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Fischer Projection Organic Lecture Series CarbohydratesCarbohydrates 1 CarbohydratesCarbohydrates Organic Lecture Series •• Carbohydrate:Carbohydrate: a polyhydroxyaldehyde, a polyhydroxyketone, or a compound that gives either of these compounds after hydrolysis 2 CarbohydratesCarbohydrates Organic Lecture Series •• Monosaccharide:Monosaccharide: a carbohydrate that cannot be hydrolyzed to a simpler carbohydrate – they have the general formula CnH2nOn, where n varies from 3 to 8 – aldose: a monosaccharide containing an aldehyde group – ketose: a monosaccharide containing a ketone group 3 Organic Lecture Series MonosaccharidesMonosaccharides • Monosaccharides are classified by their number of carbon atoms Name Formula Triose C3 H6 O3 Tetrose C4 H8 O4 Pentose C5 H10O5 Hexose C6 H12O6 Heptose C7 H14O7 Octose C8 H16O8 4 Organic Lecture Series MonosaccharidesMonosaccharides • There are only two trioses CHO CH2 OH CHOH C= O H2COH CH2 OH CH2 OH Glyceraldehyde D ihydroxyacetone HC OH (an aldotriose) (a ketotriose) H2C OH Glycerol 1,2,3-Propanetriol 5 MonosaccharidesMonosaccharidesOrganic Lecture Series CHO CH2 OH CHOH C= O CH2 OH CH2 OH Glyceraldehyde Dihydroxyacetone (an aldotriose) (a ketotriose) • Often the designations aldo- and keto- are omitted and these compounds are referred to simply as trioses, tetroses, and so forth – although these designations do not tell the nature of the carbonyl group, they at least tell the number of carbons 6 Organic Lecture Series MonosaccharidesMonosaccharides • Glyceraldehyde contains a stereocenter and exists as a pair of enantiomers CH O CH O HOHC HO C H CH 2 OH CH 2 OH (R)-Glyceraldehyde (S)-Glyceraldehyde 7 Organic Lecture Series • Glyceraldehyde contains a stereocenter and exists as a pair of enantiomers CH O CH O HOHC HO C H CH 2 OH CH 2 OH (R)-Glyceraldehyde (S)-Glyceraldeh yd e HO CHO OHC OH CH2OH CH2OH 8 Organic Lecture Series • Fischer projection: a two dimensional representation for showing the configuration of carbohydrates – horizontal lines represent bonds projecting forward – vertical lines represent bonds projecting to the rear – the only atom in the plane of the paper is the stereocenter CHO convert to a CH O Fischer projection H C OH H OH CH2 OH CH 2 OH . (R)-Glyceraldehyde (R)-Glyceraldeh yd e (three-dimensional (Fischer projection) representation) 9 Organic Lecture Series D,L Monosaccharides In 1891, Emil Fischer made the arbitrary assignments of D- and L- to the enantiomers of glyceraldehyde (aldehyde is C1-at the top). CH O CHO HOH HO H CH 2 OH CH2 OH D-Glyceraldehyde L-Glyceraldehyde 25 25 [α]DD = +13.5 [α] = -13.5 -OH to Right -OH to Left 10 Organic Lecture Series • According to the conventions proposed by Fischer – D-monosaccharide: a monosaccharide that has the same configuration at its penultimate carbon as D-glyceraldehyde; that is, its -OH is on the right when written as a Fischer projection – L-monosaccharide: a monosaccharide that has the same configuration at its penultimate carbon as L-glyceraldehyde; that is, its -OH is on the left when written as a Fischer projection 11 Organic Lecture Series • Here are the two most abundant D-aldotetroses and the two most abundant D-aldopentoses • The configuration is assigned at the next to last C in the chain CHO CHO CHO CHO H OH H H H OH HO H H OH H OH H OH H OH HOHOH H CH2 OH CH2 OH CH2 OH CH2 OH D-Erythrose D-Threose D-Ribose 2-Deoxy-D- ribose 12 Organic Lecture Series • And the three most abundant hexoses CHO CHO CH OH 2 H OH H OH C O HO H HO H HO H H OH HO H H OH H OH H OH H OH CH OH CH OH CH OH 2 2 2 D-Glucose D-Galactose D-Fructose 13 Organic Lecture Series Amino Sugars • Amino sugar: a sugar that contains an -NH2 group in place of an -OH group – only three amino sugars are common in nature – N-acetyl-D-glucosamine is a derivative of D- glucosamine CHO CHO CH O CH O O 2 H NH2 H2 N H H NH2 H NHCCH3 HO H HO H HO H HO H H OH H OH HO 4 H H OH H OH H OH H OH H OH CH2 OH CH2 OH CH 2 OH CH 2 OH D-Glucosamine D-Mannosamine D-Galactosamine N-Acetyl-D- glucosamine 14 Cyclic Structure Organic Lecture Series • Monosaccharides have hydroxyl and carbonyl groups in the same molecule and exist almost entirely as five- and six- membered cyclic hemiacetals – anomeric carbon: the new stereocenter created as a result of cyclic hemiacetal formation – anomers: carbohydrates that differ in configuration at their anomeric carbons 15 Organic Lecture Series Haworth Projections • Haworth projections – five- and six- CH2OH membered H OH hemiacetals are OH O H Anomeric Carbon represented as planar pentagons or OH H hexagons, as the case H OH may be, viewed through the edge H – they are most HOH2C O commonly written with H H Anomeric Carbon the anomeric carbon H OH on the right and the OH OH hemiacetal oxygen to the back right 16 Organic Lecture Series α-D-Glucopyranose α-D-Glucose 6 CH2OH H 5 H OH O 4 H 1 Anomeric Carbon 2 OH 3 OH H OH 17 Organic Lecture Series α-D-Ribofuranose α-D-Ribose 5 H CH2OH O 4 H H 1 Anomeric Carbon H 3 2 OH OH OH 18 Organic Lecture Series • Haworth projections CH2OH the designation β- H H means that the - OH O OH on the H Anomeric Carbon anomeric carbon OH OH α is cis to the H OH terminal -CH2OH; α- means that it is trans to the CH2OH β terminal -CH2OH H OH OH O H Anomeric Carbon OH H H OH 19 Haworth Projections Organic Lecture Series 1 CHO redraw to show the -OH CH2 OH H OH on carbon-5 close to the 5 OH aldehyde on carbon-1 H HO H H O C OH H H OH HO 1 H Groups on the right side go H 5 OH down on the Haworth. H OH CH2 OH D-Glucose anomeric anomeric carbon carbon CH2 OH CH2 OH O H O OH(β) H H H + H OH H OH H HO H HO OH(α) H OH H OH β-D-Glucopyranose α-D-Glucopyranose (β-D-Glucose) ( α-D-Glucose) 20 Organic Lecture Series Haworth Projections – six-membered hemiacetal rings are shown by the infix -pyran-pyran – five-membered hemiacetal rings are shown by the infix -furan-furan O O Furan Pyran 21 Organic Lecture Series Conformational Formulas – five-membered rings are close to being planar that Haworth projections are adequate to represent furanoses HOCH HOCH 2 O H 2 O OH ( β) H H HH H OH ( α) H H OH OH OH H α-D-Ribofuranose β-2-Deoxy-D-ribofuranose (α-D-Ribose) (β-2-Deoxy-D-ribose) 22 Organic Lecture Series other monosaccharides also form five-membered cyclic hemiacetals here are the five-membered cyclic hemiacetals of D-fructose 1 CH 2 OH 1 2 C= O (β) HOCH2 O CH 2 OH 3 HOCH2 O OH 2 HO H 5 H HO 4 5 H HO 2 H OH H OH(α) H CH 2 OH H 5 OH 1 HO H 6 HO H CH 2 OH α-D-Fructofuranose D-Fructose β-D-Fructofuranose (α-D-Fructose) (β-D-Fructose) 23 Organic Lecture Series – for pyranoses, the six-membered ring is more accurately represented as a chair conformation OH H OH H H O H OH HO HO HO OH HO O H OH H OH H H H H β-D-Glucopyranose rotate about (β-D-Glucose) C-1 to C-2 bond H OH H OH H H O HO OH HO HO H HO H H OH H OH H O H OH α-D-Glucopyranose (α-D-Glucose) 24 Organic Lecture Series – compare the orientations of groups on carbons 1-5 in the Haworth and chair projections of β-D-glucopyranose, in each case they are up-down-up-down-up respectively 6 CH OH All Groups axial 2 6 5 O H OH(β) 4 CH2 OH H HO O 4 OH H 1 HO 5 HO H 3 2 OH( β) 3 2 OH 1 H OH β-D-Glucopyranose β-D-Glucopyranose (Haworth projection) (chair conformation) 25 Organic Lecture Series • Mutarotation: the change in specific rotation that occurs when an α or β form of a carbohydrate is converted to an equilibrium mixture of the two [α] after % Present at Mon os accharide [α] Mutarotation Equilibrium α-D-glucose +112.0 +52.7 36 β-D-glucose +18.7 +52.7 64 Slight preference for equatorial α-D-galactose +150.7 +80.2 28 β-D-galactose +52.8 +80.2 72 CH2 OH CH2 OH HO O HO O HO HO OH (β) OH HO OH (α) β-D -Glu cop yranose 25 α-D -Glucopyranose [α]D +18.7 25 26 [α]D +112 Glycosides Organic Lecture Series • Glycoside: a carbohydrate in which the - OH of the anomeric carbon is replaced by -OR – methyl β-D-glucopyranoside (methyl β-D- glucoside) glycosidic bond CH2 OH CH2 OH CH2 OH O O H OH O OCH3 H H H + H H + CH OH H H + OH H 3 OH H OH H -H2 O HO H HO H HO OCH3 H OH H OH H OH β-D-Glucopyranose Methyl β-D-gluco- Methyl α-D-gluco- (β-D-Glucose) pyranoside pyranoside ( Methyl β-D-glucoside) (Methyl α-D-glucoside) 27 Glycosides Organic Lecture Series • Glycosidic bond: the bond from the anomeric carbon of the glycoside to an - OR group • Glycosides are named by listing the name of the alkyl or aryl group bonded to oxygen followed by the name of the carbohydrate with the ending -e replaced by -ide – methyl β-D-glucopyranoside – methyl α-D-ribofuranoside 28 N-Glycosides Organic Lecture Series • The anomeric carbon of a cyclic hemiacetal also undergoes reaction with the N-H group of an amine to form an N-glycoside – N-glycosides of the purine and pyrimidine bases are structural units of nucleic acids H N N N N N N Pyrimidine Purine 29 Organic Lecture Series N N Pyrimidine O NH2 O CH HN N HN 3 O N O N O N H H H Uracil Cy to sine Thymine 30 Organic Lecture Series H N N N N Purine NH2 O N N HN N N N N H2 N N H H Adenine Guanine 31 Organic Lecture Series N-Glycosides – the β-N-glycoside formed between D- ribofuranose and cytosine NH2 N a β-N-glycosidic bond O N HOCH2 O H H H H anomeric HO OH carbon 32 Reduction to Organic Lecture Series Alditols • The carbonyl group of a monosaccharide can be reduced to an hydroxyl group by a variety of reducing agents, including NaBH4 and H2/M (metal catalyst) CHO CH2 OH H OH H OH CH2 OH HO O HO H HO H HO NaBH4 OH H OH H OH OH H OH H OH β-D-Glucopyranose CH2 OH CH2 OH D-Glucose D-Glucitol (D-Sorbitol) “Sugar alcohol” additive 33 Organic Lecture Series other alditols which
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