1. 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

2. 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

4. National Academies Press (2012)
“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..”

5. What if a MAJOR cell component was invisible by standard microscopy?
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
Light microscopy micrograph of Cryptococcus neoformans
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

6. Unique to yeast – NO!
Electron microscopic thin section of Escherichia coli K1
Amako et al. (1988) J Bacteriol 170:4960
Electron microscopic thin section of Klebsiella pneumoniae
Amako et al. (1988) J Bacteriol 170:4960

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

8. Eukaryotic cell surface
The “glycocalyx” surrounding a fibroblast – glycans stained black
extracellular
lipid bilayer
fibroblast
intracellular
Martinez-Palomo, A., et al. Cancer Res. 29, , 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

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

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

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

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

13. 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

14. 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

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

16. glucose
fructose
Generalized Ketose
Generalized Aldose

17. Generalized Aldose
Glycoaldehyde

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

19. Fischer projection
D-glyceraldehyde

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

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

22. diasteriomers & enantiomers
Enantiomers & Diasteriomers * *
carbons
asymmetric carbons
diaster- iomers
diasteriomers & enantiomers 3 1 2 4 5 8 6 16 * * *
Highest numbered asymmetric carbon = reference carbon

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

24. Monosaccharides equilibrate between open chain and ring forms
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

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

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

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

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

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

30. 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

31. 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

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

33. 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

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

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

36. 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

37. 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

38. 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

39. 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

40. 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

41. 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.
(α1-4 Glc α1-4 Glc)n
α1-6 Glc branches

42. 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

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

44. Oligosaccharides: Molecular diversity of glycans
Polypeptides
Glycans
Building blocks
amino acids
monosaccharides
Number of different monomers
20 common
9 common
Linkage sites per monomer 1
3-4
Possible linkage configurations 2
Possible homodimer structures
6-8
Linkage modes
linear
linear or branched

45. Three different amino acids (Ala, Ser, Tyr) – 6 structures Ala-Ser-Tyr   
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 …

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

47. Major Glycoconjugates of Eukaryotes
Glycoproteins
Glycolipids
Proteoglycans

48. 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

49. 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

50. What are:
Glycobiology?
Glycosciences?
Glycomics?

51. Glycobiology
The study of the biological functions, structures, recognition and biosynthesis of glycans (sugar chains, saccharides) in the context of the biological scaffolds to which they are attached (e.g. glycolipids & glycoproteins).

52. Glycosciences Glycobiology & Glycochemistry, including…
-Chemical synthesis -Chemoenzymatic synthesis -Metabolic engineering -Glycomimetics -Glycan conformation and structure -Material Sciences -Plant and bacterial polysaccharides

53. Glycomics - Analytical glycosciences -Glycan bioinformatics
“Glycome” – The total complement of glycans in a cell or organism

54. Glycobiology resources
Oxford University Press, New York
Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY. Content freely available at: