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Birkholz CHM 106 CH6
Carbohydrates Chapter 6
| Question | Answer |
|---|---|
| Simple sugars | provide NRG |
| Complex ones are starches and insoluble fibers found in | plants; cellulose |
| Monosaccharides | simplest; one sugar; sweet tasting; general formula Cn(H2O)n; glucose |
| Disaccharides | two monosaccharides; can be split via hydrolysis; C12H22O11 (sucrose, table sugar); splits into glucose and fructose |
| Oligosaccharides | three to nine monosaccharides; blood typing groups |
| Polysaccharides | ten or more monosaccharides |
| Soluble fiber | mix with H2O forms gel like substance and swells; slows sugar absorption; oatmeal, legumes, apples, carrots |
| Insoluble fiber | do not mix with H2O; laxative effect; cellulose, grains, seeds, cabbage |
| Alcohols | has OH group Primary, secondary, and tertiary alcohols—named based on how many alkyl (CH3) groups bound to the C |
| Aldehydes | carbonyl group; H-C=O |
| Ketones | like aldehydes; alkyl or aromatic group on both sides of the carbonyl; H3C–C-CH3 |
| Aldose | monosaccharide with aldehyde; glucose |
| Ketose | monosaccharide with ketone; fructose |
| Functional Groups in Monosaccharides | Alcohol, Aldehydes, Ketones, Aldose, Ketose |
| Glucose 4 ; ____________ 24 = 16 stereoisomers | chiral centers Fun fact- the intersections on Fischer projects are presumed to be chiral centers |
| Fischer Projection is a | a two-dimensional representation of a three-dimensional organic molecule by projection |
| Aldose—glyceraldehyde—C3H6O3; 1 chiral center; only 2 ____________ | enantiomers |
| Chiral center is on the plane of the paper; wedges—_________; dashes—__________ | in front; behind |
| Horizontal lines— ____________; vertical lines—______________ | wedges; dashes |
| D-sugars | the –OH on the chiral center farthest from carbonyl group on RIGHT side |
| L-sugars | the –OH on the chiral center farthest from the carbonyl group on LEFT side |
| Diastereomers | stereoisomers that are NOT enantiomers; not exact mirror images |
| D-galactose and D-talose are _________ of D-glucose | diastereomers |
| Glucose (dextrose on food labels) broken down in____________; diabetics problem | cells |
| Building block for sucrose, lactose, polysaccharides | amylose, amylopectin, glycogen, and cellulose |
| __________—diastereomer that differs at just one chiral center; galactose and glucose | Epimer |
| ______________—cranberries; bacteria attaches to it rather than other carbohydrates in bladder | Mannose |
| ____________ —sweetest monosaccharide; 1.5 X sweeter than table sugar | Fructose |
| Ring formation | a five-membered ring with an oxygen in it is called a furanose (another common form, a six-membered ring, is called a pyranose). |
| Linear structures do not show how most monosaccharides actually are structured. True or false | True |
| Pentoses and hexoses (five- and six-carbon monosaccharides) bend back on themselves to form_________. | rings There are 2 diastereomers formed. they are sometimes called anomers. That means they differ in 3D space at the anomeric center; the anomeric center is the C=O. |
| When opposite charges on different functional groups within the monosaccharide attract strongly enough, new bonds are formed and other bonds are broken. True or False | True |
| The __________ group present in aldehydes and ketones is very polar and highly reactive. | carbonyl |
| The partially positive carbon in the carbonyl attracts the lone pairs of electrons on the oxygen of a hydroxyl that is ____________ ____________. | partially negative. |
| If a bond forms between this carbon and oxygen, the new pattern formed is called a ____________, new functional group | _hemiacetal |
| Hydroxyl on ___ bends around and reacts carbonyl on C1 | C5 |
| Produces two possible ring structures | D and L D and L notation is determined based on the chiral carbon farthest from the C=O carbonyl group (penultimate carbon). |
| 5C and an O form the ring and one C remains outside the ring and forms | Forms a hemiacetal ring |
| __________ (#) possible ring structures because the hydroxyl group can be on top or bottom of the ring | Two |
| Interconvertible forms known as | anomers |
| _________ carbon—the carbonyl carbon that reacted to form the hemiacetal ring; bonded to two oxygen atoms | Anomeric |
| Anomers in this case known as ______ and _________ | alpha and beta |
| Alpha—if the OH on anomeric C is _____ to C6 (C not in ring) | trans |
| Beta—if OH on anomeric C is ____ to C6 (C not in ring) | cis |
| Pyranose | six membered ring; C6 always drawn on top |
| __________ —five membered ring; C1 and C6 remain outside of the ring | Furanose |
| ___________ group (anomeric C) can undergo oxidation or reduction | Carbonyl group |
| Aldehyde oxidizes carboxylic acid; produces a ________ ________ | sugar acid Example |
| Aldehyde reduces to an alcohol; produces a___________ __________ | sugar alcohol |
| ________ sugar—easily oxidized and reducing other substances; all monosaccharides | Reducing |
| Monosaccharides—have a ________ group; form two anomers; 'free' anomeric carbon at the carbonyl that is highly polar | hemiacetal |
| Fructose and ketoses can rearrange to form _________ in the presence of oxidizing agents | aldoses |
| __________or similar premise used to monitor glucose in urine for diabetics ________ test —tests for aldose; undergoes oxidation while reducing Cu+2 | Benedicts , Benedict's |
| Aldose or ketose can be reduced to sugar __________ | alcohol |
| Sugar alcohols have _______ taste but not the calories; sorbitol (6C), xylitol (5C), and erythritol (4C) | sweet |
| Body can produce _________ ____________ when glucose levels are high—sugar cataracts | sugar alcohols |
| Disaccharides—two monosaccharides joined together by a _____________ rxn. | condensation |
| Glycoside | free hydroxyl on anomeric C reacts with hydroxyl on another monosaccharide |
| Glyosidic bond | bond that connects the two glycosides |
| A disaccharide can be split into | two monosaccharide units. |
| Ordinary table sugar,________ , C12H22O11, is a disaccharide that can be broken up, through hydrolysis, into the monosaccharide's glucose and fructose. | sucrose |
| Two essential pentose monosaccharides that are monosaccharides. (hint DNA) | Deoxyribose and ribose Ribose has 5 carbons and all -OH will be on the same side. Deoxyribose has 5 carbons and have 3 -H and only 2 -OH on same side. |
| Name the bonds for the following disaccharides. Sucrose | one unit of glucose and one unit of fructose Look for a hexose bonded with a pentose (6 to 5) |
| Name the bonds for the following disaccharides. Lactose | one unit of galactose and one unit of glucose (look for the two -OH's between two H) |
| Name the bonds for the following disaccharides. Maltose | two units of glucose-Look for two -OH's on top closest to the 6 carbon) |
| Important Disaccharides: | Maltose, Lactose, and Sucrose |
| Maltose- type of sugar it forms? How is it formed? Example of a product | Malt sugar; formed from breakdown of starch; malted barley; beer Germination of the grain; starch in grain converted to maltose (hydrolysis); dry and roast grains; converted to alcohol by yeast; reducing sugar Alpha (1-4) α-D-glucose—D-glucose |
| Lactose-type of sugar it forms? How is it formed? Example of a product | Milk sugar; don't have or no longer produce lactase means lactose intolerance; undigested lactose broken down by bacteria leads to cramping and gas; reducing sugar Beta (1-4) β-D-galactose—D- glucose |
| Sucrose-type of sugar it forms? How is it formed? Example of a product | Table sugar; most abundant in nature; sugar cane and sugar beets; NOT a reducing sugar α-Β-(1-2) α-D-glucose—β-D- fructose; both anomeric C are bonded |
| Polysaccharides | Plants and animals store glucose as starch and glycogen; α-glucose Cellulose--β-glucose |
| Storage polysaccharides | a polysaccharide that occurs in a living organism as a form of stored energy amylose, amylopectin, and glycogen |
| Structural polysaccharides | β-glucose; Cellulose is used in the cell walls of plants. Chitin is a key structural polysaccharide of invertebrates found, for example, in the exoskeletons of crustaceans and insects. |
| Starch is a mixture of | amylose (20%) and amylopectin 80% |
| Amylose | (polymer found in starch) 250-4000 D-glucose α (1-4) bonded in a continuous long chain; coil like a spring. Straight-chain polymer of D-glucose units 20% of starch; soluble in water It contains α-1,4-glycosidic bonds between two glucose units |
| Amylopectin | (type of polymer found in starch) branched-chain polymer of D-glucose units. 80% of starch; Insoluble in water It contains α-1,4-glycosidic bonds between two glucose units in the straight chain and α-1,6-glycosidic bonds at the branching |
| Glycogen | animal storage; liver and muscles; like amylopectin except branching occurs every 12 units; hydrolyzed to glucose in liver; large amount of branching allows for quick hydrolysis |
| Cellulose contains | Cellulose contains β (1→4)-bonded glucose units. |
| Bond configuration of cellulose | completely alters the overall structure of cellulose compared with that of amylose. |
| Amylose coils, and doesn't brandch. There fore the β-bonded chain of cellulose is ____________ . | straight |
| Straight chains of cellulose align and form a strong rigid___________. | forming a strong, rigid ( structure.) |
| Why eat cellulose? | Can't digest cellulose, but it is still an important part of our diet because it assists with digestive movement in the small and large intestine. |
| Chitin | makes up exoskeleton of insects, crustaceans, cell walls of fungi Β-D-glucose (N-acetylglucosamine) with β (1→4) Strong material; surgical thread that biodegrades; waterproof— added to makeup and lotions |
| Blood types based on (What macronutrient?) | carbohydrates |
| Oligosaccharide | 3-4 monosaccharides on cell surface- (Birkholz answer ) Explaination- (is a saccharide polymer containing a small number (typically two to ten) of monosaccharides (simple sugars).) |
| All blood types have | N-acetylglucosamine, galactose and fucose |
| Universal donor- who and why? | Universal donors are those with an O negative blood type. O- lacks Rh factor O negative blood can be used in transfusions for any blood type. |
| Universal acceptor- who and why? | AB+ has antigens for both blood types and positive Rh factor |
| Heparin | polysaccharide that prevents clotting; highly ionic repeating disaccharide units—oxidized monosaccharide and D-glucosamine |
| (Blood) Polysaccharide group known as (hint glyco...) | glycosaminoglycans |
| blood group A | has AN-acetylgalactosamine antigens on the red blood cells with anti-B antibodies in the plasma |
| blood group B | second galactose has B antigens with anti-A antibodies in the plasma |
| blood group O | has no antigens, but both anti-A and anti-B antibodies in the plasma |
| blood group AB | has both A and B antigens, but no antibodies |
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