Number of Carbohydrate Units

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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
Transcript
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 = 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?
  • Functional Group Aldose = aldehyde Ketose = ketone
  • Bonus:
  • Can you name a common example of each?
  • D or L Isomer
  • The orientation of the OH group furthest from the most
  • oxidized end of a carbohydrate.
  • The bottom OH on a properly drawn Fischer Projection
  • Size of Ring Furanose = 5 member ring - Ald/Ket + OH 4 carbons a way Pyranose = 6 member ring - Ald/Ket + OH 5 carbons away Anomers
  • Definition:
  • Diastereomers that differ in the configuration/orientation around the
  • OH group on the carbon capable of mutarotation
  • (hemiacetalor 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. D-allose D-altrose D-glucose D-gulose L-talose Drawing Pyranose Rings Hemiacetal reaction
  • Number the chain to decrease mistakes
  • Left OH’s Up
  • Right OH’s Down
  • #6 - CH2OH group up for D-isomers
  • #1/5 Carbons React R-side OH are down L-side OH are up Drawing Furanose Rings #2/5 Carbons React R-side OH are down L-side OH are up 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 Hemiacetals, Acetals, Hemiketals, and Ketals
  • Hemiacetals and Hemiketals
  • Capable of mutarotation
  • React easily
  • Reducing sugars
  • Acetals and Ketals
  • Not Capable of mutarotation
  • Not Reactive (hydrolysis)
  • Not Reducing sugars
  • Monosaccharides Disaccharides Polysaccharides 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 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
  • Mutarotation
  • Process by which anomers are interconverted
  • Equilibrium between cyclic and chain form.
  • Occurs because hemiacetal carbon can open/close
  • Oxidation Reactions Mild Oxidation Ald CA -“onic” acid -“aric” acid Strong Oxidation Ald CA Alc  CA Reduction Reaction Reduction Ald Alc -“itol” acid Kiliani-Fischer Reaction Carbon Chain Gains a Carbon 3C  4C Aldehyde Carboxylic Acid Cyanohydrin Aldehyde Cyanohydrin Rxn Reduction Rxn Hydrolysis Rxn Redox Tests
  • 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/di general tests
  • Functional Groups:
  • Free Aldehydes
  • α-hydroxyketones
  • Hemiacetal
  • Dehydration/Hydrolysis Carbohydrate molecules are joined by Dehydration Reactions (-H2O) Di/Oligio/Polysaccharides are broken apart by Hydrolysis Reactions (+H2O) Dehydration/Hydrolysis Carbohydrate molecules are joined by Dehydration Reactions (-H2O) Di/Oligio/Polysaccharides are broken apart by Hydrolysis Reactions (+H2O) Miscellaneous Applications Sweeteners Antigens / Blood Types
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