Structural characterization of multibranched oligosaccharides from seal milk by a combination of off-line high-performance liquid chromatography-matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry and sequential exoglycosidase digestion

Analytical Biochemistry

Volumn 388, Issue 2, 2009, Pages 242-253

  Kinoshita, Mitsuhiro ^a   Ohta, Hiroko ^a   Higaki, Kanata ^a   Kojima, Yoko ^a   Urashima, Tadasu ^b   Nakajima, Kazuki ^c   Suzuki, Minoru ^c   Kovacs, Kit M ^d   Lydersen, Christian ^d   Hayakawa, Takao ^a   Kakehi, Kazuaki ^a  

^a KINKI UNIVERSITY   (Japan)

^b OBIHIRO UNIVERSITY OF AGRICULTURE AND VETERINARY MEDICINE   (Japan)

^c Japan Science and Technology Agency   (Japan)

^d NORWEGIAN POLAR INSTITUTE   (Norway)

Author keywords

Exoglycosidase digestion; HPLC; MALDI TOF MS; Milk oligosaccharide; Multibranched polylactosamine type oligosaccharide

Indexed keywords

DESORPTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INDUCTIVELY COUPLED PLASMA; MASS SPECTROMETRY; MATRIX ALGEBRA; MIXTURES; SEALS;

2-AMINOBENZOIC ACID; EXOGLYCOSIDASE; HIGH MOLECULAR MASS; HPLC; MALDI TOF MS; MATRIX ASSISTED LASER DESORPTION; MATRIX-ASSISTED LASER DESORPTION/IONIZATION-TIME-OF-FLIGHT MASS SPECTROMETRY; STRUCTURAL CHARACTERIZATION;

OLIGOSACCHARIDES;

ANTHRANILIC ACID; CARBOHYDRATE; FUCOSE; GLYCOCONJUGATE; GLYCOSIDASE; LACTOSAMINE; LACTOSE; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; COLOSTRUM; DIGESTION; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MILK; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL; PROTEIN ISOLATION; SEAL;

ANIMALIA; CYSTOPHORA (MAMMALIA);

EID: 64249110543     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2009.03.004     Document Type: Article

References (48)

1. Feizi T. Demonstration by monoclonal antibodies that carbohydrate structures of glycoproteins and glycolipids are onco-developmental antigens. Nature 314 (1985) 53-57
2. Osanai T., Feizi T., Chai W., Lawson A.M., Gustavsson M.L., Sudo K., Araki M., Araki K., and Yuen C.T. Two families of murine carbohydrate ligands for E-selectin. Biochem. Biophys. Res. Commun. 218 (1996) 610-615
3. Feizi T. Carbohydrate-mediated recognition systems in innate immunity. Immunol. Rev. 173 (2000) 79-88
4. Podbielska M., Fredriksson S.A., Nilsson B., Lisowska E., and Krotkiewski H. ABH blood group antigens in O-glycans of human glycophorin A. Arch. Biochem. Biophys. 429 (2004) 145-153
5. Kobata A., Yamashita K., and Tachibana Y. Oligosaccharides from human milk. Methods Enzymol. 50 (1978) 216-220
6. Newburgh D.S., and Neubauer S.H. Handbook of Milk Composition (1995), Academic Press, San Diego
7. 1H-NMR spectroscopy of primary structures of variously fucosylated neutral oligosaccharides based on the iso-lacto-N-octaose core. Eur. J. Biochem. 271 (2004) 1172-1186
8. Urashima T., Asakuma S., and Messer M. Comprehensive Glycoscience (2007), Elsevier, Amsterdam
9. Jenness R., Regehr E.A., and Sloan R.E. Comparative biochemical studies of milk: II. Dialyzable carbohydrates. Comp. Biochem. Physiol. 13 (1964) 339-352
10. Messer M. Identification of N-acetyl-4-O-acetylneuraminyl-lactose in echidna milk. Biochem. J. 139 (1974) 415-420
11. Messer M., and Green B. Milk carbohydrates of marsupials: II. Quantitative and qualitative changes in milk carbohydrates during lactation in the tammar wallaby (Macropus eugenii). Austral. J. Biol. Sci. 32 (1979) 519-531
12. Kamerling J.P., Dorland L., van Halbeek H., Vliegenthart J.F., Messer M., and Schauer R. Structural studies of 4-O-acetyl-α-N-acetylneuraminyl-(2→3)-lactose, the main oligosaccharide in echidna milk. Carbohydr. Res. 100 (1982) 331-340
13. Urashima T., Saito T., Tsuji Y., Taneda Y., Takasawa T., and Messer M. Chemical characterization of sialyl oligosaccharides isolated from tammar wallaby (Macropus eugenii) milk. Biochim. Biophys. Acta 1200 (1994) 64-72
14. Urashima T., Saito T., Nakamura T., and Messer M. Oligosaccharides of milk and colostrum in non-human mammals. Glycoconj. J. 18 (2001) 357-371
15. Urashima T., Yamamoto M., Nakamura T., Arai I., Saito T., Namiki M., Yamaoka K., and Kawahara K. Chemical characterisation of the oligosaccharides in a sample of milk of a white-nosed coati, Nasua narica (Procyonidae: Carnivora). Comp. Biochem. Physiol. A 123 (1999) 187-193
16. Nakamura T., Urashima T., Mizukami T., Fukushima M., Arai I., Senshu T., Imazu K., Nakao T., Saito T., Ye Z., Zuo H., and Wu K. Composition and oligosaccharides of a milk sample of the giant panda, Ailuropoda melanoleuca. Comp. Biochem. Physiol. B 135 (2003) 439-448
17. Urashima T., Arita M., Yoshida M., Nakamura T., Arai I., Saito T., Arnould J.P., Kovacs K.M., and Lydersen C. Chemical characterisation of the oligosaccharides in hooded seal (Cystophora cristata) and Australian fur seal (Arctocephalus pusillus doriferus) milk. Comp. Biochem. Physiol. B 128 (2001) 307-323
18. Urashima T., Nakamura T., Nakagawa D., Noda M., Arai I., Saito T., Lydersen C., and Kovacs K.M. Characterization of oligosaccharides in milk of bearded seal (Erignathus barbatus). Comp. Biochem. Physiol. B 138 (2004) 1-18
19. Urashima T., Nakamura T., Teramoto K., Arai I., Saito T., Komatsu T., and Tsubota T. Chemical characterization of sialyl oligosaccharides in milk of the Japanese black bear, Ursus thibetanus japonicus. Comp. Biochem. Physiol. B 139 (2004) 587-595
20. Urashima T., Nakamura T., Yamaguchi K., Munakata J., Arai I., Saito T., Lydersen C., and Kovacs K.M. Chemical characterization of the oligosaccharides in milk of high Arctic harbour seal (Phoca vitulina vitulina). Comp. Biochem. Physiol. A 135 (2003) 549-563
21. Urashima T., Sato H., Munakata J., Nakamura T., Arai I., Saito T., Tetsuka M., Fukui Y., Ishikawa H., Lydersen C., and Kovacs K.M. Chemical characterization of the oligosaccharides in beluga (Delphinapterus leucas) and Minke whale (Balaenoptera acutorostrata) milk. Comp. Biochem. Physiol. B 132 (2002) 611-624
22. Amano J., Messer M., and Kobata K. Structures of the oligosaccharides isolated from milk of the platypus. Glycoconj. J. 2 (1985) 121-135
23. Finke B., Stahl B., Pfenninger A., Karas M., Daniel H., and Sawatzki G. Analysis of high-molecular-weight oligosaccharides from human milk by liquid chromatography and MALDI-MS. Anal. Chem. 71 (1999) 3755-3762
24. Pfenninger A., Karas M., Finke B., Stahl B., and Sawatzki G. Mass spectrometric investigations of human milk oligosaccharides. Adv. Exp. Med. Biol. 501 (2001) 279-284
25. Reinhold V.N., Reinhold B.B., and Costello C.E. Carbohydrate molecular weight profiling, sequence, linkage, and branching data: ES-MS and CID. Anal. Chem. 67 (1995) 1772-1784
26. Morelle W., and Michalski J.C. Glycomics and mass spectrometry. Curr. Pharm. Des. 11 (2005) 2615-2645
27. Chai W., Piskarev V., and Lawson A.M. Negative-ion electrospray mass spectrometry of neutral underivatized oligosaccharides. Anal. Chem. 73 (2001) 651-657
28. Chai W., Piskarev V., and Lawson A.M. Branching pattern and sequence analysis of underivatized oligosaccharides by combined MS/MS of singly and doubly charged molecular ions in negative-ion electrospray mass spectrometry. J. Am. Soc. Mass Spectrom. 13 (2002) 670-679
29. Hodge J.E., and Hofreiter B.T. Determination of reducing sugars and carbohydrates. Methods Carbohydr. Chem. 1 (1962) 308-394
30. Anumula K.R., and Dhume S.T. High resolution and high sensitivity methods for oligosaccharide mapping and characterization by normal phase high performance liquid chromatography following derivatization with highly fluorescent anthranilic acid. Glycobiology 8 (1998) 685-694
31. Nakano M., Kakehi K., Tsai M.H., and Lee Y.C., Detailed structural features of glycan chains derived from α1-acid glycoproteins of several different animals: the presence of hypersialylated, O-acetylated sialic acids but not disialyl residues. Glycobiology 14 (2004) 431-441
32. Naka R., Kamoda S., Ishizuka A., Kinoshita M., and Kakehi K. Analysis of total N-glycans in cell membrane fractions of cancer cells using a combination of serotonin affinity chromatography and normal phase chromatography. J. Proteome Res. 5 (2006) 88-97
33. Saito T., Itoh T., and Adachi S. Presence of two neutral disaccharides containing N-acetylhexosamine in bovine colostrum as free forms. Biochim. Biophys. Acta 801 (1984) 147-150
34. Saito T., Itoh T., and Adachi S. Chemical structure of three neutral trisaccharides isolated in free form from bovine colostrum. Carbohydr. Res. 165 (1987) 43-51
35. Urashima T., Kusaka Y., Nakamura T., Saito T., Maeda N., and Messer M. Chemical characterization of milk oligosaccharides of the brown bear, Ursus arctos yesoensis. Biochim. Biophys. Acta 1334 (1997) 247-255
36. Brew K., Vanaman T.C., and Hill R.L. The role of α-lactalbumin and the A protein in lactose synthetase: a unique mechanism for the control of a biological reaction. Proc. Natl. Acad. Sci. USA 59 (1968) 491-497
37. Rajput B., Shaper N.L., and Shaper J.H. Transcriptional regulation of murine β1,4-galactosyltransferase in somatic cells: analysis of a gene that serves both a housekeeping and a mammary gland-specific function. J. Biol. Chem. 271 (1996) 5131-5142
38. Davis D.T., Holt C., and Christie W.W. Biochemistry of Lactation (1983), Elsevier, Amsterdam
39. Gopal P.K., and Gill H.S. Oligosaccharides and glycoconjugates in bovine milk and colostrums. Br. J. Nutr. 84 Suppl. 1 (2000) S69-S74
40. 1H-NMR spectroscopy and fast-atom-bombardment mass spectrometry: Evidence for a new core structure, the para-lacto-N-octaose. Eur. J. Biochem. 215 (1993) 361-371
41. Kawashima H., Yamamoto K., Osawa T., and Irimura T. Purification and characterization of UDP-GlcNAc:Galβ1-4Glc(NAc) β-1,3-N-acetylglucosaminyltransferase (poly-N-acetyllactosamine extension enzyme) from calf serum. J. Biol. Chem. 268 (1993) 27118-27126
42. Piller F., and Cartron J.P. UDP-GlcNAc:Galβ1-4Glc(NAc) β1-3-N-acetylglucosaminyltransferase: identification and characterization in human serum. J. Biol. Chem. 258 (1983) 12293-12299
43. van den Eijnden D.H., Koenderman A.H., and Schiphorst W.E. Biosynthesis of blood group i-active polylactosaminoglycans: partial purification and properties of an UDP-GlcNAc:N-acetyllactosaminide β1-3-N-acetylglucosaminyltransferase from Novikoff tumor cell ascites fluid. J. Biol. Chem. 263 (1988) 12461-12471
44. Ujita M., Misra A.K., McAuliffe J., Hindsgaul O., and Fukuda M. Poly-N-acetyllactosamine extension in N-glycans and core 2- and core 4-branched O-glycans is differentially controlled by i-extension enzyme and different members of the β1,4-galactosyltransferase gene family. J. Biol. Chem. 275 (2000) 15868-15875
45. Chen G.Y., Kurosawa N., and Muramatsu T. A novel variant form of murine β-1,6-N-acetylglucosaminyltransferase forming branches in poly-N-acetyllactosamines. Glycobiology 10 (2000) 1001-1011
46. Inaba N., Hiruma T., Togayachi A., Iwasaki H., Wang X.H., Furukawa Y., Sumi R., Kudo T., Fujimura K., Iwai T., Gotoh M., Nakamura M., and Narimatsu H. A novel i-branching β-1,6-N-acetylglucosaminyltransferase involved in human blood group I antigen expression. Blood 101 (2003) 2870-2876
47. Magnet A.D., and Fukuda M. Expression of the large I antigen forming β-1,6-N-acetylglucosaminyltransferase in various tissues of adult mice. Glycobiology 7 (1997) 285-295
48. Domon B., and Costello C.E. Structure elucidation of glycosphingolipids and gangliosides using high-performance tandem mass spectrometry. Biochemistry 27 (1988) 1534-1543