Concept, strategy and realization of lectin-based glycan profiling.

Lectins are a diverse group of carbohydrate-binding proteins. Each lectin has its own specificity profile. It is believed that lectins exist in all living organisms that produce glycans. From a practical viewpoint, lectins have been used extensively in biochemical fields including proteomics due to their usefulness as detection and enrichment tools for specific glycans. Nevertheless, they have often been underestimated as probes, especially compared with antibodies, because of their low affinity and broad specificity. However, together with the concept of glycomics, such properties of lectins are now considered to be suitable for the task of 'profiling' in order to cover a wider range of ligands. Recently there has been rapid movement in the field of proteomics aimed at the investigation of glycan-related biomarkers. This is partly because of limitations of the present approach of simply following changes in protein-level expression, without paying sufficient attention to the fact and effects of glycosylation. The trend is reflected in the frequent use of lectins in the contexts of glycoprotein enrichment and glycan profiling. However, there are many aspects to be considered in using lectins, which differ considerably from antibodies. In this article, the author, as a developer of two unique methodologies, frontal affinity chromatography (FAC) and the lectin microarray, describes critical points concerning the use of lectins, together with the concept, strategy and means to achieve advances in these emerging glycan profiling technologies.

[1]  C. Neusüss,et al.  Glycoprotein characterization combining intact protein and glycan analysis by capillary electrophoresis-electrospray ionization-mass spectrometry. , 2006, Analytical chemistry.

[2]  Xin Liu,et al.  Mass spectrometry-based glycomics strategy for exploring N-linked glycosylation in eukaryotes and bacteria. , 2006, Analytical chemistry.

[3]  S. Hase,et al.  Determination of lectin-sugar binding constants by microequilibrium dialysis coupled with high performance liquid chromatography. , 1991, Journal of biochemistry.

[4]  David C Schriemer,et al.  Micro-Scale Frontal Affinity Chromatography with Mass Spectrometric Detection: A New Method for the Screening of Compound Libraries. , 1998, Angewandte Chemie.

[5]  N. Sharon Lectins: Carbohydrate-specific Reagents and Biological Recognition Molecules , 2007, Journal of Biological Chemistry.

[6]  J. Hirabayashi,et al.  Sugar Binding Properties of the Two Lectin Domains of the Tandem Repeat-type Galectin LEC-1 (N32) of Caenorhabditis elegans , 2001, The Journal of Biological Chemistry.

[7]  L. Mahal Glycomics: towards bioinformatic approaches to understanding glycosylation. , 2008, Anti-cancer agents in medicinal chemistry.

[8]  J. Hirabayashi,et al.  Frontal affinity chromatography: sugar–protein interactions , 2007, Nature Protocols.

[9]  J. Hirabayashi,et al.  Application of reinforced frontal affinity chromatography and advanced processing procedure to the study of the binding property of a Caenorhabditis elegans galectin. , 2001, Journal of chromatography. A.

[10]  N. Uchiyama,et al.  Analysis of the sugar‐binding specificity of mannose‐binding‐type Jacalin‐related lectins by frontal affinity chromatography – an approach to functional classification , 2008, The FEBS journal.

[11]  S. Fort,et al.  Screening for galectin-3 inhibitors from synthetic lacto-N-biose libraries using microscale affinity chromatography coupled to mass spectrometry. , 2006, The Journal of organic chemistry.

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

[13]  H. Nakagawa,et al.  Three-dimensional elution mapping of pyridylaminated N-linked neutral and sialyl oligosaccharides. , 1995, Analytical biochemistry.

[14]  J. Hirabayashi,et al.  Multistage mass spectrometric sequencing of keratan sulfate-related oligosaccharides. , 2006, Analytical chemistry.

[15]  J. Hirabayashi,et al.  Comparative analysis of carbohydrate‐binding properties of two tandem repeat‐type Jacalin‐related lectins, Castanea crenata agglutinin and Cycas revoluta leaf lectin , 2005, The FEBS journal.

[16]  M. Wilkins,et al.  Progress with gene‐product mapping of the Mollicutes: Mycoplasma genitalium , 1995, Electrophoresis.

[17]  Hailong Zhang,et al.  Congruent strategies for carbohydrate sequencing. 2. FragLib: an MSn spectral library. , 2005, Analytical chemistry.

[18]  R. Cummings,et al.  Fractionation of asparagine-linked oligosaccharides by serial lectin-Agarose affinity chromatography. A rapid, sensitive, and specific technique. , 1982, The Journal of biological chemistry.

[19]  A. Kuno,et al.  Evanescent-field fluorescence-assisted lectin microarray: a new strategy for glycan profiling , 2005, Nature Methods.

[20]  J. Hirabayashi,et al.  The Sclerotinia sclerotiorum agglutinin represents a novel family of fungal lectins remotely related to the Clostridium botulinum non-toxin haemagglutinin HA33/A , 2007, Glycoconjugate Journal.

[21]  R. Ishikawa,et al.  Analysis of glycoprotein-derived oligosaccharides in glycoproteins detected on two-dimensional gel by capillary electrophoresis using on-line concentration method. , 2006, Journal of chromatography. A.

[22]  J. Hirabayashi,et al.  Frontal affinity chromatography as a tool for elucidation of sugar recognition properties of lectins. , 2003, Methods in enzymology.

[23]  A. Kuno,et al.  Development of a lectin microarray based on an evanescent-field fluorescence principle. , 2006, Methods in enzymology.

[24]  Soichi Wakatsuki,et al.  Structural analysis of the human galectin-9 N-terminal carbohydrate recognition domain reveals unexpected properties that differ from the mouse orthologue. , 2008, Journal of molecular biology.

[25]  Naoyuki Taniguchi,et al.  Comparison of the methods for profiling glycoprotein glycans--HUPO Human Disease Glycomics/Proteome Initiative multi-institutional study. , 2007, Glycobiology.

[26]  T. Irimura,et al.  The amino acids involved in the distinct carbohydrate specificities between macrophage galactose-type C-type lectins 1 and 2 (CD301a and b) of mice. , 2008, Biochimica et biophysica acta.

[27]  A. Kobata A journey to the world of glycobiology , 2000, Glycoconjugate Journal.

[28]  Yehia Mechref,et al.  Comparative glycomic mapping through quantitative permethylation and stable-isotope labeling. , 2007, Analytical chemistry.

[29]  H. Nomoto,et al.  Frontal affinity chromatography of ovalbumin glycoasparagines on a concanavalin A-sepharose column. A quantitative study of the binding specificity of the lectin. , 1985, The Journal of biological chemistry.

[30]  Y. Mechref,et al.  Miniaturized separation techniques in glycomic investigations. , 2006, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[31]  T. Feizi Progress in deciphering the information content of the ‘glycome’ – a crescendo in the closing years of the millennium , 2000, Glycoconjugate Journal.

[32]  Simon J North,et al.  Mass spectrometric analysis of N- and O-glycosylation of tissues and cells. , 2006, Current opinion in structural biology.

[33]  N. Kasai,et al.  Autoradiography of ganglioside antigens separated by high-performance thin-layer chromatography with their antibodies. , 1984, Journal of biochemistry.

[34]  Catherine E Costello,et al.  Glycoform quantification of chondroitin/dermatan sulfate using a liquid chromatography-tandem mass spectrometry platform. , 2006, Biochemistry.

[35]  Y. Ikeda,et al.  A glycomic approach to the identification and characterization of glycoprotein function in cells transfected with glycosyltransferase genes , 2001, Proteomics.

[36]  Yassir A. Ahmed,et al.  Towards GAG glycomics: analysis of highly sulfated heparins by MALDI-TOF mass spectrometry. , 2007, Glycobiology.

[37]  E. Gahtan,et al.  Erratum to “Probing neural circuits in the zebrafish: a suite of optical techniques” [Methods 30 (2003) 49–63] , 2003 .

[38]  A. Kuno,et al.  Evidence that Agaricus bisporus agglutinin (ABA) has dual sugar-binding specificity. , 2006, Biochemical and biophysical research communications.

[39]  C. F. Brewer,et al.  Multivalent protein-carbohydrate interactions: isothermal titration microcalorimetry studies. , 2004, Methods in enzymology.

[40]  K. Kasai,et al.  Quantitative analysis of affinity chromatography of trypsin. A new technique for investigation of protein-ligand interaction. , 1975, Journal of biochemistry.

[41]  W. Dijk,et al.  Structural assessment of theN-linked oligosaccharides of cell-CAM 105 by lectin-agarose affinity chromatography , 2005, Glycoconjugate Journal.

[42]  J. Hirabayashi,et al.  Comparative analysis by frontal affinity chromatography of oligosaccharide specificity of GlcNAc-binding lectins, Griffonia simplicifolia lectin-II (GSL-II) and Boletopsis leucomelas lectin (BLL). , 2006, Journal of biochemistry.

[43]  Y Hasegawa,et al.  Kinetic measurement of the interaction between an oligosaccharide and lectins by a biosensor based on surface plasmon resonance. , 1994, European journal of biochemistry.

[44]  J. Hirabayashi Lectin-based structural glycomics: Glycoproteomics and glycan profiling , 2004, Glycoconjugate Journal.

[45]  J. Hirabayashi,et al.  Glycome project: Concept, strategy and preliminary application to Caenorhabditis elegans , 2001, Proteomics.

[46]  T. Irimura,et al.  Interaction of immobilized recombinant mouse C-type macrophage lectin with glycopeptides and oligosaccharides. , 1994, Biochemistry.

[47]  Toshihiko Oka,et al.  Oligosaccharide specificity of galectins: a search by frontal affinity chromatography. , 2002, Biochimica et biophysica acta.

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

[49]  A. Kuno,et al.  Optimization of evanescent‐field fluorescence‐assisted lectin microarray for high‐sensitivity detection of monovalent oligosaccharides and glycoproteins , 2008, Proteomics.

[50]  T. Ikenaka,et al.  Structure analyses of oligosaccharides by tagging of the reducing end sugars with a fluorescent compound. , 1978, Biochemical and biophysical research communications.

[51]  N. Uchiyama,et al.  High-throughput analysis of lectin-oligosaccharide interactions by automated frontal affinity chromatography. , 2006, Methods in enzymology.

[52]  R. Field,et al.  Emerging glycomics technologies. , 2007, Nature chemical biology.

[53]  K. Yamashita,et al.  Galectin-4 Binds to Sulfated Glycosphingolipids and Carcinoembryonic Antigen in Patches on the Cell Surface of Human Colon Adenocarcinoma Cells* , 2005, Journal of Biological Chemistry.

[54]  David F. Smith,et al.  Phylogenetic and specificity studies of two-domain GNA-related lectins: generation of multispecificity through domain duplication and divergent evolution. , 2007, The Biochemical journal.

[55]  R Apweiler,et al.  On the frequency of protein glycosylation, as deduced from analysis of the SWISS-PROT database. , 1999, Biochimica et biophysica acta.

[56]  Katsutoshi Takahashi,et al.  A strategy for identification of oligosaccharide structures using observational multistage mass spectral library. , 2005, Analytical chemistry.

[57]  Koichi Kato,et al.  Mechanistic elucidation of the formation of reduced 2-aminopyridine-derivatized oligosaccharides and their application in matrix-assisted laser desorption/ionization mass spectrometry. , 2005, Rapid communications in mass spectrometry : RCM.

[58]  J. Hirabayashi,et al.  Frontal Affinity Chromatography: Systematization for Quantitative Interaction Analysis Between Lectins and Glycans , 2007 .

[59]  J. Hirabayashi,et al.  Molecular characterization and oligosaccharide-binding properties of a galectin from the argasid tick Ornithodoros moubata. , 2007, Glycobiology.

[60]  N. Kochibe,et al.  Systematic fractionation of oligosaccharides of human immunoglobulin G by serial affinity chromatography on immobilized lectin columns. , 1987, Analytical biochemistry.

[61]  J. Hirabayashi,et al.  Reinforcement of frontal affinity chromatography for effective analysis of lectin-oligosaccharide interactions. , 2000, Journal of chromatography. A.

[62]  Peter H. Seeberger,et al.  Synthesis and medical applications of oligosaccharides , 2007, Nature.

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

[64]  J. Hirabayashi,et al.  Isolation and characterization of l-rhamnose-binding lectin, which binds to microsporidian Glugea plecoglossi, from ayu (Plecoglossus altivelis) eggs. , 2008, Developmental and comparative immunology.

[65]  Hisashi Narimatsu,et al.  Strategy for simulation of CID spectra of N-linked oligosaccharides toward glycomics. , 2006, Journal of proteome research.

[66]  U. Nilsson,et al.  Design and synthesis of galectin inhibitors. , 2003, Methods in enzymology.

[67]  J. Hirabayashi,et al.  Systematic comparison of oligosaccharide specificity of Ricinus communis agglutinin I and Erythrina lectins: a search by frontal affinity chromatography. , 2007, Journal of biochemistry.

[68]  D. Ashline,et al.  Congruent strategies for carbohydrate sequencing. 3. OSCAR: an algorithm for assigning oligosaccharide topology from MSn data. , 2005, Analytical chemistry.

[69]  Carolyn R. Bertozzi,et al.  Essentials of Glycobiology , 1999 .

[70]  Noritada Kaji,et al.  Rapid analysis of oligosaccharides derived from glycoproteins by microchip electrophoresis. , 2006, Journal of chromatography. A.

[71]  Kiyoko F. Aoki-Kinoshita,et al.  Frontiers in glycomics: Bioinformatics and biomarkers in disease An NIH White Paper prepared from discussions by the focus groups at a workshop on the NIH campus, Bethesda MD (September 11–13, 2006) , 2008, Proteomics.