Thin layer chromatography for the separation and analysis of acidic carbohydrates

Journal of Liquid Chromatography and Related Technologies

Volumn 32, Issue 11-12, 2009, Pages 1711-1732

  Zhang, Zhenqing ^a   Xiao, Zhongping ^a,b   Linhardt, Robert J ^a,c  

^a RENSSELAER POLYTECHNIC INSTITUTE   (United States)

^b OCEAN UNIVERSITY OF CHINA   (China)

^c RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

Disaccharides; Monosaccharides; Oligosacharides; Thin layer chromatography

Indexed keywords

ACIDIC CARBOHYDRATES; COUNTERIONS; DERIVATIZATIONS; DISACCHARIDES; MONOSACCHARIDES; NATURAL PRODUCTS; NATURAL SOURCES; NEGATIVE CHARGE; OLIGOSACHARIDES; POLAR MOLECULES; STATIONARY PHASIS;

CARBOHYDRATES; CHROMATOGRAPHIC ANALYSIS; GLUCOSE; POLYSACCHARIDES; THIN FILMS;

THIN LAYER CHROMATOGRAPHY;

CARBOHYDRATE DERIVATIVE; DISACCHARIDE; MONOSACCHARIDE; OLIGOSACCHARIDE;

ACIDITY; ANALYTIC METHOD; CARBOHYDRATE ANALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION; DERIVATIZATION; ELECTRIC POTENTIAL; HUMAN; NONHUMAN; QUANTITATIVE ANALYSIS; REPRODUCIBILITY; REVIEW; SEPARATION TECHNIQUE; THIN LAYER CHROMATOGRAPHY;

EID: 70349753162     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826070902956402     Document Type: Review

References (53)

1. Lederer, M. Inorganic thin layer chromatography. Chromatogr. Rev. 1967, 9, 115-121
2. Leppard, J.P. Thin-layer-chromatographic equipment. Biochem. J. 1972, 130, 58P-59P.
3. Okumura, T.; Kadono, T.; Nakatani, M. Thin-layer chromatography on silica gel-sintered plates. J. Chromatogr. 1972, 74, 73-84.
4. Jost, W.; Hauck, H.E. The use of modified silica gels in TLC and HPTLC. Adv. Chromatogr. 1987, 27, 129-165.
5. Poole, C.F. Thin-layer chromatography: challenges and opportunities. J. Chromatogr. A. 2003, 1000, 963-984.
6. Sherma, J. Recent advances in the thin-layer chromatography of pesticides: a review. J. AOAC Int. 2003, 86, 602-611.
7. Sherma, J. Review of advances in the thin layer chromatography of pesticides: 2004-2006. J. Environ. Sci. Health B. 2007, 42, 429-440.
8. Sherma, J. Thin-layer chromatography in food and agricultural analysis. J. Chromatogr. A. 2000, 880, 129-147.
9. Touchstone, J.C. Thin-layer chromatographic procedures for lipid separation. J. Chromatogr. B Biomed. Appl. 1995, 671, 169-195.
10. Taki, T.; Ishikawa, D. TLC blotting: application to microscale analysis of lipids and as a new approach to lipid-protein interaction. Anal. Biochem. 1997, 251, 135-143.
11. Onodera, K.; Morisawa, Y. Paper chromatography of diethyl dithioacetals of 2-amino-2-deoxyhexoses, uronic acids, and neutral monosaccharides. Anal. Biochem. 1961, 2, 263-266.
12. Young, D.S.; Jackson, A.J. Thin-layer chromatography of urinary carbohydrates. A comparative evaluation of procedures. Clin. Chem. 1970, 16, 954-959.
13. Garbutt, J.L. Inexpensive adsorbents for thin-layer chromatography of carbohydrates. J. Chromatogr. 1964, 15, 90-92.
14. Anderson, D.M.W.; Stoddart, J.F. Separations of sugars on "Chromagrams". Carbohyd. Res. 1966, 1, 417-418.
15. Hay, G.W.; Lewis, B.A.; Smith, F. Thin-film chromatography in the study of carbohydrates. J. Chromatogr. 1963, 11, 479-486.
16. Lato, M.; Brunelli, B.; Ciuffini, G.; Mezzetti, T. Bidimensional thin-layer chromatography of carbohydrates on silica gel impregnated with boric acid. J. Chromatogr. 1968, 34, 26-34.
17. Adachi, S. Thin-layer chromatography of carbohydrates in the presence of Bisulfite. J. Chromatogr. 1965, 17, 295-299.
18. Paget, M.; Coustenoble, P. Thin layer chromatography of oses and osides encountered in enzymopathies affecting the glucides. Ann. Biol. Clin. (Paris). 1967, 25, 1239-1247.
19. Valdivieso, V.D.; Schwabe, A.D. Absorption of medium-chain lipids from the rat cecum. Am. J. Dig. Dis. 1966, 11, 474-479.
20. Wolfrom, M.L.; LderKremer, R.M.; Schwab, G. Quantitative thin-layer chromatography of sugars on microcrystalline cellulose. J. Chromatogr. 1966, 22, 474.
21. Buchan, J.; Savage, R. Paper chromatography of some starch conversion products. Analyst. 1952, 77, 401-406.
22. Harris, G.; MacWillian, I. A dipping technique for revealing sugars on paper chromatograms. Chem. Ind. 1954, 249.
23. Anderson, K.; Li, S.C.; Li, Y.T. Diphenylamine-aniline-phosphoric acid reagent, a versatile spray reagent for revealing glycoconjugates on thin-layer chromatography plates. Anal. Biochem. 2000, 287, 337-339.
24. Svennerholm, L. Quantitative estimation of sialic acids. II. A colorimetric resorcinol-hydrochloric acid method. Biochim. Biophys. Acta. 1957, 24, 604-611.
25. Zanetta, J.P.; Timmerman, P.; Leroy, Y. Determination of constituents of sulphated proteoglycans using a methanolysis procedure and gas chromatography=mass spectrometry of heptafluorobutyrate derivatives. Glycoconj. J. 1999, 16, 617-627. (Pubitemid 30453739)
26. Zanetta, J.-P.; Vitiello, F.; Vincendon, G. Gangliosides from rat cerebellum: demonstration of considerable heterogeneity using a new solvent for thin layer chromatography. Lipids. 1980, 15, 1055-1061. (Pubitemid 11149449)
27. Muthing, J.; Unland, F.; Heitmann, D.; Orlich, M.; Hanisch, F.G.; Peter-Katalinic, J.; Knauper, V.; Tschesche, H.; Kelm, S.; Schauer, R. Different binding capacities of influenza A and Sendai viruses to gangliosides from human granulocytes. Glycoconj. J. 1993, 10, 120-126. (Pubitemid 23168580)
28. Muthing, J.; Unland, F. A comparative assessment of TLC overlay technique and microwell adsorption assay in the examination of influenza A and Sendai virus specificities towards oligosaccharides and sialic acid linkages of gangliosides. Glycoconj. J. 1994, 11, 486-492. (Pubitemid 24363377)
29. Kasama, T.;Hisano, Y.; Nakajima,M.; Handa, S.; Taki, T. Microscale analysis of glycosphingolipids by TLC blotting=secondary ion mass spectrometry: a novel blood group A-active glycosphingolipid and changes in glycosphingolipid expression in rat mammary tumour cells with different metastatic potentials. Glycoconj. J. 1996, 13, 461-469.
30. Taki, T.; Rokukawa, C.; Kasama, T.; Handa, S. Human hepatoma gangliosides: occurrence of a novel I-type glycolipid with NeuAc alpha 2-6Gal structure. Cancer Res. 1992, 52, 4805-4811.
31. Itonori, S.; Shirai, T.; Kiso, Y.; Ohashi, Y.; Shiota, K.; Ogawa, T. Glycosphingolipid composition of rat placenta: changes associated with stage of pregnancy. Biochem. J. 1995, 307 (Pt 2), 399-405.
32. Nyiredy, S. The role of planar chromatography in medicinal plant research. J. AOAC Int. 2001, 84, 1219-1231. (Pubitemid 33610556)
33. Chai, W.; Leteux, C.; Lawson, A.M.; Stoll, M.S. On-line overpressure thin-layer chromatographic separation and electrospray mass spectrometric detection of glycolipids. Anal. Chem. 2003, 75, 118-125.
34. Stoll, M.S.; Feizi, T.; Loveless, R.W.; Chai, W.; Lawson, A.M.; Yuen, C.T. Fluorescent neoglycolipids. Improved probes for oligosaccharide ligand discovery. Eur. J. Biochem. 2000, 267, 1795-1804.
35. Chai, W.; Feizi, T.; Yuen, C.T.; Lawson, A.M. Nonreductive release of O-linked oligosaccharides from mucin glycoproteins for structure=function assignments as neoglycolipids: application in the detection of novel ligands for E-selectin. Glycobiology. 1997, 7, 861-872.
36. Chai, W.; Rosankiewicz, J.R.; Lawson, A.M. TLC-LSIMS of neoglycolipids of glycosaminoglycan disaccharides and of oxymercuration cleavage products of heparin fragments that contain unsaturated uronic acid. Carbohydr. Res. 1995, 269, 111-124.
37. Feizi, T.; Stoll, M.S.; Yuen, C.T.; Chai, W.; Lawson, A.M. Neoglycolipids: probes of oligosaccharide structure, antigenicity, and function. Methods Enzymol. 1994, 230, 484-519.
38. Reiffova, K.; Nemcova, R. Thin-layer chromatography analysis of fructooligosaccharides in biological samples. J. Chromatogr. A. 2006, 1110, 214-221.
39. van Houdenhoven, F.E.; de Wit, P.J.; Visser, J. Large-scale preparation of galacturonic acid oligomers by matrix-bound polygalacturonase. Carbohydr. Res. 1974, 34, 233-239.
40. Zhang, Z.; Yu, G.; Zhao, X.; Liu, H.; Guan, H.; Lawson, A.M.; Chai, W. Sequence analysis of alginate-derived oligosaccharides by negative-ion electrospray tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 2006, 17, 621-630.
41. Suzuki, H.; Suzuki, K.; Inoue, A.; Ojima, T. A novel oligoalginate lyase from abalone, Haliotis discus hannai, that releases disaccharide from alginate polymer in an exolytic manner. Carbohydr. Res. 2006, 341, 1809-1819.
42. Lanning, M.C.; Cohen, S.S. The detection and estimation of 2-ketohexonic acids. J. Biol. Chem. 1951, 189, 109-114.
43. Capila, I.; Linhardt, R.J. Heparin-protein interactions. Angew. Chem. Int. Ed. Engl. 2002, 41, 391-412.
44. Longas, M.O.; Meyer, K. Sequential hydrolysis of hyaluronate by beta-glucuronidase and beta-N-acetylhexosaminidase. Biochem. J. 1981, 197, 275-282.
45. Shimada, E.; Matsumura, G. Thin-layer chromatography of hyaluronate oligosaccharides. J. Biochem. 1984, 96, 721-725.
46. Weissmann, B.; Meyer, K.; Sampson, P.; Linker, A. Isolation of oligosaccharides enzymatically produced from hyaluronic acid. J. Biol. Chem. 1954, 208, 417-429.
47. Reissig, J.L.; Storminger, J.L.; Leloir, L.F. A modified colorimetric method for the estimation of N-acetylamino sugars. J. Biol. Chem. 1955, 217, 959-966.
48. Good, T.A.; Bessman, S.P. Determination of glucosamine and galactosamine using borate buffers for modification of the Elson-Morgan and Morgan- Elson reactions. Anal. Biochem. 1964, 9, 253-262.
49. Saamanen, A.M.; Tammi, M. Determination of unsaturated glycosaminoglycan disaccharides by spectrophotometry on thin-layer chromatographic plates. Anal. Biochem. 1984, 140, 354-359.
50. Shimada, E.; Kudoh, N.; Tomioka, M.; Matsumura, G. Separation of unsaturated chondroitin sulfate disaccharides in thin-layer chromatography on silica gel and their quantitative determination by densitometry. Chem. Pharm. Bull. (Tokyo). 1987, 35, 1503-1508.
51. Shinomiya, K.; Hoshi, Y.; Imanari, T. Sensitive detection of unsaturated disaccharides from chondroitin sulphates by thin-layer chromatography as their dansylhydrazine derivatives. J. Chromatogr. 1989, 462, 471-474. (Pubitemid 19047390)
52. Zhang, Z.; Xie, J.; Zhang, F.; Linhardt, R.J. Thin-layer chromatography for the analysis of glycosaminoglycan oligosaccharides. Anal. Biochem. 2007, 371, 118-120.
53. Zhang, Z.; Xie, J.; Liu, J.; Linhardt, R.J. Tandem MS can distinguish hyaluronic acid from N-acetylheparosan. J. Am. Soc. Mass Spectrom. 2008, 19, 82-90.