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Copyright 2005 Pearson Education, Inc.

publishing as Benjamin Cummings

Why study Carbon?


Polymer

Monomer

Elements

Carbohydrate

Monosaccharides

C, H, O

Lipid

Glycerol + 3 fatty acid


chains

C, H, O

Protein

Amino acid

C, H, O, N, S

Nucleic acid

Nucleotide

C, H, O, N, P

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Tetravalence of Carbon
Covalent compatibility (valence e-)
Hydrogen

Oxygen

Nitrogen

Carbon

(valence = 1)

(valence = 2)

(valence = 3)

(valence = 4)

Figure 4.4

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Organic Chemistry
Prefix indicates # C

Suffix indicates bond type

Meth- = 1

-ane = all single bonds

Eth- = 2

-ene = at least one double bond

Pro- = 3

-yne = at least one triple bond

But- = 4
Pent- = 5
Hex- = 6

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Hydrocarbons
Found in many of a cells organic molecules
Fat droplets (stained red)

Triglyceride

100 m
Figure 4.6 A, B

(a) A fat molecule

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(b) Mammalian adipose cells

Isomers
structural, geometric and
enantiomers

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Isomers
Molecules with same
molecular formula but
different structures
different chemical
properties
Structure ~
function

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Isomers: Structural, Geometric, Enantiomers


H

H
H
(a) Structural isomers

X
C

Copyright
ure 4.7
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H
H

H
C

CO2H

CO2H

NH2
CH3

X
C

(c) Enantiomers

(b) Geometric isomers

NH2
CH3

Structural isomers
Molecules differ in structural arrangement of
atoms

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High Fructose Corn Syrup

Structural Isomers
Glucose and Fructose

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High Fructose Corn Syrup (HFCS)

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HFCS Step 1 = Starch to Glucose


Industrial processing takes corn (which is a
starch/polysaccharide) and breaks it down into glucose.

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

HFCS Step 2: Glucose to Fructose Isomer


Mechanically convert
glucose (cheaper) into
its fructose isomer.
Fructose is sweeter
than glucose
Structure influences
chemical properties
(taste)

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The Result?
The result is a mixture that consists of 55%
fructose and 45% glucose
Consistency is gel-like and easy to dissolve
when cooking

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I mess with your


hormones!
Leptin
Ghrelin
Insulin
Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Leptin
Produced by fat cells (adipose)

Travels to brain (hypothalamus)


Turns off the hunger cell
(suppresses ghrelin)
Turns on the satiety cell
Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Ghrelin
Produced in stomach

Travels to brain
(hypothalamus) to turn
off the satiety cell
Before a meal

After a meal

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Glucose vs. Fructose


Glucose

Stimulates insulin
secretion so that the
sugar can be transported
into cells where it can be
used for cell. resp

Increases production of
leptin that regulates
appetite and fat storage

Suppresses production
of ghrelin hormone which
regulates food intake
Low gherlin = low
hunger

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Fructose

Acts like fat

Does NOT stimulate


insulin or leptin and
does NOT suppress
ghrelin

Travels to the liver and


initiates lipogenesis

In fruit, fructose is
coupled with fiber and is
processed differently

HFCS Effects
Interferes
with bodys
satiety
hormones

Makes you
feel hungry
faster, less
satisfying.

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Hunger Hormones and Obesity


Youre FAT!
Fat makes leptin
Obesity =
High leptin, high insulin,
low gherlin
SEEMS BACKWARDS!

WHY? (think diabetes)


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Back to isomers

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Geometric isomers
Molecules differ in arrangement around C=C
double bond
same covalent partnerships
Cis

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Trans

Enantiomer (stereo) isomers


Molecules which are mirror images of each other
Left-handed & right-handed versions
L versions are biologically active

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Enantiomers
Are important in the pharmaceutical industry

Figure 4.8

L-Dopa

D-Dopa

(effective against
Parkinsons disease)

(biologically
inactive)

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Form affects function


Thalidomide
prescribed to pregnant women in 50s & 60s
reduced morning sickness, but
stereoisomer caused severe birth defects

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Functional Groups: Distinctive Properties


Are the chemically reactive groups of atoms within an
organic molecule

Six functional groups:


Hydroxyl

Amino

Carboxyl

Sulfhydryl

Carbonyl

Phosphate

Affect reactivity

hydrophilic
increase solubility in water
Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Functional Groups
Give organic molecules distinctive chemical
properties. Affects reactivity.
Estradiol

OH
CH3

Identical Carbonskeleton
HO

Female lion
OH
CH3
CH3

O
Figure 4.9

Male lion

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Testosterone

Different
functional group

Hydroxyl
OH
organic compounds with OH = alcohols

names typically end in -ol


ethanol

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Carbonyl
C=O
O double bonded to C

if C=O at end molecule = aldelhyde


if C=O in middle of molecule = ketone

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Carboxyl
COOH
C double bonded to O & single bonded to OH
group
compounds with COOH = acids
fatty acids, amino acids

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Amino
-NH2
compounds with NH2 = amines
amino acids

NH2 acts as base


ammonia picks up H+ from solution

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Sulfhydryl
SH
S bonded to H

compounds with SH = thiols


SH groups stabilize the structure of proteins

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Phosphate
PO4

PO4 are anions with 2 negative charges

function of PO4 is to transfer energy


between organic molecules (ATP)

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings