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

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