1. Sylvia S. Mader Copyright © The McGraw Hill Companies Inc. Permission required for reproduction or display PowerPoint® Lecture Slides are prepared by Dr. Isaac Barjis, Biology Instructor BIOLOGY 10th Edition 1 The Chemistry of Organic Molecules Chapter 3: pp. 37-58 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. © The McGraw Hill Companies, Inc./John Thoeming, photographer

2. 2 Outline Organic vs Inorganic Functional Groups and Isomers Macromolecules Carbohydrates Lipids Proteins Nucleic Acids

3. 3 Organic Molecules Organic molecules contain carbon and hydrogen atoms bonded to other atoms Organic molecules are a diverse group Four types of organic molecules (biomolecules) exist in organisms: Carbohydrates Lipids Proteins Nucleic Acids

4. 4 Organic versus Inorganic Molecules

5. 5 Carbon Atom Carbon atoms: Contain a total of 6 electrons Only four electrons in the outer shell Very diverse as one atom can bond with up to four other atoms Often bonds with other carbon atoms to make hydrocarbons Can produce long carbon chains like octane Can produce ring forms like cyclohexane

6. 6 Octane & Cyclohexane Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. octane cyclohexane

7. 7 Functional Groups Functional groups are clusters of specific atoms bonded to the carbon skeleton with characteristic structure and functions Always react in the same manner, regardless of where attached Determine activity and polarity of large organic molecules Many functional groups, but only a few are of major biological importance Depending on its functional groups, an organic molecule may be both acidic and hydrophilic Nonpolar organic molecules are hydrophobic (cannot dissolve in water) unless they contain a polar functional group

8. 8 Isomers Isomers - organic molecules that have: Identical molecular formulas, but Differing internal arrangement of atoms Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. glyceraldehyde dihydroxyacetone OH HH HCCCH O HO HCCCH H

9. Hexose Isomers 9

10. 10 Macromolecules Carbohydrates, lipids, proteins, and nucleic acids are called macromolecules because of their large size. Usually consist of many repeating units Resulting molecule is a polymer (many parts) Repeating units are called monomers E.g. amino acids (monomer) are linked to form a protein (polymer) Some examples:

11. 11 Common Foods Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. © The McGraw Hill Companies, Inc./John Thoeming, photographer

12. 12 Dehydration and Hydrolysis Dehydration - Removal of water molecule Used to connect monomers together to make polymers Polymerization of glucose monomers to make starch Hydrolysis - Addition of water molecule Used to disassemble polymers into monomer parts Digestion of starch into glucose monomers Specific enzymes required for each reaction Accelerate reaction Are not used in the reaction Are not changed by the reaction

13. Short polymerUnlinked monomer Dehydration reaction Longer polymer Dehydration

14. Hydrolysis

15. Dehydration and Hydrolysis 15

16. 16 Synthesis and Degradation of Polymers monomer dehydration reaction monomer hydrolysis reaction H2OH2O OHH H b. Degradation of a biomolecule a. Synthesis of a biomolecule H2OH2O monomer Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

17. 17 Carbohydrates Monosaccharides: Are a single sugar molecule such as glucose, ribose, deoxyribose Are with a backbone of 3 to 7 carbon atoms (most have 6 carbon). Disaccharides: Contain two monosaccharides joined by dehydration reaction Lactose is composed of galactose and glucose and is found in milk. Sucrose (table sugar) is composed of glucose and fructose Polysaccharides - Are polymers of monosaccharides Polysaccharides as Energy Storage Molecules Starch, Glycogen Polysaccharides as Structural Molecules Cellulose, Chitin

18. 18 Popular Models for Representing Glucose Molecules C 6 H 12 O 6 a. b. c.d. Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. © Steve Bloom/Taxi/Getty CH 2 OH C C H C HO O C H OH C H H H CH 2 OH H HO H OH H H O OO

19. 19 Synthesis and Degradation of Maltose, a Disaccharide glucose C 6 H 12 O 6 water monosaccharidedisaccharidewater glucose C 6 H 12 O 6 monosaccharide ++ dehydration reaction hydrolysis reaction maltose C 12 H 22 O 11 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. CH 2 OH OO H OH H HO CH 2 OH O O O H2OH2O O O glucosefructose sucrose O CH 2 OH Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. CH 2 OH

20. 20 Carbohydrates: Monosaccharides Single sugar molecules Quite soluble and sweet to taste Examples Glucose (blood), fructose (fruit) and galactose Hexoses - Six carbon atoms Isomers of C 6 H 12 O 6 Ribose and deoxyribose (in nucleotides) Pentoses – Five carbon atoms C 5 H 10 O 5 & C 5 H 10 O 4

21. 21 Carbohydrates: Disaccharides Contain two monosaccharides joined by dehydration reaction Soluble and sweet to taste Examples Lactose is composed of galactose and glucose and is found in milk Sucrose (table sugar) is composed of glucose and fructose Maltose is composed of two glucose molecules

22. 22 Carbohydrates: Polysaccharides Polymers of monosaccharides Low solubility; not sweet to taste Polysaccharides as Energy Storage Molecules Starch found in plant Polymer of glucose Few side branches Used for short-term energy storage Amylose (unbranched) and amylopectin (branched) are the two forms of starch found in plants Glycogen is the storage form of glucose in animals. Highly branched polymer of glucose with many side branches Glycogen in liver and muscles

23. 23 Carbohydrates: Polysaccharides Polysaccharides as Structural Molecules Cellulose is a polymer of glucose which forms microfibrils Primary constituent of plant cell walls Main component of wood and many natural fibers Indigestible by most animals Chitin is a polymer of glucose with an amino group attached to each glucose Very resistant to wear and digestion Primary constituent of arthropod exoskeletons (e.g. Crab) and cell walls of fungi

24. Complex Carbohydrates 24

25. 25 Starch Structure and Function a. Starch starch granule 250  m Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. © Jeremy Burgess/SPL/Photo Researchers, Inc.

26. 26 Glycogen Structure and Function b. Glycogen glycogen granule 150 nm Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. © Don W. Fawcett/Photo Researchers, Inc.

27. 27 Cellulose Structure and Function cellulose fiber cellulose fibers Plant cell wall microfibrils glucose molecules 5,000 m Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. © Science Source/J.D. Litvay/Visuals Unlimited

28. 28 Carbohydrates as Structural Materials Plants cell wall consist of cellulose Cell wall of fungi and shell of crab contain chitin Bacterial cell wall contain peptidoglycan c. Cell walls contain peptidoglycan. b. Shell contains chitin. a. Cell walls contain cellulose. Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. a: © Brand X Pictures/PunchStock; b: © Ingram Publishing/Alamy; c: © H. Pol/CNRI/SPL/Photo Researchers, Inc.

29. 29 Lipids Lipids are varied in structure Insoluble in water Long chains of repeating CH 2 units Renders molecule nonpolar Lack polar groups

30. 30 Lipids Fat provides insulation and energy storage in animals Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. © Paul Nicklen/National Geographic/Getty

31. 31 Types of Lipids

32. 32 Types of Lipids: Triglycerides Fats and oils contain two molecular units: glycerol and fatty acids. Dehydration Synthesis of Triglyceride from Glycerol and Three Fatty Acids Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. + COH H H C H C C H H H H COH H COH COH H C H C O C H C H H C H H H C H C H H C H H H C HO H C H C C O C H HHH C H C H C H H C O HO C H H C H H H C H HHH C H C H C H H C O C H H C H H H C H HHH C H C H C H H C O H C H HHH C H C H C H H H + a. Formation of a fat 3 H 2 O glycerol3 fatty acidsfat molecule3 water molecules dehydration reaction kink hydrolysis reaction

33. 33 Types of Lipids: Triglycerides C H HHH C H C H C H H C O HO C H H C H H C H H C H C H C H H C H C H C H H C H C H C H H C H H H C H H HC H HHH C H C H C H H C O C H H C H H C H H C H HHH C H C H C H H C H H C H H C H H unsaturated fatty acid with double bonds (yellow) corncorn oil milkbutter unsaturated fat saturated fatty acid with no double bondssaturated fat b.Types of fatty acidsc.Types of fats C H H Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

34. 34 Types of Lipids: Triglycerides Triglycerides (Fats) Long-term energy storage Consist of a backbone of one glycerol molecule Glycerol is a water ‑ soluble compound with three hydroxyl groups. Three fatty acids attached to each glycerol molecule Long hydrocarbon chain Saturated - no double bonds between carbons e.g. in fats (butter) Unsaturated - 1 or more than1 double bonds between carbons e.g. in oils Carboxylic acid at one end Carboxylic acid connects to –OH on glycerol in dehydration reaction

35. Animal and Plant Fats Most plant fats are unsaturated and most animal fats are saturated. Butter and lard are solids at room temperature. Too much saturated and trans fats can lead to atherosclerosis. Lipids containing deposits called plaques build up within the walls of blood vessels, reducing blood flow.

36. Atherosclerosis

37. 37 Types of Lipids: Phospholipids Phospholipids Derived from triglycerides Glycerol backbone Two fatty acids attached instead of three Third fatty acid replaced by phosphate group The fatty acids are nonpolar and hydrophobic The phosphate group is polar and hydrophilic Molecules self arrange when placed in water Polar phosphate “heads” next to water Nonpolar fatty acid “tails” overlap and exclude water Spontaneously form double layer & a sphere

38. 38 Types of Lipids: Phospholipids Phospholipids Form Membranes Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. b. Plasma membrane of a cell inside celloutside cell Polar Head phosphate a. Phospholipid structure fatty acids glycerol Nonpolar Tails 1 CH 2 O 2 CH O –O–O OPO 3 CH 2 R O O O CH 2 CH 3 C O C CH 2 CH CH 2 CH 3 CH 2 =

39. 39 Types of Lipids: Steroids & Waxes Steroids Cholesterol, testosterone, estrogen Skeletons of four fused carbon rings Waxes Long-chain fatty acid bonded to a long-chain alcohol High melting point Waterproof Resistant to degradation

40. CONNECTION Anabolic steroids pose health risks Anabolic steroids are natural and synthetic variants of the male hormone testosterone – Build up bone and muscle mass – Can cause serious health problems

41. Anabolic Steroids  Anabolic steroids are synthetic variants of the male hormone testosterone – which generally causes a build up in muscle mass in males during puberty and maintains masculine traits.  Positive uses of anabolic steroids  As a prescription drug, anabolic steroids are used to treat general anemia and diseases that destroy body muscle.

42. Negative effects of Anabolic Steroids Violent mood swings (“Roid Rage”) Deep Depression Alter cholesterol levels leading to high blood pressure and increasing risk of cardiovascular problems. Reduces the bodies natural output of male sex hormones – shrunken testicles, reduced sex drive, infertility, and breast enlargement in men. In women, use has been linked to menstrual cycle disruption and development of masculine characteristics.

43. 43 Waxes a.b. Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. a: © Das Fotoarchiv/Peter Arnold, Inc.; b: © Martha Cooper/Peter Arnold, Inc.

44. 44 Proteins Functions Support proteins Keratin - makes up hair and nails Collagen - support many of the body’s structures e.g. tendons, skin Enzymes – Almost all enzymes are proteins Acts as organic catalysts to accelerate chemical reactions within cells Transport – Hemoglobin; membrane proteins Defense – Antibodies Hormones are regulatory proteins that influence the metabolism of cells e.g. insulin Motion – Muscle proteins, microtubules

45. 45 Protein Subunits: The Amino Acids Proteins are polymers of amino acids Each amino acid has a central carbon atom (the alpha carbon) to which are attached a hydrogen atom, an amino group –NH 2, A carboxylic acid group –COOH, and one of 20 different types of –R (remainder) groups There are 20 different amino acids that make up proteins Amino acids differ according to their particular R group

46. Protein Structure 46

47. 47 Structural Formulas for the 20 Amino Acids proline (Pro)valine (Val)phenylalanine (Phe)methionine (Met)leucine (Leu) glutamine (Gln) threonine (Thr)asparagine (Asn) aspartic acid (Asp)arginine (Arg)histidine (His) cysteine (Cys)serine (Ser) tyrosine (Tyr) glutamic acid (Glu) lysine (Lys) H H3N+H3N+ C CH H3CH3CCH 3 C O O–O– H O O CC (CH 2 ) 2 S CH 3 CH 2 C H H3N+H3N+ C O O–O– H3N+H3N+ H CH CH 3 H3N+H3N+ C H O–O– H2N+H2N+ H C C H O–O– CH 2 H2CH2C H C H3N+H3N+ C O O–O– SH H3N+H3N+ CC O O–O– H CH 2 OH O O–O– C CH 2 OH H3N+H3N+ C Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. O O–O– C H (CH 2 ) 2 H3N+H3N+ NH 2 O C O O–O– C H C CH 2 H3N+H3N+ NH 2 O H O O–O– C C H3N+H3N+ OH CH 3 CH H H3N+H3N+ CC O O–O– CH 2 COO – H C CH 2 H3N+H3N+ C O O–O– N+H3N+H3 H C C –O–OO C O O–O– H3N+H3N+ H C (CH 2 ) 3 NH C NH 2 N+H2N+H2 H3N+H3N+ C O O–O– H3N+H3N+ C C H CH 2 NH N+HN+H O–O– O H CC C Sample Amino Acids with Polar (Hydrophilic) R Groups Sample Amino Acids with Ionized R Groups Sample Amino Acids with Nonpolar (Hydrophobic) R Groups C

48. 48 Proteins: The Polypeptide Backbone A peptide bond is a covalent bond between two amino acids (AA) COOH of one AA covalently bonds to the NH 2 of the next AA Two AAs bonded together – Dipeptide Three AAs bonded together – Tripeptide Many AAs bonded together – Polypeptide Characteristics of a protein determined by composition and sequence of AA’s A protein may contain more than one polypeptide chain Virtually unlimited number of proteins

49. Synthesis and Degradation of a Peptide dehydration reaction hydrolysis reaction water peptide bond dipeptide amino acid acidic groupamino group Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

50. 50 Protein: Levels of Structure Protein shape (3-D structure) determines the function of the protein in the organism Proteins can have up to four levels of structure Primary: Literally, the sequence of amino acids A string of beads (up to 20 different colors) Secondary: The way the amino acid chain coils or folds Describing the way a knot is tied Tertiary: Overall three-dimensional shape of a polypeptide Describing what a knot looks like from the outside Quaternary: Consists of more than one polypeptide Like several completed knots glued together

51. 51 Levels of Protein Organization (beta) sheet = pleated sheet COO – Primary Structure Secondary Structure Tertiary Structure Quaternary Structure amino acid peptide bond disulfide bond hydrogen bond (alpha) helix H3N+H3N+ This level of structure is determined by the sequence of amino acids that join to form a polypeptide. Hydrogen bonding between amino acids causes the polypeptide to form an alpha helix or a pleated sheet. Due in part to covalent bonding between R groups the polypeptide folds and twists giving it a characteristic globular shape. This level of structure occurs when two or more polypeptides join to form a single protein. Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

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53. 53 Examples of Fibrous Proteins a.b.c. Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. a: © Gregory Pace/Corbis; b: © Ronald Siemoneit/Corbis Sygma; c: © Kjell Sandved/Visuals Unlimited

54. 54 Protein-folding Diseases Assembly of AA’s into protein extremely complex Process overseen by “chaperone” molecules Inhibit incorrect interactions between R groups as polypeptide grows Defects in these chaperones can corrupt the tertiary structure of proteins Mad cow disease could be due to mis-folded proteins

55. 55 Nucleic Acids Polymers of nucleotides Very specific cell functions DNA (deoxyribonucleic acid) Double-stranded helical spiral (twisted ladder) Serves as genetic information center In chromosomes RNA (ribonucleic acid) Part single-stranded, part double-stranded Serves primarily in assembly of proteins In nucleus and cytoplasm of cell

56. 56 The Nucleotides of Nucleic Acids Three components: A phosphate group, A pentose sugar (ribose or deoxyribose), and A nitrogenous base (4 kinds in DNA, 3 kinds in RNA, 3 common to both Nucleotide subunits connected end-to-end to make nucleic acid Sugar of one connected to the phosphate of the next Sugar-phosphate backbone

57. 57 Nucleotides pentose sugar nitrogen- containing base phosphate deoxyribose (in DNA)ribose (in RNA) cytosinethymine in DNAuracil in RNA a. Nucleotide structure c. Pyrimidines versus purines b. Deoxyribose versus ribose adenineguanine Pyrimidines Purines Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

58. 58 DNA Structure A T b. Double helixa. Space-filling model A A T T G G C C G P C Guanine Thymine Adenine CytosineSugar Phosphate S Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. © Photodisk Red/Getty Images

59. 59 RNA Structure Guanine Uracil Adenine CytosineRibose Phosphate P S Backbone Nitrogen-containing bases S S S S P P P P G C A U Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

60. 60 Complementary Base Pairing N adenine (A) sugar thymine (T) cytosine (C)guanine (G) sugar c. Complementary base pairing Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

61. 61 Comparison of DNA & RNA

62. 62 Other Nucleic Acids ATP (adenosine triphosphate) is composed of adenine, ribose, and three phosphates In cells, one phosphate bond is hydrolyzed – Yields: The molecule ADP (adenosine diphosphate) An inorganic phosphate molecule p i Energy Other energy sources used to put ADP and p i back together again

63. 63 ATP + + adenosine ATP triphosphateadenosinediphosphatephosphate energy ADP adenosinetriphosphate H2OH2O PPP PPP b. a.c. Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. c: © Jennifer Loomis/Animals Animals/Earth Scenes

64. 64 Review Organic vs Inorganic Functional Groups and Isomers Macromolecules Carbohydrates Lipids Proteins Nucleic Acids

65. Sylvia S. Mader Copyright © The McGraw Hill Companies Inc. Permission required for reproduction or display PowerPoint® Lecture Slides are prepared by Dr. Isaac Barjis, Biology Instructor BIOLOGY 10th Edition 65 The Chemistry of Organic Molecules Chapter 3: pp. 37-58 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. © The McGraw Hill Companies, Inc./John Thoeming, photographer