Erythro and Threo. Terms used for diastereomers with two adjacent chiral Carbons, without symmetric ends. For symmetric molecules, use meso or d,l.
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1 Erythro and Threo Terms used for diastereomers with two adjacent chiral Carbons, without symmetric ends. For symmetric molecules, use meso or d,l.
2 Aldotetroses This also works for non O (Use regular rules) O O O O O O O O O O O O C 2 O O C 2 O O D-(-)-Erythrose D-(-)-Threose zig-zag Fischer erythro same side (syn) opposite sides (anti) threo opposite sides (anti) same side (syn)
3 Epimers Sugars that differ only in their stereochemistry at a single carbon.
4 Cyclic Structure for Glucose Glucose cyclic hemiacetal formed by reaction of -CO with -O on C5. D-glucopyranose
5 Anomers
6 Reactions of monosaccharides Normal chemical reactions related to the presence of C=O in aldehyde and ketone groups O groups Special reactions due to the large number of very closely spaced functional groups in the molecule
7 Reactions of carbohydrates Epimerization Enediol Rearrangement emiacetal Formation Reduction Oxidation Osazone Formation Chain Shortening Chain Lengthening
8 Epimerization In base, on C2 may be removed to form enolate ion. Reprotonation may change the stereochemistry of C2.
9 Enediol Rearrangement In base, the position of the C=O can shift. Chemists use acidic or neutral solutionsof sugars to preserve their identity.
10 Formation of Glycosides React the sugar with alcohol in acid. Since the open chain sugar is in equilibrium with its - and -hemiacetal, both anomers of the acetal are formed. Aglycone is the term used for the group bonded to the anomeric carbon.
11 Ether Formation Conversion of all -O groups to -OR, Modified Williamson synthesis After converting sugar to acetal, stable in base. elps to purify by recrystallization from water.
12 Ester Formation Acetic anhydride with pyridine catalyst converts all the free oxygens to acetate esters.
13 Reduction to Alditols The carbonyl group of a monosaccharide can be reduced to a hydroxyl group by a variety of reducing agents, including NaB 4 and 2 /M O CO O O + O C 2 O 2 Ni O C 2 O O O O C 2 O D-Glucose D-Glucitol (D-Sorbitol)
14 Reduction of Simple Sugars C=O of aldoses or ketoses can be reduced to C-O by NaB 4 or 2 /Ni. Name the sugar alcohol by adding -itol to the root name of the sugar. Reduction of D-glucose produces D-glucitol, commonly called D-sorbitol. Reduction of D-fructose produces a mixture of D-glucitol and D-mannitol.
15 Sorbitol About 60% as sweet as sucrose Sugar substitute for diabetics Used in manufactured of sweets Sugar-free really means sucrose-free Moisturing creams ( Sorbolene )
16 Pentanepentols
17 Nonreducing Sugars Glycosides are acetals, stable in base, so they do not react with Tollens reagent. Disaccharides and polysaccharides are also acetals, nonreducing sugars.
18 Oxidation by Tollens Reagent Tollens reagent reacts with aldehyde, but the base promotes enediol rearrangements, ketoses react too. Sugars that give a silver mirror with Tollens are called reducing sugars.
19 Oxidation by Bromine Bromine water oxidizes aldehyde, but not ketone or alcohol; forms aldonic acid.
20 Oxidation to Aldonic Acids Oxidation of the Aldehyde group of an aldose to a carboxyl group can be carried out using Tollens, Benedict s, or Fehling s solutions O RC + A g( N 3 ) 2 + Tollens' solution N 3, 2 O O RCO - + N 4 + Ag Precipitates as a silver mirror O RC + citrate or tartrate buffer Cu 2 + RCO - + Cu 2 O Precipitates as a red solid O
21 Oxidation to Aldonic Acids 2-Ketoses are also oxidized by these reagents because, under the conditions of the oxidation, 2-ketoses equilibrate with isomeric aldoses C 2 O C=O CO C-O CO CO (C O) n (C O) n (C O) n C 2 O C 2 O C 2 O A 2-ketose An enediol An aldose
22 Oxidation by Nitric Acid Nitric acid oxidizes the aldehyde and the terminal alcohol; forms aldaric acid.
23 Stereochemistry L D L Rotate 180 D 2,3-dihydroxybutanedioic acid meso achiral diastereomer, (optically inactive overall) (+)-tartaric acid: [ ] D = +12 m.p. 170 C (-)-tartaric acid: [ ] D = -12 m.p. 170 C meso-tartaric acid: [ ] D = 0 m.p. 140 C
24 Aldaric Acids
25 Question #1 Which of the following aldaric acids are optically active? C and D A B C D E No stereocenter meso R, R S, S meso
26 Question #2 Draw a hexose that would give the same aldaric acid product as D-Glucose O CO O CO O O O + O O O C 2 O C 2 O d-(+)- glucose D diastereomers L- (+)- gulose Core of alcohols - mild oxidation or strong oxidation X O O O O X Same product No Symmetry
27 Question #2 Draw a hexose that would give the same aldaric acid product as D-Glucose O CO O CO O O O + O O O C 2 O C 2 O d-(+)- glucose D diastereomers L- (+)- gulose Core of alcohols - mild oxidation or strong oxidation X O O O O X Same product No Symmetry
28 Question #3 There are four D-aldopentoses. Draw Fischer projections of each of them. Then draw Fischer projections of the aldaric acids they would yield. Which of those aldaric acids would be optically inactive? O O O O C 2 O D-Ribose O O O O C 2 O D-Arabinose O O O O O O C 2 O D-Xylose O O C 2 O D-Lyxose (2R, 3R, 4R) (2S, 3R, 4R) (2R, 3S, 4R) (2S, 3S, 4R)
29 Question #3 There are four D-aldopentoses. Draw Fischer projections of each of them. Then draw Fischer projections of the aldaric acids they would yield. Which of those aldaric acids would be optically O O inactive? D-Ribose O O O O O O O O O O O O O O O O O O O O O O O O O O D-Arabinose D-Xylose D-Lyxose MESO (S,S) MESO (S,S)
30 Osazone Formation Both C1 and C2 react with phenylhydrazine.
31 Osazone Sugars that differ in configuration only at the -carbon Give the same product.
32 Question #4 Select the compounds that would produce the same osazone. A and D, B and C
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[1] [Department of Civil and Environmental Engineering, University of California, Davis, CA 95616]
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