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Modification of pectin with UV-absorbing substitutents and its effect on the structural and hydrodynamic properties of the water-soluble derivatives

Morris, Gordon, Hromadkova, Z., Ebringerova, A., Malovakova, A., Alfoldi, J. and Harding, S. E. (2002) Modification of pectin with UV-absorbing substitutents and its effect on the structural and hydrodynamic properties of the water-soluble derivatives. Carbohydrate Polymers, 48 (4). pp. 351-359. ISSN 0144-8617

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Abstract

Citrus pectin with a low degree of methyl esterification (LMP) and its deesterified form, potassium pectate (KP), were modified with a low amount of UV-absorbing substituents. For this purpose, two different substitution reactions were used (a) alkylation of hydroxyl groups with p-carboxybenzyl bromide in aqueous alkali and (b) alkylation of the carboxylate group with benzyl bromide in the DMSO/TBAI/catalyst system. Chemical and spectroscopic methods reveal a low degree of substitution (DS<0.1) for the derivatives. The hydrodynamic properties were assessed by analytical ultracentrifugion, viscometry, and HPGPC. The results indicate that the introduction of small amounts of p-carboxybenzyl ether groups practically had no effect on the hydrodynamic properties in the case of KP, whereas, it was accompanied with a decrease of the molecular mass for LMP. The degradation was more pronounced during the benzyl esterification of LMP. The results confirmed that LMP is susceptible to chain cleavage due to β-elimination during both modification reactions. However, KP seems to be more tolerant of the reaction conditions. © 2002 Elsevier Science Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: Analytical ultracentrifuge Benzyl ester Calcium pectate Carboxybenzyl ether Hydrodynamic properties Low methylesterified pectin NMR spectroscopy Alkylation Chemical modification Derivatives Esterification Hydrodynamics Nuclear magnetic resonance spectroscopy Substitution reactions Ultraviolet radiation Methylesterified pectin Biopolymers Citrus
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
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Language of Original Document: English
Correspondence Address: Ebringerová, A.; Institute of Chemistry, Slovak Academy of Sciences, Dubravska cesta 9, 842 38 Bratislava, Slovakia; email: chemebri@savba.sk
References: Abel-Azim, A.-A.A., Atta, A.M., Farahat, M.S., Boutros, W., Determination of the intrinsic viscosity of polymeric compounds through a single specific viscosity measurement (1998) Polymer, 39, pp. 6827-6833; Alföldi, J., Palov�ík, R., Peciar, C., Hirsch, J., Ková�, P., Conformation of some derivatives of methyl 4-deoxy-α- and β-l-threo-hex-4-enopyranuronate (1975) Carbohydrate Research, 44, pp. 133-137; Bax, A., Summers, M.F., Proton and carbon-13 assignments from sensitivity enhanced detection of heteronuclear multiple-bond connectivity (1986) Journal of the American Chemical Society, 108, pp. 2093-2094; Chapman, H.D., Morris, V.J., Selvendran, R.R., O'Neill, M.A., Static and dynamic light scattering studies of pectic polysaccharides from the middle lamellae and primary cell walls of cider apples (1987) Carbohydrate Research, 165, pp. 53-68; Colquhoun, I.J., De Ruiter, G.A., Schols, H.A., Voragen, A.G.J., Identification by NMR spectroscopy of oligosaccharides obtained by treatment of the hairy regions of apple pectin with rhamnogalacturonase (1990) Carbohydrate Research, 206, pp. 131-144; Crescenzi, V., Callegaro, L., Esters of pectic and pectinic acids, their manufacture and uses (1993) Chemical Abstracts, 120, p. 301518. , WO 9314129; Daub, G.H., Castle, R.N., The synthesis of some substituted benzyl iodides (1954) Journal of Organic Chemistry, 19, pp. 1571-1574; Della Valle, F., Romeo, A., (1987) Hyaluronic acid esters and their medical and cosmetic uses and formulation, , Pat. Eur. 216453; Ebringerová, A., Banzragch, D., Malovíková, A., Ka�uráková, M., Characterization of pectins isolated from Mongolian plants (1993) Journal of Carbohydrate Chemistry, 12, pp. 1057-1071; Ebringerová, A., Novotná, Z., Ka�uráková, M., Machová, E., Chemical modification of beechwood xylan with p-carboxybenzyl bromide (1996) Journal of Applied Polymer Science, 62, pp. 1043-1047; Ebringerová, A., Alföldi, J., Hromádková, Z., Pavlov, G.M., Harding, S.E., Water-soluble p-carboxybenzylated beechwood 4-O-methylglucurono-xylan: Structural features and properties (2000) Carbohydrate Polymers, 42, pp. 123-131; Gralén, N., (1944) Sedimentation and diffusion measurements on cellulose and cellulose derivatives, , PhD Dissertation, University of Uppsala, Sweden; Harding, S.E., The intrinsic viscosity of biological macromolecules. Progress in measurement, interpretation and application to structure in dilute solutions (1997) Progress in Biophysics and Molecular Biology, 68, pp. 207-262; Van Holde, K.E., (1985) Physical biochemistry, (Second ed.), , New Jersey: Prentice-Hall; Johansson, M.H., Samuelson, O., Epimerization and degradation of 2-O-(4-O-α-d-Glucopyranosyluronic acid)-d-xylitol (1977) Carbohydrate Research, 54, pp. 295-299; Jumel, K., (1994) Molecular size of interacting and degrading polysaccharides, , PhD Thesis, University of Nottingham; Jumel, K., Browne, P., Kennedy, J.F., (1992) Laser light scattering in biochemistry, , S.R. Harding, D.B. Sattelle & V.A. Bloomfield, Cambridge: Royal Society of Chemistry, Chapter 2; Keenan, M.H.J., Belton, P.S., Matthew, J.A., Howson, S.J., A 13C NMR study of sugar beet pectin (1985) Carbohydrate Research, 138, pp. 168-170; Klavons, J.A., Bennet, R.D., Preparation of alkyl esters of pectin and pectinic acid (1995) Journal of Food Science, 60, pp. 513-515; Kravtchencko, T.P., Pilnik, W., A simplified method for the determination of the intrinsic viscosity of pectin solutions by classical viscometry (1990) Gums and stabilisers for the food industry, 5, pp. 281-286. , G.O. Phillips, P.A. Williams & D.J. Wedlock, Oxford: IRL Press; Kwam, B.J., Atzori, M., Toffanin, R., Paoletti, S., Biviano, F., 1H- and 13C NMR studies on solutions of hyaluronic acid esters and salts in methyl sulfoxide: Comparison of hydrogen-bond patterns and conformational behaviour (1992) Carbohydrate Research, 230, pp. 1-13; Laue, T.M., Stafford III, W.F., Modern applications of analytical ultracentrifugation (1999) Annual Reviews in Biophysics and Biomolecular Structure, 28, pp. 75-100; Morris, G.A., (2001) Hydrodynmaic investigation of polysaccharides and their interactions with casein, , PhD Thesis, University of Nottingham; Morris, G.A., Ebringerová, A., Harding, S.E., Hromádková, Z., UV tagging leaves the structural integrity of an arabino(4-O-methylglucurono)xylan polysaccharide unaffected (1999) Progress in Colloid Polymer Science, 113, pp. 201-204; Morris, G.A., Foster, T.J., Harding, S.E., The effect of degree of esterification on the hydrodynamic properties of citrus pectin (2000) Food Hydrocolloids, 14, pp. 227-235; Odonmazhig, P., Badgaa, D., Ebringerová, A., Alföldi, J., Structures of pectic polysaccharides isolated from the Siberian apricot (Armenica siberica Lam.) (1992) Carbohydrate Research, 226, pp. 353-358; Pavlov, G.M., The concentration dependence of sedimentation for polysaccharides (1997) European Biophysics Journal, 25, pp. 385-398; Philo, J.S., An improved function for fitting sedimentation velocity data for low-molecular-weight solutes (1997) Biophysical Journal, 72, pp. 435-444; Ralston, G., (1993) Introduction to analytical ultracentrifugation, , California: Beckman Instruments; Ryden, P.M., Colquhoun, I.J., Selvendran, R.R., Investigation of structural features of the pectic polysaccharides of onion by 13C NMR spectroscopy (1989) Carbohydrate Research, 185, pp. 233-237; Schleucher, J., Schwendiger, M., Sattler, M., Smidt, P., Schedletzky, O., Glaser, S.J., Sorensen, O.W., Griesinger, C., A general enhancement scheme in heteronuclear multidimensional NMR employing pulsed field gradients (1994) Journal of Biomolecular NMR, 4, pp. 301-306; Schols, H.A., Posthumus, M.A., Voragen, A.G.J., Structural features of hairy regions of pectins isolated from apple juice by the liquefaction process (1990) Carbohydrate Research, 206, pp. 117-129; Schols, H.A., Bakx, E.J., Schipper, D., Voragen, A.G.J., A xylogalacturonan subunit present in the modified hairy region of apple pectin (1995) Carbohydrate Research, 279, pp. 265-279; Stafford, I.I.I.W.F., Boundary analysis in sedimentation transport experiments: A procedure for obtaining sedimentation coefficient distributions using the time derivative of the concentration profile (1992) Analytical Biochemistry, 203, pp. 295-301; Stafford III, W.F., Methods for obtaining sedimentation coefficient distributions (1992) Analytical ultracentrifugation in biochemistry and polymer science, , S.E. Harding, A.J. Rowe & J.C. Horton, Cambridge: Royal Society of Chemistry, Chapter 20; Tanford, C., (1961) Physical chemistry of macromolecules, , New York: Wiley, Chapter 6; Thomas, J.R., Darvill, A.G., Albersheim, P., Isolation and characterization of the pectic polysaccharide rhamnogalacturonan Ii from walls of suspension-cultured rice cells (1989) Carbohydrate Research, 185, pp. 261-277; Tjan, S.B., Voragen, A.G.J., Pilnik, W., Analysis of some partly and fully esterified oligogalactopyranuronic acids by PMR spectrometry at 220 MHz (1974) Carbohydrate Research, 34, pp. 15-32

Depositing User: Gordon Morris
Date Deposited: 13 May 2011 13:04
Last Modified: 04 Jul 2011 14:11
URI: http://eprints.hud.ac.uk/id/eprint/10441

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