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Glycobiology resources

Glycobiology resources. “Thorough, detailed, comprehensive”. “Concise, clear introduction”. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY. FREE – http :// www.ncbi.nlm.nih.gov/books/NBK1908 & coming soon: https://www.ncbi.nlm.nih.gov/books/NBK310274.

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Glycobiology resources

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  1. Glycobiology resources “Thorough, detailed, comprehensive” “Concise, clear introduction” Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY. FREE – http://www.ncbi.nlm.nih.gov/books/NBK1908 & coming soon: https://www.ncbi.nlm.nih.gov/books/NBK310274 Oxford University Press, New York Schnaar RL “Glycobiology Simplified” J Leuk Biol 99:825

  2. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  3. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  4. The mammalian cell surface ? The “glycocalyx” revealed (glycans stained with ruthinium red) extracellular extracellular https://en.wikipedia.org//wiki/Plasma_membrane lipid bilayer lipid bilayer intracellular fibroblast fibroblast intracellular Krijnse Locker J. & Schmid S.L. PLoS Biol 11, e1001639, 2013 Martinez-Palomo, A., et al. Cancer Res. 29, 925-937, 1969 “Every eukaryotic cell is covered with a dense and complex array of glycans.” … in fact… “Evolution has failed to generate a [single] living cell devoid of surface glycosylation”- A. Varki

  5. A MAJOR cell component invisible to standard phase microscopy Light (phase) micrograph of Cryptococcus neoformans Steenbergen et al. (2003) Microbes and Infection 5:667 Light (phase) micrograph of Cryptococcus neoformans capsule delineated by India ink. The inner circle represents the fungal cell, with the wide outer circle being the capsule. Steenbergen et al. (2003) Microbes and Infection 5:667 Scanning electron micrograph of C. neoformans yeast cells. Van Duin et al. (2004) Antimicrobial Agents and Chemotherapy 48:2014

  6. Evolution has failed to generate a living cell devoid of surface glycosylation Electron microscopic thin section ofEscherichia coli K1 Amako et al. (1988) J Bacteriol 170:4960 Electron microscopic thin section ofKlebsiella pneumoniae Amako et al. (1988) J Bacteriol 170:4960

  7. Tropical Forest Canopy Cohen & Varki (2010) OMICS 4:455 Ajit Varki, “Perspectives on the Future of Glycobiology,” Athens, GA, 14-Mar-2011

  8. The Cell Surface Textbook image Real image fibroblast Martinez-Palomo, A., et al. Cancer Res. 29, 925-937, 1969

  9. Glycobiology = Language (semiotics) Cohen & Varki (2010) OMICS 4:455 Rosetta Stone, British Museum

  10. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  11. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  12. Carbohydrates – the building blocks of Glycobiology (CH2O)n = “carbo” “hydrate” Generalized Aldose Generalized Ketose

  13. D-fructose D-glucose

  14. Sugar diversity – structurally and functionally – is all about STEREOCHEMISTRY Enantiomers: mirror images of each other that are not superimposable. In sugar nomenclature, enantiomers get a letter “D” or “L” Diastereomers: stereoisomers that are not enantiomers. In sugar nomenclature, diastereomers get different names

  15. Enantiomers Mirror images of each other that are not superimposable. In sugar nomenclature, enantiomers get a letter “D” or “L” * * D-glyceraldehyde L-glyceraldehyde * Highest numbered asymmetric carbon = reference carbon

  16. Fischer projection D-glyceraldehyde

  17. Diasteriomers Stereoisomers that are not enantiomers. In sugar nomenclature, diastereomers get different names * * * Highest numbered asymmetric carbon = reference carbon

  18. Enantiomers & Diasteriomers * * * * * Highest numbered asymmetric carbon = reference carbon

  19. * * * * * * Second Edition * epimers: differ in one stereogenic center Essentials of Glycobiology

  20. Monosaccharides are predominantly in RING FORM at equilibrium. • Free sugars equilibrate between open chain and ring forms. • Two ring forms (anomeric configurations) are possible, α and β Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

  21. Determining anomeric configuration Step 1: D or L? Highest numbered asymeric carbon Lee & Lee (1999) J Chinese Chem Soc 46:283-291

  22. Monosaccharide conformation – Chair configurations Taylor & Drickamer (2006) Introduction to Glycobiology, 2nd edition

  23. Just nine monosaccharides are responsible for building nearly all mammalian glycans. • glucose, galactose, mannose • N-acetylglucosamine, N-acetylgalactosamine • xylose • glucuronic acid • fucose • sialic acid • All are six-membered rings (5 carbons, 1 oxygen) varying in the substituents at each carbon (mostly hydroxyls). • Seven are closely structurally related to glucose.

  24. Seven eukaryotic sugars and their relationship to glucose Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

  25. Two important terminal eukaryotic sugars Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

  26. Glycan properties for molecular recognition and binding energy Galactose Glucose Mannose Sialic Acid

  27. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  28. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  29. Glycosidic bonds link sugars together (lactose) When a glycosidic bond is formed the anomeric configuration is “locked” Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

  30. Nomenclature: -Name the non-reducing (left-most) sugar (Gal) -Name the anomeric configuration (β) -Name the anomeric carbon number (1) -Name the substituted carbon number (4) -Name the substituted sugar (Glc) RESULT: Gal β1-4 Glc Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

  31. Nomenclature: Branches are placed in parentheses NeuAc α2-3 Gal β1-4 (Fuc α1-3) GlcNAc

  32. Varki et al. (2009) Proteomics. 9:5398

  33. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  34. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  35. Sugars, polysaccharides, oligosaccharides and glycans • Sugars: often from plants or breakdown products of plant polysaccharides. • Examples: glucose, sucrose (glucose α1-2 fructose), maltose (Glc α1-4 Glc), lactose (Gal β1-4 Glc). • Polysaccharides: long polymers (linear or branched) of a single monosaccharide • Examples: Cellulose, amylose (starch), glycogen, chitin • Oligosaccharides: groups of monosaccharides (typically 3 or more) in linear or branched glycosidic linkage • Seldom found as free structures – components of glycans • Glycans: Oligosaccharides on proteins or lipids • Examples: Glycoproteins, glycolipids

  36. Examples of polysaccharides: Cellulose Most abundant organic compound on Earth. ~90% of cotton fiber, 50% of wood, 33% of all plant matter. (β1-4 Glc β1-4 Glc)n Intra- and inter-strand hydrogen bonding provides strength Material sciences http://en.wikipedia.org/wiki/Cellulose

  37. Examples of polysaccharides: Amylose Linear (amylose) and branched (amylopectin) forms are the carbohydrates of starch. This major food source is enzymatically broken down to glucose during digestion… (α1-4 Glc α1-4 Glc)n …and during ethanol production α1-6 Glc branches http://en.wikipedia.org/wiki/Amylopectin

  38. Examples of polysaccharides: Glycogen Tissue storage form of glucose (primarily in the liver & muscle). “Animal Starch” – same general structure as plant starch, but more branched & compact. Broken down to glucose at need to quickly increase blood glucose levels. α1-6 Glc branches (α1-4 Glc α1-4 Glc)n http://en.wikipedia.org/wiki/Glycogen

  39. Examples of polysaccharides: Chitin Among the most abundant of organic molecules on Earth, it is the main component of the cell walls of fungi, the exoskeletons of arthropods such as insects and crustaceans (e.g., crabs, lobsters and shrimps). (β1-4 GlcNAc β1-4 GlcNAc)n http://en.wikipedia.org/wiki/Chitin

  40. oligosaccharides as molecular language Cohen & Varki (2010) OMICS 4:455 Rosetta Stone, British Museum

  41. Oligosaccharides: Molecular diversity of glycans

  42. Three different amino acids (Ala, Ser, Tyr) – 6 structures Ala-Ser-Tyr Ala-Tyr-Ser Ser-Ala-Tyr Ser-Tyr-Ala Tyr-Ala-Ser Tyr-Ser-Ala Three different sugars (Glc, Gal, Man) – 1,056 structures …

  43. Gal a1-2 Glc a1-2 Man a1- Gal a1-3 Glc a1-2 Man a1- Gal a1-4 Glc a1-2 Man a1- Gal a1-6 Glc a1-2 Man a1- Gal b1-2 Glc a1-2 Man a1- Gal b1-3 Glc a1-2 Man a1- Gal b1-4 Glc a1-2 Man a1- Gal b1-6 Glc a1-2 Man a1- Gal a1-2 Glc a1-3 Man a1- Gal a1-3 Glc a1-3 Man a1- Gal a1-4 Glc a1-3 Man a1- Gal a1-6 Glc a1-3 Man a1- Gal b1-2 Glc a1-3 Man a1- Gal b1-3 Glc a1-3 Man a1- Gal b1-4 Glc a1-3 Man a1- Gal b1-6 Glc a1-3 Man a1- Gal a1-2 Glc a1-4 Man a1- Gal a1-3 Glc a1-4 Man a1- Gal a1-4 Glc a1-4 Man a1- Gal a1-6 Glc a1-4 Man a1- Gal b1-2 Glc a1-4 Man a1- Gal b1-3 Glc a1-4 Man a1- Gal b1-4 Glc a1-4 Man a1- Gal b1-6 Glc a1-4 Man a1- Gal a1-2 Glc a1-6 Man a1- Gal a1-3 Glc a1-6 Man a1- Gal a1-4 Glc a1-6 Man a1- Gal a1-6 Glc a1-6 Man a1- Gal b1-2 Glc a1-6 Man a1- Gal b1-3 Glc a1-6 Man a1- Gal b1-4 Glc a1-6 Man a1- Gal b1-6 Glc a1-6 Man a1- Gal a1-2 Glc b1-2 Man a1- Gal a1-3 Glc b1-2 Man a1- Gal a1-4 Glc b1-2 Man a1- Gal a1-6 Glc b1-2 Man a1- Gal b1-2 Glc b1-2 Man a1- Gal b1-3 Glc b1-2 Man a1- Gal b1-4 Glc b1-2 Man a1- Gal b1-6 Glc b1-2 Man a1- Gal a1-2 Glc b1-3 Man a1- Gal a1-3 Glc b1-3 Man a1- Gal a1-4 Glc b1-3 Man a1- Gal a1-6 Glc b1-3 Man a1- Gal b1-2 Glc b1-3 Man a1- Gal b1-3 Glc b1-3 Man a1- Gal b1-4 Glc b1-3 Man a1- Gal b1-6 Glc b1-3 Man a1- Gal a1-2 Glc b1-4 Man a1- Gal a1-3 Glc b1-4 Man a1- Gal a1-4 Glc b1-4 Man a1- Gal a1-6 Glc b1-4 Man a1- Gal b1-2 Glc b1-4 Man a1- Gal b1-3 Glc b1-4 Man a1- Gal b1-4 Glc b1-4 Man a1- Gal b1-6 Glc b1-4 Man a1- Gal a1-2 Glc b1-6 Man a1- Gal a1-3 Glc b1-6 Man a1- Gal a1-4 Glc b1-6 Man a1- Gal a1-6 Glc b1-6 Man a1- Gal b1-2 Glc b1-6 Man a1- Gal b1-3 Glc b1-6 Man a1- Gal b1-4 Glc b1-6 Man a1- Gal b1-6 Glc b1-6 Man a1- Gal a1-2 Glc a1-2 Man b1- Gal a1-3 Glc a1-2 Man b1- Gal a1-4 Glc a1-2 Man b1- Gal a1-6 Glc a1-2 Man b1- Gal b1-2 Glc a1-2 Man b1- Gal b1-3 Glc a1-2 Man b1- Gal b1-4 Glc a1-2 Man b1- Gal b1-6 Glc a1-2 Man b1- Gal a1-2 Glc a1-3 Man b1- Gal a1-3 Glc a1-3 Man b1- Gal a1-4 Glc a1-3 Man b1- Gal a1-6 Glc a1-3 Man b1- Gal b1-2 Glc a1-3 Man b1- Gal b1-3 Glc a1-3 Man b1- Gal b1-4 Glc a1-3 Man b1- Gal b1-6 Glc a1-3 Man b1- Gal a1-2 Glc a1-4 Man b1- Gal a1-3 Glc a1-4 Man b1- Gal a1-4 Glc a1-4 Man b1- Gal a1-6 Glc a1-4 Man b1- Gal b1-2 Glc a1-4 Man b1- Gal b1-3 Glc a1-4 Man b1- Gal b1-4 Glc a1-4 Man b1- Gal b1-6 Glc a1-4 Man b1- Gal a1-2 Glc a1-6 Man b1- Gal a1-3 Glc a1-6 Man b1- Gal a1-4 Glc a1-6 Man b1- Gal a1-6 Glc a1-6 Man b1- Gal b1-2 Glc a1-6 Man b1- Gal b1-3 Glc a1-6 Man b1- Gal b1-4 Glc a1-6 Man b1- Gal b1-6 Glc a1-6 Man b1- Gal a1-2 Glc b1-2 Man b1- Gal a1-3 Glc b1-2 Man b1- Gal a1-4 Glc b1-2 Man b1- Gal a1-6 Glc b1-2 Man b1- Gal b1-2 Glc b1-2 Man b1- Gal b1-3 Glc b1-2 Man b1- Gal b1-4 Glc b1-2 Man b1- Gal b1-6 Glc b1-2 Man b1- Gal a1-2 Glc b1-3 Man b1- Gal a1-3 Glc b1-3 Man b1- Gal a1-4 Glc b1-3 Man b1- Gal a1-6 Glc b1-3 Man b1- Gal b1-2 Glc b1-3 Man b1- Gal b1-3 Glc b1-3 Man b1- Gal b1-4 Glc b1-3 Man b1- Gal b1-6 Glc b1-3 Man b1- Gal a1-2 Glc b1-4 Man b1- Gal a1-3 Glc b1-4 Man b1- Gal a1-4 Glc b1-4 Man b1- Gal a1-6 Glc b1-4 Man b1- Gal b1-2 Glc b1-4 Man b1- Gal b1-3 Glc b1-4 Man b1- Gal b1-4 Glc b1-4 Man b1- Gal b1-6 Glc b1-4 Man b1- Gal a1-2 Glc b1-6 Man b1- Gal a1-3 Glc b1-6 Man b1- Gal a1-4 Glc b1-6 Man b1- Gal a1-6 Glc b1-6 Man b1- Gal b1-2 Glc b1-6 Man b1- Gal b1-3 Glc b1-6 Man b1- Gal b1-4 Glc b1-6 Man b1- Gal b1-6 Glc b1-6 Man b1- Gal a1-2 Man a1-2 Glc a1- Gal a1-3 Man a1-2 Glc a1- Gal a1-4 Man a1-2 Glc a1- Gal a1-6 Man a1-2 Glc a1- Gal b1-2 Man a1-2 Glc a1- Gal b1-3 Man a1-2 Glc a1- Gal b1-4 Man a1-2 Glc a1- Gal b1-6 Man a1-2 Glc a1- Gal a1-2 Man a1-3 Glc a1- Gal a1-3 Man a1-3 Glc a1- Gal a1-4 Man a1-3 Glc a1- Gal a1-6 Man a1-3 Glc a1- Gal b1-2 Man a1-3 Glc a1- Gal b1-3 Man a1-3 Glc a1- Gal b1-4 Man a1-3 Glc a1- Gal b1-6 Man a1-3 Glc a1- Gal a1-2 Man a1-4 Glc a1- Gal a1-3 Man a1-4 Glc a1- Gal a1-4 Man a1-4 Glc a1- Gal a1-6 Man a1-4 Glc a1- Gal b1-2 Man a1-4 Glc a1- Gal b1-3 Man a1-4 Glc a1- Gal b1-4 Man a1-4 Glc a1- Gal b1-6 Man a1-4 Glc a1- Gal a1-2 Man a1-6 Glc a1- Gal a1-3 Man a1-6 Glc a1- Gal a1-4 Man a1-6 Glc a1- Gal a1-6 Man a1-6 Glc a1- Gal b1-2 Man a1-6 Glc a1- Gal b1-3 Man a1-6 Glc a1- Gal b1-4 Man a1-6 Glc a1- Gal b1-6 Man a1-6 Glc a1- Gal a1-2 Man b1-2 Glc a1- Gal a1-3 Man b1-2 Glc a1- Gal a1-4 Man b1-2 Glc a1- Gal a1-6 Man b1-2 Glc a1- Gal b1-2 Man b1-2 Glc a1- Gal b1-3 Man b1-2 Glc a1- Gal b1-4 Man b1-2 Glc a1- Gal b1-6 Man b1-2 Glc a1- Gal a1-2 Man b1-3 Glc a1- Gal a1-3 Man b1-3 Glc a1- Gal a1-4 Man b1-3 Glc a1- Gal a1-6 Man b1-3 Glc a1- Gal b1-2 Man b1-3 Glc a1- Gal b1-3 Man b1-3 Glc a1- Gal b1-4 Man b1-3 Glc a1- Gal b1-6 Man b1-3 Glc a1- Gal a1-2 Man b1-4 Glc a1- Gal a1-3 Man b1-4 Glc a1- Gal a1-4 Man b1-4 Glc a1- Gal a1-6 Man b1-4 Glc a1- Gal b1-2 Man b1-4 Glc a1- Gal b1-3 Man b1-4 Glc a1- Gal b1-4 Man b1-4 Glc a1- Gal b1-6 Man b1-4 Glc a1- Gal a1-2 Man b1-6 Glc a1- Gal a1-3 Man b1-6 Glc a1- Gal a1-4 Man b1-6 Glc a1- Gal a1-6 Man b1-6 Glc a1- Gal b1-2 Man b1-6 Glc a1- Gal b1-3 Man b1-6 Glc a1- Gal b1-4 Man b1-6 Glc a1- Gal b1-6 Man b1-6 Glc a1- Gal a1-2 Man a1-2 Glc b1- Gal a1-3 Man a1-2 Glc b1- Gal a1-4 Man a1-2 Glc b1- Gal a1-6 Man a1-2 Glc b1- Gal b1-2 Man a1-2 Glc b1- Gal b1-3 Man a1-2 Glc b1- Gal b1-4 Man a1-2 Glc b1- Gal b1-6 Man a1-2 Glc b1- Gal a1-2 Man a1-3 Glc b1- Gal a1-3 Man a1-3 Glc b1- Gal a1-4 Man a1-3 Glc b1- Gal a1-6 Man a1-3 Glc b1- Gal b1-2 Man a1-3 Glc b1- Gal b1-3 Man a1-3 Glc b1- Gal b1-4 Man a1-3 Glc b1- Gal b1-6 Man a1-3 Glc b1- Gal a1-2 Man a1-4 Glc b1- Gal a1-3 Man a1-4 Glc b1- Gal a1-4 Man a1-4 Glc b1- Gal a1-6 Man a1-4 Glc b1- Gal b1-2 Man a1-4 Glc b1- Gal b1-3 Man a1-4 Glc b1- Gal b1-4 Man a1-4 Glc b1- Gal b1-6 Man a1-4 Glc b1- Gal a1-2 Man a1-6 Glc b1- Gal a1-3 Man a1-6 Glc b1- Gal a1-4 Man a1-6 Glc b1- Gal a1-6 Man a1-6 Glc b1- Gal b1-2 Man a1-6 Glc b1- Gal b1-3 Man a1-6 Glc b1- Gal b1-4 Man a1-6 Glc b1- Gal b1-6 Man a1-6 Glc b1- Gal a1-2 Man b1-2 Glc b1- Gal a1-3 Man b1-2 Glc b1- Gal a1-4 Man b1-2 Glc b1- Gal a1-6 Man b1-2 Glc b1- Gal b1-2 Man b1-2 Glc b1- Gal b1-3 Man b1-2 Glc b1- Gal b1-4 Man b1-2 Glc b1- Gal b1-6 Man b1-2 Glc b1- Gal a1-2 Man b1-3 Glc b1- Gal a1-3 Man b1-3 Glc b1- Gal a1-4 Man b1-3 Glc b1- Gal a1-6 Man b1-3 Glc b1- Gal b1-2 Man b1-3 Glc b1- Gal b1-3 Man b1-3 Glc b1- Gal b1-4 Man b1-3 Glc b1- Gal b1-6 Man b1-3 Glc b1- Gal a1-2 Man b1-4 Glc b1- Gal a1-3 Man b1-4 Glc b1- Gal a1-4 Man b1-4 Glc b1- Gal a1-6 Man b1-4 Glc b1- Gal b1-2 Man b1-4 Glc b1- Gal b1-3 Man b1-4 Glc b1- Gal b1-4 Man b1-4 Glc b1- Gal b1-6 Man b1-4 Glc b1- Gal a1-2 Man b1-6 Glc b1- Gal a1-3 Man b1-6 Glc b1- Gal a1-4 Man b1-6 Glc b1- Gal a1-6 Man b1-6 Glc b1- Gal b1-2 Man b1-6 Glc b1- Gal b1-3 Man b1-6 Glc b1- Gal b1-4 Man b1-6 Glc b1- Gal b1-6 Man b1-6 Glc b1- Man a1-2 Glc a1-2 Gal a1- Man a1-3 Glc a1-2 Gal a1- Man a1-4 Glc a1-2 Gal a1- Man a1-6 Glc a1-2 Gal a1- Man b1-2 Glc a1-2 Gal a1- Man b1-3 Glc a1-2 Gal a1- Man b1-4 Glc a1-2 Gal a1- Man b1-6 Glc a1-2 Gal a1- Man a1-2 Glc a1-3 Gal a1- Man a1-3 Glc a1-3 Gal a1- Man a1-4 Glc a1-3 Gal a1- Man a1-6 Glc a1-3 Gal a1- Man b1-2 Glc a1-3 Gal a1- Man b1-3 Glc a1-3 Gal a1- Man b1-4 Glc a1-3 Gal a1- Man b1-6 Glc a1-3 Gal a1- Man a1-2 Glc a1-4 Gal a1- Man a1-3 Glc a1-4 Gal a1- Man a1-4 Glc a1-4 Gal a1- Man a1-6 Glc a1-4 Gal a1- Man b1-2 Glc a1-4 Gal a1- Man b1-3 Glc a1-4 Gal a1- Man b1-4 Glc a1-4 Gal a1- Man b1-6 Glc a1-4 Gal a1- Man a1-2 Glc a1-6 Gal a1- Man a1-3 Glc a1-6 Gal a1- Man a1-4 Glc a1-6 Gal a1- Man a1-6 Glc a1-6 Gal a1- Man b1-2 Glc a1-6 Gal a1- Man b1-3 Glc a1-6 Gal a1- Man b1-4 Glc a1-6 Gal a1- Man b1-6 Glc a1-6 Gal a1- Man a1-2 Glc b1-2 Gal a1- Man a1-3 Glc b1-2 Gal a1- Man a1-4 Glc b1-2 Gal a1- Man a1-6 Glc b1-2 Gal a1- Man b1-2 Glc b1-2 Gal a1- Man b1-3 Glc b1-2 Gal a1- Man b1-4 Glc b1-2 Gal a1- Man b1-6 Glc b1-2 Gal a1- Man a1-2 Glc b1-3 Gal a1- Man a1-3 Glc b1-3 Gal a1- Man a1-4 Glc b1-3 Gal a1- Man a1-6 Glc b1-3 Gal a1- Man b1-2 Glc b1-3 Gal a1- Man b1-3 Glc b1-3 Gal a1- Man b1-4 Glc b1-3 Gal a1- Man b1-6 Glc b1-3 Gal a1- Man a1-2 Glc b1-4 Gal a1- Man a1-3 Glc b1-4 Gal a1- Man a1-4 Glc b1-4 Gal a1- Man a1-6 Glc b1-4 Gal a1- Man b1-2 Glc b1-4 Gal a1- Man b1-3 Glc b1-4 Gal a1- Man b1-4 Glc b1-4 Gal a1- Man b1-6 Glc b1-4 Gal a1- Man a1-2 Glc b1-6 Gal a1- Man a1-3 Glc b1-6 Gal a1- Man a1-4 Glc b1-6 Gal a1- Man a1-6 Glc b1-6 Gal a1- Man b1-2 Glc b1-6 Gal a1- Man b1-3 Glc b1-6 Gal a1- Man b1-4 Glc b1-6 Gal a1- Man b1-6 Glc b1-6 Gal a1- Man a1-2 Glc a1-2 Gal b1- Man a1-3 Glc a1-2 Gal b1- Man a1-4 Glc a1-2 Gal b1- Man a1-6 Glc a1-2 Gal b1- Man b1-2 Glc a1-2 Gal b1- Man b1-3 Glc a1-2 Gal b1- Man b1-4 Glc a1-2 Gal b1- Man b1-6 Glc a1-2 Gal b1- Man a1-2 Glc a1-3 Gal b1- Man a1-3 Glc a1-3 Gal b1- Man a1-4 Glc a1-3 Gal b1- Man a1-6 Glc a1-3 Gal b1- Man b1-2 Glc a1-3 Gal b1- Man b1-3 Glc a1-3 Gal b1- Man b1-4 Glc a1-3 Gal b1- Man b1-6 Glc a1-3 Gal b1- Man a1-2 Glc a1-4 Gal b1- Man a1-3 Glc a1-4 Gal b1- Man a1-4 Glc a1-4 Gal b1- Man a1-6 Glc a1-4 Gal b1- Man b1-2 Glc a1-4 Gal b1- Man b1-3 Glc a1-4 Gal b1- Man b1-4 Glc a1-4 Gal b1- Man b1-6 Glc a1-4 Gal b1- Man a1-2 Glc a1-6 Gal b1- Man a1-3 Glc a1-6 Gal b1- Man a1-4 Glc a1-6 Gal b1- Man a1-6 Glc a1-6 Gal b1- Man b1-2 Glc a1-6 Gal b1- Man b1-3 Glc a1-6 Gal b1- Man b1-4 Glc a1-6 Gal b1- Man b1-6 Glc a1-6 Gal b1- Man a1-2 Glc b1-2 Gal b1- Man a1-3 Glc b1-2 Gal b1- Man a1-4 Glc b1-2 Gal b1- Man a1-6 Glc b1-2 Gal b1- Man b1-2 Glc b1-2 Gal b1- Man b1-3 Glc b1-2 Gal b1- Man b1-4 Glc b1-2 Gal b1- Man b1-6 Glc b1-2 Gal b1- Man a1-2 Glc b1-3 Gal b1- Man a1-3 Glc b1-3 Gal b1- Man a1-4 Glc b1-3 Gal b1- Man a1-6 Glc b1-3 Gal b1- Man b1-2 Glc b1-3 Gal b1- Man b1-3 Glc b1-3 Gal b1- Man b1-4 Glc b1-3 Gal b1- Man b1-6 Glc b1-3 Gal b1- Man a1-2 Glc b1-4 Gal b1- Man a1-3 Glc b1-4 Gal b1- Man a1-4 Glc b1-4 Gal b1- Man a1-6 Glc b1-4 Gal b1- Man b1-2 Glc b1-4 Gal b1- Man b1-3 Glc b1-4 Gal b1- Man b1-4 Glc b1-4 Gal b1- Man b1-6 Glc b1-4 Gal b1- Man a1-2 Glc b1-6 Gal b1- Man a1-3 Glc b1-6 Gal b1- Man a1-4 Glc b1-6 Gal b1- Man a1-6 Glc b1-6 Gal b1- Man b1-2 Glc b1-6 Gal b1- Man b1-3 Glc b1-6 Gal b1- Man b1-4 Glc b1-6 Gal b1- Man b1-6 Glc b1-6 Gal b1- Man a1-2 Gal a1-2 Glc a1- Man a1-3 Gal a1-2 Glc a1- Man a1-4 Gal a1-2 Glc a1- Man a1-6 Gal a1-2 Glc a1- Man b1-2 Gal a1-2 Glc a1- Man b1-3 Gal a1-2 Glc a1- Man b1-4 Gal a1-2 Glc a1- Man b1-6 Gal a1-2 Glc a1- Man a1-2 Gal a1-3 Glc a1- Man a1-3 Gal a1-3 Glc a1- Man a1-4 Gal a1-3 Glc a1- Man a1-6 Gal a1-3 Glc a1- Man b1-2 Gal a1-3 Glc a1- Man b1-3 Gal a1-3 Glc a1- Man b1-4 Gal a1-3 Glc a1- Man b1-6 Gal a1-3 Glc a1- Man a1-2 Gal a1-4 Glc a1- Man a1-3 Gal a1-4 Glc a1- Man a1-4 Gal a1-4 Glc a1- Man a1-6 Gal a1-4 Glc a1- Man b1-2 Gal a1-4 Glc a1- Man b1-3 Gal a1-4 Glc a1- Man b1-4 Gal a1-4 Glc a1- Man b1-6 Gal a1-4 Glc a1- Man a1-2 Gal a1-6 Glc a1- Man a1-3 Gal a1-6 Glc a1- Man a1-4 Gal a1-6 Glc a1- Man a1-6 Gal a1-6 Glc a1- Man b1-2 Gal a1-6 Glc a1- Man b1-3 Gal a1-6 Glc a1- Man b1-4 Gal a1-6 Glc a1- Man b1-6 Gal a1-6 Glc a1- Man a1-2 Gal b1-2 Glc a1- Man a1-3 Gal b1-2 Glc a1- Man a1-4 Gal b1-2 Glc a1- Man a1-6 Gal b1-2 Glc a1- Man b1-2 Gal b1-2 Glc a1- Man b1-3 Gal b1-2 Glc a1- Man b1-4 Gal b1-2 Glc a1- Man b1-6 Gal b1-2 Glc a1- Man a1-2 Gal b1-3 Glc a1- Man a1-3 Gal b1-3 Glc a1- Man a1-4 Gal b1-3 Glc a1- Man a1-6 Gal b1-3 Glc a1- Man b1-2 Gal b1-3 Glc a1- Man b1-3 Gal b1-3 Glc a1- Man b1-4 Gal b1-3 Glc a1- Man b1-6 Gal b1-3 Glc a1- Man a1-2 Gal b1-4 Glc a1- Man a1-3 Gal b1-4 Glc a1- Man a1-4 Gal b1-4 Glc a1- Man a1-6 Gal b1-4 Glc a1- Man b1-2 Gal b1-4 Glc a1- Man b1-3 Gal b1-4 Glc a1- Man b1-4 Gal b1-4 Glc a1- Man b1-6 Gal b1-4 Glc a1- Man a1-2 Gal b1-6 Glc a1- Man a1-3 Gal b1-6 Glc a1- Man a1-4 Gal b1-6 Glc a1- Man a1-6 Gal b1-6 Glc a1- Man b1-2 Gal b1-6 Glc a1- Man b1-3 Gal b1-6 Glc a1- Man b1-4 Gal b1-6 Glc a1- Man b1-6 Gal b1-6 Glc a1- Man a1-2 Gal a1-2 Glc b1 Man a1-3 Gal a1-2 Glc b1 Man a1-4 Gal a1-2 Glc b1 Man a1-6 Gal a1-2 Glc b1 Man b1-2 Gal a1-2 Glc b1 Man b1-3 Gal a1-2 Glc b1 Man b1-4 Gal a1-2 Glc b1 Man b1-6 Gal a1-2 Glc b1 Man a1-2 Gal a1-3 Glc b1 Man a1-3 Gal a1-3 Glc b1 Man a1-4 Gal a1-3 Glc b1 Man a1-6 Gal a1-3 Glc b1 Man b1-2 Gal a1-3 Glc b1 Man b1-3 Gal a1-3 Glc b1 Man b1-4 Gal a1-3 Glc b1 Man b1-6 Gal a1-3 Glc b1 Man a1-2 Gal a1-4 Glc b1 Man a1-3 Gal a1-4 Glc b1 Man a1-4 Gal a1-4 Glc b1 Man a1-6 Gal a1-4 Glc b1 Man b1-2 Gal a1-4 Glc b1 Man b1-3 Gal a1-4 Glc b1 Man b1-4 Gal a1-4 Glc b1 Man b1-6 Gal a1-4 Glc b1 Man a1-2 Gal a1-6 Glc b1 Man a1-3 Gal a1-6 Glc b1 Man a1-4 Gal a1-6 Glc b1 Man a1-6 Gal a1-6 Glc b1 Man b1-2 Gal a1-6 Glc b1 Man b1-3 Gal a1-6 Glc b1 Man b1-4 Gal a1-6 Glc b1 Man b1-6 Gal a1-6 Glc b1 Man a1-2 Gal b1-2 Glc b1 Man a1-3 Gal b1-2 Glc b1 Man a1-4 Gal b1-2 Glc b1 Man a1-6 Gal b1-2 Glc b1 Man b1-2 Gal b1-2 Glc b1 Man b1-3 Gal b1-2 Glc b1 Man b1-4 Gal b1-2 Glc b1 Man b1-6 Gal b1-2 Glc b1 Man a1-2 Gal b1-3 Glc b1 Man a1-3 Gal b1-3 Glc b1 Man a1-4 Gal b1-3 Glc b1 Man a1-6 Gal b1-3 Glc b1 Man b1-2 Gal b1-3 Glc b1 Man b1-3 Gal b1-3 Glc b1 Man b1-4 Gal b1-3 Glc b1 Man b1-6 Gal b1-3 Glc b1 Man a1-2 Gal b1-4 Glc b1 Man a1-3 Gal b1-4 Glc b1 Man a1-4 Gal b1-4 Glc b1 Man a1-6 Gal b1-4 Glc b1 Man b1-2 Gal b1-4 Glc b1 Man b1-3 Gal b1-4 Glc b1 Man b1-4 Gal b1-4 Glc b1 Man b1-6 Gal b1-4 Glc b1 Man a1-2 Gal b1-6 Glc b1 Man a1-3 Gal b1-6 Glc b1 Man a1-4 Gal b1-6 Glc b1 Man a1-6 Gal b1-6 Glc b1 Man b1-2 Gal b1-6 Glc b1 Man b1-3 Gal b1-6 Glc b1 Man b1-4 Gal b1-6 Glc b1 Man b1-6 Gal b1-6 Glc b1 Glc a1-2 Man a1-2 Gal a1- Glc a1-3 Man a1-2 Gal a1- Glc a1-4 Man a1-2 Gal a1- Glc a1-6 Man a1-2 Gal a1- Glc b1-2 Man a1-2 Gal a1- Glc b1-3 Man a1-2 Gal a1- Glc b1-4 Man a1-2 Gal a1- Glc b1-6 Man a1-2 Gal a1- Glc a1-2 Man a1-3 Gal a1- Glc a1-3 Man a1-3 Gal a1- Glc a1-4 Man a1-3 Gal a1- Glc a1-6 Man a1-3 Gal a1- Glc b1-2 Man a1-3 Gal a1- Glc b1-3 Man a1-3 Gal a1- Glc b1-4 Man a1-3 Gal a1- Glc b1-6 Man a1-3 Gal a1- Glc a1-2 Man a1-4 Gal a1- Glc a1-3 Man a1-4 Gal a1- Glc a1-4 Man a1-4 Gal a1- Glc a1-6 Man a1-4 Gal a1- Glc b1-2 Man a1-4 Gal a1- Glc b1-3 Man a1-4 Gal a1- Glc b1-4 Man a1-4 Gal a1- Glc b1-6 Man a1-4 Gal a1- Glc a1-2 Man a1-6 Gal a1- Glc a1-3 Man a1-6 Gal a1- Glc a1-4 Man a1-6 Gal a1- Glc a1-6 Man a1-6 Gal a1- Glc b1-2 Man a1-6 Gal a1- Glc b1-3 Man a1-6 Gal a1- Glc b1-4 Man a1-6 Gal a1- Glc b1-6 Man a1-6 Gal a1- Glc a1-2 Man b1-2 Gal a1- Glc a1-3 Man b1-2 Gal a1- Glc a1-4 Man b1-2 Gal a1- Glc a1-6 Man b1-2 Gal a1- Glc b1-2 Man b1-2 Gal a1- Glc b1-3 Man b1-2 Gal a1- Glc b1-4 Man b1-2 Gal a1- Glc b1-6 Man b1-2 Gal a1- Glc a1-2 Man b1-3 Gal a1- Glc a1-3 Man b1-3 Gal a1- Glc a1-4 Man b1-3 Gal a1- Glc a1-6 Man b1-3 Gal a1- Glc b1-2 Man b1-3 Gal a1- Glc b1-3 Man b1-3 Gal a1- Glc b1-4 Man b1-3 Gal a1- Glc b1-6 Man b1-3 Gal a1- Glc a1-2 Man b1-4 Gal a1- Glc a1-3 Man b1-4 Gal a1- Glc a1-4 Man b1-4 Gal a1- Glc a1-6 Man b1-4 Gal a1- Glc b1-2 Man b1-4 Gal a1- Glc b1-3 Man b1-4 Gal a1- Glc b1-4 Man b1-4 Gal a1- Glc b1-6 Man b1-4 Gal a1- Glc a1-2 Man b1-6 Gal a1- Glc a1-3 Man b1-6 Gal a1- Glc a1-4 Man b1-6 Gal a1- Glc a1-6 Man b1-6 Gal a1- Glc b1-2 Man b1-6 Gal a1- Glc b1-3 Man b1-6 Gal a1- Glc b1-4 Man b1-6 Gal a1- Glc b1-6 Man b1-6 Gal a1- Glc a1-2 Man a1-2 Gal b1- Glc a1-3 Man a1-2 Gal b1- Glc a1-4 Man a1-2 Gal b1- Glc a1-6 Man a1-2 Gal b1- Glc b1-2 Man a1-2 Gal b1- Glc b1-3 Man a1-2 Gal b1- Glc b1-4 Man a1-2 Gal b1- Glc b1-6 Man a1-2 Gal b1- Glc a1-2 Man a1-3 Gal b1- Glc a1-3 Man a1-3 Gal b1- Glc a1-4 Man a1-3 Gal b1- Glc a1-6 Man a1-3 Gal b1- Glc b1-2 Man a1-3 Gal b1- Glc b1-3 Man a1-3 Gal b1- Glc b1-4 Man a1-3 Gal b1- Glc b1-6 Man a1-3 Gal b1- Glc a1-2 Man a1-4 Gal b1- Glc a1-3 Man a1-4 Gal b1- Glc a1-4 Man a1-4 Gal b1- Glc a1-6 Man a1-4 Gal b1- Glc b1-2 Man a1-4 Gal b1- Glc b1-3 Man a1-4 Gal b1- Glc b1-4 Man a1-4 Gal b1- Glc b1-6 Man a1-4 Gal b1- Glc a1-2 Man a1-6 Gal b1- Glc a1-3 Man a1-6 Gal b1- Glc a1-4 Man a1-6 Gal b1- Glc a1-6 Man a1-6 Gal b1- Glc b1-2 Man a1-6 Gal b1- Glc b1-3 Man a1-6 Gal b1- Glc b1-4 Man a1-6 Gal b1- Glc b1-6 Man a1-6 Gal b1- Glc a1-2 Man b1-2 Gal b1- Glc a1-3 Man b1-2 Gal b1- Glc a1-4 Man b1-2 Gal b1- Glc a1-6 Man b1-2 Gal b1- Glc b1-2 Man b1-2 Gal b1- Glc b1-3 Man b1-2 Gal b1- Glc b1-4 Man b1-2 Gal b1- Glc b1-6 Man b1-2 Gal b1- Glc a1-2 Man b1-3 Gal b1- Glc a1-3 Man b1-3 Gal b1- Glc a1-4 Man b1-3 Gal b1- Glc a1-6 Man b1-3 Gal b1- Glc b1-2 Man b1-3 Gal b1- Glc b1-3 Man b1-3 Gal b1- Glc b1-4 Man b1-3 Gal b1- Glc b1-6 Man b1-3 Gal b1- Glc a1-2 Man b1-4 Gal b1- Glc a1-3 Man b1-4 Gal b1- Glc a1-4 Man b1-4 Gal b1- Glc a1-6 Man b1-4 Gal b1- Glc b1-2 Man b1-4 Gal b1- Glc b1-3 Man b1-4 Gal b1- Glc b1-4 Man b1-4 Gal b1- Glc b1-6 Man b1-4 Gal b1- Glc a1-2 Man b1-6 Gal b1- Glc a1-3 Man b1-6 Gal b1- Glc a1-4 Man b1-6 Gal b1- Glc a1-6 Man b1-6 Gal b1- Glc b1-2 Man b1-6 Gal b1- Glc b1-3 Man b1-6 Gal b1- Glc b1-4 Man b1-6 Gal b1- Glc b1-6 Man b1-6 Gal b1- Glc a1-2 Gal a1-2 Man a1- Glc a1-3 Gal a1-2 Man a1- Glc a1-4 Gal a1-2 Man a1- Glc a1-6 Gal a1-2 Man a1- Glc b1-2 Gal a1-2 Man a1- Glc b1-3 Gal a1-2 Man a1- Glc b1-4 Gal a1-2 Man a1- Glc b1-6 Gal a1-2 Man a1- Glc a1-2 Gal a1-3 Man a1- Glc a1-3 Gal a1-3 Man a1- Glc a1-4 Gal a1-3 Man a1- Glc a1-6 Gal a1-3 Man a1- Glc b1-2 Gal a1-3 Man a1- Glc b1-3 Gal a1-3 Man a1- Glc b1-4 Gal a1-3 Man a1- Glc b1-6 Gal a1-3 Man a1- Glc a1-2 Gal a1-4 Man a1- Glc a1-3 Gal a1-4 Man a1- Glc a1-4 Gal a1-4 Man a1- Glc a1-6 Gal a1-4 Man a1- Glc b1-2 Gal a1-4 Man a1- Glc b1-3 Gal a1-4 Man a1- Glc b1-4 Gal a1-4 Man a1- Glc b1-6 Gal a1-4 Man a1- Glc a1-2 Gal a1-6 Man a1- Glc a1-3 Gal a1-6 Man a1- Glc a1-4 Gal a1-6 Man a1- Glc a1-6 Gal a1-6 Man a1- Glc b1-2 Gal a1-6 Man a1- Glc b1-3 Gal a1-6 Man a1- Glc b1-4 Gal a1-6 Man a1- Glc b1-6 Gal a1-6 Man a1- Glc a1-2 Gal b1-2 Man a1- Glc a1-3 Gal b1-2 Man a1- Glc a1-4 Gal b1-2 Man a1- Glc a1-6 Gal b1-2 Man a1- Glc b1-2 Gal b1-2 Man a1- Glc b1-3 Gal b1-2 Man a1- Glc b1-4 Gal b1-2 Man a1- Glc b1-6 Gal b1-2 Man a1- Glc a1-2 Gal b1-3 Man a1- Glc a1-3 Gal b1-3 Man a1- Glc a1-4 Gal b1-3 Man a1- Glc a1-6 Gal b1-3 Man a1- Glc b1-2 Gal b1-3 Man a1- Glc b1-3 Gal b1-3 Man a1- Glc b1-4 Gal b1-3 Man a1- Glc b1-6 Gal b1-3 Man a1- Glc a1-2 Gal b1-4 Man a1- Glc a1-3 Gal b1-4 Man a1- Glc a1-4 Gal b1-4 Man a1- Glc a1-6 Gal b1-4 Man a1- Glc b1-2 Gal b1-4 Man a1- Glc b1-3 Gal b1-4 Man a1- Glc b1-4 Gal b1-4 Man a1- Glc b1-6 Gal b1-4 Man a1- Glc a1-2 Gal b1-6 Man a1- Glc a1-3 Gal b1-6 Man a1- Glc a1-4 Gal b1-6 Man a1- Glc a1-6 Gal b1-6 Man a1- Glc b1-2 Gal b1-6 Man a1- Glc b1-3 Gal b1-6 Man a1- Glc b1-4 Gal b1-6 Man a1- Glc b1-6 Gal b1-6 Man a1- Glc a1-2 Gal a1-2 Man b1- Glc a1-3 Gal a1-2 Man b1- Glc a1-4 Gal a1-2 Man b1- Glc a1-6 Gal a1-2 Man b1- Glc b1-2 Gal a1-2 Man b1- Glc b1-3 Gal a1-2 Man b1- Glc b1-4 Gal a1-2 Man b1- Glc b1-6 Gal a1-2 Man b1- Glc a1-2 Gal a1-3 Man b1- Glc a1-3 Gal a1-3 Man b1- Glc a1-4 Gal a1-3 Man b1- Glc a1-6 Gal a1-3 Man b1- Glc b1-2 Gal a1-3 Man b1- Glc b1-3 Gal a1-3 Man b1- Glc b1-4 Gal a1-3 Man b1- Glc b1-6 Gal a1-3 Man b1- Glc a1-2 Gal a1-4 Man b1- Glc a1-3 Gal a1-4 Man b1- Glc a1-4 Gal a1-4 Man b1- Glc a1-6 Gal a1-4 Man b1- Glc b1-2 Gal a1-4 Man b1- Glc b1-3 Gal a1-4 Man b1- Glc b1-4 Gal a1-4 Man b1- Glc b1-6 Gal a1-4 Man b1- Glc a1-2 Gal a1-6 Man b1- Glc a1-3 Gal a1-6 Man b1- Glc a1-4 Gal a1-6 Man b1- Glc a1-6 Gal a1-6 Man b1- Glc b1-2 Gal a1-6 Man b1- Glc b1-3 Gal a1-6 Man b1- Glc b1-4 Gal a1-6 Man b1- Glc b1-6 Gal a1-6 Man b1- Glc a1-2 Gal b1-2 Man b1- Glc a1-3 Gal b1-2 Man b1- Glc a1-4 Gal b1-2 Man b1- Glc a1-6 Gal b1-2 Man b1- Glc b1-2 Gal b1-2 Man b1- Glc b1-3 Gal b1-2 Man b1- Glc b1-4 Gal b1-2 Man b1- Glc b1-6 Gal b1-2 Man b1- Glc a1-2 Gal b1-3 Man b1- Glc a1-3 Gal b1-3 Man b1- Glc a1-4 Gal b1-3 Man b1- Glc a1-6 Gal b1-3 Man b1- Glc b1-2 Gal b1-3 Man b1- Glc b1-3 Gal b1-3 Man b1- Glc b1-4 Gal b1-3 Man b1- Glc b1-6 Gal b1-3 Man b1- Glc a1-2 Gal b1-4 Man b1- Glc a1-3 Gal b1-4 Man b1- Glc a1-4 Gal b1-4 Man b1- Glc a1-6 Gal b1-4 Man b1- Glc b1-2 Gal b1-4 Man b1- Glc b1-3 Gal b1-4 Man b1- Glc b1-4 Gal b1-4 Man b1- Glc b1-6 Gal b1-4 Man b1- Glc a1-2 Gal b1-6 Man b1- Glc a1-3 Gal b1-6 Man b1- Glc a1-4 Gal b1-6 Man b1- Glc a1-6 Gal b1-6 Man b1- Glc b1-2 Gal b1-6 Man b1- Glc b1-3 Gal b1-6 Man b1- Glc b1-4 Gal b1-6 Man b1- Glc b1-6 Gal b1-6 Man b1- Gal a1-2 (Glc a1-3) Man a1- Gal a1-2 (Glc a1-4) Man a1- Gal a1-2 (Glc a1-6) Man a1- Gal a1-3 (Glc a1-2) Man a1- Gal a1-3 (Glc a1-4) Man a1- Gal a1-3 (Glc a1-6) Man a1- Gal a1-4 (Glc a1-2) Man a1- Gal a1-4 (Glc a1-3) Man a1- Gal a1-4 (Glc a1-6) Man a1- Gal a1-6 (Glc a1-2) Man a1- Gal a1-6 (Glc a1-3) Man a1- Gal a1-6 (Glc a1-4) Man a1- Gal b1-2 (Glc a1-3) Man a1- Gal b1-2 (Glc a1-4) Man a1- Gal b1-2 (Glc a1-6) Man a1- Gal b1-3 (Glc a1-2) Man a1- Gal b1-3 (Glc a1-4) Man a1- Gal b1-3 (Glc a1-6) Man a1- Gal b1-4 (Glc a1-2) Man a1- Gal b1-4 (Glc a1-3) Man a1- Gal b1-4 (Glc a1-6) Man a1- Gal b1-6 (Glc a1-2) Man a1- Gal b1-6 (Glc a1-3) Man a1- Gal b1-6 (Glc a1-4) Man a1- Gal a1-2 (Glc b1-3) Man a1- Gal a1-2 (Glc b1-4) Man a1- Gal a1-2 (Glc b1-6) Man a1- Gal a1-3 (Glc b1-2) Man a1- Gal a1-3 (Glc b1-4) Man a1- Gal a1-3 (Glc b1-6) Man a1- Gal a1-4 (Glc b1-2) Man a1- Gal a1-4 (Glc b1-3) Man a1- Gal a1-4 (Glc b1-6) Man a1- Gal a1-6 (Glc b1-2) Man a1- Gal a1-6 (Glc b1-3) Man a1- Gal a1-6 (Glc b1-4) Man a1- Gal b1-2 (Glc b1-3) Man a1- Gal b1-2 (Glc b1-4) Man a1- Gal b1-2 (Glc b1-6) Man a1- Gal b1-3 (Glc b1-2) Man a1- Gal b1-3 (Glc b1-4) Man a1- Gal b1-3 (Glc b1-6) Man a1- Gal b1-4 (Glc b1-2) Man a1- Gal b1-4 (Glc b1-3) Man a1- Gal b1-4 (Glc b1-6) Man a1- Gal b1-6 (Glc b1-2) Man a1- Gal b1-6 (Glc b1-3) Man a1- Gal b1-6 (Glc b1-4) Man a1- Gal a1-2 (Glc a1-3) Man b1- Gal a1-2 (Glc a1-4) Man b1- Gal a1-2 (Glc a1-6) Man b1- Gal a1-3 (Glc a1-2) Man b1- Gal a1-3 (Glc a1-4) Man b1- Gal a1-3 (Glc a1-6) Man b1- Gal a1-4 (Glc a1-2) Man b1- Gal a1-4 (Glc a1-3) Man b1- Gal a1-4 (Glc a1-6) Man b1- Gal a1-6 (Glc a1-2) Man b1- Gal a1-6 (Glc a1-3) Man b1- Gal a1-6 (Glc a1-4) Man b1- Gal b1-2 (Glc a1-3) Man b1- Gal b1-2 (Glc a1-4) Man b1- Gal b1-2 (Glc a1-6) Man b1- Gal b1-3 (Glc a1-2) Man b1- Gal b1-3 (Glc a1-4) Man b1- Gal b1-3 (Glc a1-6) Man b1- Gal b1-4 (Glc a1-2) Man b1- Gal b1-4 (Glc a1-3) Man b1- Gal b1-4 (Glc a1-6) Man b1- Gal b1-6 (Glc a1-2) Man b1- Gal b1-6 (Glc a1-3) Man b1- Gal b1-6 (Glc a1-4) Man b1- Gal a1-2 (Glc b1-3) Man b1- Gal a1-2 (Glc b1-4) Man b1- Gal a1-2 (Glc b1-6) Man b1- Gal a1-3 (Glc b1-2) Man b1- Gal a1-3 (Glc b1-4) Man b1- Gal a1-3 (Glc b1-6) Man b1- Gal a1-4 (Glc b1-2) Man b1- Gal a1-4 (Glc b1-3) Man b1- Gal a1-4 (Glc b1-6) Man b1- Gal a1-6 (Glc b1-2) Man b1- Gal a1-6 (Glc b1-3) Man b1- Gal a1-6 (Glc b1-4) Man b1- Gal b1-2 (Glc b1-3) Man b1- Gal b1-2 (Glc b1-4) Man b1- Gal b1-2 (Glc b1-6) Man b1- Gal b1-3 (Glc b1-2) Man b1- Gal b1-3 (Glc b1-4) Man b1- Gal b1-3 (Glc b1-6) Man b1- Gal b1-4 (Glc b1-2) Man b1- Gal b1-4 (Glc b1-3) Man b1- Gal b1-4 (Glc b1-6) Man b1- Gal b1-6 (Glc b1-2) Man b1- Gal b1-6 (Glc b1-3) Man b1- Gal b1-6 (Glc b1-4) Man b1- Gal a1-2 (Man a1-3) Glc a1- Gal a1-2 (Man a1-4) Glc a1- Gal a1-2 (Man a1-6) Glc a1- Gal a1-3 (Man a1-2) Glc a1- Gal a1-3 (Man a1-4) Glc a1- Gal a1-3 (Man a1-6) Glc a1- Gal a1-4 (Man a1-2) Glc a1- Gal a1-4 (Man a1-3) Glc a1- Gal a1-4 (Man a1-6) Glc a1- Gal a1-6 (Man a1-2) Glc a1- Gal a1-6 (Man a1-3) Glc a1- Gal a1-6 (Man a1-4) Glc a1- Gal b1-2 (Man a1-3) Glc a1- Gal b1-2 (Man a1-4) Glc a1- Gal b1-2 (Man a1-6) Glc a1- Gal b1-3 (Man a1-2) Glc a1- Gal b1-3 (Man a1-4) Glc a1- Gal b1-3 (Man a1-6) Glc a1- Gal b1-4 (Man a1-2) Glc a1- Gal b1-4 (Man a1-3) Glc a1- Gal b1-4 (Man a1-6) Glc a1- Gal b1-6 (Man a1-2) Glc a1- Gal b1-6 (Man a1-3) Glc a1- Gal b1-6 (Man a1-4) Glc a1- Gal a1-2 (Man b1-3) Glc a1- Gal a1-2 (Man b1-4) Glc a1- Gal a1-2 (Man b1-6) Glc a1- Gal a1-3 (Man b1-2) Glc a1- Gal a1-3 (Man b1-4) Glc a1- Gal a1-3 (Man b1-6) Glc a1- Gal a1-4 (Man b1-2) Glc a1- Gal a1-4 (Man b1-3) Glc a1- Gal a1-4 (Man b1-6) Glc a1- Gal a1-6 (Man b1-2) Glc a1- Gal a1-6 (Man b1-3) Glc a1- Gal a1-6 (Man b1-4) Glc a1- Gal b1-2 (Man b1-3) Glc a1- Gal b1-2 (Man b1-4) Glc a1- Gal b1-2 (Man b1-6) Glc a1- Gal b1-3 (Man b1-2) Glc a1- Gal b1-3 (Man b1-4) Glc a1- Gal b1-3 (Man b1-6) Glc a1- Gal b1-4 (Man b1-2) Glc a1- Gal b1-4 (Man b1-3) Glc a1- Gal b1-4 (Man b1-6) Glc a1- Gal b1-6 (Man b1-2) Glc a1- Gal b1-6 (Man b1-3) Glc a1- Gal b1-6 (Man b1-4) Glc a1- Gal a1-2 (Man a1-3) Glc b1- Gal a1-2 (Man a1-4) Glc b1- Gal a1-2 (Man a1-6) Glc b1- Gal a1-3 (Man a1-2) Glc b1- Gal a1-3 (Man a1-4) Glc b1- Gal a1-3 (Man a1-6) Glc b1- Gal a1-4 (Man a1-2) Glc b1- Gal a1-4 (Man a1-3) Glc b1- Gal a1-4 (Man a1-6) Glc b1- Gal a1-6 (Man a1-2) Glc b1- Gal a1-6 (Man a1-3) Glc b1- Gal a1-6 (Man a1-4) Glc b1- Gal b1-2 (Man a1-3) Glc b1- Gal b1-2 (Man a1-4) Glc b1- Gal b1-2 (Man a1-6) Glc b1- Gal b1-3 (Man a1-2) Glc b1- Gal b1-3 (Man a1-4) Glc b1- Gal b1-3 (Man a1-6) Glc b1- Gal b1-4 (Man a1-2) Glc b1- Gal b1-4 (Man a1-3) Glc b1- Gal b1-4 (Man a1-6) Glc b1- Gal b1-6 (Man a1-2) Glc b1- Gal b1-6 (Man a1-3) Glc b1- Gal b1-6 (Man a1-4) Glc b1- Gal a1-2 (Man b1-3) Glc b1- Gal a1-2 (Man b1-4) Glc b1- Gal a1-2 (Man b1-6) Glc b1- Gal a1-3 (Man b1-2) Glc b1- Gal a1-3 (Man b1-4) Glc b1- Gal a1-3 (Man b1-6) Glc b1- Gal a1-4 (Man b1-2) Glc b1- Gal a1-4 (Man b1-3) Glc b1- Gal a1-4 (Man b1-6) Glc b1- Gal a1-6 (Man b1-2) Glc b1- Gal a1-6 (Man b1-3) Glc b1- Gal a1-6 (Man b1-4) Glc b1- Gal b1-2 (Man b1-3) Glc b1- Gal b1-2 (Man b1-4) Glc b1- Gal b1-2 (Man b1-6) Glc b1- Gal b1-3 (Man b1-2) Glc b1- Gal b1-3 (Man b1-4) Glc b1- Gal b1-3 (Man b1-6) Glc b1- Gal b1-4 (Man b1-2) Glc b1- Gal b1-4 (Man b1-3) Glc b1- Gal b1-4 (Man b1-6) Glc b1- Gal b1-6 (Man b1-2) Glc b1- Gal b1-6 (Man b1-3) Glc b1- Gal b1-6 (Man b1-4) Glc b1- Glc a1-2 (Man a1-3) Gal a1- Glc a1-2 (Man a1-4) Gal a1- Glc a1-2 (Man a1-6) Gal a1- Glc a1-3 (Man a1-2) Gal a1- Glc a1-3 (Man a1-4) Gal a1- Glc a1-3 (Man a1-6) Gal a1- Glc a1-4 (Man a1-2) Gal a1- Glc a1-4 (Man a1-3) Gal a1- Glc a1-4 (Man a1-6) Gal a1- Glc a1-6 (Man a1-2) Gal a1- Glc a1-6 (Man a1-3) Gal a1- Glc a1-6 (Man a1-4) Gal a1- Glc b1-2 (Man a1-3) Gal a1- Glc b1-2 (Man a1-4) Gal a1- Glc b1-2 (Man a1-6) Gal a1- Glc b1-3 (Man a1-2) Gal a1- Glc b1-3 (Man a1-4) Gal a1- Glc b1-3 (Man a1-6) Gal a1- Glc b1-4 (Man a1-2) Gal a1- Glc b1-4 (Man a1-3) Gal a1- Glc b1-4 (Man a1-6) Gal a1- Glc b1-6 (Man a1-2) Gal a1- Glc b1-6 (Man a1-3) Gal a1- Glc b1-6 (Man a1-4) Gal a1- Glc a1-2 (Man b1-3) Gal a1- Glc a1-2 (Man b1-4) Gal a1- Glc a1-2 (Man b1-6) Gal a1- Glc a1-3 (Man b1-2) Gal a1- Glc a1-3 (Man b1-4) Gal a1- Glc a1-3 (Man b1-6) Gal a1- Glc a1-4 (Man b1-2) Gal a1- Glc a1-4 (Man b1-3) Gal a1- Glc a1-4 (Man b1-6) Gal a1- Glc a1-6 (Man b1-2) Gal a1- Glc a1-6 (Man b1-3) Gal a1- Glc a1-6 (Man b1-4) Gal a1- Glc b1-2 (Man b1-3) Gal a1- Glc b1-2 (Man b1-4) Gal a1- Glc b1-2 (Man b1-6) Gal a1- Glc b1-3 (Man b1-2) Gal a1- Glc b1-3 (Man b1-4) Gal a1- Glc b1-3 (Man b1-6) Gal a1- Glc b1-4 (Man b1-2) Gal a1- Glc b1-4 (Man b1-3) Gal a1- Glc b1-4 (Man b1-6) Gal a1- Glc b1-6 (Man b1-2) Gal a1- Glc b1-6 (Man b1-3) Gal a1- Glc b1-6 (Man b1-4) Gal a1- Glc a1-2 (Man a1-3) Gal b1- Glc a1-2 (Man a1-4) Gal b1- Glc a1-2 (Man a1-6) Gal b1- Glc a1-3 (Man a1-2) Gal b1- Glc a1-3 (Man a1-4) Gal b1- Glc a1-3 (Man a1-6) Gal b1- Glc a1-4 (Man a1-2) Gal b1- Glc a1-4 (Man a1-3) Gal b1- Glc a1-4 (Man a1-6) Gal b1- Glc a1-6 (Man a1-2) Gal b1- Glc a1-6 (Man a1-3) Gal b1- Glc a1-6 (Man a1-4) Gal b1- Glc b1-2 (Man a1-3) Gal b1- Glc b1-2 (Man a1-4) Gal b1- Glc b1-2 (Man a1-6) Gal b1- Glc b1-3 (Man a1-2) Gal b1- Glc b1-3 (Man a1-4) Gal b1- Glc b1-3 (Man a1-6) Gal b1- Glc b1-4 (Man a1-2) Gal b1- Glc b1-4 (Man a1-3) Gal b1- Glc b1-4 (Man a1-6) Gal b1- Glc b1-6 (Man a1-2) Gal b1- Glc b1-6 (Man a1-3) Gal b1- Glc b1-6 (Man a1-4) Gal b1- Glc a1-2 (Man b1-3) Gal b1- Glc a1-2 (Man b1-4) Gal b1- Glc a1-2 (Man b1-6) Gal b1- Glc a1-3 (Man b1-2) Gal b1- Glc a1-3 (Man b1-4) Gal b1- Glc a1-3 (Man b1-6) Gal b1- Glc a1-4 (Man b1-2) Gal b1- Glc a1-4 (Man b1-3) Gal b1- Glc a1-4 (Man b1-6) Gal b1- Glc a1-6 (Man b1-2) Gal b1- Glc a1-6 (Man b1-3) Gal b1- Glc a1-6 (Man b1-4) Gal b1- Glc b1-2 (Man b1-3) Gal b1- Glc b1-2 (Man b1-4) Gal b1- Glc b1-2 (Man b1-6) Gal b1- Glc b1-3 (Man b1-2) Gal b1- Glc b1-3 (Man b1-4) Gal b1- Glc b1-3 (Man b1-6) Gal b1- Glc b1-4 (Man b1-2) Gal b1- Glc b1-4 (Man b1-3) Gal b1- Glc b1-4 (Man b1-6) Gal b1- Glc b1-6 (Man b1-2) Gal b1- Glc b1-6 (Man b1-3) Gal b1- Glc b1-6 (Man b1-4) Gal b1- Man a1-4 Gal a1-3 Glc b1 Man a1-6 Gal a1-3 Glc b1 Man b1-2 Gal a1-3 Glc b1 Man b1-3 Gal a1-3 Glc b1 Man b1-4 Gal a1-3 Glc b1 Man b1-6 Gal a1-3 Glc b1 Man a1-2 Gal a1-4 Glc b1 Man a1-3 Gal a1-4 Glc b1 Man a1-4 Gal a1-4 Glc b1 Man a1-6 Gal a1-4 Glc b1 Man b1-2 Gal a1-4 Glc b1 Man b1-3 Gal a1-4 Glc b1 Man b1-4 Gal a1-4 Glc b1 Man b1-6 Gal a1-4 Glc b1 Man a1-2 Gal a1-6 Glc b1 Man a1-3 Gal a1-6 Glc b1

  44. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  45. The Glyco World saccharides, glycosides & glycans • Glycans: the "missing mass" of the biological universe • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycans • Major glycans of eukaryotes

  46. Major Glycans of Eukaryotes • Glycoproteins • Glycolipids • Proteoglycans

  47. Major Glycans of Eukaryotes • Glycoproteins • Glycolipids • Proteoglycans

  48. Glycans are large hydrated surface components of glycoproteins HIV gp120 Burton DR et al (2012) Cell Host & Microbe 4:396

  49. HIV gp120 Doores K J et al. (2010) PNAS 107:17107

  50. 18 kDa protein 1.5 kDa GPI anchor Proteins fold onto themselves… glycans spread out in space 3 kDa N-linkedglycans 1 kDa N-linkedglycan membrane Essentials of Glycobiology Thy-1cell-cell interaction protein Second Edition

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