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Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Functional Group Structural Formula OH Hydroxyl Found In Example H H C C H carbohydrates, proteins, nucleic acids, lipids OH H H Ethanol O Carbonyl H C C C carbohydrates, nucleic acids H H C H proteins, lipids C OH H Acetic acid H N O C OH Amino O H Acetaldehyde O Carboxyl H HO O H C C H H proteins, nucleic acids N H CH3 Alanine COOH Sulfhydryl S H H C CH2 S H proteins NH2 Cysteine O– Phosphate O OH OH H O– H P O C C C H H H O O P O– nucleic acids O– Glycerol phosphate H Methyl C H H HO O H C C NH2 H C H H Alanine proteins 1 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. X W X C Z W C Y Y Z Mirror 2 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Cellular Structure Polymer Monomer Carbohydrate CH2OH O H H OH HO H Starch grains in a chloroplast Starch OH Monosaccharide P P Nucleic Acid G P T A P Nitrogenous base P T G A C P P P P C p A P P A T C P Chromosome P P P O Phosphate group 5-carbon sugar OH DNA strand Nucleotide CH3 Protein H Ala Val Val Intermediate filament Sel Polypeptide N Ala H C C H OH O Amino acid Lipid O H H H H H H H H H H H HO C C C C C C C C C C C C H H H H H H H H H H H H Adipose cell with fat droplets Triglyceride Fatty acid 3 4 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. H 2O H 2O HO H HO HO H H a. Dehydration reaction HO HO H H HO H b. Hydrolysis reaction 5 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. 3-carbon Sugar H O 5-carbon Sugars 5 CH2OH C O 1 H H C 2 OH C OH 3 5 H Glyceraldehyde 4 H H H 3 H 2 OH CH2OH OH Ribose 4 H H 5 OH 1 H 3 H 2 OH CH2OH 6 O OH 1 6-carbon Sugars H Deoxyribose H H OH 4 HO 3 H 6 O 1 OH 2 OH 6 O H H Glucose CH2OH 5 HO H 4 OH 5 H OH 3 H Fructose OH 2 CH2OH 1 CH2OH 4 H H OH 3 H O OH 1 H H 2 OH Galactose 6 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. CH2OH 5 H O C OH H H 1 H C OH C H 2 HO H C OH C OH C OH 4 H H 5 6 H OH H C 3 H OH C C2 H OH 4 OH H 5 C 3 H 6 C C O H O 3 O H OH C H C2 H OH H C 1 OH α-glucose or β-glucose C 1 4 C H 5 CH2OH C H C OH 4 OH C 3 H H O H C2 OH C 1 H OH 7 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. H H H H C OH C O HO C H H C H H C O H C OH H HO C H C OH HO C H H C OH H C OH H C OH H C OH C O H C OH HO C OH H C OH C OH H Fructose Structural isomer H Glucose Stereoisomer H Galactose 8 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. CH2OH H HO H OH H + OH CH2OH O O H H OH α-glucose a. CH2OH HO H H OH OH H Fructose H CH2OH HO H 2O CH2OH O H OH H H CH2OH O H O OH Sucrose H H OH CH OH 2 OH H H HO O H OH H H CH2OH H H O O H OH H OH H OH H OH Maltose b. 9 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. CH2OH H 4 HO O H OH H H CH2OH O H 1 OH H OH a-glucose H OH H H OH OH O H α-1 H H H OH OH H H OH H b. + Amylopectin 7.5 µm 6 linkage α-1 H OH H H H OH α-1 O CH2OH O Amylose CH2OH O H H H OH H O OH H OH 4 linkages CH2OH O H H OH H O H a. CH2OH O CH2 O H Glycogen 4 linkage c. 3.3 µm b: © Asa Thoresen/Photo Researchers, Inc.; c: © J.Carson/Custom Medical Stock Photo 10 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. CH2OH H 4 HO CH2OH O H OH H H OH OH H 1 H O H O H OH H H OH O H H OH H H O H H O CH2OH β-1 β-glucose CH2OH OH O H OH H H OH O H 4 linkages a. b. 500 µm b: © J.D. Litvay/Visuals Unlimited 11 12 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Nitrogenous base NH2 7N 1 O 9 P O 5 5 8 Phosphate group -O 6 N 4 2 N 3 CH2 O- O 1 4 3 2 OH in RNA OH Sugar H in DNA 13 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. O NH2 5΄ 5΄ 1΄ 4΄ 3΄ P H C N C C N N C C H Phosphodiester bonds O 4΄ 1΄ 3΄ P 2΄ 5΄ C N C C N H N C C NH 2 H H C H C C N N Guanine O NH2 2΄ 5΄ N H H Adenine O Pyrimidines P Purines Phosphate group H 3C N C O H Cytosine (both DNA and RNA) H C C C N O N H H C C O H C H Thymine (DNA only) C N N H C O H Uracil (RNA only) b. O 1΄ 4΄ 3΄ 5-carbon sugar 2΄ Nitrogenous base P 5΄ O 1΄ 4΄ 3΄ OH a. 2΄ 3΄ 14 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Sugar–phosphate “backbone” P A P T G C Phosphodiester bonds T P OH 3΄ end A P Hydrogen bonds between nitrogenous bases P 5΄ end 15 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. P P P G P T T P A Deoxyribosephosphate backbone G A C P P A C P P Bases P P P C A P P Hydrogen bonding P occurs between base-pairs P G A T P DNA P P Ribose-phosphate backbone G P U A Bases U P P RNA G 16 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Nitrogenous base (adenine) NH2 O –O P O– O O P O– P 5 N1 8 O O 6 7 N Triphosphate group O 5 CH2 9 N 4 N 2 3 O– O 1 4 3 2 OH OH 5-carbon sugar 17 18 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. H H R N C C H O OH H H R N C C H O Amino acid OH Amino acid H 2O H H R N C C H O H R N C C H O OH Dipeptide 19 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Nonpolar Polar uncharged CH3 H3 N+ C C CH3 Nonaromatic H 3N + CH2 H3 C C C H O CH2 H3 CH3 C OH H 3N + C C O– O H O Threonine (Thr) CH3 H3 CH H C C O– N+ C H O O– O– N+ C C H O O– CH2 C CH2 H 3N + CH2 H 3N + H O Glycine (Gly) C C H O CH2 Aromatic H 3N + C C H O Phenylalanine (Phe) Special function H 3N + CH2 CH2 H 3N + C C O– C H 3N + H O Tryptophan (Trp) C H O Tyrosine ( Tyr) H O O– NH2 C C H O C O– NH2+ NH CH2 Lysine ( Lys) C O– C CH2 CH2 NH C NH3+ CH2 CH2 CH N H Histidine (His) O– Glutamine (Gln) OH NH+ HC Aspartic acid (Asp) C Asparagine (Asn) H O Leucine (Leu) O– NH2 O O– CH2 H3 C C C CH2 CH3 C N+ H O Glutamic acid (Glu) C H 3N + C H NH2 O O– CH2 C CH2 O– O– CH3 Isoleucine (Ile) H 3N + C C H O Serine (Ser) CH3 C C H O Valine (Val) CH3 C O– CH2 H 3N + CH N+ O OH O– H O Alanine (Ala) H Charged CH2 CH2 O– H 3N + C C O– H O Arginine (Arg) CH3 CH2 CH2 CH2 CH NH2+ S H CH2 S CH2 C O Proline (Pro) O– H3 N+ CH2 C C H O Methionine (Met) O– H 3N + C C H O Cysteine (Cys) O– 20 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. O C C N O H O O C N (CH2)4 C H C C N C R R C C H R H S S C N H H C NH3+ Lonic bond C N C C O O– O O C Hydrogen bond N CH3 CH3 N C C C C O van der Waals attraction CH2 Disulfide bridge N C C O a. b. CH 3 c. d. CH 3 H Hydrophobic exclusion CH 3 CH 3 C CH 3 CH 3 CH 2 C CH 3 e. 21 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Primary Structure R C C H O H H O N C C R R N C C H H O H H N C R The primary structure can fold into a pleated sheet, or turn into a helix Secondary Structure Secondary Structure β-pleated sheet Tertiary Structure α-helix Quaternary Structure 22 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Misfolded protein Cap Chaperone protein ATP ATP + P Correctly folded protein Chance for protein to refold 23 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Properly folded protein Denaturation Denatured protein 24 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Structural Formula H Structural Formula H O H H H H H H H H H H H H H H H H H H C O C C C C C C C C C C C C C C C C C C H O H H H H H H H H H H H H H H H H H H H H H H H H O H H H H H H H O H H H H H H H H H H H H H H H H H H H H H H C O C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H Space-Filling Model a. H H H H H H H H H C O C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H O H H H H H H H H H H H H H H H H H H C O C C C C C C C C C C C C C C C C C C H H H C O C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H C O C C C C C C C C C C C C C C C C C C H O H H H H H H H H H H H H H H H H H H H H H H H H Space-Filling Model b. 25 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. CH3 H 3C CH H 3C CH CH2 CH CH2 a. Terpene (citronellol) CH2 CH2 CH2 CH2 H 3C CH3 OH CH CH2 CH3 CH CH3 CH3 HO b. Steroid (cholesterol) 26 Nonpolar Hydrophobic Tails Polar Hydrophilic Heads Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. CH2 N+(CH3)3 CH2 O O P O– Choline Phosphate Glycerol F a t t y a c i d a. H H 2C C O O O CH2 C OC O CH CH CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH CH2 CH CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3 CH3 F a t t y a c i d b. c. d. 27 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Water Lipid head (hydrophilic) Lipid tail (hydrophobic) a. Water Water b. 28