Carbon and the Molecular Diversity of Life

Transcription

1 LECTURE PRESENTATIONS For CAMPBELL BIOLOGY, NINTH EDITION Jane B. Reece, Lisa A. Urry, Michael L. Cain, Steven A. Wasserman, Peter V. Minorsky, Robert B. Jackson Chapter 4 Carbon and the Molecular Diversity of Life Lectures by Erin Barley Kathleen Fitzpatrick

2 Overview: Carbon: The Backbone of Life Living organisms are made up of chemicals based mostly on the element carbon, e.g. proteins, DNA, carbohydrates

3 Concept 4.1: Organic chemistry is the study of carbon compounds Organic chemistry is the study of carbon compounds i.e. organic compounds Most organic compounds contain hydrogen atoms in addition to carbon atoms Carbon is unparalleled in its ability to form large, complex, and diverse molecules Range from simple molecules like methane To colossal ones like proteins

4 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 Organic chemistry was redefined as, The study of carbon compounds, irrespective of their origin

5 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

6 Figure 4.2 EXPERIMENT Water vapor CH 4 Atmosphere Electrode Condenser Cooled rain containing organic molecules Cold water H 2 O sea Sample for chemical analysis

7 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

8 The Formation of Bonds with Carbon Carbon is tetravalent, has 4 electrons in its valence shell This allows it to form four covalent bonds with a variety of atoms This ability makes large, complex molecules possible This bonding versatility of carbon over hydrogen, oxygen and nitrogen, allows it to form many diverse molecules, including carbon skeletons

9 The Formation of Bonds with Carbon 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

10 Figure 4.3 Name and Comment Molecular Formula Structural Formula Ball-and- Stick Model Space-Filling Model (a) Methane CH 4 (b) Ethane C 2 H 6 (c) Ethene (ethylene) C 2 H 4

11 Molecular Diversity Arising from Carbon Skeleton Variation 1)Length, shape and arrangement (branching or ring) 2)Presence and location of double and/or triple bonds Animation: Carbon Skeletons

12 Hydrocarbons Are molecules consisting of carbon & hydrogen Are found in many of a cell s organic molecules Hydrocarbons can undergo reactions that release a large amount of energy Fat droplets (stained red) (a) A fat molecule 100 µm (b) Mammalian adipose cells

13 Isomers Are compounds with the same molecular formula but different structures and hence different properties E.g. Butane (C 4 H 10 ) vs Isobutane (C 4 H 10 ) Three types of isomers are a) Structural b) Geometric c) Enantiomers

14 a) Structural Isomers Differ in the covalent arrangement of their atoms The number of possible isomers increases as the number of carbon skeleton increases in size E.g. C 4 H 10 has 2 isomers C 8 H 18 has 18 isomers C 20 H 42 has isomers

15 b) Geometric Isomers Have the same covalent partnerships, but differ in their spatial arrangements around a carbon-carbon double bond. Dramatically affect the biological activities eg rhodopsin in eye changes from cis to trans in response to light Cis isomer: The two Xs are on the same side. Trans isomer: The two Xs are on opposite sides.

16 c) Enantiomers are isomers that are mirror images of each other CO 2 H CO 2 H H H NH 2 NH 2 CH 3 CH 3

17 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 Animation: L-Dopa

18 Figure 4.8 Drug Condition Effective Enantiomer Ineffective Enantiomer Ibuprofen Pain; inflammation S-Ibuprofen R-Ibuprofen Albuterol Asthma R-Albuterol S-Albuterol

19 Concept 4.3: A few chemical groups are key to the functioning of biological molecules Functional groups are the parts of molecules involved in chemical reactions Are the chemically reactive groups of atoms within an organic molecule Give organic molecules distinctive chemical properties The number and arrangement of functional groups give each molecule its unique properties

20 Functional groups contd. The basic structure of testosterone (male hormone) and estradiol (female hormone) is identical Both are steroids with four fused carbon rings, but they differ in the functional groups attached to the rings.

21 Functional groups contd. Seven important ones in the chemistry of life Hydroxyl Carbonyl Carboxyl Amino Sulfhydryl Phosphate Methyl

22 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 Propanal FUNCTIONAL PROPERTIES Is polar as a result of the electrons spending more time near the electronegative oxygen atom. Can form hydrogen bonds with water molecules, helping dissolve organic compounds such as sugars. A ketone and an aldehyde may be structural isomers with different properties, as is the case for acetone and propanal. 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). Acts as an acid; can donate an H + because the covalent bond between oxygen and hydrogen is so polar: Nonionized Ionized Found in cells in the ionized form with a charge of 1 and called a carboxylate ion.

23 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): Nonionized Found in cells in the ionized form with a charge of 1+. Ionized Two sulfhydryl groups can react, forming a covalent bond. This cross-linking helps stabilize protein structure. 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. 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). Molecules containing phosphate groups have the potential to react with water, releasing energy. Addition of a methyl group to DNA, or to molecules bound to DNA, affects the expression of genes. Arrangement of methyl groups in male and female sex hormones affects their shape and function.

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

25 Figure 4.9b Carbonyl STRUCTURE EXAMPLE Acetone Propanal Ketones if the carbonyl group is within a carbon skeleton Aldehydes if the carbonyl group is at the end of the carbon skeleton A ketone and an aldehyde may be structural isomers with different properties, as is the case for acetone and propanal. 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). NAME OF COMPOUND FUNCTIONAL PROPERTIES

26 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 Acetic acid Nonionized Ionized Found in cells in the ionized form with a charge of 1 and called a carboxylate ion.

27 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 Glycine Nonionized Ionized Found in cells in the ionized form with a charge of 1.

28 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 Cysteine 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.

29 Figure 4.9f Phosphate STRUCTURE Organic phosphates NAME OF COMPOUND EXAMPLE Glycerol phosphate 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). Molecules containing phosphate groups have the potential to react with water, releasing energy. FUNCTIONAL PROPERTIES

30 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 5-Methyl cytidine Arrangement of methyl groups in male and female sex hormones affects their shape and function.

31 ATP: An Important Source of Energy for Cellular Processes One phosphate molecule, adenosine triphosphate (ATP), is the primary energytransferring molecule in the cell ATP consists of an organic molecule called adenosine attached to a string of three phosphate groups Adenosine

32 The Chemical Elements of Life: A Review The versatility of carbon Makes possible the great diversity of organic molecules Thus diversity of BIOLOGICAL FORMS

33 You should now be able to: 1. Explain how carbon s electron configuration explains its ability to form large, complex, diverse organic molecules 2. Describe how carbon skeletons may vary and explain how this variation contributes to the diversity and complexity of organic molecules 3. Distinguish among the three types of isomers: structural, geometric, and enantiomer

34 4. Name the major functional groups found in organic molecules; describe the basic structure of each functional group and outline the chemical properties of the organic molecules in which they occur 5. Explain how ATP functions as the primary energy transfer molecule in living cells