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1 Part 4. Carbohydrates As Bioorganic Molecules Сontent Pages 4.1 1 Part 4. Carbohydrates as bioorganic molecules Сontent Pages 4.1. General information……………………….. 3 4.2. Classification of carbohydrates …….. 4 4.3. Monosaccharides (simple sugar)…….. 4 4.3.1. Monosaccharides classification……………………….. 5 4.3.2. Stereochemical properties of monosaccharides. … 6 4.3.2.1. Chiral carbon atom…………………………………. 6 4.3.2.2. D-, L-configurations of optical isomers ……….. 8 4.3.2.3. Optical activity of enantiomers. Racemate. …… 9 4.3.3. Open chain (acyclic) and closed chain (cyclic) forms of monosaccharides. Haworth projections ……………… 9 4.3.4. Pyranose and furanose forms of sugars ……………. 10 4.3.5. Mechanism of cyclic form of aldoses and ketoses formation ………………………………………………………………….. 11 4.3.6. Anomeric carbon …………………………………………. 14 4.3.7. α and β anomers ………………………………………… 14 4.3.8. Chair and boat 3D conformations of pyranoses and envelope 3D conformation of furanoses ……………………. 15 4.3.9. Mutarotation as a interconverce of α and β forms of D-glucose ………………………………………………………………… 15 4.3.10. Important monosaccharides .............................. 17 4.3.11. Physical and chemical properties of monosaccharides ………………………………………………………… 18 4.3.11.1. Izomerization reaction (with epimers forming). 18 4.3.11.2. Oxidation of monosaccharides…………………. 18 4.3.11.3. Reducing Sugars …………………………………. 19 4.3.11.4. Visual tests for aldehydes ……………………… 21 4.3.11.5. Reduction of monosaccharides ……………….. 21 4.3.11.6. Glycoside bond and formation of Glycosides (Acetals) ……………………………………………………………….. 22 4.3.12. Natural sugar derivatives ................................... 24 4.3.12.1. Deoxy sugars ............................................... 24 4.3.12.2. Amino sugars …………………………………….. 24 4.3.12.3. Sugar phosphates ………………………………… 26 4.4. Disaccharides ………………………………… 26 4.4.1. Reducing and non reducing disaccharides ………. 27 4.4.2. Nomenclature of Disaccharides …………………….. 28 4.4.3. The main representatives of disaccharides ………. 29 4.5. Oligosaccharides …………………………… 34 4.5.1. Mammalian oligosaccharides .............................. 34 2 4.5.2. Plant oligosaccharides ........................................ 35 4.6. Polysaccharides (Glycans) …………….. 36 4.6.1. Homopolysaccharides …………………………………. 37 4.6.1.1. Starch and glycogen as storage homopolysaccharides ……………………………………………… 37 4.6.1.2. Cellulose……………………………………………… 40 4.6.1.3. Chitin………………………………………………….. 42 4.6.1.4. Inulin………………………………………………….. 46 4.6.1.5. Dextrans……………………………………………… 47 4.6.2. Heteropolysaccharides ....................................... 47 4.6.2.1. Pectins ……………………………………………….. 48 4.6.2.2. Natural gums ……………………………………… 49 4.6.2.3. Hemicelluloses ……………………………………… 49 4.6.2.4. Agar …………………………………………………… 52 4.6.2.5. Mammalian heteropolysaccharides: glycosaminoglycans ………………………………………………… 53 4.6.2.6. Proteoglycans as proteins conjugated with glycosaminoglycans ………………………………………………… 58 4.6.2.7. Proteoglycan aggregates ………………………….. 59 4.6.2.8. Murein as the heteropolysaccharide of the bacterial cell wall …………………………………………………… 60 4 . 7 . Glycoconjugates ......................... 63 4.7.1. N-linked Glycoproteins ..................................... 65 4.7.2. O-linked glycoproteins ........................................ 66 4.7.3. The role of glycosylation reactions and glycosyltransferases in AB0 Blood group system functioning …………………………………………………………… 67 3 Part 4. Carbohydrates as bioorganic molecules 4.1. General information Carbohydrates are polyhydroxy aldehydes or ketones (the simplest carbohydrates, or monosaccharides), or substances that yield such compounds on hydrolysis (large carbohydrate molecules called polysaccharides): hydrolysis cellulose → D-glucose (polysaccharide) (monosaccharide) The general empirical structure for carbohydrates is (CH 2O) n suggesting that they are carbon "hydrates“. For example, the empirical formula of glucose is C 6H12 O6, which can also be written (CH 2O) 6 or C 6(H 2O) 6. But although many common carbohydrates conform to the empirical formula (CH 2O) n, others do not; some carbohydrates also contain nitrogen, phosphorus, or sulfur. Carbohydrates are the most abundant biomolecules in nature. They are not genetically encoded and are produced in a form of glucose by photosynthesis in plants – this process is a direct link between solar energy and the chemical bond energy in living organisms: Carbohydrates (mainly starch in plants and glycogen in animals) are the source of rapid energy production Some of carbohydrates are the structural elements in the cell walls of bacteria ( peptidoglycan or murein ), plants ( cellulose ) and animals ( chitin ). Glycosaminoglycans of extracellular matrix also play a structural role, and some gel-like carbohydrates play the role of "lubricant" for joints. Carbohydrates may be linked to proteins and lipids with glycoproteins and glycolipids forming. Such conjugated carbohydrates are important in cell-cell communication and in interactions between cells and other elements in the cellular environment (e.g., other cells, hormones, and viruses). For example, they are involved in the recognition and adhesion of cells, promote the realization of antigenic function 4 Carbohydrates may be also the components of several metabolic pathways and some of them are the substrates for the fats, non-essential amino acids and steroids synthesis. Glucuronic acid , which is a product of glucose oxidation, is used to neutralize the products of proteins decay in the intestine, as well as in the metabolism of bile pigments. Disorders of the carbohydrates metabolism are characteristic of a number of diseases (diabetes mellitus, liver and nervous system damage), or cause a number of pathological conditions (intolerance to lactose, fructose, galactosemia, glycogenosis and aglycogenosis). Carbohydrates and their derivatives are used in medical practice: glucose 40%; cardiac glycosides (e.g., digitalis), blood substitute dextran. 4.2. Classification of carbohydrates There are three major classes of carbohydrates: • monosaccharides, • oligosaccharides, • polysaccharides Monosaccharides consist of a single polyhydroxy aldehyde (aldoses) or ketone unit (ketoses). The most abundant monosaccharide in nature is the sixcarbon D-glucose. Oligosaccharides consist of short chains of monosaccharide units joined together by characteristic glycosidic linkages . The most abundant are the disaccharides with two monosaccharide units – for example, sucrose (consists of the six-carbon sugars D-glucose and D-fructose joined covalently). All common names of monosaccharides and disaccharides have ending with the suffix "-ose". Most oligosaccharides having three or more units do not occur as free entities but are joined to lipids or proteins in structures called glycoconjugates . Polysaccharides consist of long chains that have hundreds or thousands of monosaccharide units. Polysaccharides that have the same monosaccharide units are called homopolysaccharides ; when they consist of the different monosaccharide units – there are heteropolysaccharides . Some polysaccharides, such as cellulose, occur in linear chains, whereas others, such as glycogen, have branched chains. The most abundant homopolysaccharides, starch and cellulose made by plants, consist of recurring units of D-glucose, but they differ in the type of glycosidic linkage. 4.3. Monosaccharides (simple sugar) Monosaccharides are the carbohydrates that cannot be hydrolyzed to simpler carbohydrates. They have the general formula CnH2n On, where n > 3. 5 They are colorless, crystalline solids, soluble in water but insoluble in nonpolar solvents. One of the carbon atoms of these substances is double-bonded to an oxygen atom to form a carbonyl group ; each of the other carbon atoms has a hydroxyl group . 4.3.1. Monosaccharides classification They may be subcategorized as aldoses or ketoses , if the molecule contains an aldehyde or ketone functional groups respectively. Aldoses have a carbonyl group in the form of an aldehyde on the end of the carbon chain and ketoses have a ketone group somewhere along the sugar backbone. The simplest ketose is dihydroxyacetone while the simplest aldose is glyceraldehyde , which can be found as either the L or D enantiomer. Monosaccharides may be also classified based on the number of carbon atoms as trioses (n=3), tetroses (n=4), pentoses (n=5), hexoses (n=6), heptose (n=7), etc. So dihydroxyacetone and glyceraldehyde are trioses, the example of tetrose is erythrulose, penthoses – ribulose, ribose and xylulose, and hexoses – glucose, mannose, fructose and galactose (Tab. 4.1). Table 4.1. Monosaccharides classification (with examples) Trioses Tetroses Pentoses Hexoses Aldoses Aldotriose Aldotetroses Aldopentoses Aldohexoses Ketoses Ketotriose Ketotetrose Ketopentoses Ketohexoses Glucose is known as a aldohexose (a six carbon aldose) and ribose is considered an aldopentose (a five carbon aldose). 6 4.3.2. Stereochemical properties of monosaccharides. 4.3.2.1. Chiral carbon atom Chiral center or an asymmetric atom is a carbon atom in molecule, which is connected with four different groups. In order to find chiral carbon, it is necessary: Step 1. To number carbon atoms in molecule Step 2. Research all carbon atoms in molecule to find carbon atoms, which are connected with four different groups The next carbon atoms cannot be chiral centres: - Carbons in −CH 3 or −CH 2 groups - Carbon, connected with other atom via double or triple bond (for example, with oxygen in ketone group): * * CHIRAL ACHIRAL CHIRAL ACHIRAL Has 4 different Doesn’t have 4 different Has 4 different Only has 3 atoms atoms
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