Elucidation of a novel lacto-N-decaose core structure in human milk using nonlinear analytical technique combinations

Analytical Biochemistry

Volumn 421, Issue 2, 2012, Pages 680-690

  Blank, Dennis ^a   Geyer, Hildegard ^a   Maass, Kai ^a   Yamashita, Katsuko ^b   Geyer, Rudolf ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Carbohydrate structure analysis; GC MS linkage analysis; Human milk oligosaccharides; Mass spectrometry

Indexed keywords

ANTENNAS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERS; MASS SPECTROMETRY; MOLECULES; OLIGOSACCHARIDES; SACCHARIFICATION;

ANALYTICAL PROTOCOLS; HIGH MOLECULAR WEIGHT; HUMAN MILK OLIGOSACCHARIDES; LINKAGE ANALYSIS; MODULAR STRATEGY; PROOF OF PRINCIPLES; STRUCTURAL CHARACTERIZATION; STRUCTURE ANALYSIS;

STRUCTURAL ANALYSIS;

GLYCOSIDASE; LACTO N DECAOSE; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; BREAST MILK; CARBOHYDRATE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MASS SPECTROMETRY; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 84859715950     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2011.11.030     Document Type: Article

References (48)

1. T. Urashima, K. Fukuda, M. Kitaoka, M. Ohnighi, T. Terabayashi, A. Kobata, Milk Oligosaccharides, Nova Science, New York, 2011.
2. B. Stahl, S. Thurl, J. Zeng, M. Karas, F. Hillenkamp, M. Steup, G. Sawatzki, Oligosaccharides from human milk as revealed by matrix-assisted laser desorption/ionization mass spectrometry, Anal. Biochem. 223 (1994) 218-226. (Pubitemid 24368970)
3. S. Wu, R. Grimm, J.B. German, C.B. Lebrilla, Annotation and structural analysis of sialylated human milk oligosaccharides, J. Proteome Res. 10 (2011) 856-868.
4. S. Wu, N. Tao, J.B. German, R. Grimm, C.B. Lebrilla, The development of an annotated library of neutral human milk oligosaccharides, J. Proteome Res. 9 (2010) 4138-4151.
5. L. Bode, Human milk oligosaccharides: prebiotics and beyond, Nutr. Rev. 67 (Suppl. 2) (2009) S183-S191.
6. D.S. Newburg, G.M. Ruiz-Palacios, M. Altaye, P. Chaturvedi, J. Meinzen-Derr, L. Guerrero Mde, A.L. Morrow, Innate protection conferred by fucosylated oligosaccharides of human milk against diarrhea in breastfed infants, Glycobiology 14 (2004) 253-263. (Pubitemid 38324941)
7. G.M. Ruiz-Palacios, L.E. Cervantes, P. Ramos, B. Chavez-Munguia, D.S. Newburg, Campylobacter jejuni binds intestinal H(O) antigen (Fucα1, 2Galß,1 4GlcNAc), and fucosyloligosaccharides of human milk inhibit its binding and infection, J. Biol. Chem. 278 (2003) 14112-14120. (Pubitemid 36799958)
8. P. Hong, M.R. Ninonuevo, B. Lee, C. Lebrilla, L. Bode, Human milk oligosaccharides reduce HIV-1-gp120 binding to dendritic cell-specific ICAM3-grabbing non-integrin (DC-SIGN), Br. J. Nutr. 101 (2009) 482-486.
9. A.P. Vos, M. Haarman, A. Buco, M. Govers, J. Knol, J. Garssen, B. Stahl, G. Boehm, L. M'Rabet, A specific prebiotic oligosaccharide mixture stimulates delayedtype hypersensitivity in a murine influenza vaccination model, Int. Immunopharmacol. 6 (2006) 1277-1286. (Pubitemid 43884995)
10. A. El-Hawiet, E.N. Kitova, P. Kitov, L. Eugenio, K.K. Ng, G.L. Mulvey, T.C. Dingle, A. Szpacenko, G.D. Armstrong, J.S. Klassen, Binding of clostridium difficile toxins to human milk oligosaccharides, Glycobiology 21 (2011) 1217-1227.
11. S. Thurl, M. Munzert, J. Henker, G. Boehm, B. Müller-Werner, J. Jelinek, B. Stahl, Variation of human milk oligosaccharides in relation to milk groups and lactational periods, Br. J. Nutr. 104 (2010) 1261-1271.
12. C. Kunz, S. Rudloff, W. Baier, N. Klein, S. Strobel, Oligosaccharides in human milk: structural, functional, and metabolic aspects, Annu. Rev. Nutr. 20 (2000) 699-722.
13. A. Kobata, Structures and application of oligosaccharides in human milk, Proc. Jpn. Acad. Ser. B. Phys. Biol. Sci. 86 (2010) 731-747.
14. n after pyrene derivatization of variously fucosylated oligosaccharides with branched decaose cores from human milk, Glycobiology 19 (2009) 601-614.
15. A. Kobata, Possible application of milk oligosaccharides for drug development, Chang Gung Med. J. 26 (2003) 621-636.
16. A. Pfenninger, M. Karas, B. Finke, B. Stahl, Structural analysis of underivatized neutral human milk oligosaccharides in the negative ion mode by nanoelectrospray MS(n) (part 2: application to isomeric mixtures), J. Am. Soc. Mass Spectrom. 13 (2002) 1341-1348. (Pubitemid 36875989)
17. A. Pfenninger, M. Karas, B. Finke, B. Stahl, Structural analysis of underivatized neutral human milk oligosaccharides in the negative ion mode by nanoelectrospray MS(n) (part 1: methodology), J. Am. Soc. Mass Spectrom. 13 (2002) 1331-1340. (Pubitemid 36875988)
18. M. Rohmer, B. Meyer, M. Mank, B. Stahl, U. Bahr, M. Karas, 3-Aminoquinoline acting as matrix and derivatizing agent for MALDI MS analysis of oligosaccharides, Anal. Chem. 82 (2010) 3719-3726.
19. M. Rohmer, D. Baeumlisberger, B. Stahl, U. Bahr, M. Karas, Fragmentation of neutral oligosaccharides using the MALDI LTQ Orbitrap, Int. J. Mass Spectrom. 305 (2011) 199-208.
20. nfor structural determination of fucosylated and sialylated oligosaccharides labeled with a pyrene derivative, Glycobiology 19 (2009) 592-600.
21. P. Zhang, Y. Zhang, X. Xue, C. Wang, Z. Wang, L. Huang, Relative quantitation of glycans using stable isotopic labels 1-(d0/d5) phenyl-3-methyl-5-pyrazolone by mass spectrometry, Anal. Biochem. 418 (2011) 1-9.
22. L. Han, C.E. Costello, Investigation of structures and fragmentation pathways by electron transfer dissociation of permethylated milk sugars, Glycobiology 20 (2010) 1514-1515.
23. K. Mariño, J.A. Lane, J.L. Abrahams, W.B. Struwe, D.J. Harvey, M. Marotta, R.M. Hickey, P.M. Rudd, Method for milk oligosaccharide profiling by 2-aminobenzamide labeling and hydrophilic interaction chromatography, Glycobiology 21 (2011) 1317-1330.
24. H. Kogelberg, V.E. Piskarev, Y. Zhang, A.M. Lawson, W. Chai, Determination by electrospray mass spectrometry and 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. (Pubitemid 38373050)
25. K. Goto, K. Fukuda, A. Senda, T. Saito, K. Kimura, K.E. Glander, K. Hinde, W. Dittus, L.A. Milligan, M.L. Power, O.T. Oftedal, T. Urashima, Chemical characterization of oligosaccharides in the milk of six species of New and Old world monkeys, Glycoconj. J. 27 (2010) 703-715.
26. W. Chai, V.E. Piskarev, Y. Zhang, A.M. Lawson, H. Kogelberg, Structural determination of novel lacto-N-decaose and its monofucosylated analogue from human milk by electrospray tandem mass spectrometry and 1H NMR spectroscopy, Arch. Biochem. Biophys. 434 (2005) 116-127. (Pubitemid 40040477)
27. A. Kobata, Isolation of oligosaccharides from human milk, Methods Enzymol. 28 (1972) 262-271.
28. A. Kobata, K. Yamashita, Y. Tachibana, Oligosaccharides from human milk, Methods Enzymol. 50 (1978) 216-220.
29. K. Yamashita, T. Mizuochi, A. Kobata, Analysis of oligosaccharides by gel filtration, Methods Enzymol. 83 (1982) 105-126.
30. Y. Tachibana, K. Yamashita, A. Kobata, Oligosaccharides of human milk: structural studies of di- and trifucosyl derivatives of lacto-N-octaose and lacto-N-neoctaose, Arch. Biochem. Biophys. 188 (1978) 83-89. (Pubitemid 8344460)
31. K. Yamashita, Y. Tachibana, A. Kobata, Oligosaccharides ofhumanmilk: isolation characterization of two new nonasaccharides monofucosyllacto-N-octaose and monofucosyllacto-N-neooctaose, Biochemistry 15 (1976) 3950-3955.
32. K.R. Anumula, Quantitative determination of monosaccharides in glycoproteins by high-performance liquid chromatography with highly sensitive fluorescence detection, Anal. Biochem. 220 (1994) 275-283. (Pubitemid 24261169)
33. M. Wuhrer, C.A. Koeleman, A.M. Deelder, Two-dimensional HPLC separation with reverse-phase-nano-LC-MS/MS for the characterization of glycan pools after labeling with 2-aminobenzamide, Methods Mol. Biol. 534 (2009) 79-91.
34. H. Geyer, M. Wuhrer, A. Resemann, R. Geyer, Identification and characterization of keyhole limpet hemocyanin N-glycans mediating crossreactivity with Schistosoma mansoni, J. Biol. Chem. 280 (2005) 40731-40748. (Pubitemid 41780564)
35. M. Wuhrer, M.L. Robijn, C.A. Koeleman, C.I. Balog, R. Geyer, A.M. Deelder, C.H. Hokke, A novel Gal(β1-4)Gal(β1-4)Fuc(α1-6)-core modification attached to the proximal N-acetylglucosamine of keyhole limpet haemocyanin (KLH) Nglycans, Biochem. J. 378 (2004) 625-632. (Pubitemid 38367252)
36. I. Ciucanu, C.E. Costello, Elimination of oxidative degradation during the per- O-methylation of carbohydrates, J. Am. Chem. Soc. 125 (2003) 16213-16219. (Pubitemid 38020645)
37. J. Jang-Lee, S.J. North, M. Sutton-Smith, D. Goldberg, M. Panico, H. Morris, S. Haslam, A. Dell, Glycomic profiling of cells and tissues by mass spectrometry: fingerprinting and sequencing methodologies, Methods Enzymol. 415 (2006) 59-86. (Pubitemid 44751091)
38. K. Maass, R. Ranzinger, H. Geyer, C.W. Von der Lieth, R. Geyer, "Glyco- Peakfinder" - de novo composition analysis of glycoconjugates, Proteomics 7 (2007) 4435-4444.
39. A. Ceroni, K. Maass, H. Geyer, R. Geyer, A. Dell, S.M. Haslam, GlycoWorkbench: a tool for the computer-assisted annotation of mass spectra of glycans, J. Proteome Res. 7 (2008) 1650-1659.
40. C.W. von der Lieth, A.A. Freire, D. Blank, M.P. Campbell, A. Ceroni, D.R. Damerell, A. Dell, R.A. Dwek, B. Ernst, R. Fogh, M. Frank, H. Geyer, R. Geyer, M.J. Harrison, K. Henrick, S. Herget, W.E. Hull, J. Ionides, H.J. Joshi, J.P. Kamerling, B.R. Leeflang, T. Lütteke, M. Lundborg, K. Maass, A. Merry, R. Ranzinger, J. Rosen, L. Royle, P.M. Rudd, S. Schloissnig, R. Stenutz, W.F. Vranken, G. Widmalm, S.M. Haslam, EUROCarbDB: an open-access platform for glycoinformatics, Glycobiology 21 (2011) 493-502.
41. S.M. Haslam, G.C. Coles, H.R. Morris, A. Dell, Structural characterization of the N-glycans of Dictyocaulus viviparus: discovery of the Lewis(x) structure in a nematode, Glycobiology 10 (2000) 223-229. (Pubitemid 30193023)
42. H. Geyer, S. Schmitt, M. Wuhrer, R. Geyer, Structural analysis of glycoconjugates by on-target enzymatic digestion and MALDI-TOF-MS, Anal. Chem. 71 (1999) 476-482.
43. J.P. Parente, P. Cardon, Y. Leroy, J. Montreuil, B. Fournet, G. Ricart, A convenient method for methylation of glycoprotein glycans in small amounts by using lithium methylsulfinyl carbanion, Carbohydr. Res. 141 (1985) 41-47.
44. R. Geyer, H. Geyer, Saccharide linkage analysis using methylation and other techniques, Methods Enzymol. 230 (1994) 86-108.
45. R. Geyer, H. Geyer, S. Kühnhardt, W. Mink, S. Stirm, Capillary gas chromatography of methylhexitol acetates obtained upon methylation of N-glycosidically linked glycoprotein oligosaccharides, Anal. Biochem. 121 (1982) 263-274. (Pubitemid 12052003)
46. R. Geyer, H. Geyer, S. Kühnhardt, W. Mink, S. Stirm, Methylation analysis of complex carbohydrates in small amounts: capillary gas chromatography-mass fragmentography of methylalditol acetates obtained from N-glycosidically linked glycoprotein oligosaccharides, Anal. Biochem. 133 (1983) 197-207. (Pubitemid 13009680)
47. 13C- nuclear magnetic resonance spectroscopy. Evidence for a new core structure iso-lacto-N-octaose, Glycoconj. J. 6 (1989) 169-182.
48. B. Domon, C.E. Costello, A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates, Glycoconj. J. 5 (1988) 397-409. (Pubitemid 19031141)