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Carbohydrates

Carbohydrates. Carbohydrate. hydrate of carbon – C n (H 2 O) m Glucose -blood sugar- C 6 H 12 O 6 or C 6 (H 2 O) 6 Sucrose -table sugar- C 12 H 22 O 11 or C 12 (H 2 O) 11. Not all carbohydrates have this exact form – old habits die slow or sometimes never at all. Monosaccharides.

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Carbohydrates

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  1. Carbohydrates

  2. Carbohydrate • hydrate of carbon – Cn(H2O)m • Glucose -blood sugar- C6H12O6 or C6(H2O)6 • Sucrose -table sugar- C12H22O11 or C12(H2O)11

  3. Not all carbohydrates have this exact form – old habits die slow or sometimes never at all

  4. Monosaccharides • Formula CnH2nOn • One carbon is either an aldehyde or ketone • The suffix ose indicates that the molecule is a carbohydrate • Use prefix to indicate number of carbons tri , tetr, pent, hex • Aldose – contain an aldehyde group • Ketose – contain a ketone group

  5. Aldohexoses carbohydrates or saccharides aldehyde function six carbons Monosaccharides • Aldohexoses other examples: ketotetrose, aldotriose, ketopentose

  6. A B D C Fischer Projections • Emil Fischer (late 1800’s) • Side groups come out of the plane (towards you) • Vertical groups go back away from you

  7. Naming Aldotriose and aldotetrose Remember ET goes home left at T

  8. Naming AldoPentose RAXL – Ribose, Araginose, Xylose, Lyxose Right – Top – Middle – Top/Middle

  9. Naming Aldohexoses • All Altrose Gladly Make Gum in Gallon Tanks • Bottom – all right • 2 up – 4x4 • 3 up – 2x2 like Noahs Ark • 4 up – alternate

  10. R/S and D/L • R = D - dextrorotatory • S = L - levarotatory • D – A monosaccharide with the Penultimate OH group on the right in a Fischer Projection • L - A monosaccharide with the penultimate OH group on the left in a Fischer Projection OK, so what’s a penultimate????

  11. Ketoses triose * • Note: The ketone is located on carbon #2 tetrose pentoses Penultimate is the next To last carbon hexoses *

  12. Amino Sugars • Contain an NH2 group instead of an OH • 1st three are common in nature

  13. Cyclic structure of monsacharides • It’s the hemiacetal reaction all over • We draw them as Haworth Projections • Practice practice practice From yahoo images

  14. Reactions of Monosacharides • Practice From yahoo images

  15. The two Most Significant Sugars • Ketose • D-Fructose • Known as “fruit sugar” • Found combined with glucosein the disaccharide sucrose • Aldose • -D-glucose • -The most important • monosaccharide • -White solid • -Formula C6H12O6 • - Sugar used in our bodies

  16. Multiple Sugars • Monosaccharides – Single Carbohydrate unit • Disaccharides - two monosaccharides combined • Oligosaccharides - three to ten monosaccharides • Polsaccharide – More than ten monoscharides

  17. Three Disaccharides • Sucrose • Lactose • Maltose

  18. Disaccharides * • Sucrose • A disaccharide • One D-glucose andone D-Fructose • Connected by two anomeric carbons:C-1on glucose and C-2on fructose linkages:linkage on glucose andlinkage on fructose

  19. Disaccharides * • Sucrose • Anomeric C are tied-upon both sugars • No oxidation can occurno hemi-acetals • Sucrose is a non-reducing sugar • Hydrolyzed by enzymes to form a mixture ofglucose and fructose - “invert sugar”

  20. -C-1 -C-2 Disaccharides * • Sucrose

  21. Disaccharides * • Lactose • A disaccharide • One D-galactose andone D-glucose • Connected by an  linkagebetween D-Galactose C-1 and D-Glucose C-4 • Known as an -1,4 linkage • Found in mammalian milk

  22. -1,4 linkage Lactose Disaccharides

  23. Disaccharides * • Maltose • A disaccharide • Two D-glucose monomers • Connected by an  linkagebetween C-1 and C-4 • Known as an -1,4 linkage (two D-glucose molecules) • An ingredient in most syrups • “Malt sugar”

  24. -1,4 linkage Disaccharides

  25. Polysaccharides * • Starch - Amylose • Many units of -D-glucose • Linkages are -1,4 (same as Maltose) • Between 1000-2000 glucoseunits (polyglucose) • Random coils or helix

  26. Polysaccharides * • Starch - Amylopectin • Also many units of -D-glucose • Linkages are -1,4 and -1,6 • Lots of branching • 20 to 25 glucose monomers inthe straight chain and then branching • A total of 105 to 106glucose molecules • Use Iodine (I2) to test for starches

  27. Polysaccharides * • Glycogen • Animal energy storage (about 400 g in us) • -D-glucose polymer • Similar to amylopectin but smaller chains • Linkages are -1,4 and -1,6 (branching) • 10 to 20 glucose monomers in thestraight chain and then branching • A total of 105 to 106glucose molecules

  28. Polysaccharides * • Cellulose • Linear polymer of D-glucose • Linkages are -1,4 ! • The most abundant molecule inliving tissues • Cotton is about 95% cellulose • 300 to 3000 glucose units • Form fibrous rods

  29. Polysaccharides * • Cellulose • We cannot digest cellulose •  glucose linkages! • Many bacteria and fungihave necessary enzyme • Ruminant mammals carrythese bacteria • Termites also have necessarymicroorganisms

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