Orthogonal Technologies for NISTmAb N-Glycan Structure Elucidation and Quantitation

[1]  R. Dwek,et al.  Variations in oligosaccharide-protein interactions in immunoglobulin G determine the site-specific glycosylation profiles and modulate the dynamic motion of the Fc oligosaccharides. , 1997, Biochemistry.

[2]  Akira Okazaki,et al.  Comparison of biological activity among nonfucosylated therapeutic IgG1 antibodies with three different N-linked Fc oligosaccharides: the high-mannose, hybrid, and complex types. , 2007, Glycobiology.

[3]  C. Lebrilla,et al.  Evidence for long-range glycosyl transfer reactions in the gas phase , 2002, Journal of the American Society for Mass Spectrometry.

[4]  S L Morrison,et al.  Effect of C2-associated carbohydrate structure on Ig effector function: studies with chimeric mouse-human IgG1 antibodies in glycosylation mutants of Chinese hamster ovary cells. , 1998, Journal of immunology.

[5]  Alain Balland,et al.  Asparagine-linked Oligosaccharides Present on a Non-consensus Amino Acid Sequence in the CH1 Domain of Human Antibodies , 2009, The Journal of Biological Chemistry.

[6]  John E. Schiel,et al.  Universal proteolysis and MS(n) for N- and O-glycan branching analysis. , 2013, Journal of mass spectrometry : JMS.

[7]  John E. Schiel,et al.  LC-MS/MS biopharmaceutical glycoanalysis: identification of desirable reference material characteristics , 2012, Analytical and Bioanalytical Chemistry.

[8]  D. Harvey.  Halogeno-substituted 2-aminobenzoic acid derivatives for negative ion fragmentation studies of N-linked carbohydrates. , 2005, Rapid communications in mass spectrometry : RCM.

[9]  O. Salas-Solano,et al.  Investigation of sample preparation artifacts formed during the enzymatic release of N-linked glycans prior to analysis by capillary electrophoresis. , 2009, Analytical chemistry.

[10]  J. Thomas-Oates,et al.  Sodium-cationized oligosaccharides do not appear to undergo 'internal residue loss' rearrangement processes on tandem mass spectrometry. , 1998, Rapid communications in mass spectrometry : RCM.

[11]  D. Harvey.  Collision-induced fragmentation of negative ions from N-linked glycans derivatized with 2-aminobenzoic acid. , 2005, Journal of mass spectrometry : JMS.

[12]  Thomas K. Villiger,et al.  Evaluating the impact of cell culture process parameters on monoclonal antibody N-glycosylation. , 2014, Journal of biotechnology.

[13]  M Ohlin,et al.  Does endogenous glycosylation prevent the use of mouse monoclonal antibodies as cancer therapeutics? , 1993, Immunology today.

[14]  Yehia Mechref,et al.  Structural characterization of oligosaccharides using MALDI-TOF/TOF tandem mass spectrometry. , 2003, Analytical chemistry.

[15]  Gregory C Flynn,et al.  Analysis of N-glycans from recombinant immunoglobulin G by on-line reversed-phase high-performance liquid chromatography/mass spectrometry. , 2007, Analytical biochemistry.

[16]  Louise Royle,et al.  Proposal for a standard system for drawing structural diagrams of N‐ and O‐linked carbohydrates and related compounds , 2009, Proteomics.

[17]  R. Dwek,et al.  A rapid high-resolution high-performance liquid chromatographic method for separating glycan mixtures and analyzing oligosaccharide profiles. , 1996, Analytical biochemistry.

[18]  Y. Mechref,et al.  Electrophoretic analysis of N-glycans on microfluidic devices. , 2007, Analytical chemistry.

[19]  D. Harvey,et al.  Electrospray ionization-ion trap mass spectrometry for structural analysis of complex N-linked glycoprotein oligosaccharides. , 1998, Analytical chemistry.

[20]  Hailong Zhang,et al.  Toward a Platform for Comprehensive Glycan Sequencing* , 2013, Molecular & Cellular Proteomics.

[21]  Michael Pierce,et al.  Tools for glycomics: relative quantitation of glycans by isotopic permethylation using 13CH3I. , 2007, Glycobiology.

[22]  K. Anumula,et al.  Advances in fluorescence derivatization methods for high-performance liquid chromatographic analysis of glycoprotein carbohydrates. , 2006, Analytical biochemistry.

[23]  R. Jefferis,et al.  IgG‐Fc‐mediated effector functions: molecular definition of interaction sites for effector ligands and the role of glycosylation , 1998, Immunological reviews.

[24]  John E. Schiel.  Glycoprotein analysis using mass spectrometry: unraveling the layers of complexity , 2012, Analytical and Bioanalytical Chemistry.

[25]  D. Ashline,et al.  Carbohydrate structural isomers analyzed by sequential mass spectrometry. , 2007, Analytical chemistry.

[26]  Alain Van Dorsselaer,et al.  Characterization of therapeutic antibodies and related products. , 2013, Analytical chemistry.

[27]  Bradley D Prater,et al.  Automated sample preparation facilitated by PhyNexus MEA purification system for oligosaccharide mapping of glycoproteins. , 2007, Analytical biochemistry.

[28]  R. Linhardt,et al.  C-2 Epimerization of N-Acetylglucosamine in an Oligosaccharide Derived From Heparan Sulfate , 1996 .

[29]  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.

[30]  Pauline M. Rudd,et al.  GlycoBase and autoGU: tools for HPLC-based glycan analysis , 2008, Bioinform..

[31]  L. Taylor,et al.  Characterization of monoclonal antibody glycosylation: comparison of expression systems and identification of terminal alpha-linked galactose. , 1997, Analytical biochemistry.

[32]  Yannis-Nicolas François,et al.  Full antibody primary structure and microvariant characterization in a single injection using transient isotachophoresis and sheathless capillary electrophoresis-tandem mass spectrometry. , 2014, Analytical chemistry.

[33]  B. Domon,et al.  Structural assignment of permethylated oligosaccharide subunits using sequential tandem mass spectrometry. , 1998, Analytical chemistry.

[34]  Wolfgang Lindner,et al.  Comparison of hydrophilic-interaction, reversed-phase and porous graphitic carbon chromatography for glycan analysis. , 2011, Journal of chromatography. A.

[35]  James E. Bailey,et al.  Engineered glycoforms of an antineuroblastoma IgG1 with optimized antibody-dependent cellular cytotoxic activity , 1999, Nature Biotechnology.

[36]  Yehia Mechref,et al.  High-throughput solid-phase permethylation of glycans prior to mass spectrometry. , 2008, Rapid communications in mass spectrometry : RCM.

[37]  Alexander Makarov,et al.  Dynamic range of mass accuracy in LTQ orbitrap hybrid mass spectrometer , 2006, Journal of the American Society for Mass Spectrometry.

[38]  A. Tarentino,et al.  Peptide-N4-(N-acetyl-beta-glucosaminyl) asparagine amidase and endo-beta-N-acetylglucosaminidase from Flavobacterium meningosepticum. , 1987, Methods in enzymology.

[39]  F. Maley,et al.  Characterization of glycoproteins and their associated oligosaccharides through the use of endoglycosidases. , 1989, Analytical biochemistry.

[40]  Ying Qing Yu,et al.  N- and O-glycosylation analysis of etanercept using liquid chromatography and quadrupole time-of-flight mass spectrometry equipped with electron-transfer dissociation functionality. , 2014, Analytical chemistry.

[41]  Quynh-Thu Le,et al.  Cetuximab-induced anaphylaxis and IgE specific for galactose-alpha-1,3-galactose. , 2008, The New England journal of medicine.

[42]  R. Dwek,et al.  Glycosylation changes of IgG associated with rheumatooid arthritis can activate complement via the mannose-binding protein , 1995, Nature Medicine.

[43]  Pauline M Rudd,et al.  Multiplexed analytical glycomics: rapid and confident IgG N-glycan structural elucidation. , 2011, Journal of proteome research.

[44]  K. Shitara,et al.  The Absence of Fucose but Not the Presence of Galactose or Bisecting N-Acetylglucosamine of Human IgG1 Complex-type Oligosaccharides Shows the Critical Role of Enhancing Antibody-dependent Cellular Cytotoxicity* , 2003, The Journal of Biological Chemistry.

[45]  P. Rudd,et al.  Separation of 2-aminobenzamide labeled glycans using hydrophilic interaction chromatography columns packed with 1.7 microm sorbent. , 2010, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

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

[47]  David J. Harvey,et al.  HPLC-based analysis of serum N-glycans on a 96-well plate platform with dedicated database software. , 2008, Analytical biochemistry.

[48]  D. Harvey,et al.  Characterization of oligosaccharide composition and structure by quadrupole ion trap mass spectrometry. , 1997, Rapid communications in mass spectrometry : RCM.

[49]  V. Reinhold,et al.  Detailed characterization of carbohydrate linkage and sequence in an ion trap mass spectrometer: glycosphingolipids. , 1998, Analytical biochemistry.

[50]  F. Sörgel,et al.  Reversed-phase liquid-chromatographic mass spectrometric N-glycan analysis of biopharmaceuticals , 2013, Analytical and Bioanalytical Chemistry.

[51]  A. Varki,et al.  Production platforms for biotherapeutic glycoproteins. Occurrence, impact, and challenges of non-human sialylation , 2012, Biotechnology & genetic engineering reviews.

[52]  John R. Engen,et al.  Analytical tools for characterizing biopharmaceuticals and the implications for biosimilars , 2012, Nature Reviews Drug Discovery.

[53]  R. B. Trimble,et al.  Identification of distinct endoglycosidase (endo) activities in Flavobacterium meningosepticum: endo F1, endo F2, and endo F3. Endo F1 and endo H hydrolyze only high mannose and hybrid glycans. , 1991, The Journal of biological chemistry.

[54]  Alain Balland,et al.  Glutamine-linked and Non-consensus Asparagine-linked Oligosaccharides Present in Human Recombinant Antibodies Define Novel Protein Glycosylation Motifs , 2010, The Journal of Biological Chemistry.

[55]  A. van Dorsselaer,et al.  Fragmentation characteristics of permethylated oligosaccharides using a matrix-assisted laser desorption/ionization two-stage time-of-flight (TOF/TOF) tandem mass spectrometer. , 2004, Rapid communications in mass spectrometry : RCM.

[56]  Qiang Qin,et al.  High-throughput immunoglobulin G N-glycan characterization using rapid resolution reverse-phase chromatography tandem mass spectrometry. , 2009, Analytical biochemistry.

[57]  L. R. Ruhaak,et al.  Glycan labeling strategies and their use in identification and quantification , 2010, Analytical and bioanalytical chemistry.

[58]  R. Dwek,et al.  Function and glycosylation of plant-derived antiviral monoclonal antibody , 2003, Proceedings of the National Academy of Sciences of the United States of America.

[59]  Y. Mechref,et al.  Microscale nonreductive release of O-linked glycans for subsequent analysis through MALDI mass spectrometry and capillary electrophoresis. , 2001, Analytical chemistry.

[60]  T. Seyfried,et al.  Differentiating N-linked glycan structural isomers in metastatic and nonmetastatic tumor cells using sequential mass spectrometry. , 2008, Glycobiology.

[61]  B. Reinhold,et al.  Carbohydrate molecular weight profiling, sequence, linkage, and branching data: ES-MS and CID. , 1995, Analytical Chemistry.

[62]  Y. C. Lee.  High-performance anion-exchange chromatography for carbohydrate analysis. , 1990, Analytical biochemistry.

[63]  R. Dwek,et al.  Structural and quantitative analysis of N-linked glycans by matrix-assisted laser desorption ionization and negative ion nanospray mass spectrometry. , 2008, Analytical biochemistry.

[64]  J. Cipollo,et al.  A glycomics platform for the analysis of permethylated oligosaccharide alditols , 2007, Journal of the American Society for Mass Spectrometry.

[65]  Justin M. Prien,et al.  The high mannose glycans from bovine ribonuclease B isomer characterization by ion trap MS , 2009, Journal of the American Society for Mass Spectrometry.

[66]  B. Domon,et al.  Structural analysis of permethylated oligosaccharides by electrospray tandem mass spectrometry. , 1997, Analytical chemistry.

[67]  V. Nizet,et al.  EndoS2 is a unique and conserved enzyme of serotype M49 group A Streptococcus that hydrolyses N-linked glycans on IgG and α1-acid glycoprotein , 2013, The Biochemical journal.

[68]  N. Karamanos,et al.  Derivatization of carbohydrates for chromatographic, electrophoretic and mass spectrometric structure analysis. , 2003, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[69]  D. Ashline,et al.  Congruent strategies for carbohydrate sequencing. 1. Mining structural details by MSn. , 2005, Analytical chemistry.

[70]  K. Anumula.  Single tag for total carbohydrate analysis. , 2014, Analytical biochemistry.

[71]  P. Bondarenko,et al.  High-mannose glycans on the Fc region of therapeutic IgG antibodies increase serum clearance in humans. , 2011, Glycobiology.

[72]  D. Suckau,et al.  Correct primary structure assessment and extensive glyco-profiling of cetuximab by a combination of intact, middle-up, middle-down and bottom-up ESI and MALDI mass spectrometry techniques , 2013, mAbs.

[73]  Pauline M Rudd,et al.  Automated, high-throughput IgG-antibody glycoprofiling platform. , 2013, Analytical chemistry.

[74]  Wolfgang Lindner,et al.  HILIC analysis of fluorescence-labeled N-glycans from recombinant biopharmaceuticals , 2010, Analytical and bioanalytical chemistry.

[75]  Pauline M Rudd,et al.  A systematic approach to protein glycosylation analysis: a path through the maze. , 2010, Nature chemical biology.

[76]  Qiang Qin,et al.  Mass spectrometric-based stable isotopic 2-aminobenzoic acid glycan mapping for rapid glycan screening of biotherapeutics. , 2010, Analytical chemistry.

[77]  Justin M. Prien,et al.  A multi-method approach toward de novo glycan characterization: a Man-5 case study. , 2010, Glycobiology.

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

[79]  Richard D Cummings,et al.  Symbol nomenclature for glycan representation , 2009, Proteomics.