Macromolecules

• Monomers and Polymers • R-OH hydroxyl – Dehydration synthesis • Carbohydrates • R-SH sulfhydryl – Sugars and starches • R-C=O carbonyl • Lipids – Fats and oils • R-COOH carboxyl – Phospholipids • R-NH2 amino – How soap works • R-PO4 phosphate

• R-CH3 methyl 7 Sept. 2012

Each has a Ionizable Functional Groups balance point Ionizable Functional Groups

Carboxylic acid Amine Carboxylic acid Amine

R-COOH R-CH2N-H HOH R-COOH R-CH2N-H HOH pK pKa pKb a pKb Most H Most Most H Most organic organic organic organic Acids Acids Acids Acids 3 to 5 H 8 to 11 3-to-5 H 8-to-11 - + - + R-COO H + - R-COO H + - R-CH2N-H OH R-CH2N-H OH H H At normal pH these are charged ions

Isomers are molecules with the same H Isomers can have very different effects molecular formula but different structures and H C H H H C properties H H H H H H H (a) Structural isomers H C C C C C H H C C C H H H H – Structural H H H H H

X X H X (b) Geometric isomers C C C C Carvone

H H X H Caroway Spearmint – Geometric CO2H CO2H

Ibuprofen (c) Enantiomers C C H NH NH H – Enantiomers 2 2 CH 3 CH3

Figure 4.7 A-C

1 Figure 5.2

1 2 3

Unlinked monomer Macromolecules Dehydration Synthesis make by • Carbohydrates taking water away • Lipids 1 2 3 4 Longer polymer • Proteins • Nucleic Acids 1 2 3 4

Hydrolysis

Split by water

1 2 3

Simple sugars can be coupled together by Monosaccharides vary in Length and Dehydration Synthesis Geometry Triose sugars Pentose sugars Hexose sugars

(C3H6O3) (C5H10O5) (C6H12O6) CH OH CH2OH CH OH CH OH 2 2 2 O O O H H H H O O O O O H 1– 4 H H H H H H H C C C C H H H 1 glycosidic 4 H OH H OH H OH H linkage OH H H C OH Glucose + Glucose OH H O OH H C OH H C OH H C OH HO OH HO O OH H C OH = Maltose H C OH HO C H HO C H H H H H OH OH OH OH H H C OH H C OH HO C H H2O Aldoses Aldoses Glucose Maltose H C OH H C OH H C OH Glucose Glyceraldehyde H H C OH H C OH

Ribose H H CH2OH CH2OH CH2OH CH2OH Glucose Galactose O O O 1–2 O H H H H H H H H 1 glycosidic 2 H H H OH H HO OH H linkage OH H H HO H O O H C OH H C OH H C OH HO CH2OH HO CH2OH C O C O C O Glucose + Fructose H OH OH H H OH OH H H C OH H C OH HO C H = Sucrose H2O Glucose Fructose Sucrose H H C OH H C OH

Ketoses Ketoses Dihydroxyacetone H C OH H C OH

H H C OH Figure 5.5 Ribulose H Figure 5.3 Fructose

5 and 6 Carbon Sugars CIRCULARIZE in Water Cellulose To FORM RINGS

10 !m

0.5 !m

Cellulose molecules!

! Glucose monomer! Fig. 5-8

2 Fig. 5-7bc Fats or triglycerides (glycerol + 3 fatty acids)

Glycerol + Fatty acid H H H H H H H H O H H H H H H H H H C O H C C C C C C C C H C C C C C C C C HO H H H H H H H H H H H H H H H H C OH

H C OH Dehydration reaction 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 H C C C C C C C C 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 H Fat molecule C C C C C C C C 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 H 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 Figure 5.11 hydrophilic or hydrophobic?

FATS OILS WHY? Solid Liquid What are trans fats?

Like Unsaturated or Fig 5-12 Saturated Polyunsaturated

• Phospholipids Phospholipid Bilayer – Glycerol + 2 fatty acids + phosphate

+ CH2 N(CH3)3 Choline CH2 O How will Phosphate O P O – O phospholipids CH CH CH Hydrophilic head 2 2 Glycerol O O behave in water? C O C O

Fatty acids Hydrophilic “head” Form Hydrophobic Boundaries Hydrophobic tails “tails” (a) Structural formula

3