater. Lett., 59, pp. 971-975
  • Yang, Y., Gu, Z., Zhang, G., (2009) J. Agric. Food Chem., 57, pp. 7125-7130
  • Joshi, S.S., Mebel, A.M., (2007) Polymer, 48, pp. 3893-3901
  • Frampton, M.J., Claridge, T.D.W., Latini, G., Brovelli, S., Cacialli, F., Anderson, H.L., (2008) Chem. Commun., pp. 2797-2799
  • Wulff, G., Avgenaki, G., Guzmann, M.S.P., (2005) J. Cereal Sci., 41, pp. 239-249
  • Tapanapunnitikul, O., Chaiseri, S., Peterson, D.G., Thompson, D.B., (2008) J. Agric. Food Chem., 56, pp. 220-226
  • Sinha, A.K., Sharma, U.K., Sharma, N., (2008) Int. J. Food Sci. Nutr., 59, pp. 299-326
  • Karathanos, V.T., Mourtzinos, I., Yannakopoulou, K., Andrikopoulos, N.K., (2007) Food Chem., 101, pp. 652-658
  • De Roos, K.B., (2006) Trends Food Sci. Technol., 17, pp. 236-243
  • Heinemann, F., Escher, C., Conde-Petit, B., (2005) Food Sci. Technol., 38, pp. 885-894
  • Egawa, T., Kameyama, A., Takeuch, H., (2006) J. Mol. Struct., 794, pp. 92-102
  • Cocinero, E.J., Lesarri, A., Ecija, P., Grabow, J.-U., Fernandez, J.A., Castaño, F., (2010) Phys. Chem. Chem. Phys., 12, pp. 12486-12493
  • Yu, X., Houtman, C., Atalla, R.H., (1996) Carbohydr. Res., 292, pp. 129-141
  • (2004) TINKER - Software Tools for Molecular Design, Version 4.2
  • Homans, S.W., (1990) Biochemistry, 29, pp. 9110-9118
  • Momany, F.A., Willett, J.L., Schnupf, U., (2009) Carbohydr. Polym., 78, pp. 978-986
  • Dapprich, S., Komáromi, I., Byun, K.S., Morokuma, K., Frisch, M.J., (1999) J. Mol. Struct. (Theochem), 462, pp. 1-21
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Fox, D.J., (2009) Gaussian 09, Revision A.1, , Gaussian, Inc. Wallingford, CT
  • Hirao, H., Morokuma, K., (2010) J. Phys. Chem. Lett., 1, pp. 901-906
  • Lundberg, M., Sasakura, Y., Zheng, G., Morokuma, K., (2010) J. Chem. Theory Comput., 6, pp. 1413-1427
  • Rajapandian, V., Subramanian, V., (2011) J. Phys. Chem. A, 115, pp. 2866-2876
  • Poully, J.-C., Grégoire, G., Schermann, J.-P., (2009) J. Phys. Chem., 113, pp. 8020-8026
  • Zheng, A., Chen, L., Yang, J., Yue, Y., Ye, Ch., Lu, X., Deng, F., (2005) Chem. Commun., pp. 2474-2476
  • Altun, A., Yokoyama, S., Morokuma, K., (2008) J. Phys. Chem. B, 112, pp. 6814-6827
  • Li, X., Chung, L.W., Mizuno, H., Mayawaki, A., Morokuma, K., (2010) J. Phys. Chem. B, 114, pp. 1114-1126
  • Becke, A.D., (1993) J. Chem. Phys., 98, pp. 5648-5652
  • Stephens, P.J., Devlin, F.J., Chabalowski, C.F., Frisch, M.J., (1994) J. Phys. Chem., 98, pp. 11623-11627
  • Iikura, H., Tsuneda, T., Yanai, T., Hirao, K., (2001) J. Chem. Phys., 115, pp. 3540-3544
  • Yanai, T., Tew, D.P., Handy, N.C., (2004) Chem. Phys. Lett., 393, pp. 51-57
  • Stewart, J.J.P., (2007) J. Mol. Model., 13, pp. 1173-1213
  • Cornell, W.D., Cieplak, P., Bayly, C.I., Gould, I.R., Merz Jr., K.M., Ferguson, D.M., Spellmeyer, D.C., Kollman, P.A., (1995) J. Am. Chem. Soc., 117, pp. 5179-5197
  • Vreven, T., Byun, K.S., Komáromi, I., Dapprich, S., Montgomery Jr., J.A., Morokuma, K., Frisch, M.J., (2006) J. Chem. Theory Comput., 2, pp. 815-826
  • Cammi, R., Mennucci, B., Tomasi, J., (1999) J. Chem. Phys., 110, pp. 7627-7638
  • Zerner, M.C., (1991) Rev. Comput. Chem., 2. , Lipkowitz, K. B. Boyd, D. B. Vol. Chapter 8
  • MOS-F (Semi-Empirical Molecular Orbital Package for Spectroscopy), pp. 1998-2000. , version 4.2D; Fujitsu Laboratories, Ltd. Japan
  • Botek, E., Champagne, B., (2007) J. Chem. Phys., 127, p. 204101
  • Putseys, J.A., Lamberts, L., Delcour, J.A., (2010) J. Cereal Sci., 51, pp. 238-247
  • Buléon, A., Delage, M.M., Brisson, J., Chanzy, H., (1990) Int. J. Biol. Macromolecules, 12, pp. 25-33
  • Tapanapunnitikul, O., Chaiseri, S., Peterson, D.G., Thompson, D.B., (2008) J. Agric. Food. Chem., 56, pp. 220-226
  • Stipanovic, A.J., Stevens, E.S., (1981) Biopolymers, 20, pp. 1183-1189
  • Debie, E., Jaspers, L., Bultinck, P., Herrebout, W., Van Der Veken, B., (2008) Chem Phys. Lett., 450, pp. 426-430

Citas:

---------- APA ----------
Rodríguez, S.D., Bernik, D.L., Méreau, R., Castet, F., Champagne, B. & Botek, E. (2011) . Amylose-vanillin complexation assessed by a joint experimental and theoretical analysis. Journal of Physical Chemistry C, 115(47), 23315-23322.
http://dx.doi.org/10.1021/jp208328n
---------- CHICAGO ----------
Rodríguez, S.D., Bernik, D.L., Méreau, R., Castet, F., Champagne, B., Botek, E. "Amylose-vanillin complexation assessed by a joint experimental and theoretical analysis" . Journal of Physical Chemistry C 115, no. 47 (2011) : 23315-23322.
http://dx.doi.org/10.1021/jp208328n
---------- MLA ----------
Rodríguez, S.D., Bernik, D.L., Méreau, R., Castet, F., Champagne, B., Botek, E. "Amylose-vanillin complexation assessed by a joint experimental and theoretical analysis" . Journal of Physical Chemistry C, vol. 115, no. 47, 2011, pp. 23315-23322.
http://dx.doi.org/10.1021/jp208328n
---------- VANCOUVER ----------
Rodríguez, S.D., Bernik, D.L., Méreau, R., Castet, F., Champagne, B., Botek, E. Amylose-vanillin complexation assessed by a joint experimental and theoretical analysis. J. Phys. Chem. C. 2011;115(47):23315-23322.
http://dx.doi.org/10.1021/jp208328n