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Chapters 4 & 5

Chapters 4 & 5. Carbon and Macromolecules. CARBON. Atomic #: 6 1st level: 2 2nd Level: 4 # of bonds able to form – 4 - allows the formation of numerous different compounds - compounds that contain carbon are called ORGANIC except for a few very common ones such as CO and CO 2.

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Chapters 4 & 5

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  1. Chapters 4 & 5 Carbon and Macromolecules

  2. CARBON Atomic #: 6 1st level: 22nd Level: 4# of bonds able to form – 4- allows the formation of numerous different compounds- compounds that contain carbon are called ORGANIC except for a few very common ones such as CO and CO2

  3. Name and Comments Space-Filling Model Molecular Formula Structural Formula Ball-and-Stick Model H (a) Methane CH4 C H H H H H (b) Ethane C2H6 C H C H H H H H (c) Ethene (ethylene) C C C2H4 H H Figure 4.3 A-C • The bonding versatility of carbon • Allows it to form many diverse molecules, including carbon skeletons

  4. Carbon (valence = 4) Nitrogen (valence = 3) Hydrogen (valence = 1) Oxygen (valence = 2) O H N C Figure 4.4 • The electron configuration of carbon • Gives it covalent compatibility with many different elements

  5. BOND TYPES Covalent • single - hydrogen, carbon, nitrogen and hydroxyl • double - oxygen, carbon, nitrogen • triple - carbon, nitrogen • C-H - hydrocarbon - non-polar • C-O - polar • C-N- slightly polar

  6. H H C C C C H H C H H H H H H C H H H H H H H H H H H H C C C C C C C H H H H H H H H H H H H (a) Length H Ethane Propane H H H H H H H H H H H C C C C C C C C H H H H (b) Branching 2-methylpropane (commonly called isobutane) Butane H H H H C H (c) Double bonds H H C C C H H C C H H C C 1-Butene 2-Butene H H C C C (d) Rings Figure 4.5 A-D Cyclohexane Benzene Molecular Diversity Arising from Carbon Skeleton Variation • Carbon chains • Form the skeletons of most organic molecules • Vary in length and shape

  7. Carbon: Base of All Biological Molecules Difference between biological molecules • 1) Structure: • Isomers: same chemical formula but different structure • Structual: C4H10 • Butane • Isobutane (2-methylpropane) • Geometric: Ethene - cis and trans • - cis and trans: • L vs. D. • - left verses Right

  8. H H H C H H C H H H H H H H (a) Structural isomers H C C C C C H H C H C C H H H H H H H H H X X X C C C C (b) Geometric isomers X H H H CO2H CO2H C C (c) Enantiomers H H NH2 NH2 CH3 CH3 Figure 4.7 A-C • Three types of isomers are • Structural • Geometric • Enantiomers

  9. L-Dopa (effective against Parkinson’s disease) D-Dopa (biologically inactive) Figure 4.8 • Enantiomers • Are important in the pharmaceutical industry

  10. 2) Functional Groups • - different chemical attachments on hydrocarbons that change the reactivity • TYPES PAGE 54 • a. Hydroxyl - OH - not hydroxide • alcohols • ethane vs. ethanol • b. Carbonyl - C=O • aldehydes - on end • keytones - in middle of chain

  11. c. Carboxyl - -COOH • carboxylic acid • - weak acids • d. Amino - -NH2 • nitrogen containing • amino acids • e. Sufhydryl Group - SH thiols • stabilize proteins – disulfide bridges • f. Phosphate - PO4

  12. OH CH3 Estradiol HO Female lion OH CH3 CH3 O Testosterone Male lion Figure 4.9 • Give organic molecules distinctive chemical properties

  13. FUNCTIONAL GROUP HYDROXYL CARBONYL CARBOXYL O O OH C C OH (may be written HO ) STRUCTURE In a hydroxyl group (—OH), a hydrogen atom is bonded to an oxygen atom, which in turn is bonded to the carbon skeleton of the organic molecule. (Do not confuse this functional group with the hydroxide ion, OH–.) The carbonyl group( CO) consists of a carbon atom joined to an oxygen atom by a double bond. When an oxygen atom is double-bonded to a carbon atom that is also bonded to a hydroxyl group, the entire assembly of atoms is called a carboxyl group (—COOH).  Figure 4.10 • Some important functional groups of organic compounds

  14. Ketones if the carbonyl group is within a carbon skeleton Aldehydes if the carbonyl group is at the end of the carbon skeleton NAME OF COMPOUNDS Alcohols (their specific names usually end in -ol) Carboxylic acids, or organic acids EXAMPLE H H H H O O C C H OH C C H C H C H OH H H H H C Ethanol, the alcohol present in alcoholic beverages H H Acetic acid, which gives vinegar its sour tatste Acetone, the simplest ketone H H O H C C C H H H Propanal, an aldehyde Figure 4.10 • Some important functional groups of organic compounds

  15.  Is polar as a result of the electronegative oxygen atom drawing electrons toward itself.  Attracts water molecules, helping dissolve organic compounds such as sugars (see Figure 5.3). FUNCTIONALPROPERTIES  Has acidic properties because it is a source of hydrogen ions. The covalent bond between oxygen and hydrogen is so polar that hydrogen ions (H+) tend to dissociate reversibly; for example,  A ketone and an aldehyde may be structural isomers with different properties, as is the case for acetone and propanal. H H O O + H+ H C H C C C OH O H H  In cells, found in the ionic form, which is called a carboxylate group. Figure 4.10 • Some important functional groups of organic compounds

  16. AMINO SULFHYDRYL PHOSPHATE O H SH N P OH O (may be written HS ) H OH In a phosphate group, a phosphorus atom is bonded to four oxygen atoms; one oxygen is bonded to the carbon skeleton; two oxygens carry negative charges; abbreviated P . The phosphate group (—OPO32–) is an ionized form of a phosphoric acid group (—OPO3H2; note the two hydrogens). The amino group (—NH2) consists of a nitrogen atom bonded to two hydrogen atoms and to the carbon skeleton. The sulfhydryl group consists of a sulfur atom bonded to an atom of hydrogen; resembles a hydroxyl group in shape. Figure 4.10 • Some important functional groups of organic compounds

  17. Monomers Vs. Polymers most biological molecules are polymers Monomer - one part Polymer - many repeating part Macromolecules - combination of polymers

  18. BUILDING of POLYMERS • Polymerization reaction: 2 units form one larger unit • KEY EX: Protein synthesis Condensation Reaction or Dehydration Synthesis • bond is formed by the removal of a water • two hydroxyl groups - one molecule loses OH and one loses an H • results in a bond based on the remaining O and the H and the OH combine to form water • Requires energy and a catalyst

  19. 1 HO H 3 2 H HO Unlinked monomer Short polymer Dehydration removes a watermolecule, forming a new bond H2O 1 2 3 4 HO H Longer polymer (a) Dehydration reaction in the synthesis of a polymer Figure 5.2A The Synthesis and Breakdown of Polymers • Monomers form larger molecules by condensation reactions called dehydration reactions

  20. BREAKING UP IS HARD TO DO • Hydrolysis Reaction - addition of water to break a polymer chain • Also requires energy and enzymes - but generally gives off more energy than it uses

  21. 1 3 HO 4 2 H Hydrolysis adds a watermolecule, breaking a bond H2O 1 2 H HO 3 H HO (b) Hydrolysis of a polymer Figure 5.2B • Polymers can disassemble by Hydrolysis

  22. Dehydration Synthesis and Hydrolysis Build - anabolic - requires energy • Break - catabolic - releases energy • NOTE: COMBINATION OF MONOMERS IN DIFFERENT QUANTITIES AND PATTERNS RESULTS IN A WIDE VARIETY OF MOLECULES • eg. Alphabet

  23. Four Major Biological Molecules 1. Carbohydrates 2. Lipids 3. Proteins 4. Nucleic Acids

  24. CARBOHYDRATES Elements: CHO and sometimes N • FUNCTION: • Energy • Structure • Protection • Storage

  25. Types of Carbohydrates 1. Sugars: simplest Monomers: monosaccharides Most common glucose : C6H12O6 • Classification: • Monosaccharides: one sugar unit • Ex. Glucose - storage of solar energy via photosynthesis • Characteristics: • Two types of carbonyls: • aldehyde - carbonyl on end • ex. Glucose • ketone - carbonyl in middle • ex. fructose • carbonyl affects ring formation • placement of hydroxyl groups give different properties • Glucose and fructose

  26. Triose sugars(C3H6O3) Pentose sugars(C5H10O5) Hexose sugars(C6H12O6) H H H H O O O O C C C C H C OH H C OH H C OH H C OH H C OH H C OH HO C H HO C H Aldoses H H C OH H C OH HO C H H C OH H C OH H C OH Glyceraldehyde H C OH H C OH H Ribose H H Glucose Galactose H H H H C OH H C OH H C OH C O C O C O HO C H H C OH H C OH Ketoses H C OH H C OH H Dihydroxyacetone H C OH H C OH H C OH H Ribulose H Figure 5.3 Fructose • Examples of monosaccharides

  27. O H 1 C 6CH2OH 6CH2OH 2 CH2OH H C OH 5C H 5C O O 6 3 H O H H H H H 5 HO C H HOH H HOH 4 4C 1 C 1C 4C 4 1 OH H H H C OH O HO OH 3 2 OH OH 5 OH 2 C C 3 C 2C 3 OH H C H OH 6 H H OH OH H C OH H (a) Linear and ring forms. Chemical equilibrium between the linear and ring structures greatly favors the formation of rings. To form the glucose ring, carbon 1 bonds to the oxygen attached to carbon 5. Figure 5.4 • Monosaccharides • May be linear • Can form rings

  28. Glucose + Fructose = Sucrose

  29. Dissacharides formation of a 2 sugar unit by dehydration synthesis • glu + glu = maltose • glu + galac = lactose • glu + fruc = sucrose

  30. (a) Dehydration reaction in the synthesis of maltose. The bonding of two glucose units forms maltose. The glycosidic link joins the number 1 carbon of one glucose to the number 4 carbon of the second glucose. Joining the glucose monomers in a different way would result in a different disaccharide. CH2OH CH2OH CH2OH CH2OH O O O O H H H H H H H H 1–4glycosidiclinkage HOH HOH HOH HOH 4 1 H H H H OH OH O H OH HO HO OH O H H H H OH OH OH OH H2O Glucose Maltose Glucose CH2OH CH2OH CH2OH CH2OH O O O O 1–2glycosidiclinkage H H H H H H HOH HOH 2 1 H H HO H HO H Dehydration reaction in the synthesis of sucrose. Sucrose is a disaccharide formed from glucose and fructose.Notice that fructose,though a hexose like glucose, forms a five-sided ring. (b) OH H O O HO CH2OH HO CH2OH H OH H H OH H OH OH H2O Glucose Sucrose Fructose Figure 5.5 • Examples of disaccharides

  31. Polysaccharides: many sugar units • Chains of glucose • Type of polysaccharide dependent on the type of glucose • alpha glucose • beta glucose • differ in orientation of the hydroxyl group on the number 1 carbon alpha - down position beta - up position

  32. STORAGE POLYSACCHARIDES • 1. Starch - storage in plants - as granuals in organelles called plastids glucose monomers linked together a alpha 1-4 glucosidic linkages two forms of starch • amalose - unbranched chains • amylopectin - branched - branches from the sixth carbon • - branches about every 30 units • 2. Glycogen - storage in animals - storage in liver and muscle cells • alpha 1-4 linkage • extensivly branched • about every 10 units

  33. Chloroplast Starch 1 m Amylose Amylopectin (a) Starch: a plant polysaccharide Figure 5.6 Starch • Is the major storage form of glucose in plants

  34. Giycogen granules Mitochondria 0.5 m Glycogen Figure 5.6 (b) Glycogen: an animal polysaccharide • Glycogen • Consists of glucose monomers • Is the major storage form of glucose in animals

  35. Structural Polysaccharides provide protection and support 1. Cellulose - long unbranched, straight chains beta 1-4 linkages makes for alternating bonds makes for a very rigid structure makes up cell walls enzymes that break alpha bonds can't break beta bonds

  36. H O CH2OH C CH2OH OH H C H O O OH H H H H HO C H 4 4 1 OH H OH H HO OH H HO H C OH H OH OH H C OH H  glucose C  glucose H OH (a)  and  glucose ring structures CH2OH CH2OH CH2OH CH2OH O O O O 1 4 4 4 1 1 1 OH OH OH OH O O O O HO OH OH OH OH (b) Starch: 1– 4 linkage of  glucose monomers CH2OH CH2OH OH OH O O O O OH OH OH OH 4 O 1 HO OH O O CH2OH CH2OH OH OH (c) Cellulose: 1– 4 linkage of  glucose monomers Figure 5.7 A–C Cellulose vs. Starch • Cellulose has different glycosidic linkages than starch

  37. About 80 cellulose molecules associate to form a microfibril, the main architectural unit of the plant cell wall. Cellulose microfibrils in a plant cell wall Microfibril Cell walls  0.5 m Plant cells OH OH CH2OH CH2OH O O O O OH OH OH OH O O O O O OH CH2OH OH CH2OH Cellulose molecules CH2OH OH CH2OH OH O O O O OH OH OH OH Parallel cellulose molecules are held together by hydrogen bonds between hydroxyl groups attached to carbon atoms 3 and 6. O O O O O OH CH2OH OH CH2OH CH2OH CH2OH OH OH O O O O OH OH OH OH O O O A cellulose molecule is an unbranched  glucose polymer. O O OH CH2OH OH CH2OH Figure 5.8 • Glucose monomer Cellulose • Is a major component of the tough walls that enclose plant cells

  38. Figure 5.9 • Cellulose is difficult to digest • Cows have microbes in their stomachs to facilitate this process – mutualism

  39. Structural Polysaccharides 2. Chitin - structure of arthropod exoskeletons and cell walls of fungus differs: glucose with a nitrogen compound attached

  40. CH2OH O OH H H OH H H H NH O C CH3 OH (b) Chitin forms the exoskeleton of arthropods. This cicada is molting, shedding its old exoskeleton and emerging in adult form. (c) Chitin is used to make a strong and flexible surgical thread that decomposes after the wound or incision heals. (a) The structure of the chitin monomer. Figure 5.10 A–C • Chitin, another important structural polysaccharide • Is found in the exoskeleton of arthropods • Can be used as surgical thread

  41. LIPIDS • CHOP - mostly HYDROPHOBIC • - MOSTLY hydrocarbons • NET affect - NON-POLAR • Types: fats, phospholipids, steroids, waxes • Function: energy storage, structure, chemical commumication, repel water

  42. FATS AND OILS Structure - two parts 1. glycerol - three carbon chain with three hydroxyls 2. fatty acid - long chain of hydrocabons with a carboxyl head • carboxyl head combines with hydroxyl of glycerol by dehydration synthesis so 3 fatty acids combine with the glycerols = triglycerol or triglyceride • The massive amounts of hydrocarbons in the tail make fats NONPOLAR

  43. Fats and Oils Constructed from a glycerol and three fatty acids Result = TRIGLYCERIDE

  44. FATS vs. OILS • FATS - animal derived - solid at room temp • OILS - mostly plant derived - liquid at room temp • crucial difference? • bonding in the fatty acids

  45. Saturation vs. Unsaturation Saturated - all carbon bonds are single bonded - all possible hydrogens • straight chains • atheriosclerosis Unsaturated - carbons may have double bonds • - causes a bend in the chain • - chains can't stack as neatly

  46. Stearic acid Figure 5.12 (a) Saturated fat and fatty acid • Saturated fatty acids • Have the maximum number of hydrogen atoms possible • Have no double bonds

  47. Oleic acid cis double bond causes bending Figure 5.12 (b) Unsaturated fat and fatty acid • Unsaturated fatty acids • Have one or more double bonds

  48. PARTIALLY HYDROGENATED OILS BAD BAD BAD BAD BAD

  49. ENERGY Content of Fats and Oils 9 Cal/g • - carbs: 4 Cal/g • - protein: 4 Cal/g • - alcohol: 7 Cal/g • Protection and Insulation Ex: Blubber

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