Carbohydrates 1. Steven E. Massey, Ph.D. Assistant Professor Bioinformatics Department of Biology University of Puerto Rico Río Piedras
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1 Carbohydrates 1 Steven E. Massey, Ph.D. Assistant Professor Bioinformatics Department of Biology University of Puerto Rico Río Piedras Office & Lab: NCN#343B Tel: ext stevenemassey@gmail.com
2 Carbohydrates are the most abundant type of biological molecule on earth They are used for energy storage, have a role in central metabolism and structural roles Carbohydrates are polyhydroxy aldehydes or ketones Many have the formula (CH2O)n Monosaccharides have a single aldehyde or ketone unit Oligosaccharides are short chains of monosaccharides Disaccharides are double units of monosaccharides Polysaccharides are 20 or more units of monosaccharides
3 Monosaccharides are either aldehydes or ketones with 2 or more hydroxyl groups Divided into aldoses and ketoses (from aldehydes and ketones, respectively) Triose 3 carbons Tetrose 4 carbons Pentose 5 carbons Hexose 6 carbons Heptose 7 carbons All (except dihydroxyacetone) have at least one chiral center By convention, there are two enantiomers, D and L
4 Examples of monosaccharides The prefix aldoor keto- denotes whether it is an aldehyde or ketose, respectively
5 Enantiomers are mirror images of each other An easy way to remember: L stands for left (anti-clockwise) D stands for derecha (right) The order of atoms attached to the chiral carbon is dictated by the location of the hydroxyl Most naturally occurring sugars are in their D-form
6 There can be 2n stereoisomers for a molecule with n chiral centers Glyceraldehyde has 21, while glucose has 24 (16) The chiral center furthest from the carbonyl group determines the name of the molecule (D or L) For aldoses: Those in which the conformation is the same as D-glyceraldehyde are D isomers Those in which the conformation is the same as L-glyceraldehyde are L isomers
7 Pink denotes a chiral center
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10 Dihydroxyacetone does not have a chiral center
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12 Epimers are sugars that differ only in the configuration around one carbon atom (not the major chiral center) Eg. D-glucose, D-mannose and D-galactose D-mannose and D-galactose vary at the second and fourth carbon positions respectively
13 Some sugars occur naturally in their L form Eg. L-arabinose
14 Monosaccharides are commonly rings, and this conformation predominates in aqueous solution The ring structures are formed by the reaction of alcohols with aldehydes / ketones are called hemiacetals or hemiketals
15 Taking the example of glucose, the open form may form a closed form by the reaction of the terminal aldehyde group with C5-OH There are two potential configurations (anomers); α and β α means that the -OH below the level of the plane Mutarotation converts the two anomers
16 6 membered rings are called pyranoses The two anomers of glucose are called α-d-glucopyranose and β-d-glucopyranose 5 membered rings are called furanoses; these are less stable and less common for aldoses More common for ketoses eg. fructose
17 Ketohexoses also have α and β anomeric forms. The naming convention is the same as for aldohexoses; the α form -OH is below the plane, the β is above the level of the plane D-fructose readily forms a furanose ring with a hemiketal linkage β-d-fructose is the most common form of fructose
18 Haworth perspective formulas are used to show the ring structures of monosaccharides The bold lines come OUT of the page However, monosaccharides are really not planar, but instead have a chair conformation Note: Conformations can be interconverted without breaking covalent bonds Configurations can be interconverted only by breaking bonds
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20 Hexose derivatives In addition to simple hexoses there are a variety of derivatives, where a hydroxyl group is replaced. With an amine group glucosamine, galactosamine, mannosamine The amine group is usually reacted with acetic acid, as in the case of N-acetylglucosamine. This compound is found in bacterial cell walls
21 A phosphate group eg glucose 6-phosphate The phosphate group is often used to activate the sugar, prior to further chemical reactions (eg. glycolysis)
22 Monosaccharides are reducing This means they can reduce cupric ions (Cu2+) to cuprous ions (Cu+; red in colour) Fehling s reaction is a test for the presence of reducing sugars; used for many years to test for diabetes. The amount of sugar was quantitized by making a red color on making Cu+
23 Disaccharides are formed when a hydroxyl group of one sugar reacts with the anomeric carbon of another This is called an O-glycosidic bond The formation of maltose leaves a free hemiacetal group, thus it is a reducing sugar Not all disaccharides are reducing sugars By convention, the reducing end is at the right
24 Maltose is formed from 2 D-glucoses and is found in seeds Its formula is: α-d-glucopyranosyl-(1->4)-d-glucopyranose Glc(α1->4)Glc Lactose is formed from D-glucose and D-galactose and is found in milk Gal(β1->4)Glc Sucrose is derived from glucose and fructose and is only found in plants - it is non-reducing as it does not have a free anomeric carbon, both are joined hence the symbol Its abbreviation is Glc(α1<->2β)Fru and can also be represented as Fru(β2<->1α)Glc
25 Trehalose is formed from two α D-glucoses Glc(α1<->1α)Glc Found in insects and fungi, it is also non-reducing, hence the symbol
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