I. Chapter 5 Summary. II. Nucleotides & Nucleic Acids. III. Lipids
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1 I. Chapter 5 Summary A. Simple Sugars (CH 2 O) n : 1. One C contains a carbonyl (C=O) rest contain - 2. Classification by functional group: aldoses & ketoses 3. Classification by number of C's: trioses, pentoses, hexoses 4. Stereochemistry: all sugars have D conformation 5. Cyclic structure: - bonds to carbonyl carbon ==> 5- or 6-member ring B. Disaccharides: 2 simple sugars joined by "glycosidic" bond between - of one and carbonyl of another 1. Table sugar 2. Maltose 3. Lactose C. Polysaccharides 1. Food Storage: starch and glycogen are polymers of glucose 2. Structural: cellulose is polymer of glucose 3. Differ in conformation of carbonyl C where sugars are joined II. Nucleotides & Nucleic Acids A. Nucleotides: Base-sugar-phosphate B. Nucleic Acids 1. Nucleotide polymer connected by phosphodiester bonds 2. RNA (RiboNucleic Acid)-nucleotides contain ribose sugar 3. DNA (DeoxyriboNucleic Acid)-nucleotides contain 2!-deoxy-ribose sugar III. Lipids A. Glycerides 1. Triglycerides: 3 fatty acids bonded to 3 -'s of glycerol by ester bonds 2. Phospholipids: Diglycerides and Amphipathic (have polar and nonpolar groups) 3. Phospholipid bilayer B. Cholesterol-sterol lipid
2 In 1953 Stanley Miller simulated what were thought to be environmental conditions in the prebiotic earth. Figure 4-02
3 Fig. 4-2: He created Building Block Molecules EXPERIMENT Water vapor CH 4 Atmosphere Electrode Condense r Cooled water containing organic molecules Cold water H 2 O sea Sample for chemical analysis Simple compounds: Formaldehyde & Hydrogen Cyanide More Complex Molecules: Amino Acids & Hydrocarbons
4 Fig. 5.2a: Common Features of Macromolecules (a) Dehydration reaction: synthesizing a polymer Short polymer Unlinked monomer Dehydration removes a water molecule, forming a new bond Longer polymer
5 Fig. 5.2b: Common Features of Macromolecules (b) Hydrolysis: breaking down a polymer
6 Chapter 5: Biological Building Block Molecules are the units (Monomers) of Macromolecules Monomer Monosaccharide (Simple Sugar) Simple Polymer Oligosaccharide Complex Polymer (Macromolecule) Polysaccharide (Complex Carbohydrate) Nucleotide Oligonucleotide Nucleic Acid Amino Acid Peptide Polypeptide Protein
7 What do Macromolecules Do?
8 Common Features of Macromolecules - Shape
9 Common Features of Macromolecules
10 Fig. 2.18: Important Concept The Function of a macromolecule is determined by its Molecular Shape (conformation) & Composition Macromolecules such as proteins work by interacting with other molecules. These interactions depend on the molecules having complementary shapes that fit together (like a lock and key)
11 Chapter 5: Biological Building Block Molecules are the units (Monomers) of Macromolecules Monomer Monosaccharide (Simple Sugar) Simple Polymer Oligosaccharide Complex Polymer (Macromolecule) Polysaccharide (Complex Carbohydrate) Nucleotide Oligonucleotide Nucleic Acid Amino Acid Peptide Polypeptide Protein
12 Number of Carbon atoms: 3 C s Triose 4 C s Tetrose 5 C s Pentose 6 C s Hexose O R-C-R O R-C-H Note: suffix ose indicates a sugar
13 Fig. 5.3a: Trioses Aldose (Aldehyde Sugar) Ketose (Ketone Sugar) Trioses: 3-carbon sugars (C 3 H 6 O 3 ) Chiral Carbon D- because is on the right D - Glyceraldehyde Dihydroxyacetone
14 is on the right D is on the left L D-Glyceraldehyde L-Glyceraldehyde
15 3 Chiral Carbons 4 Chiral Carbons 3 Chiral Carbons
16 Fig. 5.4a: Linear and ring forms of glucose Pentoses and Hexoses form ring structures in water when one of the groups forms a bond to the carbonyl group Linear and ring forms CH 2 CH 2 Assume C s at vertices and H s at ends of lines O O -CH 2 O CH 2 -CH 2 O α-d-glucose β-d-glucose β-d-fructose β-d-ribose
17 Figure 5.5a: Disaccharides 1 4 glycosidic linkage Glucose Glucose Maltose CH 2 O O CH 2 Malt Sugar Glucose-Glucose O HO CH 2 O O CH 2 Milk Sugar Galactose-Glucose O CH 2 O -CH 2 O O Table Sugar Glucose-Fructose CH 2
18 Figure 5.7: Polysaccharides Starch & Cellulose (a) α and β glucose ring structures α Glucose β Glucose (b) Starch: 1 4 linkage of α glucose monomers (b) Cellulose: 1 4 linkage of β glucose monomers
19 Fig. 5.6: Starch & Glycogen Food Storage Polysaccharides. Chloroplast Starch granules Amylopectin (a) Starch: a plant polysaccharide 1 µm Amylose Mitochondria Glycogen granules (b) Glycogen: 0.5 µm an animal polysaccharide Glycogen
20 LE 5-8 Fig. 5.8: Structural Polysaccharides - Cellulose Cell walls Cellulose microfibrils in a plant cell wall Microfibril 0.5 µm Plant cells Cellulose molecules β Glucose monomer
21 Structural Polysaccharides - Chitin β (1 4) Glycosidic Bond similar to cellulose Chitin forms the hard exterior exoskeleton of insects It is also used to make biodegradable surgical threads
22 Lipids Lipids are a diverse group of molecules that are primarily water-insoluble and include: Fats Triglycerides Oils Waxes Phospholipids Biological Steroids Membranes Carotenoids
23 Fatty Acids Acyl chain (16 18 carbons) Straight conformation Bent (kinked) conformation
24 Fig 5.10: Triglycerides Triglycerides consist of 3 fatty acids bonded to the three hydroxyl (-O-H) groups of a molecule of glycerol (ester bonds) Dehydration (condensation) Reaction Acyl chains can be saturated or unsaturated
25 (a) Saturated fat Fig 5.12: Triglycerides Structural formula of a saturated fat molecule Stearic acid, a saturated fatty acid (b) Unsaturated fat Structural formula of an unsaturated fat molecule Oleic acid, an unsaturated fatty acid cis double bond causes bending
26 Fig 5.12: Phospholipids Hydrophobic tails Hydrophilic head Choline Phosphate Glycerol Fatty acids Hydrophilic head Hydrophobic tails
27 Fig 5.13 / 7.2: Phospholipids Assemble to Form Membrane Bilayers Fig 7.2 Phospholipid bilayers form impermeable membranes that enclose and compartmentalize cells
28 Fig 5.14: Steroids are lipid molecules (water insoluble) based on a hydrocarbon structure with four fused rings The Polar - group makes this molecule amphipathic
29 Monomer Monosaccharide (Simple Sugar) Simple Polymer Oligosaccharide Complex Polymer (Macromolecule) Polysaccharide (Complex Carbohydrate) Nucleotide Oligonucleotide Nucleic Acid Amino Acid Peptide Polypeptide Protein
30 Adenine Phosphate N-Glycosidic Bond Adenosine 5 -monophosphate (AMP) Phosphoester Bond RNA RiboNucleic Acid DNA DeoxyriboNucleic Acid
31 Fig. 5.26: The components of Nucleic Acids 5 end 5 C Sugar-phosphate backbone Nitrogenous bases Pyrimidines 3 C Nucleoside Phosphodiester Bond Nitrogenous base Cytosine (C) Thymine (T, in DNA) Uracil (U, in RNA) 5 C Purines 5 C 3 C Phosphate group (b) Nucleotide 3 C Sugar (pentose) 1 C Adenine (A) Guanine (G) 3 end (a) Polynucleotide, or nucleic acid Sugars Deoxyribose (in DNA) Ribose (in RNA) (c) Nucleoside components
32 Fig. 5.28: The DNA double helix and its replication. 5 end 3 end Sugar-phosphate backbone Base pair (joined by hydrogen bonding) Old strands Nucleotide about to be added to a new strand 5 end New strands 3 end 5 end 5 end 3 end
A disaccharide is formed when a dehydration reaction joins two monosaccharides. This covalent bond is called a glycosidic linkage.
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