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The Glyco World saccharides, glycosides & glycans

The Glyco World saccharides, glycosides & glycans. What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources.

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The Glyco World saccharides, glycosides & glycans

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  1. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

  2. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

  3. “Understanding the structures and functions of glycans is central to understanding biology.” “… Glycoscience researchers have developed a knowledge base that can be used to address many of today’s major research problems. When combined with current tools, it is a powerful resource to better understand human, plant, and microbial biology..” National Academies Press (2012)

  4. What if a MAJOR cell component was invisible by standard microscopy? Light microscopy micrograph of Cryptococcus neoformans Steenbergen et al. (2003) Microbes and Infection 5:667 Light microscopy 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 microscopy of C. neoformans yeast cells. Van Duin et al. (2004) Antimicrobial Agents and Chemotherapy 48:2014

  5. Unique to yeast – NO! 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

  6. ? Tiny sugar “decorations”..added as an afterthought The Eukaryotic Cell Surface Lodish, et al. (1995) Molecular Cell Biology 3rd ed.

  7. Eukaryotic cell surface The “glycocalyx” surrounding a fibroblast– glycans stained black extracellular lipid bilayer fibroblast intracellular Martinez-Palomo, A., et al. Cancer Res. 29, 925-937, 1969 “Every eukaryotic cell is covered with a dense and complex array of glycans, which also feature prominently in extracellular matrix and secreted soluble molecules.” … in fact… “Evolution has failed to generate a [single] living cell devoid of surface glycosylation” - A. Varki

  8. Tropical Forest Canopy Ajit Varki, “Perspectives on the Future of Glycobiology,” Athens, GA, 14-Mar-2011

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

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

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

  12. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

  13. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

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

  15. Generalized Aldose fructose glucose Generalized Ketose

  16. Generalized Aldose Glycoaldehyde

  17. Enantiomers: mirror images of each other that are not superimposable. Diastereomers: stereoisomers that are not enantiomers. Generalized Aldose

  18. Fischer projection D-glyceraldehyde

  19. Enantiomers * * D-glyceraldehyde L-glyceraldehyde * Highest numbered asymmetric carbon = reference carbon

  20. Diasteriomers * * * Highest numbered asymmetric carbon = reference carbon

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

  22. * * * * * * Second Edition * epimers: differ in only stereogenic center Essentials of Glycobiology

  23. Monosaccharides 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

  24. Determining anomeric configuration [PDB] Same direction as reference carbon = α Different direction from reference carbon = β Lee & Lee (1999) J Chinese Chem Soc 46:283-291

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

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

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

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

  29. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

  30. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

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

  32. 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

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

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

  35. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

  36. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

  37. Sugars, polysaccharides, oligosaccharides and glycoconjugates • Simple mono- or disaccharides: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 (e.g. 3 or more) in linear or branched glycosidic linkage • Examples: Sugars groups bound to proteins or lipids to form glycoconjugates (see below) • Glycoconjugates • Examples: Glycoproteins, glycolipids, proteoglycans

  38. 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

  39. 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

  40. 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

  41. 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

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

  43. Oligosaccharides: Molecular diversity of glycans

  44. 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 …

  45. 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

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

  47. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

  48. The Glyco World saccharides, glycosides & glycans • What’s the (sugar) buzz? • Carbohydrates: The language of glycoscience • The glycosidic bond and glycan nomenclature • Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates • Definitions and resources

  49. What are: Glycobiology? Glycosciences? Glycomics?

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