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Number of Carbohydrate Units.

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Presentation on theme: "Number of Carbohydrate Units."— Presentation transcript:

1 Number of Carbohydrate Units

2 Monosaccharides = single unit
Disaccharides = two units Oligiosaccharide = 3-10 units Polysaccharide = 11+ units Bonus: Can you name the most common Mono (4), Di(3), and Poly(4)-saccharides

3 Number of Carbons

4 3C = Triose 4C = Tetrose 5C = Pentose 6C = Hexose 7C = Heptose Most common are 5 and 6 Carbon Carbohydrate Bonus: Can you name the most common pentose? Can you name the most common hexoses?

5 Functional Group

6 Aldose = aldehyde Ketose = ketone Bonus: Can you name a common example of each?

7 D or L Isomer

8 The orientation of the OH group furthest from the most
oxidized end of a carbohydrate. The bottom OH on a properly drawn Fischer Projection

9 Size of Ring

10 Furanose = 5 member ring - Ald/Ket + OH 4 carbons a way
Pyranose = 6 member ring - Ald/Ket + OH 5 carbons away

11 Anomers

12 Definition: Diastereomers that differ in the configuration/orientation around the OH group on the carbon capable of mutarotation (hemiacetal or hemiketal carbon) BUDA (Beta Up, Down Alpha) Beta - Up Down - Alpha

13 Epimers

14 Definition: Two monosaccharide's that differ in the configuration around a single carbon. D-allose D-altrose D-glucose D-gulose L-talose

15 Drawing Pyranose Rings

16 Number the chain to decrease mistakes
Left OH’s Up Right OH’s Down #6 - CH2OH group up for D-isomers Hemiacetal reaction #1/5 Carbons React R-side OH are down L-side OH are up

17 Drawing Furanose Rings

18 #2/5 Carbons React R-side OH are down L-side OH are up

19 Drawing Disaccharides

20 Formed by a dehydration reaction
Draw a disaccharide given two monosaccharide's and the linkage Name disaccharides First ring (yl ending), Second normal “Sucrose” α-D-glucopyranosyl-(1,2)- β-D-fructofuranose “Lactose” β -D-galactopyranosyl-(1,4)-α-D-glucopyranose

21 Hemiacetals, Acetals, Hemiketals, and Ketals

22 Hemiacetals and Hemiketals
Capable of mutarotation React easily Reducing sugars Acetals and Ketals Not Capable of mutarotation Not Reactive (hydrolysis) Not Reducing sugars

23 Monosaccharide’s

24 4 Most Common Monosaccharide's
Structural Isomers D-Glucose aldohexose pyranose bloodsugar, cellular respiration D-Galactose milk, yogurt, cell membranes D-Fructose ketohexose furanose honey, sweetest sugar D-Ribose aldopentose DNA

25 Disaccharides

26 3 Most Common Disaccharides
Maltose α-D-Glucose + α-D-Glucose α-1,4 beer, starch breakdown product Lactose β-D-Galactose + α-D-Glucose β-1,4 milk sugar Sucrose α-D-Glucose + β-D-Fructose α-β-1,2 table sugar

27 Polysaccharides

28 4 Most Common Polysaccharide's
Starch Amylose α-1,4 helix plant energy storage Amylopectin α-1,4 (main) α-1,6 (side) treelike Glycogen similar to amylopectin animal energy storage Cellulose β-1,4 linear/ sheets plant structural storage

29 Starch

30 Amylose: α-D-Glucose units α-1,4-glycosidic bonds Forms coils/helical/telephone structure Energy storage for plants Amylopectin: α-D-Glucose units α-1,4-glycosidic bonds, branched every 25 glucose with a α-1,6-glycosidic bond Forms tree like structure Energy storage for plants

31 Glycogen

32 Glycogen: α-D-Glucose units α-1,4-glycosidic bonds, branched every 12-18 glucose with a α-1,6-glycosidic bond Forms tree like structure Similar to amylopectin, but more branched Energy storage for animals

33 Cellulose

34 or Cellulose: 25-1300 β-D-Glucose units β-1,4-glycosidic bonds
Forms linear chains, strong H-bonds leads to the formation of sheets Resistant to hydrolysis, indigestible by humans Most abundant organic substance in nature Chief structural component of plants and wood or

35 Mutarotation

36 Process by which anomer’s are interconverted
Equilibrium between cyclic and chain form. Occurs because hemiacetal carbon can open/close

37 Oxidation Reactions

38 Mild Oxidation Ald  CA -“onic” acid -“aric” acid Strong Oxidation Ald  CA Alc  CA

39 Reduction Reaction

40 Reduction Ald  Alc -“itol” acid

41 Kiliani-Fischer Reaction

42 Carbon Chain Gains a Carbon 3C  4C Cyanohydrin Rxn Aldehyde Reduction
Carboxylic Acid Hydrolysis

43 Redox Tests

44 Redox Tests for Carbohydrates:
Benedicts/Fehling/ Barfoeds – Cu+2  Cu2O (s) “Blue  Brick Red ppt Tollens – Reduce Ag+  Ag (s) “Silver Mirror” Sugar is Oxidized, Metals are Reduced general tests mono/di Functional Groups: Free Aldehydes α-hydroxyketones Hemiacetal

45 Dehydration/Hydrolysis

46 Carbohydrate molecules are joined by Dehydration Reactions (-H2O)
Di/Oligio/Polysaccharides are broken apart by Hydrolysis Reactions (+H2O)

47 Dehydration/Hydrolysis

48 Carbohydrate molecules are joined by Dehydration Reactions (-H2O)
Di/Oligio/Polysaccharides are broken apart by Hydrolysis Reactions (+H2O)

49 Miscellaneous Applications

50 Sweeteners Antigens / Blood Types

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