Number of Carbohydrate Units
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Transcript of Number of Carbohydrate Units
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Number of Carbohydrate Units
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Monosaccharides = single unitDisaccharides = two unitsOligiosaccharide = 3-10 unitsPolysaccharide = 11+ units
Bonus:• Can you name the most common Mono (4), Di(3), and Poly(4)-saccharides
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Number of Carbons
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3C = Triose4C = Tetrose5C = Pentose6C = Hexose7C = Heptose
Most common are 5 and 6 Carbon Carbohydrate
Bonus:• Can you name the most common pentose?• Can you name the most common hexoses?
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Functional Group
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Aldose = aldehyde Ketose = ketone
Bonus:• Can you name a common example of each?
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D or L Isomer
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• The orientation of the OH group furthest from the most oxidized end of a carbohydrate.• The bottom OH on a properly drawn Fischer Projection
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Size of Ring
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Furanose = 5 member ring - Ald/Ket + OH 4 carbons a way
Pyranose = 6 member ring - Ald/Ket + OH 5 carbons away
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Anomers
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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
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Epimers
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Definition:Two monosaccharide's that differ in the configuration around a single carbon.
OH
O
H OH
H OH
H OH
H OH
OH
O
OH HH OHH OHH OH
OH
O
H OHOH HH OHH OH
OH
O
H OHH OHOH HH OH
OH
O
H OH
H OH
H OH
OH H
D-allose D-altrose D-glucose D-gulose L-talose
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Drawing Pyranose Rings
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#1/5 CarbonsReact
L-side OHare up
R-side OHare down
• Number the chain to decrease mistakes• Left OH’s Up• Right OH’s Down• #6 - CH2OH group up for D-isomers
Hemiacetal reaction
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Drawing Furanose Rings
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#2/5 CarbonsReact
L-side OHare up
R-side OHare down
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Drawing Disaccharides
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• 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
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Hemiacetals, Acetals,Hemiketals, and Ketals
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O
OH
HH
H
OH
OH
H OH
HOH
Hemiacetals and Hemiketals• Capable of mutarotation• React easily• Reducing sugars
Acetals and Ketals• Not Capable of mutarotation• Not Reactive (hydrolysis)• Not Reducing sugars
O
H
HHH
OH
H
OH OH
OH
OH
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Monosaccharide’s
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4 Most Common Monosaccharide's
Structural Isomers
D-Glucose aldohexose pyranose bloodsugar, cellular
respiration
D-Galactose aldohexose pyranose milk, yogurt, cell
membranes
D-Fructose ketohexose furanose honey, sweetest sugar
D-Ribose aldopentose furanose DNAOH
O
H OH
OH H
OH H
H OH
OH
OH H
H OH
H OH
O
OH
OH
O
H OH
OH H
H OH
H OH
OH
O
H OH
H OH
H OH
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Disaccharides
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3 Most Common Disaccharides
Maltose α-D-Glucose + α-D-Glucose α-1,4beer, 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
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Polysaccharides
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4 Most Common Polysaccharide's
Starch
Amylose α-1,4 helix plant energy storage
Amylopectin α-1,4 (main)α-1,6 (side) treelike plant energy storage
Glycogen similar to amylopectin treelike animal energy storage
Cellulose β-1,4 linear/sheets
plant structural storage
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Starch
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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
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Glycogen
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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
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Cellulose
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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
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Mutarotation
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• Process by which anomer’s are interconverted• Equilibrium between cyclic and chain form.• Occurs because hemiacetal carbon can open/close
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Oxidation Reactions
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Mild OxidationAld CA
Strong OxidationAld CAAlc CA
-“onic” acid
-“aric” acid
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Reduction Reaction
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ReductionAld Alc -“itol” acid
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Kiliani-Fischer Reaction
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CyanohydrinRxn
Aldehyde CyanohydrinReduction
Rxn
Carboxylic Acid Aldehyde
HydrolysisRxn
Carbon ChainGains a Carbon
3C 4C
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Redox Tests
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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
mono/digeneral tests
Functional Groups:• Free Aldehydes• α-hydroxyketones• Hemiacetal
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Dehydration/Hydrolysis
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Carbohydrate molecules are joined by Dehydration Reactions (-H2O)Di/Oligio/Polysaccharides are broken apart by Hydrolysis Reactions (+H2O)
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Dehydration/Hydrolysis
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Carbohydrate molecules are joined by Dehydration Reactions (-H2O)Di/Oligio/Polysaccharides are broken apart by Hydrolysis Reactions (+H2O)
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Miscellaneous Applications
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Sweeteners
Antigens / Blood Types