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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 α-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 α(1→6)-linked d-glucopyranosyl backbone modified with small side chains of d-glucose branches with α(1→2), α(1→3), and α(1→4)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 α(1→3) and α(1→6)-linked d-glucopyranosyl units with α(1→3)linked branches. Class 3 dextrans (mutans) have a backbone structure of consecutive α(1→3)-linked d-glucopyranosyl units with α(1→6)-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 α(1→6)-linked d-glucopyranosyl repeating units. The dextran may have branches of smaller chains of d-glucose linked to the backbone by α(1→2)- , α(1→3)- or α(1→4)glycosidic bonds.

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

diethylaminoethyl (DEAE). Polymer elasticity is important for structural integrity.24 and inhibition of virion binding to CD4+ cells. Cross-linked dextran beads are widely used for chromatography in biochemical research and industry.. but also by the dental plaque-forming species Streptococcus mutans. 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. by having a softer or more rigid bacterial cell surface. They start with a single α(1→6) bond. to evade host phagocytes in the case of pathogenic bacteria. while high bacterial adhesion is obtained with more flexible polysaccharides and a rigid bacterial surface. Dextran sulfates are derived from dextran via sulfation. Bacteria employ dextran in biofilm formation10 or as protective coatings. They have become indispensable components in many molecular biology techniques. depending on the polysaccharide itself and the pH and ionic strength. amylose. and molecular weight. amylose. which have a characteristic distribution. such as Leuconostoc mesenteroides and Lactobacillus brevis. and in pharmaceutical and cosmetics manufacturing. which plays an important role in accommodating mechanical stress and modulating ligand binding in biological systems. and pharmaceutical industries. textile.15-17 Ion exchange chromatography utilizes dextran that has been derivatized with positively or negatively charged moieties such as carboxymethyl (CM).g. Sigma® offers a large variety of dextrans with high polydispersity and dextran molecular weight standards with low polydispersity (Mw/Mn values close to 1. enzymes.9 Laboratory experiments have demonstrated that cleavage of the pyranose rings of dextran. clinical grades of dextrans with a molecular weight range of 75-100 kDa have been used as blood-plasma volume expanders in transfusions. Other Polysaccharides Pullulans are structural polysaccharides primarily produced from starch by the fungus Aureobasidium pullulans.19 Pullulans are composed of repeating α(1→6)-linked maltotriose (D-glucopyranosyl-α(1→4)-D-glucopyranosyl-α(1→4)-Dglucose) units with the inclusion of occasional maltotetraose units.18. They are synthesized from sucrose by beneficial lactic acid bacteria. and the pyranose ring is the structural unit controlling the elasticity of the polysaccharide.The secretion of dextrans provides an opportunity for bacteria to modulate adhesion. single molecules of dextran. proteins.g. but continue linearly with α(1→4)-linked D-glucopyranosyl units. temperature.22 Dextrins are composed of D-glucopyranosyl units but have shorter chain lengths than dextrans.12 Dextrans have been investigated for the targeted and sustained delivery of drugs. and imaging agents. Dextrans have high water solubility and the solutions behave as Newtonian fluids.25 Materials Product # Image Description Molecular Formula Add to Cart . in tooth decay. diethyl(2-hydroxypropyl) aminoethyl (QAE). e. and sulfopropyl (SP).23 precipitation procedures for the quantitation of high-density lipoprotein cholesterol.0).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. and pullulan convert these different polysaccharide chains into similar structures where all the bonds of the polymer backbone can rotate and align under force.13 In medicine. Low bacterial adhesion occurs at low salt conditions with more rigid polysaccharides and a softer surface. 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. and it was confirmed that pullulan molecules behave as random coils in aqueous solution. and pullulan display identical elastic behavior as measured by atomic force microscopy. After ring cleavage. The long history of the safety of dextrans has allowed them to be used as additives to food and chemicals.20 Diffusion-ordered NMR spectroscopy has been used to achieve a simple estimation of the molecular weight of pullulan. Dextrins are usually mixtures derived from the hydrolysis of starch and have found widespread use in the food.21 The solution properties of pullulan in water have been studied. Solution viscosity depends on concentration. and these functionalized glycoconjugates represent a largely unexplored class of biocompatible and environmentally safe compounds. including the transfer of large DNA fragments from agarose gels and rapid hybridization. The hydroxyl groups present in dextran offer many sites for derivatization.14 Other applications include the use of dextrans with polyethylene glycol as components of aqueous two-phase systems for the extraction of biochemicals. Dextrans are found as bacterial extracellular polysaccharides. paper.7-200 kDa. but all are white and tasteless solids. e.

Mw 12. for GPC. for GPC. 25. for GPC.000 Dextran from Leuconostoc mesenteroides analytical standard. 670. 1. 150.000 pricing 00893 Dextran analytical standard. for GPC. for GPC. for molecular biology pricing 00268 Dextran analytical standard. Set Mp 1.000 pricing 31417 pricing D9260 pricing 31418 pricing 31419 pricing D1662 Dextran from Leuconostoc mesenteroides average mol wt 35.000-45. for GPC.000 Dextran analytical standard.000 Dextran from Leuconostoc mesenteroides average mol wt 9. for GPC.000 Dextran from Leuconostoc mesenteroides analytical standard.000 pricing 00892 Dextran analytical standard.000 pricing 00891 Dextran analytical standard. 410.000 Dextran analytical standard. for GPC. for GPC. for GPC. Mw 25.000 pricing 00895 Dextran analytical standard.86524 CM-Dextran sodium salt BioXtra pricing D9885 DEAE-Dextran hydrochloride powder pricing 30461 DEAE-Dextran hydrochloride BioReagent.000 Dextran from Leuconostoc mesenteroides analytical standard.000 pricing 00271 Dextran analytical standard. for GPC. 5. Mw 1. for GPC. 270. 12.000-11.000 pricing 00269 pricing 00270 Dextran analytical standard. for GPC. 50. for GPC.000 pricing pricing 31416 Dextran from Leuconostoc mesenteroides analytical standard.000 pricing 31420 Dextran from Leuconostoc mesenteroides analytical pricing .000 pricing 00894 Dextran analytical standard. Dextran analytical standard.000 pricing 00896 pricing 31394 31430 Dextran enzymatic synth. for GPC. Mw 5. 80.000-400.

Mw 1.000 31424 Dextran from Leuconostoc mesenteroides analytical standard.000 D4876 Dextran from Leuconostoc mesenteroides average mol wt 150.000 Dextran from Leuconostoc spp.000 D5501 Dextran from Leuconostoc mesenteroides industrial grade. Mr ~70.800.000 Dextran from Leuconostoc spp. Mw 670.000 31425 Dextran from Leuconostoc mesenteroides analytical standard. Mw 150. Mr ~40.000 31398 Dextran from Leuconostoc mesenteroides Mr ~200.000.000 31421 Dextran from Leuconostoc mesenteroides analytical standard.000 31390 Dextran from Leuconostoc spp. for GPC.000.000 D3759 Dextran from Leuconostoc mesenteroides average mol wt 48. Mr ~6.000 31423 Dextran from Leuconostoc mesenteroides analytical standard. for GPC. Mr ~100. for GPC.mesenteroides analytical standard. Mw 410. average mol wt 5.000 49297 Dextran from Leuconostoc mesenteroides analytical standard.000.000 pricing pricing pricing pricing pricing pricing pricing pricing pricing pricing pricing pricing pricing 31388 pricing 31389 pricing 09184 pricing 95771 pricing .000 31397 Dextran from Leuconostoc mesenteroides Mr ~60.500.000 Dextran from Leuconostoc spp.000-90.000 Dextran from Leuconostoc spp.000-2.400. Mw 270. Mr ~2. Mw 50. for GPC. for GPC.000 31422 Dextran from Leuconostoc mesenteroides analytical standard.000 D5376 Dextran from Leuconostoc mesenteroides average mol wt 1. for GPC. Mw 80. for GPC.000-40.

for molecular biology.000 (dextran starting material).000 pricing D2006 Dextrin from corn Type I. average mol wt >500.31392 Dextran from Leuconostoc spp.000 pricing D6001 Dextran sulfate sodium salt from Leuconostoc spp. Mr 15. pH 6-8 pricing D8906 Dextran sulfate sodium salt from Leuconostoc spp. contains 0. powder pricing D2131 Dextrin from corn commercial grade. contains 0.000-20. Mr ~500. powder pricing 31410 Dextrin from maize starch 10 pricing 31414 Dextrin from maize starch 20 pricing .500-10.5-2% phosphate buffer pricing 31404 Dextran sulfate sodium salt from Leuconostoc spp.000-25. Mr 5. average mol wt 9.000 (dextran starting material). Type II.000 Dextran cross-linked G-25 50150 µm particle size pricing 31387 pricing 01468 pricing 40359 Dextran cross-linked G-50 50150 µm pricing 94504 Dextran cross-linked G-50 2080 µm Dextran cross-linked G-50 100300 µm particle size Dextran sulfate sodium salt from Leuconostoc spp.0% phosphate buffer.5-2.000 Dextran from Leuconostoc spp.000 pricing 68263 pricing D4911 pricing D6924 Dextran sulfate sodium salt from Leuconostoc spp. mol wt 6. average Mw >500.

). Z. P.. J. I. and Vickermann. Nature. L. and Coughlin. 60. J. N. L. Bioeng. 5. Polysaccharide elasticity governed by chair-boat transitions of the glucopyranose ring. NMR spectroscopic analysis of exopolysaccharides produced by Leuconostoc citreum and Weissella confusa. J. R.R. and Leathers. glucansucrases according to strain-dependent acceptor product patterns. Biotechnol. Terg. 3. C.. 11. 202-208 (2003). 661-664 (1998). 6. Med. et al. Dextrans for targeted and sustained delivery of therapeutic and imaging agents. B..J. Robyt. 396.A. 1-25 (2000). J...H.. 1446-1455 (2008). Polym. et al. 9. Eng. 2.E. Pharmacokinetics of Dextran-70 in patients with cirrhosis and ascites undergoing therapeutic paracentesis.. Pasteur. G.. 12. 118311889 (2003). Carbohydr. Glucan-binding proteins of the oral streptococci.... M. 845-860 (2005).. Cheetham. Optimization of high molecular weight pullulan production by Aureobasidium . 7. et al. 309-335 (1874).D.. R. A. Isolation of α-lactalbumin. 18. Fragrance J.. L.H.. properties and applications. J.H.. Mp 342-710′000 pricing References 1. and bovine serum albumin from cow’s milk using gel filtration and anion-exchange chromatography including evaluation of their antigenicity. Penzol.F. β-lactoglobulin. Banas. 14. Oral Biol. 53-60 (2005). for GPC.. Size-exclusion chromatography and dynamic light scattering of dextrans in water: Explanation of ion-exclusion behaviour. 33. G.. Chromatogr. 17.. D. Mehvar... Carbohydr. 14. 338. Ver. Carbohydr. 15. Maina.. Res. Crit. powder pricing 31400 Dextrin from potato starch for microbiology pricing P4516 Pullulan from Aureobasidium pullulans suitable for substrate for pullulanase pricing 96351 Pullulan Standard Set set of analytical standards. J. 30-31 (1861).. et al. 14.Kroschwitz (ed.. in: Encyclopedia of Polymer Sci. 29. Paris. T. Bull. Porsch. Protein Expres. 24.. 65. 669. et al. et al. Rev. Wiley-VCH. Ind. A method for surveying and classifying Leuconostoc spp.M. J. 329-333 (1996). and temperature of reaction of Leuconostoc mesenteroides B-512FMCM dextransucrase. et al. R.. 32. Exp.. Chem. 4.. et al. Scheibler. Biotechnol. Hepatol. Chim. 8. Res.. 16. Dextran structural details from high-field proton NMR spectroscopy.. 10. 13.L. J..I. Neyestani. and Sundelöf. T.. Soc.-O. Kim. M. 343. Zucker-Ind. 21-30 (1994).D4894 Dextrin from potato starch Type IV. Kato. Meddens. 149-158 (1990). M.W. Pathol. Marszalek. 80... Dtsch. 69.. 257-265 (1984). Controlled Release. 25. J. 752-767 (1986). Purif. Naessens. et al. N.... Côté.W. Dextran molecular size and degree of branching as a function of sucrose concentration. 89-99 (2003). Leuconostoc dextransucrase and dextran: production. Microbiol. Biotechnol. 4. 518-523 (1998). 59-64 (2005). Br... Use of dextrans as long and hydrophilic spacer arms to improve the performance of immobilized proteins acting on macromolecules. Technol... Gibson. pH.

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