Carbohydrates A General Introduction. Graduate course in Carbohydrate Chemistry
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1 Carbohydrates A General Introduction
2 Sugar Sucrose, Saccharose, Cane sugar, Beet sugar, Table sugar β-d-fructofuranosyl-(2 1)-α-D-glucopyranoside β-d-fruf-(2 1)-α-D-Glcp
3 Sugar oney (fructose + glucose) was the main sweetener during the middle ages Cane sugar arrived in Europe with the Moors around 700 A.D. The Continental blockade (1806) during the Napoleonic wars made cane sugar unavailable Beet sugar was developed as substitute for cane sugar Sucrose, glucose (corn syrup) and inverted sugar, are the main sweeteners today
4 Sugar cane Sugar beet
5 Sucralose & lestra Chlorinated sucrose Sweetener 600x sweeter than sucrose Sucrose fatty acid ester Fat substitute
6 Inverted sugar Sucrose Glucose + Fructose [α] D =+66 [α] D =+53 [α] D = 92 Sweeter than sucrose More difficult to crystallize (e.g. in sweets, chocolate ) Glucose ( grape sugar ) is also called dextrose Fructose ( fruit sugar ) is also called laevulose
7 What is a carbohydrate? 2-Carb-1.1. Carbohydrates The generic term 'carbohydrate' includes monosaccharides, oligosaccharides and polysaccharides as well as substances derived from monosaccharides by reduction of the carbonyl group (alditols), by oxidation of one or more terminal groups to carboxylic acids, or by replacement of one or more hydroxy group(s) by a hydrogen atom, an amino group, a thiol group or similar heteroatomic groups. It also includes derivatives of these compounds. The term 'sugar' is frequently applied to monosaccharides and lower oligosaccharides. It is noteworthy that about 3% of the compounds listed by Chemical Abstracts Service (i.e. more than ) are named by the methods of carbohydrate nomenclature. Note. Cyclitols are generally not regarded as carbohydrates. Their nomenclature is dealt with in other recommendations.
8 What is a monosaccharide? 2-Carb-1.2. Monosaccharides Parent monosaccharides are polyhydroxy aldehydes -[C] n -C or polyhydroxy ketones -[C] n -C-[C] m - with three or more carbon atoms. The generic term 'monosaccharide' (as opposed to oligosaccharide or polysaccharide) denotes a single unit, without glycosidic connection to other such units. It includes aldoses, dialdoses, aldoketoses, ketoses and diketoses, as well as deoxy sugars and amino sugars, and their derivatives, provided that the parent compound has a (potential) carbonyl group.
9 Some carbohydrates C 2 Isosorbide Sucrose (cane sugar) C 2 sorbitol N 2 N N N N myo-inositol meso-tartaric acid Adenosine
10 Common Monosaccharides Glucose Mannose NAc 2-Acetamido-2-deoxyglucose Galactose
11 Monosaccharides Mammalian glycoproteins contain about 10 different monosaccharides More than 100 different monosaccharides are found in microbial glucans Common functional groups are: Amides, amines, carboxylic acids, esters, ethers, sulphates and phosphates
12 Mutarotation Glucose, [α] D =+53 in water at equilibrium [α] D =+112 [α] D =+19
13 Mutarotation of ribose hydrate (0.09%) C 2 α-pyranose (20.2%) α-furanose (7.4%) C C 2 keto-form (0.04%) β-pyranose (59.1%) β-furanose (13.2%)
14 More complications Some compounds form anhydrides or lactones 1,6-anhydro-β-D-idopyranose β-d-glucofuranurono-6,3-lactone (used in some energy drinks) and a few may even have more than one aldehyde/keto function
15 β-caryose 4,8-cyclo-3,9-di-deoxy-L-erythro-D-ido-nonose
16 Disaccharides Non-reducing Sucrose Trehalose Reducing Lactose Maltose Cellobiose Cane sugar in yeast Milk sugar Malt sugar
17 ligosaccharides N-glucans Blood group antigens Milk-oligosaccharides linked to ASN in proteins linked to ceramide (a lipid) lactose at the reducing end
18 rhamnogalacturonan II ca. 30 glycosylresidues 10 different residues
19 N-linked glucans
20 Cyclic oligosaccharides E.g. cyclodextrins, [4)-α-D-Glcp-(1 ] n α β γ δ Used to stabilize flavours and pharmaceuticals
21 Polysaccharides Energy storage Starches (amylose, glycogen, amylopectin) (glucans) Levan and inulin (fructans) Structure - cellwalls Cellulose (plants) Chitin (yeast and arthropods) Glucosaminoglucans (animals) Murein (peptidoglucan, bacteria)
22 Molasses -a thick, syrupy derivative of the juice of the sugarcane plant or the processing of sugar beet ey, let's be careful out there. Sgt. Esterhaus, ill Street Blues
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1 Biology: Macromolecules 2 Carbohydrates Carbohydrate organic compound containing carbon, hydrogen, & oxygen in a 1:2:1 ratio Meaning: hydrated carbon ratio of h:0 is 2:1 (same as in water) Source: plants
Organic Chemistry III
rganic Chemistry III (Yuki Goto, Bioorganic Chemistry Lab.) rganic chemistry of biomolecules rganic chemistry of radicals 6/6 (Wed) 6/13 (Wed) 6/20 (Wed) 6/27 (Wed) 7/4 (Wed) Examples of biomolecules?
You know from previous lectures that carbonyl react with all kinds of nucleophiles. Hydration and hemiacetal formation are typical examples.
hem 263 Nov 17, 2009 D,L onfiguration of Sugars Glyceraldehyde has only one stereogenic center and therefore has two enantiomers (mirror image) forms. A D-sugar is defined as one that has configuration
Chem 263 Nov 21, 2013
hem 263 Nov 21, 2013 arbohydrates- emiacetal Formation You know from previous lectures that carbonyl compounds react with all kinds of nucleophiles. ydration and hemiacetal formation are typical examples.