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CHAPTER 17 AND 18

CHAPTER 17 AND 18. CONCURRENT ENROLLMENT. CARBOHYDRATES. BIOMOLECULE Organic compounds essential for life BIOCHEMISTRY Study of compounds and processes associated with living organisms CARBOHYDRATES A polyhydroxyl aldehyde or ketone, or substance that yields such compounds upon hydrolysis

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CHAPTER 17 AND 18

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  1. CHAPTER 17 AND 18 CONCURRENT ENROLLMENT

  2. CARBOHYDRATES • BIOMOLECULE • Organic compounds essential for life • BIOCHEMISTRY • Study of compounds and processes associated with living organisms • CARBOHYDRATES • A polyhydroxyl aldehyde or ketone, or substance that yields such compounds upon hydrolysis • Monosaccharide • A simple carbohydrate most commonly consisting of 3 to 6 carbon atoms • Disaccharide • A carbohydrate formed by the combination of two monosaccharides • Polysaccharide • A carbohydrate formed by the combination of many monosaccharide units

  3. STEREOCHEMISTRY • Enantiomers • Mirror images like a hand or 1 and d glyceraldehyde • Chiral • A term for compounds or objects that cannot be superimposed on their mirror image • Chiral carbon • Carbon atom with four different groups attached • Learning checks on pages 535 and 537

  4. FISHER PROJECTIONS • Method to look at chiral molecules three-dimensional • With the acid group or the ketone group or the aldehyde group facing up • The farthest away chiral carbon look at the hydroxyl or amino group this tells you if it is a D or L family • If the last group is on the right side it is in the D family • If the last group is on the left side it is in the L family • Learning check page 539 and 540

  5. Continue • Levorotatory • Rotates plane-polarized light to the left • Dextrorotatory • Rotates plane-polarized light to the right • Optically active molecule • A molecule that rotates the plane of polarized light • Living organisms are made up largely of chiral substances • Both enantiomers will not be found together in the same biological system • L-lactic acid is found in muscles, while D-lactic acid is found in sour milk

  6. MONOSACCHARIDES • Table 17.1 page 541 • With an aldeyde group in a monosaccharide you have a prefix aldo- • With a ketone group you will have a prefix keto- • Learning check page 541 • Figure 17.8 gives you the family of D aldoses. MEMORIZE THESE

  7. PROPERTIES • Most monosaccharides are sugars, because they taste sweet • Table 17.2 page 543 • Monosaccharides with at least five carbons exist predominantly as CYCLIC HEMIACETALS AND HEMIKETALS • Overhead • Pyranose ring • A six-membered sugar ring system containing an oxygen atom

  8. Continue • Haworth structure • Three-dimensional carbohydrate structures • Anomeric carbon • An acetal, ketal, hemiacetal, or hemiketal carbon atom giving rise to two stereoisomers • Anomers • Stereoisomers that differ in the three-dimensional arrangement of groups at the carbon of an acetal, ketal, hemiacetal or hemiketal • Furanose ring • A five-membered sugar ring system containing an oxygen atom • Page 544 look at drawings • Anomeric carbon is to the right of the oxygen • Hydroxyl group down is α and up is β • Learning check page 546

  9. REACTIONS • Oxidation • Aldehydes and ketones that have adjacent -OH groups are oxidized by alkaline solutions containing Cu2+ • A sugar that can be reduced by Cu2+ is called a REDUCING SUGAR • Page 547 look at general reaction • Phosphate ester • Monosaccharides behave as an alcohol and reacts with an acid to form and ester • Important Intermediates in the carbohydrate metabolism • Glycoside • Another name for a carbohydrate containing an acetal or ketal group • Page 548 glycosidic linkage and learning check

  10. Important monosaccharides and disaccharides • Read pages 548-558 • Know (draw) ribose, glucose, galactose and maltose • DNA AND RNA are pentoses and are essential in protein synthesis and the transfer of genetic material • Glucose is a hexose and is found in honey and also known as blood sugar • Galactose is a hexose and similar to glucose. This is found in mammal milk

  11. Continue • Maltose is formed from two α-D-glucose linking this is malt sugar • Lactose is formed from a β-D-Galactose and α-D-glucose, this makes up 5% of cow’s milk and 7% of human milk • Surcose is formed from a α-D-glucose and β-D-fructose, found in fruits and sugar cane • Polysaccharides • Not water soluble • Table 17.4 and overhead • Starch, glycogen, cellulose

  12. CHAPTER 18 • Lipid • A biological compound that is soluble only in NONPOLAR SOLVENTS • Simple lipid • A ester-containing lipid with just two types of components: an alcohol and one or more fatty acids • Complex lipid • An ester-containing lipid with more than two types of components: an alcohol, fatty acids – plus others • Fatty acids are the fundamental building block for many lipids • They are long-chain carboxylic acids • It is the long nonpolar chain on the fatty acid that gives the oily characteristics of fats • In the physiological pH the polar head exists as the carboxylate anion – COO-

  13. FATTY ACIDS • Micelle • A spherical cluster of molecules in which the polar portions of the molecules are on the surface and the nonpolar portions are located in the interior. • Figure 18.3 page 567 • Fatty acids found in natural lipids have the following characteristics • They are usually straight-chain carboxylic acids (no branching) • The sizes of most common fatty acids range from 10 to 20 carbons • Fatty acids usually have an even number of carbon atoms (including the carboxyl group carbon) • Fatty acids can be saturated (containing no double bonds between carbons). Apart from the carboxyl group and double bonds, there are usually no other functional groups

  14. Continue • Unsaturated fatty acids usually contain double bonds in the cis- configuration • This forms kinks that result in weaker intermolecular forces, low melting points and are usually liquid at room temperature • Overheads • Essential fatty acids • Fatty acids needed for reactions in the body, but not made in the body • Linoleic acid and linolenic acid, these are found in fish and plant oils • They regulate blood pressure, blood clotting, blood lipid levels etc.

  15. STRUCTURE OF FATS AND OILS • In fats and oils, the alcohol portion is always derived from glycerol, and the acid portion comes from the fatty acids • Overhead • Learning check 18.1 570 • Fat • A triglyceride that is a solid at room temperature • Oil • A triglyceride that is a liquid at room temperature • They differ in the degree of unsaturation • Saturated fats influence blood cholesterol

  16. CHEMICAL PROPERTIES • Hydrolysis • Fats and oils can react with water (only when in the presence of acid or lipase, enzyme) it will reverse the ester formation • Glycerol and fatty acids are reformed • Learning check 18.2 page 572 • Saponification • Overhead • When triglycerides react with a strong base it will form soap (glycerol with a salt) • Sodium salts are found in the cake soaps • Potassium salts are found in shaving creams and liquid soaps • Overhead • Learning check 18.3 page 573

  17. Continue • Hydrogenation • Double bonds of unsaturated fats can be broken when reacting with hydrogen in the presence of a catalyst • This will decrease the degree of unsaturation and increase the melting point • This is how margarine and peanut butter are made • During hydrogenation some fatty acids with the common cis- configuration are isomerized into trans-form. Like margarine • Study skills page 575 • Wax • An ester of a long-chain fatty acid and a long-chain alcohol • Are water-insoluble • In nature are found on feathers, leaves or fruits • Phosphoglycrides • A complex lipid containing glycerol, fatty acids, phosphoric acid, and an alcohol component

  18. Continue • Phospholipid • A phosphorus-containing lipid • Overhead • Lecithin • A phosphoglyceride containing choline • + • HO-CH2CH2-N(CH3)3 • This makes one end hydrophilic and the rest of the molecule hydrophobic • This is very important in forming cell membranes • Cephalin • A phospholyceride containing ethanolamine or serine • + + HO-CH2CH2-NH3 and HO-CH2CH-NH3 COO-

  19. Continue • Sphingolipids • A complex lipid containing sphingosine (page 578), a fatty acid, phosphoric acid, and choline • Large amounts of sphingomyelin are found in the brain and nerve tissue • Glycolipid • A complex lipid containing a sphingosine, a fatty acid, and a carbohydrate • Page 578 • When a body cannot break down these complex lipids, due to a genetic inability to form an enzyme. This causes several human diseases like Tay-Sachs

  20. BIOLOGICAL MEMBRANES • Prokaryotic cell • A simple unicellular organism that contains no nucleus and no membrane-enclose organelles • Eukaryotic cell • A cell containing membrane-enclosed organelles, particularly a nucleus • Organelle • A membrane-encased body in the interior of a cell

  21. Continue • Most cells are made up of 40% protein and 60% lipids • Phosphoglycerides (lecithin and cephlin), sphingomyelin, and cholesterol • Fluid-mosaic model • A model of membrane structure in which proteins are embedded in a flexible lipid bilayer • Lipid bilayer • A structure found in membranes, consisting of two sheets of lipid molecules arranged so that the hydrophobic portions are facing each other • Overhead

  22. STEROIDS • A compound containing four rings fused in a particular pattern • The most abundant steroid in the human body is cholesterol (very important) • Overhead • Found in cell membranes and is the building blocks for sex hormones, vitamin D, bile salts, etc. • Synthesized in the liver • Bile salts • Yellowish brown or green liver secretion that is stored in the gallbladder

  23. HORMONES • Chemical messenger secreted by specific glands and carried by the blood to a target tissue, where it triggers a particular response • Adrenocorticoids • Produced in the adrenal glands by the kidney • Regulates the ion concentration (mainly sodium ions) in body fluids • Enhances carbohydrate metabolism • Sex hormones • Testosterone • Male hormone for development • When these steroids are given to the body it can increase muscular development but can cause testicular atrophy or a decrease in sperm count

  24. Continue • Female hormones used in the reproductive process • Estrogens • Estradiol and estrone • Progesterone • Prostaglandins • A substance derived from unsaturated fatty acids, with hormone-like effects on a number of body tissues • These can regulate menstruations, prevent conception, stimulate blood clotting, it can even be used as an aerosol for asthma • Overheads

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