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Biology 107 Carbon and Molecular Diversity. September 1, 2004. Carbon. Student Objectives: As a result of this lecture and the assigned reading, you should understand the following:

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Presentation Transcript
carbon
Carbon

Student Objectives: As a result of this lecture and the assigned reading, you should understand the following:

  • Role of carbon in life's diversity - next to water, compounds containing carbon are the most common substances in living organisms.
  • The enormous variety of carbon-based molecules is because a carbon atom has 4 outer shell electrons in a shell that holds 8.
  • Compounds with the same molecular formula but different structure are called isomers.
carbon3
Carbon

4.The unique properties of an organic compound depend not only on its carbon skeleton, but also on certain groups of atoms that are covalently linked to the skeleton. These groups of atoms are called functional groups, the name reflecting the fact that these parts of the organic molecules usually are involved in chemical reactions. See Table 4.1 in Campbell and Reece.

5. Most of these functional groups are polar, because their oxygen or nitrogen atoms are highly electronegative. The polarity tends to make compounds containing these groups hydrophilic, and therefore soluble in water - a necessary condition for their roles in water-based life. Note that many biological molecules have two or more functional groups (e.g., amino acids - contain at least one carboxyl as well as one amino group).

carbon4
Carbon
  • Organic macromolecules are polymers created through dehydration synthesis reactions that chemically link the specific monomers together with covalent bonds. Polymers are broken down through hydrolysis reactions.

7. It is the variety in polymers that accounts for the uniqueness of each organism; the monomers used to make polymers are essentially universal throughout the biological realm.

majors types of isomers
Majors Types of Isomers
  • Structural isomers (different covalent arrangements)
  • Geometric isomers (differ around double bond)
  • Enantiomers (mirror-images that differ around an asymmetric, chiral, atom)
what is chirality

(S)

“sinister”

LEFT

(R)

“rectus”

RIGHT

What is Chirality?

Immanuel Kant,

1783

“The glove of one hand cannot be used on the other”

enantiomers
ENANTIOMERS

Enantiomers have identical physical and chemical properties.

EXCEPT

Ability to rotate the plane of polarized light

and

Rate of reaction and interaction with other chiral compounds and environments

importance of chirality
Importance of Chirality

Different activities?

Same activity different potency

chirality and drug action
CHIRALITY AND DRUG ACTION

Why do enantiomers have the potential for exhibiting different pharmacodynamic and/or pharmacokinetic properties?

slide16

C

C

O-H

O

H

C

C

C

C O

Functional Groups

1. Hydroxyl

2. Carbonyl

aldehyde

ketone

slide17

H

N

H

C

C

C

C

H

O H

H

C O

N

H

O-

CO

Functional Groups

3. Carboxyl

+ H+

4. Amino

+

+ H+

slide18

C

C

C

O H

O H

S-H

O-

O

P

O

O

P

O

O-

Functional Groups

5. Sulfhydral

6. Phosphate

+ 2 H+

polymer synthesis and breakdown reactions
Polymer Synthesis and Breakdown Reactions

Synthesis of complex molecules from simpler molecules (anabolism) by dehydration synthesis reactions

Break down of complex molecules to simpler molecules (catabolism) by hydrolysis reactions

Why so many different metabolic enzymes in cells?