Carbohydrates 121409 2 slide

Carbohydrates 121409 2 slide - 1 C ARBOHYDRATES (C HS . 3...

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Unformatted text preview: 1 C ARBOHYDRATES (C HS . 3 & 4) Lia M. Nightingale, Ph.D. C ARBOHYDRATE I NTRODUCTION Contains C, H, O C(H 2 O) hydrated carbon Major source of energy for the body the brain requires ~130 g of glucose/day!! 4 kcal/g 2 Carbohydrates Simple Carbs Monosaccharides Disaccharides Complex Carbs Oligosaccharides Polysaccharides Sweet Sweet Sugars Saccharides or glycans S IMPLE C ARBOHYDRATES Monosaccharides Glucose (glu) Fructose (fru) Galactose (gal) 1 sugar 3 S IMPLE C ARBOHYDRATES Disaccharides Sucrose Glucose Fructose Lactose Glucose Galactose Maltose Glucose Glucose 2 sugars C OMPLEX C ARBOHYDRATES Oligosaccharides Raffinose (glu, fru, gal) Stachyose (glu, fru, 2 gal) 3-10 sugars 4 C OMPLEX C ARBOHYDRATES Polysaccharides Homopolysaccharides Starch Cellulose Heteropolysaccharides Pectin Gums >10 sugars 1 type of sugar >1 type of sugar N OMENCLATURE 3 C sugar = ____________ 4 C sugar = ____________ 5 C sugar = ____________ 6 C sugar = ____________ End in ose!! 5 C O C HO C H C OH H C OH H C OH H H H 2 OH D-glucose CH 2 OH C HO C H C O C OH H C OH H H 2 OH D-fructose If it contains an aldehyde, it is known as an aldose . If it contains a ketone, it is known as a ketose . N OMENCLATURE 5C aldehyde sugar = _______________ 6C aldehyde sugar = _______________ 5C ketone sugar = _______________ 6C ketone sugar = _______________ 6 D VS . L R EVIEW Position of OH on highest number chiral carbon Right = dextrorotary (D) Left = levorotary (L) NOT in reference to rotation of polarized light Most sugars are D D VS . L R EVIEW C O C HO C H C OH H C OH H C OH H 1 2 3 4 5 6 H H 2 OH Shortcut: The highest numbered chiral carbon is almost always the next to last carbon (above CH 2 OH). 7 D VS . L R EVIEW HC O C HO H 2 C OH H Glyceraldehyde L HC O C OH H 2 C OH H Glyceraldehyde D E PIMERS Isomers where the only difference is the rotation around 1C (type of diastereomer ) C O C HO C H C OH H C HO H C OH H H H 2 OH C O HC OH C C OH H C HO H C OH H H H 2 OH R R L L L R R R NBQ 8 D RAWING F ISCHER P ROJECTIONS C O C HO C H C OH H C HO H C OH H H H 2 OH CH 2 OH CHO D-sugar Simplified structures Lines signify hydroxyl groups in carbohydrate chemistry (not methyl groups)!! Remember: aldehydes = CHO P RACTICE CHO HC OH C OH H C OH H CH 2 OH ribose 9 C OMMON M ONOSACCHARIDES CH 2 OH CHO D-Glucose CH 2 OH CHO D-Galactose CH 2 OH D-Fructose O CH 2 OH C ARB S TRUCTURE Carbs are not normally in open chains Usually found in cyclic structures Cyclized aldose = hemiacetal Cyclized ketose = hemiketal Formed by intramolecular rearrangement 10 C ARB S TRUCTURE Rearrangement between anomeric carbon (contains double bonded O) and D/L hydroxyl group....
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Carbohydrates 121409 2 slide - 1 C ARBOHYDRATES (C HS . 3...

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