Number of Carbohydrate Units
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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 = exose 7C = eptose 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 O group furthest from the most oxidized end of a carbohydrate. The bottom O on a properly drawn Fischer Projection
9 Size of Ring
10 Furanose = 5 member ring Ald/Ket + O 4 carbons a way Pyranose = 6 member ring Ald/Ket + O 5 carbons away
11 Anomers
12 Definition: Diastereomers that differ in the configuration/orientation around the O 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. O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O D allose D altrose D glucose D gulose L talose
15 Drawing Pyranose Rings
16 Number the chain to decrease mistakes Left O s Up Right O s Down #6 C 2 O group up for D isomers emiacetal reaction #1/5 Carbons React R side O are down L side O are up
17 Drawing Furanose Rings
18 #2/5 Carbons React L side O are up R side O are down
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 emiacetals, Acetals, emiketals, and Ketals
22 O O O O O O emiacetals and emiketals Capable of mutarotation React easily Reducing sugars O O O O O O Acetals and Ketals Not Capable of mutarotation Not Reactive (hydrolysis) Not Reducing sugars
23 Monosaccharide s
24 Structural Isomers D Glucose D Galactose D Fructose D Ribose O 4Most Common Monosaccharide's aldohexos e aldohexos e ketohexos e aldopento se O pyranose pyranose furanose furanose O bloodsugar, cellular respiration milk, yogurt, cell membranes honey, sweetest sugar DNA O O O O O O O O O O O O O O O O O O O O
25 Disaccharides
26 3Most 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 4Most Common Polysaccharide's Starch Amylose α 1,4 helix plant energy storage Amylopectin Glycogen Cellulose α 1,4 (main) α 1,6 (side) similar to amylopectin β 1,4 treelike treelike linear/ sheets plant energy storage animal energy storage 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 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 Cellulose: β D Glucose units β 1,4 glycosidic bonds Forms linear chains, strong 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 Strong Oxidation Ald CA Alc CA aric acid
39 Reduction Reaction
40 Reduction Ald Alc itol acid
41 Kiliani Fischer Reaction
42 Carbon Chain Gains a Carbon 3C 4C Aldehyde Cyanohydrin Cyanohydrin ydrolysis Rxn Rxn Carboxylic Acid Reduction Rxn Aldehyde
43 Redox Tests
44 Redox Tests for Carbohydrates: Benedicts/Fehling/ Barfoeds Cu +2 Cu 2 O (s) Blue Brick Red ppt general tests mono/di Tollens Reduce Ag + Ag (s) Silver Mirror Sugar is Oxidized, Metals are Reduced Functional Groups: Free Aldehydes α hydroxyketones emiacetal
45 Dehydration/ydrolysis
46 Carbohydrate molecules are joined by Dehydration Reactions ( 2 O) Di/Oligio/Polysaccharides are broken apart by ydrolysis Reactions (+ 2 O)
47 Dehydration/ydrolysis
48 Carbohydrate molecules are joined by Dehydration Reactions ( 2 O) Di/Oligio/Polysaccharides are broken apart by ydrolysis Reactions (+ 2 O)
49 Miscellaneous Applications
50 Sweeteners Antigens / Blood Types
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