Derivatization of carbohydrates for chromatographic, electrophoretic and mass spectrometric structure analysis.

Carbohydrates, either alone or as constituents of glycoproteins, proteoglycans and glycolipids, are mediators of several cellular events and (patho)physiological processes. Progress in the "glycome" project is closely related to the analytical tools used to define carbohydrate structure and correlate structure with function. Chromatography, electrophoresis and mass spectrometry are the indispensable analytical tools of the on-going research. Carbohydrate derivatization is required for most of these analytical procedures. This review article gives an overview of derivatization methods of carbohydrates for their liquid chromatographic and electrophoretic separation, as well as the mass spectrometric characterization. Pre-column and on-capillary derivatization methods are presented with special emphasis on the derivatization of large carbohydrates.

[1]  N. Karamanos,et al.  Importance of high-performance liquid chromatographic analysis of serum N-acylneuraminic acids in evaluating surgical treatment in patients with early endometrial cancer. , 1999, Journal of chromatography. B, Biomedical sciences and applications.

[2]  Xuefei Wang,et al.  ANALYSIS OF CARBOHYDRATES BY CAPILLARY ZONE ELECTROPHORESIS WITH ON-CAPILLARY DERIVATIZATION , 2002 .

[3]  N. Volpi Hyaluronic acid and chondroitin sulfate unsaturated disaccharides analysis by high-performance liquid chromatography and fluorimetric detection with dansylhydrazine. , 2000, Analytical biochemistry.

[4]  M. Götte,et al.  Functions of cell surface heparan sulfate proteoglycans. , 1999, Annual review of biochemistry.

[5]  A. Taga,et al.  Capillary electrophoretic analysis of carbohydrates derivatized by in-capillary condensation with 1-phenyl-3-methyl-5-pyrazolone. , 2001, Journal of chromatography. A.

[6]  Ming‐Sun Liu,et al.  Characterization of 9-Aminopyrene-1,4,6-trisulfonate Derivatized Sugars by Capillary Electrophoresis with Laser-Induced Fluorescence Detection , 1995 .

[7]  A. Guttman,et al.  High-resolution capillary gel electrophoresis of reducing oligosaccharides labeled with 1-aminopyrene-3,6,8-trisulfonate. , 1996, Analytical biochemistry.

[8]  O. Dahlman,et al.  Efficient capillary zone electrophoretic separation of wood-derived neutral and acidic mono- and oligosaccharides. , 1996, Journal of chromatography. A.

[9]  S. Lin,et al.  An ultrasensitive chemical method for polysialic acid analysis. , 2001, Glycobiology.

[10]  M. Novotny Capillary biomolecular separations. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[11]  L. Haro,et al.  High-resolution polyacrylamide gel electrophoresis of carbohydrates derivatized with a visible dye. , 1998, Analytical biochemistry.

[12]  Z. El Rassi,et al.  Determination of cellular carbohydrates in peanut fungal pathogens and baker's yeast by capillary electrophoresis and electrochromatography. , 2001, Journal of agricultural and food chemistry.

[13]  K. Ikeda,et al.  An improved fluorometric high-performance liquid chromatography method for sialic acid determination: an internal standard method and its application to sialic acid analysis of human apolipoprotein E. , 2002, Analytical biochemistry.

[14]  R. Linhardt,et al.  Capillary electrophoresis for the analysis of glycosaminoglycans and glycosaminoglycan-derived oligosaccharides. , 2002, Biomedical chromatography : BMC.

[15]  Sandra Díaz,et al.  New sialic acids from biological sources identified by a comprehensive and sensitive approach: liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) of SIA quinoxalinones. , 1997, Glycobiology.

[16]  A. Dell,et al.  Glycoprotein Structure Determination by Mass Spectrometry , 2001, Science.

[17]  D. Harvey,et al.  Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates. , 1999, Mass spectrometry reviews.

[18]  Glycomics, Coming of Age! , 2000 .

[19]  J. Gabriel,et al.  Microemulsion electrokinetic chromatography of diphenylhydrazones of dicarbonyl sugars , 1997 .

[20]  H M Widmer,et al.  The influence of buffer composition on separation efficiency and resolution in capillary electrophoresis of 8‐aminonaphthalene‐1,3,6‐trisulfonic acid labeled monosaccharides and complex carbohydrates , 1996, Electrophoresis.

[21]  X. Gioldassi,et al.  DETERMINATION OF PHOSPHORYLATED AND SULFATED LINKAGE–REGION OLIGOSACCHARIDES IN CHONDROITIN/DERMATAN AND HEPARAN SULFATE PROTEOGLYCANS BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY , 1999 .

[22]  D. Harvey,et al.  Cationic Derivatization of Oligosaccharides with Girard's T Reagent for Improved Performance in Matrix-assisted Laser Desorption/Ionization and Electrospray Mass Spectrometry , 1996 .

[23]  M. Roberts,et al.  Separation of ι‐, κ and λ‐carrageenans by capillary electrophoresis , 2001 .

[24]  Fu-Tai A. Chen,et al.  Acid‐catalyzed reductive amination of aldoses with 8‐aminopyrene‐1,3,6‐trisulfonate , 1996, Electrophoresis.

[25]  Susumu Honda,et al.  High-performance capillary zone electrophoresis of carbohydrates in the presence of alkaline earth metal ions , 1991 .

[26]  A. Hjerpe,et al.  A Method to Quantitate Total Sialic Acid, Glucosamine, and Galactosamine in Blood Serum and Glycoconjugates by HPLC , 1998 .

[27]  A. Taga,et al.  Ultramicroanalysis of reducing carbohydrates by capillary electrophoresis with laser-induced fluorescence detection as 7-nitro-2,1,3-benzoxadiazole-tagged N-methylglycamine derivatives. , 2000, Analytical biochemistry.

[28]  Structural determination of some new oligosaccharides and analysis of the branching pattern of isomaltooligosaccharides from beer. , 1998, Carbohydrate research.

[29]  Joel T. Smith,et al.  Capillary zone electrophoresis of biological substances with surface‐modified fused silica capillaries with switchable electroosmotic flow , 1992 .

[30]  K. Yoshino,et al.  Sensitive Analysis of Oligosaccharides Derivatized with 4-Aminobenzoic Acid 2-(Diethylamino)ethyl Ester by Matrix-assisted Laser Desorption/Ionization Mass Spectrometry , 1996 .

[31]  Anders Hjerpe,et al.  Determination of twelve heparin‐ and heparan sulfate‐derived disaccharides as 2‐aminoacridone derivatives by capillary zone electrophoresis using ultraviolet and laser‐induced fluorescence detection , 2002, Electrophoresis.

[32]  N. Maness,et al.  Determination of the pattern of methyl esterification in pectin. Distribution of contiguous nonesterified residues. , 1993, Carbohydrate research.

[33]  S. Honda,et al.  Simultaneous determination of reducing monosaccharides by capillary zone electrophoresis as the borate complexes of N-2-pyridylglycamines. , 1989, Analytical biochemistry.

[34]  H. Perreault,et al.  Effect of 1-phenyl-3-methyl-5-pyrazolone labeling on the fragmentation behavior of asialo and sialylated N-linked glycans under electrospray ionization conditions. , 1999, Rapid communications in mass spectrometry : RCM.

[35]  G. Her,et al.  Linkage analysis of chromophore-labeled disaccharides and linear oligosaccharides by negative ion fast atom bombardment ionization and collisional-induced dissociation with B/E scanning. , 1993, Analytical biochemistry.

[36]  Y. Arata,et al.  Analyses of N-linked oligosaccharides using a two-dimensional mapping technique. , 1988, Analytical biochemistry.

[37]  R. Linhardt,et al.  Analysis of fluorescently labeled sugars by reversed-phase ion-pairing high-performance liquid chromatography. , 1995, Journal of chromatographic science.

[38]  R. Dwek,et al.  Rapid, sensitive sequencing of oligosaccharides from glycoproteins. , 1997, Current opinion in biotechnology.

[39]  H. Nakanishi,et al.  Rapid analysis of amino sugars by microchip electrophoresis with laser‐induced fluorescence detection , 2001, Electrophoresis.

[40]  R. Midura,et al.  Ion exchange HPLC microanalysis of chondroitin sulfate: quantitative derivatization of chondroitin lyase digestion products with 2-aminopyridine. , 1996, Glycobiology.

[41]  P. Morin,et al.  Investigation of micelles and anionic cyclodextrins as pseudostationary phases for the capillary electrophoresis separation of oligosaccharides derivatized with 2‐aminobenzamide , 1998, Electrophoresis.

[42]  W. Nashabeh,et al.  Carbohydrate analysis of a chimeric recombinant monoclonal antibody by capillary electrophoresis with laser-induced fluorescence detection. , 1999, Analytical chemistry.

[43]  P Jackson,et al.  The use of polyacrylamide-gel electrophoresis for the high-resolution separation of reducing saccharides labelled with the fluorophore 8-aminonaphthalene-1,3,6-trisulphonic acid. Detection of picomolar quantities by an imaging system based on a cooled charge-coupled device. , 1990, The Biochemical journal.

[44]  Shigeo Suzuki,et al.  A tabulated review of capillary electrophoresis of carbohydrates , 1998, Electrophoresis.

[45]  J. Gorman,et al.  Oligosaccharide characterization and quantitation using 1-phenyl-3-methyl-5-pyrazolone derivatization and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. , 1997, Analytical biochemistry.

[46]  J. Turnbull,et al.  Heparan sulfate: decoding a dynamic multifunctional cell regulator. , 2001, Trends in cell biology.

[47]  R. Helm,et al.  The use of the 2-aminobenzoic acid tag for oligosaccharide gel electrophoresis. , 2000, Carbohydrate research.

[48]  A. Hjerpe,et al.  Identity of dermatan and chondroitin sequences in dermatan sulfate chains determined by using fragmentation with chondroitinases and ion-pair high-performance liquid chromatography. , 1995, Analytical biochemistry.

[49]  K. Yoshino,et al.  Use of the derivatizing agent 4-aminobenzoic acid 2-(diethylamino)ethyl ester for high-sensitivity detection of oligosaccharides by electrospray ionization mass spectrometry. , 1995, Analytical chemistry.

[50]  M. G. O'shea,et al.  High resolution slab gel electrophoresis of 8‐amino‐1,3,6‐pyrenetrisulfonic acid (APTS) tagged oligosaccharides using a DNA sequencer , 1996, Electrophoresis.

[51]  D. Kratschmar,et al.  Analysis of oligosaccharides by MEKC with aminobenzoic alkyl esters as derivatization agents , 1999 .

[52]  J. Hirabayashi,et al.  Separation technologies for glycomics. , 2002, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[53]  M. Novotny,et al.  Capillary electrophoresis of amino sugars with laser-induced fluorescence detection. , 1991, Analytical chemistry.

[54]  B. Behnke,et al.  Nano-HPLC-mass spectrometry and MEKC for the analysis of oligosaccharides from human milk. , 2002, Biomedical chromatography : BMC.

[55]  J. Michalski,et al.  Identification of urinary oligosaccharides by matrix-assisted laser desorption ionization time-of-flight mass spectrometry. , 1998, Clinical chemistry.

[56]  S. Honda,et al.  High-performance capillary electrophoresis of unsaturated oligosaccharides derived from glycosaminoglycans by digestion with chondroitinase ABC as 1-phenyl-3-methyl-5-pyrazolone derivatives. , 1992, Journal of chromatography.

[57]  F. Che,et al.  Characterization of derivatization of sialic acid with 2‐aminoacridone and determination of sialic acid content in glycoproteins by capillary electrophoresis and high performance liquid chromatography ‐ ion trap mass spectrometry , 1999, Electrophoresis.

[58]  Gerald W. Hart,et al.  Glycosylation of Nucleocytoplasmic Proteins: Signal Transduction and O-GlcNAc , 2001, Science.

[59]  M. Okamoto,et al.  Sensitive detection and structural characterization of trimethyl(p-aminophenyl)-ammonium-derivatized oligosaccharides by electrospray ionization-mass spectrometry and tandem mass spectrometry. , 1995, Rapid communications in mass spectrometry : RCM.

[60]  P. Lerouge,et al.  Monitoring the N‐glycosylation of plant glycoproteins by fluorophore‐assisted carbohydrate electrophoresis , 2000, Electrophoresis.

[61]  R. Kuhn,et al.  Investigation of derivatization of oligosaccharides by means of reductive amination for separation in capillary electrophoresis , 1999 .

[62]  P. Camilleri,et al.  Fingerprinting of glycans as their 2‐aminoacridone derivatives by capillary electrophoresis and laserinduced fluorescence , 1996, Electrophoresis.

[63]  Q. Xia,et al.  Analysis of neutral saccharides in human milk derivatized with 2-aminoacridone by capillary electrophoresis with laser-induced fluorescence detection. , 2002, Analytical biochemistry.

[64]  M. Novotny,et al.  Sensitive, laser-assisted determination of complex oligosaccharide mixtures separated by capillary gel electrophoresis at high resolution. , 1992, Analytical chemistry.

[65]  A. Mort,et al.  Separation of 8‐aminonaphthalene‐1,3,6‐trisulfonate (ANTS)‐labeled oligomers containing galacturonic acid by capillary electrophoresis: Application to determining the substrate specificity of endopolygalacturonases , 1996, Electrophoresis.

[66]  O Hindsgaul,et al.  Analysis by capillary electrophoresis-laser-induced fluorescence detection of oligosaccharides produced from enzyme reactions. , 1995, Journal of chromatography. A.

[67]  K R Anumula,et al.  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. , 1998, Glycobiology.

[68]  E. Higgins,et al.  A method for monitoring the glycosylation of recombinant glycoproteins from conditioned medium, using fluorophore-assisted carbohydrate electrophoresis. , 1995, Analytical biochemistry.

[69]  H M Widmer,et al.  Separation of 8-aminonaphthalene-1,3,6-trisulfonic acid-labelled neutral and sialylated N-linked complex oligosaccharides by capillary electrophoresis. , 1995, Journal of chromatography. A.

[70]  P. Camilleri,et al.  Direct structural analysis of 2-aminoacridone derivatized oligosaccharides by high-performance liquid chromatography/mass spectrometric detection. , 1998, Rapid communications in mass spectrometry : RCM.

[71]  N. Schwartz,et al.  Biosynthesis and regulation of expression of proteoglycans. , 2000, Frontiers in bioscience : a journal and virtual library.

[72]  C. Lebrilla,et al.  MALDI-FTMS characterization of oligosaccharides labeled with 9-aminofluorene , 2001, Journal of the American Society for Mass Spectrometry.

[73]  Y. Mechref,et al.  Capillary electrophoresis of carboxylated carbohydrates. IV. Adjusting the separation selectivity of derivatized carboxylated carbohydrates by controlling the electrolyte ionic strength at subambient temperature and in the absence of electroosmotic flow. , 1997, Journal of chromatography. A.

[74]  R. Iozzo,et al.  The family of the small leucine-rich proteoglycans: key regulators of matrix assembly and cellular growth. , 1997, Critical reviews in biochemistry and molecular biology.

[75]  I. Lynch,et al.  A dual-detection strategy in the chromatographic analysis of 2-aminoacridone-derivatized oligosaccharides. , 1999, Analytical chemistry.

[76]  T. Raju,et al.  Species-specific variation in glycosylation of IgG: evidence for the species-specific sialylation and branch-specific galactosylation and importance for engineering recombinant glycoprotein therapeutics. , 2000, Glycobiology.

[77]  R. Midura,et al.  Microanalysis of enzyme digests of hyaluronan and chondroitin/dermatan sulfate by fluorophore-assisted carbohydrate electrophoresis (FACE). , 2000, Glycobiology.

[78]  E. Makatsori,et al.  Screening of N-acylneuraminic acids in serum and tissue specimens of mouse C57BI with Lewis' lung cancer by high-performance liquid chromatography. , 1998, Journal of chromatography. B, Biomedical sciences and applications.

[79]  N. Takahashi,et al.  Three-dimensional mapping of N-linked oligosaccharides using anion-exchange, hydrophobic and hydrophilic interaction modes of high-performance liquid chromatography. , 1996, Journal of chromatography. A.

[80]  T. Takao,et al.  Structural analysis of oligosaccharides derivatized with 4-aminobenzoic acid 2-(diethylamino)ethyl ester by matrix-assisted laser desorption/ionization mass spectrometry. , 1998, Analytical chemistry.

[81]  B. Monsarrat,et al.  Characterization of mannooligosaccharide caps in mycobacterial lipoarabinomannan by capillary electrophoresis/electrospray mass spectrometry. , 1999, Glycobiology.

[82]  S. Harata,et al.  Identification of glycosaminoglycans using high-performance liquid chromatography on a hydroxyapatite column. , 1995, Analytical biochemistry.

[83]  J. Langridge,et al.  Profiling of 2-aminoacridone derivatised glycans by electrospray ionization mass spectrometry. , 1999, Rapid communications in mass spectrometry : RCM.

[84]  H. Lingeman,et al.  Derivatization trends in capillary electrophoresis , 2000, Electrophoresis.

[85]  T. Hikita,et al.  Determination of N-acetyl- and N-glycolylneuraminic acids in gangliosides by combination of neuraminidase hydrolysis and fluorometric high-performance liquid chromatography using a GM3 derivative as an internal standard. , 2000, Analytical biochemistry.

[86]  G. Blaschke,et al.  Analysis of the antidiabetic drug acarbose by capillary electrophoresis. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[87]  P. Oefner,et al.  Capillary zone electrophoresis and micellar electrokinetic chromatography of 4‐aminobenzonitrile carbohydrate derivatives , 1994, Electrophoresis.

[88]  A. Hjerpe,et al.  Determination of iduronic acid and glucuronic acid in glycosaminoglycans after stoichiometric reduction and depolymerization using high-performance liquid chromatography and ultraviolet detection. , 1988, Analytical biochemistry.

[89]  S. Honda,et al.  Analysis of the oligosaccharides in ovalbumin by high-performance capillary electrophoresis. , 1990, Analytical biochemistry.

[90]  P. Camilleri,et al.  Efficient carbohydrate release, purification, and derivatization. , 1998, Analytical biochemistry.

[91]  B. Karger,et al.  Analysis of 1-aminopyrene-3,6,8-trisulfonate-derivatized oligosaccharides by capillary electrophoresis with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. , 1997, Analytical chemistry.

[92]  P. Lerouge,et al.  Analysis of 8-aminonaphthalene-1,3,6-trisulfonic acid labelled N-glycans by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. , 2000, Rapid communications in mass spectrometry : RCM.

[93]  M. Novotny,et al.  High-Resolution Studies of Hyaluronic Acid Mixtures through Capillary Gel Electrophoresis. , 1998, Analytical chemistry.

[94]  P. Camilleri,et al.  High resolution and rapid analysis of branched oligosaccharides by capillary electrophoresis. , 1995, Analytical biochemistry.

[95]  P. Camilleri,et al.  A probe for the versatile analysis and characterization of N-linked oligosaccharides. , 2000, Analytical chemistry.

[96]  A. Taga,et al.  Separation of disaccharides by affinity capillary electrophoresis in lectin‐containing electrophoretic solutions , 1998, Electrophoresis.

[97]  C. Castells,et al.  Precolumn derivatization of reducing carbohydrates with 4-(3-Methyl-5-oxo-2-pyrazolin-1-yl) benzoic acid. Study of reaction, high-performance liquid chromatographic separation and quantitative performance of method , 2002 .

[98]  C. Chiesa,et al.  Capillary zone electrophoresis of oligosaccharides derivatized with various aminonaphthalene sulfonic acids , 1994, Electrophoresis.

[99]  L. Colón,et al.  Determination of carbohydrates as their dansylhydrazine derivatives by capillary electrophoresis with laser‐induced fluorescence detection , 1996, Electrophoresis.

[100]  N. Karamanos,et al.  Identification of oligomeric domains within dermatan sulfate chains using differential enzymic treatments, derivatization with 2‐aminoacridone and capillary electrophoresis , 2001, Electrophoresis.

[101]  A. Guttman,et al.  Analysis of monosaccharide composition by capillary electrophoresis. , 1997, Journal of chromatography. A.

[102]  N. Dovichi,et al.  Nanomolar determination of aminated sugars by capillary electrophoresis , 1995 .

[103]  Determination of carbohydrate heterogeneity in the humanised antibody CAMPATH 1H by liquid chromatography and matrix-assisted laser desorption ionisation mass spectrometry , 1995 .

[104]  F T Chen,et al.  Quantitative analysis of sugar constituents of glycoproteins by capillary electrophoresis. , 1998, Glycobiology.

[105]  S. Folestad,et al.  On-line capillary electrophoresis with mass spectrometry detection for the analysis of carbohydrates after derivatization with 8-aminonaphthalene-1,3,6-trisulfonic acid. , 2001, Journal of chromatography. A.

[106]  N. Karamanos,et al.  Capillary electrophoresis: a superior miniaturized tool for analysis of the mono-, di-, and oligosaccharide constituents of glycan moieties in proteoglycans , 2001, Fresenius' journal of analytical chemistry.

[107]  H. Perreault,et al.  Characterization of carbohydrates using a combination of derivatization, high-performance liquid chromatography and mass spectrometry. , 1998, Journal of chromatography. A.

[108]  P. Jackson,et al.  Polyacrylamide gel electrophoresis of reducing saccharides labeled with the fluorophore 2-aminoacridone: subpicomolar detection using an imaging system based on a cooled charge-coupled device. , 1991, Analytical biochemistry.

[109]  M. Roberts,et al.  Separation of high-molecular-mass carrageenan polysaccharides by capillary electrophoresis with laser-induced fluorescence detection , 1998 .

[110]  Sumihiro Hase,et al.  Precolumn derivatization for chromatographic and electrophoretic analyses of carbohydrates , 1996 .

[111]  M. Khaledi,et al.  Efficiency studies in nonaqueous capillary electrophoresis. , 1999, Journal of chromatography. A.

[112]  R. Parekh,et al.  Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthranilic acid. , 1995, Analytical biochemistry.

[113]  B. Monsarrat,et al.  Structural characterization of Mycobacterium tuberculosis lipoarabinomannans by the combination of capillary electrophoresis and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. , 2001, Analytical chemistry.

[114]  M. G. O'shea,et al.  Analysis of starch structure using fluorophore‐assisted carbohydrate electrophoresis , 1998, Electrophoresis.

[115]  B. Domon,et al.  Capillary electrophoresis/electrospray ion trap mass spectrometry for the analysis of negatively charged derivatized and underivatized glycans. , 2002, Rapid communications in mass spectrometry : RCM.

[116]  J. Duus,et al.  Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of oligosaccharides derivatized by reductive amination and N,N-dimethylation. , 2000, Rapid communications in mass spectrometry : RCM.

[117]  G. Avigad Dansyl hydrazine as a fluorimetric reagent for thin-layer chromatographic analysis of reducing sugars. , 1977, Journal of chromatography.

[118]  H. Desaire,et al.  Combined partial acid hydrolysis and electrospray ionization-mass spectrometry for the structural determination of oligosaccharides. , 2000, Analytical chemistry.

[119]  N. Karamanos,et al.  Microemulsion electrokinetic capillary chromatography of sulfated disaccharides derived from glycosaminoglycans , 2001, Electrophoresis.

[120]  A. Theocharis,et al.  Ultrasensitive capillary electrophoresis of sulfated disaccharides in chondroitin/dermatan sulfates by laser-induced fluorescence after derivatization with 2-aminoacridone. , 1999, Journal of chromatography. B, Biomedical sciences and applications.

[121]  J. Skehel,et al.  Analysis of N-linked oligosaccharides released from glycoproteins separated by two-dimensional gel electrophoresis. , 2000, Analytical biochemistry.

[122]  Y. Ohkura,et al.  Fluorometric high-performance liquid chromatography of N-acetyl- and N-glycolylneuraminic acids and its application to their microdetermination in human and animal sera, glycoproteins, and glycolipids. , 1987, Analytical biochemistry.

[123]  S. Carr,et al.  A coordinated high-performance liquid chromatographic, capillary electrophoretic, and mass spectrometric approach for the analysis of oligosaccharide mixtures derivatized with 2-aminoacridone. , 1996, Analytical chemistry.

[124]  A. Hjerpe,et al.  Determination of N-acetyl- and N-glycolylneuraminic acids in glycoconjugates by reversed-phase high-performance liquid chromatography with ultraviolet detection , 1990 .

[125]  A. Taga,et al.  Separation of aldose enantiomers by capillary electrophoresis in the presence of optically active N-dodecoxycarbonylvalines , 1997 .

[126]  A. Helenius,et al.  Intracellular functions of N-linked glycans. , 2001, Science.

[127]  J. Nakamura,et al.  High-performance liquid chromatography of reducing carbohydrates as strongly ultraviolet-absorbing and electrochemically sensitive 1-phenyl-3-methyl-5-pyrazolone derivatives. , 1989, Analytical biochemistry.

[128]  K. Sugahara,et al.  The unusual tetrasaccharide sequence GlcAβ-3GalNAc(4-sulfate)(β1–4GlcA(2-sulfate)β1–3GalNAc(6-sulfate) found in the hexasaccharides prepared by testicular hyaluronidase digestion of shark cartilage chondroitin sulfate D , 1997 .

[129]  K R Anumula,et al.  High-sensitivity and high-resolution methods for glycoprotein analysis. , 2000, Analytical biochemistry.

[130]  K. Mopper,et al.  Reversed-phase liquid chromatographic analysis of dns-sugars : Optimization of derivatization and chromatographic procedures and applications to natural samples , 1983 .

[131]  Fu-Tai A. Chen,et al.  Profiling glycoprotein N‐linked oligosaccharide by capillary electrophoresis , 1998, Electrophoresis.

[132]  R. Kuhn,et al.  Quantitative analysis of malto-oligosaccharides by MALDI-TOF mass spectrometry, capillary electrophoresis and anion exchange chromatography , 1998 .

[133]  K. Sato,et al.  Optimization of derivatization with 2-aminobenzoic acid for determination of monosaccharide composition by capillary electrophoresis. , 1998, Analytical biochemistry.

[134]  Yehia Mechref,et al.  Capillary electrophoresis of carboxylated carbohydrates. Part 2. Selective precolumn derivatization of sialooligosaccharides derived from gangliosides with 7‐aminonaphthalene‐1,3‐disulfonic acid fluorescing tag , 1995, Electrophoresis.

[135]  X Wang,et al.  Determination of carbohydrates as their p-sulfophenylhydrazones by capillary zone electrophoresis. , 2001, Carbohydrate research.

[136]  M. Okamoto A Comparative Study on Structural Elucidation of Sialyl Oligosaccharides by Mass Spectrometry with Fast Atom Bombardment, Electrospray Ionization, and Matrix Assisted Laser Desorption/Ionization , 2001, Bioscience, biotechnology, and biochemistry.

[137]  H. Kitagawa,et al.  Microanalysis of glycosaminoglycan-derived disaccharides labeled with the fluorophore 2-aminoacridone by capillary electrophoresis and high-performance liquid chromatography. , 1995, Analytical biochemistry.

[138]  M. Novotny,et al.  Ultrasensitive fluorometric detection of carbohydrates as derivatives in mixtures separated by capillary electrophoresis. , 1991, Proceedings of the National Academy of Sciences of the United States of America.

[139]  C. Horváth,et al.  Capillary zone electrophoresis of malto-oligosaccharides derivatized with 8-aminonaphthalene-1,3,6-trisulfonic acid. , 1993, Journal of chromatography.

[140]  Y. Mechref,et al.  Capillary electrophoresis of carboxylated carbohydrates. III. Selective precolumn derivatization of glycosaminoglycan disaccharides with 7-aminonaphthalene-1,3-disulfonic acid fluorescing tag for ultrasensitive laser-induced fluorescence detection. , 1997, Analytical biochemistry.

[141]  S. Honda,et al.  Comparison of the sensitivities of various derivatives of oligosaccharides in LC/MS with fast atom bombardment and electrospray ionization interfaces. , 1996, Analytical chemistry.

[142]  K. Kakehi,et al.  3-Aminobenzamide and 3-aminobenzoic acid, tags for capillary electrophoresis of complex carbohydrates with laser-induced fluorescent detection. , 1999, Journal of chromatography. A.

[143]  S. Honda Postcolumn derivatization for chromatographic analysis of carbohydrates , 1996 .

[144]  A. Taga,et al.  Capillary electrophoretic determination of the association constant of a protein and a neutral carbohydrate by introducing mercaptoethanesulfonate tags to the carbohydrate , 1999 .

[145]  A. Mort,et al.  Use of scavenger beads to remove excess labeling reagents from capillary zone electrophoresis samples , 1998, Electrophoresis.

[146]  Y. Lee,et al.  Precolumn labeling of reducing carbohydrates with 1-(p-methoxy)phenyl-3-methyl-5-pyrazolone: analysis of neutral and sialic acid-containing oligosaccharides found in glycoproteins. , 1991, Analytical biochemistry.

[147]  R. Zeng,et al.  Analysis of 8-aminonaphthalene-1,3,6-trisulfonate-derivatized oligosaccharides by capillary electrophoresis-electrospray ionization quadrupole ion trap mass spectrometry. , 1999, Journal of chromatography. A.

[148]  A. Guttman,et al.  Capillary and slab gel electrophoresis profiling of oligosaccharides , 1995, Electrophoresis.

[149]  L A Colón,et al.  Determination of Glucose in Submicroliter Samples by CE-LIF Using Precolumn or On-Column Enzymatic Reactions. , 1997, Analytical chemistry.

[150]  W. Nashabeh,et al.  Capillary zone electrophoresis of linear and branched oligosaccharides. , 1992, Journal of chromatography.

[151]  C. Prakash,et al.  A new fluorescent tag for labeling of saccharides. , 1983, Analytical biochemistry.

[152]  M. Novotny,et al.  Resolution of the branched forms of oligosaccharides by high-performance capillary electrophoresis. , 1994, Carbohydrate research.

[153]  N. Dovichi,et al.  Metabolic cytometry: monitoring oligosaccharide biosynthesis in single cells by capillary electrophoresis. , 2000, Analytical biochemistry.

[154]  J. Strickler,et al.  Structural characterization of oligosaccharides in recombinant soluble human interferon receptor 2 using fluorophore‐assisted carbohydrate electrophoresis , 2000, Electrophoresis.

[155]  Y. Hsieh,et al.  Analysis of chitin oligosaccharides by capillary electrophoresis with laser-induced fluorescence. , 2002, Journal of chromatography. A.

[156]  M. Novotny,et al.  Capillary zone electrophoresis of oligosaccharides derivatized with N-(4-aminobenzoyl)-L-glutamic acid for ultraviolet absorbance detection. , 1997, Journal of chromatography. A.

[157]  C. Sato,et al.  Fluorescent-assisted detection of oligosialyl units in glycoconjugates. , 1999, Analytical biochemistry.

[158]  T. Goins,et al.  Relative Abundance of Oligosaccharides in CandidaSpecies as Determined by Fluorophore-Assisted Carbohydrate Electrophoresis , 2000, Journal of Clinical Microbiology.

[159]  H. Kitagawa,et al.  Recent advances in the study of the biosynthesis and functions of sulfated glycosaminoglycans. , 2000, Current opinion in structural biology.

[160]  S. Inoue,et al.  A challenge to the ultrasensitive chemical method for the analysis of oligo- and polysialic acids at a nanogram level of colominic acid and a milligram level of brain tissues. , 2001, Biochimie.

[161]  C. Noe,et al.  Determination of reducing sugars in selected beverages by capillary electrophoresis , 1999 .

[162]  N. Karamanos,et al.  A capillary zone electrophoresis method for determining N-acetylneuraminic acid in glycoproteins and blood sera. , 2002, Biomedical chromatography : BMC.

[163]  P. Meikle,et al.  Determination of oligosaccharides in Pompe disease by electrospray ionization tandem mass spectrometry. , 2002, Clinical chemistry.

[164]  Fu-Tai A. Chen,et al.  Separation of 1‐aminopyrene‐3,6,8‐trisulfonate‐labeled asparagine‐linked fetuin glycans by capillary gel electrophoresis , 1996, Electrophoresis.

[165]  T. Kindt,et al.  The structure of the Aerobacter aerogenes A3(S1) polysaccharide. II. Sequence analysis and hydrolysis studies. , 1966, Biochemistry.

[166]  M. Stefansson Assessment of alginic acid molecular weight and chemical composition through capillary electrophoresis. , 1999, Analytical Chemistry.

[167]  R. Contreras,et al.  Ultrasensitive profiling and sequencing of N-linked oligosaccharides using standard DNA-sequencing equipment. , 2001, Glycobiology.

[168]  A. Paulus,et al.  Capillary electrophoresis of ANTS labelled oligosaccharide ladders and complex carbohydrates , 1994 .

[169]  D T Li,et al.  Structural analysis of Chromophore-Labeled , 2000, Journal of the American Society for Mass Spectrometry.

[170]  F. Goubet,et al.  Polysaccharide analysis using carbohydrate gel electrophoresis: a method to study plant cell wall polysaccharides and polysaccharide hydrolases. , 2002, Analytical biochemistry.

[171]  Y. Mechref,et al.  Capillary electrophoresis of carboxylated carbohydrates. I. Selective precolumn derivatization of gangliosides with UV absorbing and fluorescent tags. , 1995, Journal of chromatography. A.

[172]  T. Tsegenidis,et al.  Analysis of neutral sugars as dinitrophenyl-hydrazones by high-performance liquid chromatography , 1987 .

[173]  T. Pritchett,et al.  Capillary gel electrophoresis separation of high‐mannose type oligosaccharides derivatized by 1‐aminopyrene‐3,6,8‐trisulfonic acid , 1995, Electrophoresis.

[174]  R. Montesino,et al.  Two-dimensional mapping of 8-amine-1,3,6-naphthalene trisulfonic acid derivatives of N-linked neutral and sialyloligosaccharides. , 1998, Analytical biochemistry.

[175]  P. Jackson,et al.  The use of polyacrylamide gel electrophoresis for the analysis of acidic glycans labeled with the fluorophore 2‐aminoacridone , 1994, Electrophoresis.