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Dextran and Related Polysaccharides

By: Vicki Caligur, BioFiles 2008, 3.10, 17.

Dextran
Historically, dextrans had been long recognized as contaminants in sugar processing and other food production. The formation of dextran in wine was shown by Pasteur to be due to the activity of microbes.1 The name dextran was created by Scheibler in 1874, who demonstrated dextran was a carbohydrate with the formula (C6H10O6)n and a positive optical rotation.2 Dextrans are polysaccharides with molecular weights 1,000 Dalton, which have a linear backbone of -linked dglucopyranosyl repeating units. Three classes of dextrans can be differentiated by their structural features. The pyranose ring structure contains five carbon atoms and one oxygen atom. Class 1 dextrans contain the (16)-linked d-glucopyranosyl backbone modified with small side chains of d-glucose branches with (12), (13), and (14)linkage (see Figure 1). The class 1 dextrans vary in their molecular weight, spatial arrangement, type and degree of branching, and length of branch chains,3-5 depending on the microbial producing strains and cultivation conditions.6,7 Isomaltose and isomaltotriose are oligosaccharides with the class 1 dextran backbone structure. Class 2 dextrans (alternans) contain a backbone structure of alternating (13) and (16)-linked d-glucopyranosyl units with (13)linked branches. Class 3 dextrans (mutans) have a backbone structure of consecutive (13)-linked d-glucopyranosyl units with (16)-linked branches. One and two-dimensional NMR spectroscopy techniques have been utilized for the structural analysis of dextrans.8

Figure 1. General structure of class 1 dextrans consisting of a linear backbone of (16)-linked d-glucopyranosyl repeating units. The dextran may have branches of smaller chains of d-glucose linked to the backbone by (12)- , (13)- or (14)glycosidic bonds.

The secretion of dextrans provides an opportunity for bacteria to modulate adhesion, e.g. in tooth decay, by having a

The secretion of dextrans provides an opportunity for bacteria to modulate adhesion, e.g. in tooth decay, by having a softer or more rigid bacterial cell surface, depending on the polysaccharide itself and the pH and ionic strength. Low bacterial adhesion occurs at low salt conditions with more rigid polysaccharides and a softer surface, while high bacterial adhesion is obtained with more flexible polysaccharides and a rigid bacterial surface. Polymer elasticity is important for structural integrity. and the pyranose ring is the structural unit controlling the elasticity of the polysaccharide. This elasticity results from a force-induced elongation of the ring structure and a final transition from a chair-like to a boat-like conformation of the glucopyranose ring, which plays an important role in accommodating mechanical stress and modulating ligand binding in biological systems.9 Laboratory experiments have demonstrated that cleavage of the pyranose rings of dextran, amylose, and pullulan convert these different polysaccharide chains into similar structures where all the bonds of the polymer backbone can rotate and align under force. After ring cleavage, single molecules of dextran, amylose, and pullulan display identical elastic behavior as measured by atomic force microscopy. Dextrans are found as bacterial extracellular polysaccharides. They are synthesized from sucrose by beneficial lactic acid bacteria, such as Leuconostoc mesenteroides and Lactobacillus brevis, but also by the dental plaque-forming species Streptococcus mutans. Bacteria employ dextran in biofilm formation10 or as protective coatings, e.g., to evade host phagocytes in the case of pathogenic bacteria.11 The physical and chemical properties of purified dextrans vary depending on the microbial strains from which they are produced and by the production method, but all are white and tasteless solids. Dextrans have high water solubility and the solutions behave as Newtonian fluids. Solution viscosity depends on concentration, temperature, and molecular weight, which have a characteristic distribution. The long history of the safety of dextrans has allowed them to be used as additives to food and chemicals, and in pharmaceutical and cosmetics manufacturing.12 Dextrans have been investigated for the targeted and sustained delivery of drugs, proteins, enzymes, and imaging agents.13 In medicine, clinical grades of dextrans with a molecular weight range of 75-100 kDa have been used as blood-plasma volume expanders in transfusions.14 Other applications include the use of dextrans with polyethylene glycol as components of aqueous two-phase systems for the extraction of biochemicals. The hydroxyl groups present in dextran offer many sites for derivatization, and these functionalized glycoconjugates represent a largely unexplored class of biocompatible and environmentally safe compounds. Cross-linked dextran beads are widely used for chromatography in biochemical research and industry. The classic application of cross-linked dextrans is as gel filtration media in packed-bed columns for the separation and purification of biomolecules with molecular weights in the range of 0.7-200 kDa.15-17 Ion exchange chromatography utilizes dextran that has been derivatized with positively or negatively charged moieties such as carboxymethyl (CM), diethylaminoethyl (DEAE), diethyl(2-hydroxypropyl) aminoethyl (QAE), and sulfopropyl (SP). Sigma offers a large variety of dextrans with high polydispersity and dextran molecular weight standards with low polydispersity (Mw/Mn values close to 1.0).

Other Polysaccharides
Pullulans are structural polysaccharides primarily produced from starch by the fungus Aureobasidium pullulans.18,19 Pullulans are composed of repeating (16)-linked maltotriose (D-glucopyranosyl-(14)-D-glucopyranosyl-(14)-Dglucose) units with the inclusion of occasional maltotetraose units.20 Diffusion-ordered NMR spectroscopy has been used to achieve a simple estimation of the molecular weight of pullulan.21 The solution properties of pullulan in water have been studied, and it was confirmed that pullulan molecules behave as random coils in aqueous solution.22 Dextrins are composed of D-glucopyranosyl units but have shorter chain lengths than dextrans. They start with a single (16) bond, but continue linearly with (14)-linked D-glucopyranosyl units. Dextrins are usually mixtures derived from the hydrolysis of starch and have found widespread use in the food, paper, textile, and pharmaceutical industries. Dextran sulfates are derived from dextran via sulfation. They have become indispensable components in many molecular biology techniques, including the transfer of large DNA fragments from agarose gels and rapid hybridization,23 precipitation procedures for the quantitation of high-density lipoprotein cholesterol,24 and inhibition of virion binding to CD4+ cells.25
Materials

Product #

Image

Description

Molecular Formula

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86524

CM-Dextran sodium salt BioXtra

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D9885

DEAE-Dextran hydrochloride powder

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30461

DEAE-Dextran hydrochloride BioReagent, for molecular biology

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00268

Dextran analytical standard, for GPC, 1,000 Dextran analytical standard, for GPC, 5,000

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00269

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00270

Dextran analytical standard, for GPC, 12,000

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00271

Dextran analytical standard, for GPC, 25,000

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00891

Dextran analytical standard, for GPC, 50,000

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00892

Dextran analytical standard, for GPC, 80,000

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00893

Dextran analytical standard, for GPC, 150,000

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00894

Dextran analytical standard, for GPC, 270,000

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00895

Dextran analytical standard, for GPC, 410,000 Dextran analytical standard, for GPC, 670,000

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00896

pricing

31394 31430

Dextran enzymatic synth. Dextran analytical standard, for GPC, Set Mp 1,000-400,000

pricing pricing

31416

Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 1,000 Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 5,000 Dextran from Leuconostoc mesenteroides average mol wt 9,000-11,000 Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 12,000 Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 25,000

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31417

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D9260

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31418

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31419

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D1662

Dextran from Leuconostoc mesenteroides average mol wt 35,000-45,000

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31420

Dextran from Leuconostoc mesenteroides analytical

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mesenteroides analytical standard, for GPC, Mw 50,000 D3759 Dextran from Leuconostoc mesenteroides average mol wt 48,000-90,000 31421 Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 80,000 D4876 Dextran from Leuconostoc mesenteroides average mol wt 150,000 31422 Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 150,000 31423 Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 270,000 31424 Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 410,000 31425 Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 670,000 49297 Dextran from Leuconostoc mesenteroides analytical standard, for GPC, Mw 1,400,000 D5376 Dextran from Leuconostoc mesenteroides average mol wt 1,500,000-2,800,000 D5501 Dextran from Leuconostoc mesenteroides industrial grade, average mol wt 5,000,000-40,000,000 31397 Dextran from Leuconostoc mesenteroides Mr ~60,000 31398 Dextran from Leuconostoc mesenteroides Mr ~200,000 Dextran from Leuconostoc spp. Mr ~6,000 Dextran from Leuconostoc spp. Mr ~40,000 31390 Dextran from Leuconostoc spp. Mr ~70,000 Dextran from Leuconostoc spp. Mr ~100,000 Dextran from Leuconostoc spp. Mr ~2,000,000 pricing pricing pricing pricing pricing pricing pricing pricing pricing pricing pricing pricing pricing

31388

pricing

31389

pricing

09184

pricing

95771

pricing

31392

Dextran from Leuconostoc spp. Mr ~500,000 Dextran from Leuconostoc spp. Mr 15,000-25,000 Dextran cross-linked G-25 50150 m particle size

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31387

pricing

01468

pricing

40359

Dextran cross-linked G-50 50150 m

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94504

Dextran cross-linked G-50 2080 m Dextran cross-linked G-50 100300 m particle size Dextran sulfate sodium salt from Leuconostoc spp. mol wt 6,500-10,000

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68263

pricing

D4911

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D6924

Dextran sulfate sodium salt from Leuconostoc spp. average mol wt 9,000-20,000

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D6001

Dextran sulfate sodium salt from Leuconostoc spp. average mol wt >500,000 (dextran starting material), contains 0.5-2.0% phosphate buffer, pH 6-8

pricing

D8906

Dextran sulfate sodium salt from Leuconostoc spp. for molecular biology, average Mw >500,000 (dextran starting material), contains 0.5-2% phosphate buffer

pricing

31404

Dextran sulfate sodium salt from Leuconostoc spp. Mr 5,000

pricing

D2006

Dextrin from corn Type I, powder

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D2131

Dextrin from corn commercial grade, Type II, powder

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31410

Dextrin from maize starch 10

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31414

Dextrin from maize starch 20

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D4894

Dextrin from potato starch Type IV, powder

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31400

Dextrin from potato starch for microbiology

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P4516

Pullulan from Aureobasidium pullulans suitable for substrate for pullulanase

pricing

96351

Pullulan Standard Set set of analytical standards, for GPC, Mp 342-710000

pricing

References

1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18.

Pasteur, L., Bull. Soc. Chim. Paris, 30-31 (1861). Scheibler, C., Z. Ver. Dtsch. Zucker-Ind., 24, 309-335 (1874). Robyt, J.F., in: Encyclopedia of Polymer Sci. Eng., J.I.Kroschwitz (ed.), 4, 752-767 (1986), Wiley-VCH. Cheetham, N.W.H., et al., Dextran structural details from high-field proton NMR spectroscopy. Carbohydr. Polym. 14, 149-158 (1990). Naessens, M., et al., Leuconostoc dextransucrase and dextran: production, properties and applications. J. Chem. Technol. Biotechnol., 80, 845-860 (2005). Kim, D., et al., Dextran molecular size and degree of branching as a function of sucrose concentration, pH, and temperature of reaction of Leuconostoc mesenteroides B-512FMCM dextransucrase. Carbohydr. Res., 338, 118311889 (2003). Ct, G.L., and Leathers, T.D., A method for surveying and classifying Leuconostoc spp. glucansucrases according to strain-dependent acceptor product patterns. J. Ind. Microbiol. Biotechnol. 32, 53-60 (2005). Maina, N.H., et al., NMR spectroscopic analysis of exopolysaccharides produced by Leuconostoc citreum and Weissella confusa. Carbohydr. Res., 343, 1446-1455 (2008). Marszalek, P.E., et al., Polysaccharide elasticity governed by chair-boat transitions of the glucopyranose ring. Nature, 396, 661-664 (1998). Banas, J.A., and Vickermann, M.M., Glucan-binding proteins of the oral streptococci. Crit. Rev. Oral Biol. Med., 14, 89-99 (2003). Meddens, M.J., et al., Br. J. Exp. Pathol., 65, 257-265 (1984). Kato, I., Fragrance J., 33, 59-64 (2005). Mehvar, R., Dextrans for targeted and sustained delivery of therapeutic and imaging agents. J. Controlled Release, 69, 1-25 (2000). Terg, R., et al., Pharmacokinetics of Dextran-70 in patients with cirrhosis and ascites undergoing therapeutic paracentesis. J. Hepatol., 25, 329-333 (1996). Porsch, B., and Sundelf, L.-O., Size-exclusion chromatography and dynamic light scattering of dextrans in water: Explanation of ion-exclusion behaviour. J. Chromatogr. A, 669, 21-30 (1994). Neyestani, T.R., et al., Isolation of -lactalbumin, -lactoglobulin, and bovine serum albumin from cows milk using gel filtration and anion-exchange chromatography including evaluation of their antigenicity. Protein Expres. Purif., 29, 202-208 (2003). Penzol, G., et al., Use of dextrans as long and hydrophilic spacer arms to improve the performance of immobilized proteins acting on macromolecules. Biotechnol. Bioeng., 60, 518-523 (1998). Gibson, L.H., and Coughlin, R.W., Optimization of high molecular weight pullulan production by Aureobasidium

18. Gibson, L.H., and Coughlin, R.W., Optimization of high molecular weight pullulan production by Aureobasidium pullulans in batch fermentations. Biotechnol. Prog., 18, 675-678 (2002). 19. Leathers, T.D., Biotechnological production and applications of pullulan. Appl. Microbiol. Biotechnol., 62, 468-473 (2003). 20. Catley, B.J., Pullulan, a relationship between molecular weight and fine structure. FEBS Lett., 10, 190-193 (1970). 21. Viel, S., et al., Diffusion-ordered NMR spectroscopy: a versatile tool for the molecular weight determination of uncharged polysaccharides. Biomacromolecules, 4, 1843- 1847 (2003). 22. Nishinari, K., et al., Solution properties of pullulan. Macromolecules, 24, 5590-5593 (1991). 23. Wahl, G.M., et al., Efficient transfer of large DNA fragments from agarose gels to diazobenzyloxymethyl-paper and rapid hybridization by using dextran sulfate. Proc. Natl. Acad. Sci. USA, 76, 3683-3687 (1979). 24. Warnick, G.R., et al., Dextran sulfate-Mg2+ precipitation procedure for quantitation of high-density-lipoprotein cholesterol. Clin. Chem., 28, 1379-1388 (1982). 25. Mitsuya H., et al., Dextran sulfate suppression of viruses in the HIV family: inhibition of virion binding to CD4+ cells. Science, 240, 646-649 (1988).