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