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Functional Structural Found Example Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Group Formula In H H carbo- hydrates, Hydroxyl OH H C C OH proteins, X X nucleic H H acids, W W Ethanol lipids

H O carbo- C O C Carbonyl H C C H hydrates, C nucleic H acids Acetaldehyde O H O Z Y Y Z Carboxyl C H C C proteins, lipids OH H OH Acetic acid

H O H H proteins, Amino N HO C C N nucleic H acids H CH 3 Alanine COOH H C CH S H Sulfhydryl S H 2 proteins NH 2 Cysteine

O– OH OH H O

Phosphate O P O– H C C C O P O– nucleic acids O H H H O– Glycerol phosphate Mirror H O H HO C C NH Methyl C H 2 proteins H C H H H Alanine 1 2

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Cellular Structure Polymer Monomer

CH2OH

H O H

HO OH Carbohydrate H OH

Starch grains in a chloroplast Starch Monosaccharide

P P P P T Nitrogenous base T G A P G A P P C P p A P C O P P A Phosphate C 5-carbon sugar Nucleic Acid Nucleic T group P P P OH P Chromosome DNA strand Nucleotide

CH H 3 Ala N C C OH Ala Val H Val Sel H O Protein Protein

Intermediate filament Polypeptide Amino acid

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 Lipid H H H H H H H H H H H

Adipose cell with fat droplets Triglyceride Fatty acid 3 4

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H2O H2O 3-carbon Sugar 5-carbon Sugars 6-carbon Sugars

H O 5 CH OH 5 CH OH 6 CH OH 6 CH OH 6 CH OH HO H HO H HO H 2 2 2 2 2 C 1 O O 5 O 5 OH OH H O H H OH O OH H C OH 4 1 4 1 H 5 2 H 2 4 1 4 1 H H H H H H OH H H OH OH H H H HO OH HO CH2OH H H H C OH 3 2 3 2 1 3 4 3 3 2 3 2 HO H HO H HO H H OH OH OH H H OH OH H H OH Glyceraldehyde Ribose Deoxyribose Glucose Fructose Galactose a. Dehydration reaction b. Hydrolysis reaction

5 6 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. CH OH 2 H 5 H H C O H H C O O H C OH C O OH C H C OH H 4 1 C H C C OH C O Structural H C OH Stereo- H C OH H C H O H 3 2 1 6 H isomer isomer H C OH 5 H OH 2 H C O O HO C H HO C H HO C H -glucose HO C H H α C C or 3 4 OH H 1 -glucose H C OH H C OH HO C H O H H β H C OH 3 C C 2 4 CH OH H C OH H C OH H C OH H C OH H OH 2 5 5 H C OH H C O OH H C OH H C OH H C OH 6 H C C H 4 OH H 1 OH C C H H H H 3 2 Fructose Glucose Galactose H OH

7 8

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CH2OH CH2OH CH2OH CH2OH O O O O H H H H H H 4 H 1 OH H OH H OH H OH H HO OH O O Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. H OH H OH H OH H OH CH OH a-glucose α-1 4 linkages 2 CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH Amylose + Amylopectin O O O O O H O H H H H H H H H H O H H H H H H + H b. 7.5 µm OH H OH OH H H OH OH H OH H H CH OH O CH OH O HO OH HO 2 HO 2 HO OH H OH O α-1 6 linkage H OH OH H H OH OH H H OH H OH H2O H OH α-glucose Fructose Sucrose Maltose CH2OH CH2 O O a. b. H H H H H H OH H O OH H

H OH H OH α-1 4 linkage Glycogen a. c. 3.3 µm b: © Asa Thoresen/Photo Researchers, Inc.; c: © J.Carson/Custom Medical Stock Photo

9 10

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CH OH CH OH CH OH 2 2 H OH 2 O H OH O O H H O H H O 4 1 H OH H H OH H O OH H H OH H HO H H H O H O H OH H OH CH2OH H OH β-glucose β-1 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. Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Nitrogenous base NH2 O 5΄

Phosphate group C C NH2 N C N N C N H 7 6 H C H C N N C C H N C C NH 2

Purines N N 5 P 5΄ H H O Adenine Guanine 1 1΄ 8 4΄ Phosphodiester bonds NH2 O O Phosphate group 3΄ 2΄ 2 C C C H C N H3C C N H H C N H 4 O N N P 5΄ H C C O H C C O H C C O 9 3 O N N N 4΄ 1΄ - Pyrimidines H H H O P O CH2 3΄ Cytosine Thymine Uracil 2΄ 5 (both DNA and RNA) (DNA only) (RNA only)

- P b. O 5΄ O O 5-carbon sugar 4΄ 1΄ 4 1 3΄ 2΄ Nitrogenous base P 5΄ O 1΄ 3 2 OH in RNA 4΄ 3΄ 2΄ OH OH H in DNA a. 3΄ Sugar 13 14

Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. P P P Deoxyribose- T P phosphate T backbone G A P G P A P C P A P C P G Sugar–phosphate Bases P A T “backbone” P P Hydrogen bonding P P occurs between base-pairs DNA P

A P P T P P G P C Ribose-phosphate backbone C A G T P P OH U Phosphodiester 3΄ end A bonds A Bases U P P Hydrogen bonds between P nitrogenous bases P G RNA 5΄ end 15 16

Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Nitrogenous base (adenine)

NH2 6 7 N Triphosphate group 5 N 1 8 O O O 5 2 – 4 O P O P O P O CH2 N N 9 3 O– O– O– O

4 1

3 2 OH OH 5-carbon sugar 17 18 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. Nonpolar Polar uncharged Charged CH – 3 OH O O H N+ C C O– C 3 CH 2 H O + – CH H3N C C O 2 Alanine (Ala) CH R CH CH H O 2 3 H H R 3 Serine – H N+ C C O CH 3 (Ser) CH3 H N+ C C O– H O 3 H C OH Glutamic acid H O (Glu) + – CH H3N C C O 3 Valine – H N C C OH H N C C OH (Val) O O H O CH2 C Threonine O NH2 H C CH (Thr) 3 CH C 2 + – H N C C O 3 H N+ C C O– Nonaromatic 3 + CH2 NH H O H O H O HC CH CH H O 3 3 + – CH C C O Isoleucine H3N C NH N O 2 Aspartic acid CH (Ile) (Asp) H H O C CH 2 CH 2 Asparagine Amino acid Amino acid + – CH H N C C O 2 3 + (Asn) H N C – 3 C O H CH H O H O 2 Leucine Histidine H N+ C C O– H N+ C C O– 3 (Leu) 3 (His) CH NH + H O H O 2 3 Glycine Glutamine CH H2O (Gly) (Gln) 2 CH2 NH 2 CH2 + C NH2 – OH H N+ C C O 3 NH H O CH NH 2 CH C Lysine 2 H N+ C C O– ( Lys) 3 CH CH CH2 2 2 R H R H O H + – – Aromatic + H N C C O H N C C O CH 3 3 2 Phenylalanine (Phe) H N+ C C O– H O H O 3 Tryptophan Tyrosine H O (Trp) ( Tyr) Arginine H N C C N C C OH (Arg)

CH 3 S H CH H O H O 2 S CH CH 2 2 CH2 CH 2 + – + – CH2 CH C – H N C C O H N C O O 3 3 C Dipeptide +

Special function function Special NH 2 O H O H O Proline Methionine Cysteine 19 (Pro) (Met) (Cys) 20

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Primary Structure

R H H O R H H O C C N C C N C C N C C C N H O R H H O R

(CH2)4 C

C R R O C H H N The primary structure can fold

+

NH3 O N into a pleated sheet, or turn into a helix

C C H N O Lonic bond C C S S C C

–

O H N O C CH3 CH3 C C O N C Secondary Structure Secondary Structure H H

O C N O C C

R C van der Waals Disulfide bridge CH 2 attraction C Hydrogen bond N C O a. b. c. d. β-pleated sheet α-helix

Tertiary Structure Quaternary Structure CH 3 H CH 3 Hydrophobic C CH 3 CH 3 exclusion CH 3 CH 2

CH 3 C CH 3 e. 21 22

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Properly folded protein

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Misfolded protein Cap

Correctly Chaperone ATP folded protein ATP + P protein Denaturation

Denatured Chance for protein to refold protein

23 24 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

CH3 Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display. H3C Structural Formula Structural Formula CH CH CH H O 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 2 CH2 H C O C C C C C C C C C C C C C C C C C C H H C O C C C C C C C C C C C C C C C C C C H H3C CH CH CH OH 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 2 2 O 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 C O C C C C C C C C C C C C C C C C C C 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 O 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 a. Terpene (citronellol) H C O C C C C C C C C C C C C C C C C C C H H C O C C C C C C C C C C C C C C C C C C H H3C CH2 CH2 CH 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 3 CH CH2 CH Space-Filling Model Space-Filling Model CH3 CH3

CH3

a. b. HO b. Steroid (cholesterol) 25 26

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CH N+(CH ) 2 3 3 Water CH 2 Lipid head O (hydrophilic)

O P O– Choline O H Phosphate Lipid tail H C C CH 2 2 (hydrophobic) Polar Hydrophilic Heads Hydrophilic Polar Glycerol O O C O C O CH F F CH CH CH a. a a 2 2 CH CH t t 2 2 CH CH t t 2 2 CH CH y y 2 2 Water CH CH a a 2 2 c c CH CH 2 2 i i CH CH 2 d d CH CH 2 CH CH 2 2 CH CH 2 2 CH CH 2 2 CH2 CH2 Nonpolar Hydrophobic Tails Nonpolar Hydrophobic Tails CH CH 2 2 CH CH 2 2 CH CH 2 2 CH CH Water 3 3 a. b. c. d. b. 27 28