Introduction

Ajit Varki1, Hudson H. Freeze2, Adriana E. Manzi1

1 University of California San Diego, La Jolla, California, 2 Sanford Children's Health Research Center and Burnham Institute for Medical Research, La Jolla, California
Publication Name:  Current Protocols in Molecular Biology
Unit Number:  null
DOI:  10.1002/0471142727.mb1700s88
Online Posting Date:  October, 2009
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Abstract

Whereas DNA, RNA, and proteins are linear polymers that can usually be directly sequenced, glycans show substantially more complexity, having branching and anomeric configurations (α and β linkages). The biosynthesis of glycans, termed glycosylation, is extremely complex, is not template‐driven, varies among different cell types, and cannot be easily predicted from simple rules. This overview discusses the stereochemistry of mono‐ and oligosaccharides and provides diagrammatic representations of monosaccharides (Fisher projections and Haworth representations) and formulas for representation of glycan chains. A glossary of terms used in glycobiology is also provided. Curr. Protoc. Mol. Biol. 88:17.0.1‐17.0.12. © 2009 by John Wiley & Sons, Inc.

Keywords: glycan; monosaccharide; glycan analysis; sugar symbols; glycoconjugate; glycobiology

     
 
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Table of Contents

  • Introduction
  • Choice of Techniques
  • Stereochemistry and Diagrammatic Representation of Monosaccharides and Oligosaccharides
  • Glossary
  • Literature Cited
  • Figures
  • Tables
     
 
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Materials

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Figures

Videos

Literature Cited

   Allen, H.J. and Kisalius, E.C. (eds.). 1992. Glycoconjugates: Composition, Structure, and Function. Marcel Dekker, New York.
   Varki, A., Cummings, R.D., Esko, J.D., Freeze, H.H., Stanley, P., Bertozzi, C.R., Hart, G.W., and Etzler, M.E. (eds.) 2009. Essentials of Glycobiology. Cold Spring Harbor Laboratory, Cold Spring Harbor, N.Y.
Key References
   Allen and Kisailus (eds.), 1992. See above.
   Bertozzi, C. and Rabuka, D. 2009. Structural basis of glycan diversity. In Essentials of Glycobiology (A. Varki, R.D. Cummings, J.D. Esko, H.H. Freeze, P. Stanley, C.R. Bertozzi, G.W. Hart, and M.E. Etzler, eds.), pp. 601‐616. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
   Bill, M.R., Revers, L., and Wilson, I.B.H. 1998. Protein Glycosylation. Kluwer Academic Publishers, Boston.
   Boons, G‐J. (ed.) 1998. Carbohydrate Chemistry. Blackie Academic & Professional, London.
   Chaplin, M.F. and Kennedy, J.F. (eds.) 1987. Carbohydrate Analysis: A Practical Approach. IRL Press, Oxford.
   Fleischer, S. and Fleischer, B. 1983. Biomembranes, part L. Methods Enzymol. 98:1‐688.
   Ginsburg, V. (ed.). 1972. Complex Carbohydrates, Part B. Methods Enzymol. Vol. 28.
   Ginsburg, V. (ed.). 1978. Complex Carbohydrates, Part C. Methods Enzymol. Vol. 50.
   Ginsburg, V. (ed.). 1982. Complex Carbohydrates, Part D. Methods Enzymol. Vol. 83.
   Ginsburg, V. (ed.). 1987. Complex Carbohydrates, Part E. Methods Enzymol. Vol. 138.
   Ginsburg, V. (ed.). 1989. Complex Carbohydrates, Part F. Methods Enzymol. Vol. 179.
   Hart, G. and Lennarz, W. 1993. Guide to techniques in glycobiology. Methods Enzymol. 230.
   Haslam, S.M., North, S.J., and Dell, A. 2006. Mass spectrometric analysis of N‐ and O‐glycosylation of tissues and cells. Curr. Opin. Struct. Biol. 16:584‐591.
   Kamerling, J., Boons, G‐J., Lee, Y., Suzuki, A., Taniguchi, N., and Voragen, A.G.J. 2007. Comprehensive glycoscience. 1‐4. Elsevier Science, London.
   Manzi, A.E. and van Halbeek, H. 1999. Glycan structure and nomenclature. In Essentials of Glycobiology. (A. Varki, R.D. Cummings, J.D. Esko, H.H. Freeze, P. Stanley, C.R. Bertozzi, G.W. Hart, and M.E. Etzler, eds.) pp. 17‐29. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
   Manzi, A.E. and van Halbeek, H. 1999. General principles for the analysis and sequencing of glycans. In Essentials of Glycobiology. (A. Varki, R.D. Cummings, J.D. Esko, H.H. Freeze, P. Stanley, C.R. Bertozzi, G.W. Hart, and M.E. Etzler, eds.) pp. 581‐598. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
   McNaught, A.D. 1997. Nomenclature of carbohydrates. Carbohydr. Res. 297:1‐92.
   McCloskey, J.A. (ed.). 1990. Mass Spectrometry. Methods Enzymol. 193.
   Stick, R.V. 2001. Carbohydrates: The sweet molecules of life. Academic Press, New York.
   Varki, A. 1991. Radioactive tracer techniques in the sequencing of glycoprotein oligosaccharides. FASEB J. 5:226‐235.
   Vliegenthart, J.F.G., Dorland, L., and van Halbeek, H. 1983. NMR spectroscopy of carbohydrates. Adv. Carbohydr. Chem. Biochem. 41:209‐378.
   Whistler, R. and Wolfram, F. (eds.). 1968‐1980. Methods in Carbohydrate Chemistry, Vols I‐VIII. Academic Press, San Diego.
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