Number of Carbohydrate Units

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Transcription:

Number of Carbohydrate Units

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

Number of Carbons

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?

Functional Group

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

D or L Isomer

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

Size of Ring

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

Anomers

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

Epimers

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

Drawing Pyranose Rings

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

Drawing Furanose Rings

#2/5 Carbons React L side O are up R side O are down

Drawing Disaccharides

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

emiacetals, Acetals, emiketals, and Ketals

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

Monosaccharide s

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

Disaccharides

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

Polysaccharides

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

Starch

Amylose: 25 1300 α D Glucose units α 1,4 glycosidic bonds Forms coils/helical/telephone structure Energy storage for plants Amylopectin: 25 1300 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

Glycogen

Glycogen: 25 1300 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

Cellulose

Cellulose: 25 1300 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

Mutarotation

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

Oxidation Reactions

Mild Oxidation Ald CA onic acid Strong Oxidation Ald CA Alc CA aric acid

Reduction Reaction

Reduction Ald Alc itol acid

Kiliani Fischer Reaction

Carbon Chain Gains a Carbon 3C 4C Aldehyde Cyanohydrin Cyanohydrin ydrolysis Rxn Rxn Carboxylic Acid Reduction Rxn Aldehyde

Redox Tests

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

Dehydration/ydrolysis

Carbohydrate molecules are joined by Dehydration Reactions ( 2 O) Di/Oligio/Polysaccharides are broken apart by ydrolysis Reactions (+ 2 O)

Dehydration/ydrolysis

Carbohydrate molecules are joined by Dehydration Reactions ( 2 O) Di/Oligio/Polysaccharides are broken apart by ydrolysis Reactions (+ 2 O)

Miscellaneous Applications

Sweeteners Antigens / Blood Types

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