Carbon and the Molecular Diversity of Life Chapter 4 Carbon and the Molecular Diversity of Life

Overview: Carbon: The Backbone of Life Living organisms consist mostly of carbon-based compounds Carbon is unparalleled in its ability to form large, complex, and diverse molecules Proteins, DNA, carbohydrates, and other molecules that distinguish living matter are all composed of carbon compounds © 2011 Pearson Education, Inc.

Figure 4.1 Figure 4.1 What properties make carbon the basis of all life?

Concept 4.1: Organic chemistry is the study of carbon compounds Organic chemistry is the study of compounds that contain carbon Organic compounds range from simple molecules to colossal ones Most organic compounds contain hydrogen atoms in addition to carbon atoms © 2011 Pearson Education, Inc.

Vitalism, the idea that organic compounds arise only in organisms, was disproved when chemists synthesized these compounds Mechanism is the view that all natural phenomena are governed by physical and chemical laws © 2011 Pearson Education, Inc.

Organic Molecules and the Origin of Life on Earth Stanley Miller’s classic experiment demonstrated the abiotic synthesis of organic compounds Experiments support the idea that abiotic synthesis of organic compounds, perhaps near volcanoes, could have been a stage in the origin of life © 2011 Pearson Education, Inc.

Cooled “rain” containing organic molecules Cold water Figure 4.2 EXPERIMENT “Atmosphere” CH4 Water vapor Electrode NH3 H2 Condenser Cooled “rain” containing organic molecules Cold water Figure 4.2 Inquiry: Can organic molecules form under conditions believed to simulate those on the early Earth? H2O “sea” Sample for chemical analysis

Concept 4.2: Carbon atoms can form diverse molecules by bonding to four other atoms Electron configuration is the key to an atom’s characteristics Electron configuration determines the kinds and number of bonds an atom will form with other atoms © 2011 Pearson Education, Inc.

The Formation of Bonds with Carbon With four valence electrons, carbon can form four covalent bonds with a variety of atoms This ability makes large, complex molecules possible In molecules with multiple carbons, each carbon bonded to four other atoms has a tetrahedral shape However, when two carbon atoms are joined by a double bond, the atoms joined to the carbons are in the same plane as the carbons © 2011 Pearson Education, Inc.

Name and Comment Molecular Formula Structural Formula Ball-and- Figure 4.3 Name and Comment Molecular Formula Structural Formula Ball-and- Stick Model Space-Filling Model (a) Methane CH4 (b) Ethane C2H6 Figure 4.3 The shapes of three simple organic molecules. (c) Ethene (ethylene) C2H4

The electron configuration of carbon gives it covalent compatibility with many different elements The valences of carbon and its most frequent partners (hydrogen, oxygen, and nitrogen) are the “building code” that governs the architecture of living molecules © 2011 Pearson Education, Inc.

Hydrogen (valence  1) Oxygen (valence  2) Nitrogen (valence  3) Figure 4.4 Hydrogen (valence  1) Oxygen (valence  2) Nitrogen (valence  3) Carbon (valence  4) Figure 4.4 Valences of the major elements of organic molecules.

Carbon atoms can partner with atoms other than hydrogen; for example: Carbon dioxide: CO2 Urea: CO(NH2)2 © 2011 Pearson Education, Inc.

Figure 4.UN01 Urea Figure 4.UN01 In-text figure, p. 61

Molecular Diversity Arising from Carbon Skeleton Variation Carbon chains form the skeletons of most organic molecules Carbon chains vary in length and shape © 2011 Pearson Education, Inc.

Animation: Carbon Skeletons Right-click slide/select “Play” © 2011 Pearson Education, Inc. 16

2-Methylpropane (isobutane) Figure 4.5 (a) Length (c) Double bond position Ethane Propane 1-Butene 2-Butene (b) Branching (d) Presence of rings Figure 4.5 Four ways that carbon skeletons can vary. Butane 2-Methylpropane (isobutane) Cyclohexane Benzene

(a) Length Ethane Propane Figure 4.5a Figure 4.5 Four ways that carbon skeletons can vary.

(commonly called isobutane) Figure 4.5b (b) Branching Figure 4.5 Four ways that carbon skeletons can vary. Butane 2-Methylpropane (commonly called isobutane)

(c) Double bond position Figure 4.5c (c) Double bond position 1-Butene 2-Butene Figure 4.5 Four ways that carbon skeletons can vary.

(d) Presence of rings Cyclohexane Benzene Figure 4.5d Figure 4.5 Four ways that carbon skeletons can vary. Cyclohexane Benzene

Hydrocarbons Hydrocarbons are organic molecules consisting of only carbon and hydrogen Many organic molecules, such as fats, have hydrocarbon components Hydrocarbons can undergo reactions that release a large amount of energy © 2011 Pearson Education, Inc.

(a) Part of a human adipose cell (b) A fat molecule Figure 4.6 Nucleus Fat droplets Figure 4.6 The role of hydrocarbons in fats. 10 m (a) Part of a human adipose cell (b) A fat molecule

Nucleus Fat droplets 10 m Figure 4.6a Figure 4.6 The role of hydrocarbons in fats. 10 m

Isomers Isomers are compounds with the same molecular formula but different structures and properties Structural isomers have different covalent arrangements of their atoms Cis-trans isomers have the same covalent bonds but differ in spatial arrangements Enantiomers are isomers that are mirror images of each other © 2011 Pearson Education, Inc.

Animation: Isomers Right-click slide / select “Play” © 2011 Pearson Education, Inc. 26

(a) Structural isomers Figure 4.7 (a) Structural isomers (b) Cis-trans isomers cis isomer: The two Xs are on the same side. trans isomer: The two Xs are on opposite sides. Figure 4.7 Three types of isomers, compounds with the same molecular formula but different structures. (c) Enantiomers CO2H CO2H H NH2 NH2 H CH3 CH3 L isomer D isomer

(a) Structural isomers Figure 4.7a (a) Structural isomers Figure 4.7 Three types of isomers, compounds with the same molecular formula but different structures.

cis isomer: The two Xs are on the same side. Figure 4.7b (b) Cis-trans isomers cis isomer: The two Xs are on the same side. trans isomer: The two Xs are on opposite sides. Figure 4.7 Three types of isomers, compounds with the same molecular formula but different structures.

(c) Enantiomers CO2H CO2H H NH2 NH2 H CH3 CH3 L isomer D isomer Figure 4.7c (c) Enantiomers CO2H CO2H H NH2 NH2 H CH3 CH3 Figure 4.7 Three types of isomers, compounds with the same molecular formula but different structures. L isomer D isomer

Enantiomers are important in the pharmaceutical industry Two enantiomers of a drug may have different effects Usually only one isomer is biologically active Differing effects of enantiomers demonstrate that organisms are sensitive to even subtle variations in molecules © 2011 Pearson Education, Inc.

Animation: L-Dopa Right-click slide / select “Play” © 2011 Pearson Education, Inc. 32

Effective Enantiomer Ineffective Enantiomer Pain; inflammation Figure 4.8 Effective Enantiomer Ineffective Enantiomer Drug Condition Pain; inflammation Ibuprofen S-Ibuprofen R-Ibuprofen Figure 4.8 The pharmacological importance of enantiomers. Albuterol Asthma R-Albuterol S-Albuterol

Concept 4.3: A few chemical groups are key to the functioning of biological molecules Distinctive properties of organic molecules depend on the carbon skeleton and on the molecular components attached to it A number of characteristic groups can replace the hydrogens attached to skeletons of organic molecules © 2011 Pearson Education, Inc.

The Chemical Groups Most Important in the Processes of Life Functional groups are the components of organic molecules that are most commonly involved in chemical reactions The number and arrangement of functional groups give each molecule its unique properties © 2011 Pearson Education, Inc.

Estradiol Testosterone Figure 4.UN02 Figure 4.UN02 In-text figure, p. 63

The seven functional groups that are most important in the chemistry of life: Hydroxyl group Carbonyl group Carboxyl group Amino group Sulfhydryl group Phosphate group Methyl group © 2011 Pearson Education, Inc.

Figure 4.9 Exploring: Some Biologically Important Chemical Groups Figure 4.9-a CHEMICAL GROUP Hydroxyl Carbonyl Carboxyl STRUCTURE (may be written HO—) NAME OF COMPOUND Alcohols (Their specific names usually end in -ol.) Ketones if the carbonyl group is within a carbon skeleton Carboxylic acids, or organic acids Aldehydes if the carbonyl group is at the end of the carbon skeleton EXAMPLE Ethanol Acetone Acetic acid Figure 4.9 Exploring: Some Biologically Important Chemical Groups Propanal FUNCTIONAL PROPERTIES • Is polar as a result of the electrons spending more time near the electronegative oxygen atom. • A ketone and an aldehyde may be structural isomers with different properties, as is the case for acetone and propanal. • Acts as an acid; can donate an H+ because the covalent bond between oxygen and hydrogen is so polar: • Can form hydrogen bonds with water molecules, helping dissolve organic compounds such as sugars. • Ketone and aldehyde groups are also found in sugars, giving rise to two major groups of sugars: ketoses (containing ketone groups) and aldoses (containing aldehyde groups). Nonionized Ionized • Found in cells in the ionized form with a charge of 1 and called a carboxylate ion.

Figure 4.9 Exploring: Some Biologically Important Chemical Groups Figure 4.9-b Amino Sulfhydryl Phosphate Methyl (may be written HS—) Amines Thiols Organic phosphates Methylated compounds Glycine Cysteine Glycerol phosphate 5-Methyl cytidine • Acts as a base; can pick up an H+ from the surrounding solution (water, in living organisms): • Two sulfhydryl groups can react, forming a covalent bond. This “cross-linking” helps stabilize protein structure. • Contributes negative charge to the molecule of which it is a part (2– when at the end of a molecule, as above; 1– when located internally in a chain of phosphates). • Addition of a methyl group to DNA, or to molecules bound to DNA, affects the expression of genes. Figure 4.9 Exploring: Some Biologically Important Chemical Groups • Arrangement of methyl groups in male and female sex hormones affects their shape and function. • Cross-linking of cysteines in hair proteins maintains the curliness or straightness of hair. Straight hair can be “permanently” curled by shaping it around curlers and then breaking and re-forming the cross-linking bonds. • Molecules containing phosphate groups have the potential to react with water, releasing energy. Nonionized Ionized • Found in cells in the ionized form with a charge of 1+.

Hydroxyl STRUCTURE NAME OF COMPOUND EXAMPLE FUNCTIONAL PROPERTIES Figure 4.9a Hydroxyl STRUCTURE Alcohols (Their specific names usually end in -ol.) NAME OF COMPOUND (may be written HO—) EXAMPLE • Is polar as a result of the electrons spending more time near the electronegative oxygen atom. FUNCTIONAL PROPERTIES Figure 4.9 Exploring: Some Biologically Important Chemical Groups Ethanol • Can form hydrogen bonds with water molecules, helping dissolve organic compounds such as sugars.

Carbonyl STRUCTURE NAME OF COMPOUND EXAMPLE FUNCTIONAL PROPERTIES Figure 4.9b Carbonyl STRUCTURE Ketones if the carbonyl group is within a carbon skeleton NAME OF COMPOUND Aldehydes if the carbonyl group is at the end of the carbon skeleton EXAMPLE A ketone and an aldehyde may be structural isomers with different properties, as is the case for acetone and propanal. FUNCTIONAL PROPERTIES Ketone and aldehyde groups are also found in sugars, giving rise to two major groups of sugars: ketoses (containing ketone groups) and aldoses (containing aldehyde groups). Figure 4.9 Exploring: Some Biologically Important Chemical Groups Acetone Propanal

Carboxyl • Acts as an acid; can donate an H+ because the Figure 4.9c Carboxyl STRUCTURE Carboxylic acids, or organic acids NAME OF COMPOUND EXAMPLE • Acts as an acid; can donate an H+ because the covalent bond between oxygen and hydrogen is so polar: FUNCTIONAL PROPERTIES Figure 4.9 Exploring: Some Biologically Important Chemical Groups Acetic acid Nonionized Ionized • Found in cells in the ionized form with a charge of 1– and called a carboxylate ion.

Amino • Acts as a base; can • Found in cells in the STRUCTURE Amines Figure 4.9d Amino STRUCTURE Amines NAME OF COMPOUND EXAMPLE • Acts as a base; can pick up an H+ from the surrounding solution (water, in living organisms): FUNCTIONAL PROPERTIES Figure 4.9 Exploring: Some Biologically Important Chemical Groups Glycine Nonionized Ionized • Found in cells in the ionized form with a charge of 1.

Sulfhydryl • Two sulfhydryl groups can • Cross-linking of cysteines Figure 4.9e Sulfhydryl STRUCTURE Thiols NAME OF COMPOUND (may be written HS—) EXAMPLE • Two sulfhydryl groups can react, forming a covalent bond. This “cross-linking” helps stabilize protein structure. FUNCTIONAL PROPERTIES • Cross-linking of cysteines in hair proteins maintains the curliness or straightness of hair. Straight hair can be “permanently” curled by shaping it around curlers and then breaking and re-forming the cross-linking bonds. Figure 4.9 Exploring: Some Biologically Important Chemical Groups Cysteine

• Contributes negative Figure 4.9f Phosphate STRUCTURE Organic phosphates NAME OF COMPOUND EXAMPLE • Contributes negative charge to the molecule of which it is a part (2– when at the end of a molecule, as at left; 1– when located internally in a chain of phosphates). FUNCTIONAL PROPERTIES Figure 4.9 Exploring: Some Biologically Important Chemical Groups Glycerol phosphate • Molecules containing phosphate groups have the potential to react with water, releasing energy.

• Addition of a methyl group Figure 4.9g Methyl STRUCTURE Methylated compounds NAME OF COMPOUND EXAMPLE • Addition of a methyl group to DNA, or to molecules bound to DNA, affects the expression of genes. FUNCTIONAL PROPERTIES Figure 4.9 Exploring: Some Biologically Important Chemical Groups • Arrangement of methyl groups in male and female sex hormones affects their shape and function. 5-Methyl cytidine

ATP: An Important Source of Energy for Cellular Processes One phosphate molecule, adenosine triphosphate (ATP), is the primary energy-transferring molecule in the cell ATP consists of an organic molecule called adenosine attached to a string of three phosphate groups © 2011 Pearson Education, Inc.

Figure 4.UN03 a. b. Figure 4.UN03 Figure legend question, Figure 4.9

Figure 4. UN04 Adenosine Figure 4.UN04 In-text figure, p. 66

The Chemical Elements of Life: A Review The versatility of carbon makes possible the great diversity of organic molecules Variation at the molecular level lies at the foundation of all biological diversity © 2011 Pearson Education, Inc.

Reacts with H2O Adenosine Adenosine Energy ATP Inorganic phosphate ADP Figure 4. UN05 Reacts with H2O Adenosine Adenosine Energy ATP Inorganic phosphate ADP Figure 4.UN05 In-text figure, p. 66

Figure 4. UN07 Figure 4.UN07 Test Your Understanding, question 2

Figure 4. UN08 Figure 4.UN08 Test Your Understanding, question 5

Figure 4. UN09 Figure 4.UN09 Test Your Understanding, question 6

Figure 4. UN10 Figure 4.UN10 Test Your Understanding, question 11

Figure 4. UN11 Figure 4.UN11 Appendix A: answer to Figure 4.4 legend question

Figure 4. UN12 Figure 4.UN12 Appendix A: answer to Figure 4.7 legend question

Figure 4. UN13 Figure 4.UN13 Appendix A: answer to Concept Check 4.2, question 1

Figure 4. UN14 Figure 4.UN14 Appendix A: answer to Concept Check 4.3, question 3

Figure 4. UN15 Figure 4.UN15 Appendix A: answer to Test Your Understanding, question 9