Carbohydrates - General Description
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1 arbohydrates - General Description A. Polyhydroxy Aldehydes or Ketones ARBN AIN B. Serve a variety of functions ARBN AIN ARBN AIN 1. Energy storage (Glucose, Glycogen, Starch) 2. Structural Support (ellulose, hitin) 3. Biochemical ontrol (DNA, Glycoproteins). ydrates of arbon - General formula: n(2)n, n=1,2,3... D. Saccharides - from Latin saccharum (sugar) 1. Monosaccharides - simple sugars 2. Disaccharides, trisaccharides, tetrasaccharides, ligosaccharides 4. Polysaccharides
2 arbohydrates - General Nomenclature A. -SE ending - Glucose, Galactose, Sucrose, ellulose B. lassification by Number of arbons Tri + ose = Triose Tetra + ose = Tetrose Penta + ose = Pentose. lassification by Functional Groups 1. Aldoses contain the aldehyde functional group. 2. Ketoses contain the ketone functional group. D. ombining A, B, and 2 an aldopentose 2 a ketohexose 2
3 arbohydrates - Simple Structures A. Simple Monosaccharide Structures D-Glyceraldehyde Dihydroxyacetone (A simple aldose) (A simple ketose) B. Note: Glyceraldehyde exists in two enantiomeric forms D
4 arbohydrates - Simple Structures Important Aldopentoses Important Aldohexoses 2 2 D-ribose 2-deoxy-D-ribose 2 D-glucose 2 D-galactose Glucose and Galactose are epimers
5 arbohydrates - Simple Structures An Important Ketohexose D-fructose D-glucose omparison of the structures of D-fructose and D-glucose D-fructose
6 arbohydrates - Simple Structures What is L-Glucose? D-Glucose and L-Glucose are enantiomers Most naturally occurring monosaccharides are from the D-series. 2 2 D-Glucose L-Glucose
7 Absolute onfigurations of the D-Aldoses
8 Absolute onfigurations of the D-Ketoses
9 arbohydrates - yclic Structures Previously Studied Reactions of Aldehydes and Ketones
10 6 arbohydrates - yclic Structures 1 yclic Forms of Glucose anomers
11 arbohydrates - yclic Structures In solution, glucose exists in a variety of forms.
12 arbohydrates - Reducing Sugars Glucose is a reducing sugar u 2+ u2 The small amount of aldehyde present in a glucose solution is sufficient to reduce the copper ion from 2+ to 1+.
13 arbohydrates - yclic Structures yclic Forms of ther arbohydrates
14 arbohydrates - yclic Structures β-d-glucopyranose β-d-galactopyranose
15 arbohydrates - Reducing Sugars Because they exist to a small extent in the aldehyde form in solution, most other simple sugars are reducing sugars.
16 arbohydrates - Reducing Sugars Because they exist to a small extent in the aldehyde form in solution, most other simple sugars are reducing sugars.
17 arbohydrates - Glycoside Formation
18 arbohydrates - Glycoside Formation The linkage between the sugar and the alcohol is called a glycosidic linkage and must be designated as α or β. Glycosides of simple monosaccharides are not reducing sugars because the aldehyde functional group is no longer present. The alcohol which attaches through the glycosidic can be another carbohydrate.
19 arbohydrates - Glycoside Formation
20 arbohydrates - Sugar Phosphates
21 arbohydrates - Acidic Sugars 2 D-Glucose D-Glucuronic Acid A building block for hyaluronic acid
22 arbohydrates - Amino Sugars 2 N 2 2 N 3 D-Glucosamine N-acetyl-D-Glucosamine Building block for chitin, the exoskeleton of crustaceans
23 arbohydrates - Sugar Sulphates - S - 2 S N - D-Glucuronic Acid 2-sulfate S - N-sulfo-D-Glucosamine 6-sulfate Building blocks for heparin
24 Monosaccharides - Physical Properties 1) Most monosaccharides are crystalline solids at room temperature and are very soluble in water where they can form highly viscous solutions. 2) Monosaccharides are slightly soluble in alcohols (methanol, ethanol) and are insoluble in less polar solvents (ethers, hydrocarbons). 3) Many monosaccharides taste sweet. 4) A solution of a reducing sugar may contain a mixture of α anomers, β anomers, and acyclic structures. The structures rapidly interconvert to form an equilibrium mixture. (This interconversion is called mutarotation.) 5) Usually, only a single form of a carbohydrate is drawn when drawing a carbohydrate in solution.
25 Mutarotation of Glucose alpha anomer oxo form beta anomer [α]d = +112º [α]d = +19º Equilibrium Mixture 36% 64% [α]d = +53º
26 Mutarotation of Glucose
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