Abstract
Xyloglucan in water solution turns into a gel with addition of alcohol such as methanol and ethanol. In regard to this phenomenon, we investigated the adhesive property of alcohol to xyloglucan and proposed the mechanism of the gelation by molecular dynamics (MD) simulation of a xyloglucan in water, water/methanol, and water/ethanol solution for 10 ns. The alcohol molecules showed its adhesive property to the xyloglucan and made the swelling-shrinking motion of the xyloglucan slow. Alcohol molecules solvated to the xyloglucan mainly in hydrophobic way so as to fill the void of water hydration shell, resulting in reformation of the hydrogen-bond network of water molecules around the solute. We also found that alcohol molecules have strong tendency to hydrogen-bond on xylose O3 in xyloglucan. According to these results, we proposed the gelation mechanism of xyloglucan in water/alcohol solution.
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References
Basma M, Sundara S, Calgan D, Venali T, Woods RJ (2001) Solvated ensemble averaging in the calculation of partial atomic charges. J Comput Chem 22:1125–1137. doi:10.1002/jcc.1072
Berendsen HJC, Postma JPM, van Gunsteren WF, DiNola A, Haak JR (1984) Molecular dynamics with coupling to an external bath. J Chem Phys 81:3684–3690. doi:10.1063/1.448118
Case DA, Pearlman DA, Caldwell JW, Cheatham TEI, Wang J, Ross WS, Simmerling C, Darden T, Merz KM, Stanton RV, Cheng A et al (2002) AMBER 7. Univ of California, San Francisco
Dixit S, Crain J, Poon WC, Finney JL, Soper AK (2002) Molecular segregation observed in a concentrated alcohol–water solution. Nature 416:829–832. doi:10.1038/416829a
Engelsen SB, Monteiro C, de Penhoat CH, Perez S (2001) The diluted aqueous solvation of carbohydrates as inferred from molecular dynamics simulations and NMR spectroscopy. Biophys Chem 93:103–127. doi:10.1016/S0301-4622(01)00215-0
Essmann U, Perera L, Berkowitz ML, Darden T, Lee H, Pedersen LG (1995) A smooth particle mesh Ewald method. J Chem Phys 103:8577–8593. doi:10.1063/1.470117
Gibeault DM, Garpita NC (1993) Structural models of primary cell walls in flowering plants: consistency of molecular structure with the physical properties of the walls during growth. Plant J 3:1–30. doi:10.1111/j.1365-313X.1993.tb00007.x
Hayashi T (1989) Xyloglucans in the primary cell wall. Annu Rev Plant Physiol Plant Mol Biol 40:139–168. doi:10.1146/annurev.pp.40.060189.001035
Hayashi T, Takeda T, Ogawa K, Mitsuishi Y (1994a) Effects of the degree of polymerization on the binding of xyloglucans to cellulose. Plant Cell Physiol 35:893–899
Hayashi T, Ogawa K, Mitsuishi Y (1994b) Characterization of the adsorption of xyloglucan to cellulose. Plant Cell Physiol 35:1199–1205
Jorgensen WL, Chandrasekhar J, Madura JD, Impey RW, Klein ML (1983) Comparison of simple potential functions for simulating liquid water. J Chem Phys 79:926–935. doi:10.1063/1.445869
Kirschner KN, Woods RJ (2001a) Solvent interactions determine carbohydrate conformation. Proc Natl Acad Sci USA 98:10541–10545. doi:10.1073/pnas.191362798
Kirschner KN, Woods RJ (2001b) Quantum mechanical study of the nonbonded forces in water-methanol complexes. J Phys Chem A 105:4150–4155. doi:10.1021/jp004413y
Kooiman P (1961) The constitution of Tamarindus-amyloid. Recl Trav Chim Pays-bas 80:849–865
Levy S, York WS, Stuike-Prill R, Meyer B, Staehelin LA (1991) Simulations of the static and dynamic molecular conformations of xyloglucan. The role of the fucosylated sidechain in surface-specific sidechain folding. Plant J 1:195–215. doi:10.1111/j.1365-313X.1991.00195.x
Masuya M 2003. NSOL. http://biocomputing.cc/nsol/
Nishi N, Takahashi S, Matsumoto M, Tanaka A, Muraya K, Takamuku T, Yamaguchi T (1995) Hydrogen-bonded cluster formation and hydrophobic solute association in aqueous solutions of ethanol. J Phys Chem 99:462–468. doi:10.1021/j100001a068
Noskov SY, Lamoureux G, Roux B (2005) Molecular dynamics study of hydration in ethanol–water mixtures using a polarizable force field. J Phys Chem B 109:6705–6713. doi:10.1021/jp045438q
Ogawa K, Hayashi T, Okamura K (1990) Conformational analysis of xyloglucans. Int J Biol Macromol 12:218–222. doi:10.1016/0141-8130(90)90036-A
Ryckaert JP, Ciccotti G, Berendsen HJC (1977) Numerical integration of the cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes. J Comput Phys 23:327–341. doi:10.1016/0021-9991(77)90098-5
Stillinger FH (1980) Water revisited. Science 209:451–457. doi:10.1126/science.209.4455.451
Takamuku T, Yamaguchi T, Asato M, Matsumoto M, Nishi N (2000) Structure of clusters in methanol–water binary solutions studied by mass spectrometry and X-ray diffraction. Z Naturforsch 55 a:513–525
Taylor IEP, Atkins EDT (1985) X-ray diffraction studies on the xyloglucan from tamarind (Tamarindus indica) seed. FEBS Lett 181:300–302. doi:10.1016/0014-5793(85)80280-5
Umemura M, Yuguchi Y (2005) Conformational folding of xyloglucan side chains in aqueous solution from molecular dynamics simulation. Carbohydr Res 340:2520–2532. doi:10.1016/j.carres.2005.08.017
Wakisaka A, Komatsu S, Usui Y (2001) Solute-solvent and solvent-solvent interactions evaluated through clusters isolated from solutions: Preferential solvation in water-alcohol mixtures. J Mol Liq 90:175–184. doi:10.1016/S0167-7322(01)00120-9
Wang Q, Ellis PR, Ross–Murphy SB, Burchard W (1997) Solution characteristics of the xyloglucan extracted from Detarium senegalense Gmelin. Carbohydr Polym 33:115–124. doi:10.1016/S0144-8617(97)00026-X
Wang J, Cieplak P, Kollman PA (2000) How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? J Comput Chem 21:1049–1074. doi:10.1002/1096-987X(200009)21:12<1049::AID-JCC3>3.0.CO;2-F
White EV, Rao PS (1953) Constitution of the polysaccharide from Tamarind seed. J Am Chem Soc 75:2617–2619. doi:10.1021/ja01107a018
Whittaker ET, Robinson G (1967) The calculus of observations: a treatise on numerical mathematics, 4th edn. Dover, New York, pp 334–336
Woods RJ, Dwek RA, Edge CJ, Fraser-Reid B (1995) Molecular mechanical and molecular dynamical simulations of glycoproteins and oligosaccharides. 1. GLYCAM_93 parameter development. J Phys Chem 99:3832–3846. doi:10.1021/j100011a061
Yamaguchi T (1999) New horizons in hydrogen bonded clusters in solution. Pure Appl Chem 71:1741–1751. doi:10.1351/pac199971091741
Yamanaka S, Yuguchi Y, Urakawa H, Kajiwara K, Shirakawa M, Yamatoya K (2000) Gelation of tamarind seed polysaccharide xyloglucan in the presence of ethanol. Food Hydrocoll 14:125–128. doi:10.1016/S0268-005X(99)00057-0
Yuguchi Y, Kumagai T, Wu M, Hirotsu T, Hosokawa J (2004) Gelation of xyloglucan in water/alcohol systems. Cellulose 11:203–208. doi:10.1023/B:CELL.0000025427.60557.40
Zhong Y, Warren GL, Patel S (2007) Thermodynamic and structural properties of methanol-water solutions using nonadditive interaction models. J Comput Chem 29:1142–1152. doi:10.1002/jcc.20877
Acknowledgments
The authors thank T. Hirotsu, K. Kanayama, and other colleagues for useful discussions and criticism. This work was partially supported by the Ministry of Education, Science and Culture, Japan (support of young researchers with a term to Y.Y.).
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Umemura, M., Yuguchi, Y. Solvation of xyloglucan in water/alcohol systems by molecular dynamics simulation. Cellulose 16, 361–371 (2009). https://doi.org/10.1007/s10570-009-9278-0
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DOI: https://doi.org/10.1007/s10570-009-9278-0