Types of Carbohydrates Section 17.1 Four Types of Carbohydrates Monosaccharides Contain a single sugar unit Examples: glucose and fructose Disaccharides Contain two monosaccharides units joined through bridging oxygen atoms AKA glycosidic bond Examples: sucrose and lactose Four Types, continued Oligosaccharides Three to ten monosaccharide units joined by glycosidic bonds Polysaccharides Long, often highly branched, chains of monosaccharides Examples: starch, glycogen, and cellulose Monosaccharides Composed of carbon, hydrogen and oxygen Most follow the general formula (CH2O)n All names end in –ose Two types Ketose – monosaccharide that contains a ketone carbonyl group Aldose – monosaccharide that contains an aldehyde carbonyl group Ketose OR Aldose? O O CH CH2OH CH CH2OH C O HO C H OH H C OH OH H C OH H C OH C O H C OH H C OH HO C H HO C H H C OH H C OH H C H C OH H C OH H C CH2OH CH2OH CH2OH CH2OH Ketose OR Aldose O O CH CH2OH CH CH2OH C O HO C H OH H C OH OH H C OH H C OH C O H C OH H C OH HO C H HO C H H C OH H C OH H C H C OH H C OH H C CH2OH CH2OH CH2OH CH2OH Another system – number of carbons Another system of nomenclature tells us the number of carbon atoms in the main skeleton. 3 carbon triose 4 carbon tetrose 5 carbon pentose 6 carbon hexose Etc. Triose, tetrose, pentose, etc? O O CH O CH CH H C OH CH2OH H C OH HO C H H C OH H C OH H C OH H C OH H C OH CH2OH CH2OH Answers O O CH O CH CH H C OH CH2OH C OH HO C H H C OH H C OH H C OH H C OH H C OH CH2OH Triose H Pentose CH2OH Hexose Combining the two systems O CH2OH O CH CH H C H OH CH2OH HO H C C C C O HO C H H C OH H C OH OH H OH H C OH Aldose Triose CH2OH Aldotriose Aldose D-Glyceraldehyde Hexose Aldohexose D-Glucose CH2OH Ketose Hexose Ketohexose D-Fructose Stereochemistry: different spatial arrangements of atoms Enantiomers Chiral molecules 2 stereoisomers Molecules that exist as enantiomers that are (they have a right & nonsuperimposable left version) mirror images of one Chiral carbon another a carbon that has 4 different groups attached to it Chiral Objects Chiral compounds have the same number of atoms arranged differently in space. A chiral carbon atom has four different groups attached. Mirror Images The three-dimensional structure of a chiral compound has a mirror image. Your hands are chiral. Try to superimpose your thumbs, palms, back of hands, and little fingers. Is it possible? Why or why not? Important in biochemistry because our biochemical processes will recognize & act on only ONE of the chiral compounds. The other compound is foreign to us. Chiral or NOT? Determine if there is a chiral carbon in each compound. Cl C CH3 H CH2CH3 A Cl H C CH3 H B Solution Cl Cl H C CH3 CH2CH3 A Yes, 4 different groups are attached to the second C atom H C CH3 H B No, the 2 H atoms are identical D and L Notation D,L tells to which of the two chiral isomers we are referring. If the –OH group on the next to the bottom carbon atom points to the right, the isomer is a D-isomer; if it points left, the isomer is L. The D form is usually the isomer found in nature. D notation H C O H C OH H C OH CH2OH Right = D Glucose H C O H C OH HO C H H C OH H C OH CH 2OH D-Glucose D or L? Homework Complete problems 17.3 and 17.4 on page 472; 17.5 and 17.6 on page 474-5; 17.24, 17.25, and 17.26 on page 493 Importance of Glucose Most important sugar in the human body. Glucose is broken down in glycolysis and other pathways to release energy for body functions The concentration of glucose in the blood is carefully controlled by insulin and glucagon. Normal blood glucose levels are 100-120 mg/100mL Importance of Glucose Insulin stimulates the uptake of the excess glucose by most of the cells in the body. 1-2 hrs after eating the glucose levels return to normal. If glucose concentrations drop too low, the individual feels lightheaded and shaky. When this happens, glucagon stimulates the liver to release glucose in the blood. Diabetes / Hypoglycemia and Glucose Type I diabetes or diabetes mellitus – caused by the inability to produce the hormone insulin; If untreated, end up with high blood sugar Type II diabetes or adult-onset diabetes – caused by insulin resistance (body fails to properly use insulin) combined with a relative insulin deficiency; If untreated, end up with high blood sugar Hypoglycemia – caused by the over excretion of insulin in response to a rise in blood sugar; If untreated, end up with low blood sugar Structure of glucose In reality, the open-chain form of glucose is present in very small concentrations in cells. In most cases, the cyclic intramolecular hemiacetal is formed. The hydroxyl group on C-5 reacts with the aldehyde group to form a hemiacetal. Two isomers are formed because a new chiral carbon is created. 6 CH2OH 5 O 1 H HO H H CH 2 3 4 α-D-glucose O H H 1 4 OH H OH OH 3 H H OH 6 CH2OH 2 5 O OH H OH OH H 4 H 5 OH 1 OH 6 CH2OH D-glucose OH 3 β-D-glucose H H H 2 OH Steps for drawing Haworth Structures for D-Glucose 1. Break the double bond 2. Move the H from the –OH group on C5 to the O on C1 3. Connect the ring structure by bonding the O on C5 directly to C1 4. Write –OH groups on the right (C2, C4) down 5. Write –OH groups on the left (C3) up 6. The new –OH on C1 has two possibilites: down for form, up for form α-D-glucose CH2OH H C OH O H C OH HO C H H HO C OH H2 C C H H O OH H H OH H H OH OH β-D-glucose CH2OH HO C H O H C H OH OH H O HO C H OH H HO H2 C C C OH H H OH OH H H You Try This One! Write the cyclic form of -D-galactose H O C H C OH HO C H HO C H H C OH CH 2OH Solution -D-galactose H C OH H C OH CH2OH O HO OH C H OH C H CH2 C H o OH OH OH OH Benedict’s reagent Benedict’s reagent – a basic buffer solution that contains Cu2+ ions It readily oxidizes the aldehyde group of aldoses to form a brick red Cu2O precipitate. It will also oxidize ketoses because of the –OH group on the carbon next to the carbonyl group. Reducing Sugars Reducing sugar – a sugar that can be oxidized by Benedict’s reagent All monosaccharides and the common disaccharides (except sucrose) are reducing sugars. Use of Benedict’s reagent Benedict’s reagent was commonly used to qualitatively monitor excess glucose in the urine by diabetics to insure proper dosage of insulin. These have been replaced by blood glucose tests that are more accurate.