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Carbon and the molecular diversity of life. (Chapter 4) презентация
Содержание
- 1. Carbon and the molecular diversity of life. (Chapter 4)
- 2. Overview: Carbon: The Backbone of Life Living
- 3. Figure 4.1
- 4. Concept 4.1: Organic chemistry is the study
- 5. Vitalism, the idea that organic compounds arise
- 6. Organic Molecules and the Origin of Life
- 7. Figure 4.2 EXPERIMENT “Atmosphere” Electrode Condenser CH4
- 8. Concept 4.2: Carbon atoms can form diverse
- 9. The Formation of Bonds with Carbon With
- 10. Figure 4.3 Name and Comment Molecular Formula
- 11. The electron configuration of carbon gives it
- 12. Figure 4.4 Hydrogen (valence = 1) Oxygen
- 13. Carbon atoms can partner with atoms other
- 14. Figure 4.UN01 Urea
- 15. Molecular Diversity Arising from Carbon Skeleton Variation
- 16. Animation: Carbon Skeletons Right-click slide/select “Play”
- 17. Figure 4.5 (a) Length Ethane 1-Butene (c)
- 18. Figure 4.5a (a) Length Ethane Propane
- 19. Figure 4.5b (b) Branching Butane 2-Methylpropane (commonly called isobutane)
- 20. Figure 4.5c 1-Butene (c) Double bond position 2-Butene
- 21. Figure 4.5d (d) Presence of rings Cyclohexane Benzene
- 22. Hydrocarbons Hydrocarbons are organic molecules consisting of
- 23. Figure 4.6 Nucleus Fat droplets (b) A
- 24. Figure 4.6a Nucleus Fat droplets 10 μm
- 25. Isomers Isomers are compounds with the same
- 26. Animation: Isomers Right-click slide / select “Play”
- 27. Figure 4.7 (a) Structural isomers (b) Cis-trans
- 28. Figure 4.7a (a) Structural isomers
- 29. Figure 4.7b (b) Cis-trans isomers cis isomer:
- 30. Figure 4.7c (c) Enantiomers CO2H CO2H CH3
- 31. Enantiomers are important in the pharmaceutical industry
- 32. Animation: L-Dopa Right-click slide / select “Play”
- 33. Figure 4.8 Drug Ibuprofen Albuterol Condition Effective
- 34. Concept 4.3: A few chemical groups are
- 35. The Chemical Groups Most Important in the
- 36. Figure 4.UN02 Estradiol Testosterone
- 37. The seven functional groups that are most
- 38. Figure 4.9-a STRUCTURE CHEMICAL GROUP Hydroxyl NAME
- 39. Figure 4.9-b Amino Sulfhydryl Phosphate Methyl Methylated
- 40. Figure 4.9a STRUCTURE EXAMPLE Alcohols (Their specific
- 41. Figure 4.9b Carbonyl STRUCTURE EXAMPLE Ketones if
- 42. Carboxyl STRUCTURE EXAMPLE Carboxylic acids, or organic
- 43. Amino Amines Glycine STRUCTURE EXAMPLE • Acts as
- 44. Sulfhydryl Thiols (may be written HS—)
- 45. Figure 4.9f Phosphate STRUCTURE EXAMPLE NAME OF
- 46. Figure 4.9g Methyl STRUCTURE EXAMPLE NAME OF
- 47. ATP: An Important Source of Energy for
- 48. Figure 4.UN03 a. b.
- 49. Figure 4. UN04 Adenosine
- 50. The Chemical Elements of Life: A Review
- 51. Figure 4. UN05 Adenosine Adenosine Reacts with H2O Inorganic phosphate ATP ADP Energy
- 52. Figure 4. UN07
- 53. Figure 4. UN08
- 54. Figure 4. UN09
- 55. Figure 4. UN10
- 56. Figure 4. UN11
- 57. Figure 4. UN12
- 58. Figure 4. UN13
- 59. Figure 4. UN14
- 60. Figure 4. UN15
Слайд 2Overview: Carbon: The Backbone of Life
Living organisms consist mostly of carbon-based
Carbon is unparalleled in its ability to form large, complex, and diverse molecules
Proteins, DNA, carbohydrates, and other molecules that distinguish living matter are all composed of carbon compounds
Слайд 4Concept 4.1: Organic chemistry is the study of carbon compounds
Organic chemistry
Organic compounds range from simple molecules to colossal ones
Most organic compounds contain hydrogen atoms in addition to carbon atoms
Слайд 5Vitalism, the idea that organic compounds arise only in organisms, was
Mechanism is the view that all natural phenomena are governed by physical and chemical laws
Слайд 6Organic Molecules and the Origin of Life on Earth
Stanley Miller’s classic
Experiments support the idea that abiotic synthesis of organic compounds, perhaps near volcanoes, could have been a stage in the origin of life
Слайд 7Figure 4.2
EXPERIMENT
“Atmosphere”
Electrode
Condenser
CH4
H2
NH3
Water vapor
Cooled “rain”
containing
organic
molecules
Cold
water
Sample for chemical analysis
H2O
“sea”
Слайд 8Concept 4.2: Carbon atoms can form diverse molecules by bonding to
Electron configuration is the key to an atom’s characteristics
Electron configuration determines the kinds and number of bonds an atom will form with other atoms
Слайд 9The Formation of Bonds with Carbon
With four valence electrons, carbon can
This ability makes large, complex molecules possible
In molecules with multiple carbons, each carbon bonded to four other atoms has a tetrahedral shape
However, when two carbon atoms are joined by a double bond, the atoms joined to the carbons are in the same plane as the carbons
Слайд 10Figure 4.3
Name and
Comment
Molecular
Formula
(a) Methane
(b) Ethane
CH4
Ball-and-
Stick Model
Space-Filling
Model
(c) Ethene
(ethylene)
C2H6
C2H4
Structural
Formula
Слайд 11The electron configuration of carbon gives it covalent compatibility with many
The valences of carbon and its most frequent partners (hydrogen, oxygen, and nitrogen) are the “building code” that governs the architecture of living molecules
Слайд 13Carbon atoms can partner with atoms other than hydrogen; for example:
Carbon
Urea: CO(NH2)2
Слайд 15Molecular Diversity Arising from Carbon Skeleton Variation
Carbon chains form the skeletons
Carbon chains vary in length and shape
Слайд 17Figure 4.5
(a) Length
Ethane
1-Butene
(c) Double bond position
2-Butene
Propane
(b) Branching
(d) Presence of rings
Butane
2-Methylpropane
(isobutane)
Cyclohexane
Benzene
Слайд 22Hydrocarbons
Hydrocarbons are organic molecules consisting of only carbon and hydrogen
Many organic
Hydrocarbons can undergo reactions that release a large amount of energy
Слайд 25Isomers
Isomers are compounds with the same molecular formula but different structures
Structural isomers have different covalent arrangements of their atoms
Cis-trans isomers have the same covalent bonds but differ in spatial arrangements
Enantiomers are isomers that are mirror images of each other
Слайд 27Figure 4.7
(a) Structural isomers
(b) Cis-trans isomers
(c) Enantiomers
cis isomer: The two Xs
are
trans isomer: The two Xs
are on opposite sides.
CO2H
CO2H
CH3
H
NH2
L isomer
NH2
CH3
H
D isomer
Слайд 29Figure 4.7b
(b) Cis-trans isomers
cis isomer: The two Xs
are on the same
trans isomer: The two Xs
are on opposite sides.
Слайд 31Enantiomers are important in the pharmaceutical industry
Two enantiomers of a drug
Usually only one isomer is biologically active
Differing effects of enantiomers demonstrate that organisms are sensitive to even subtle variations in molecules
Слайд 33Figure 4.8
Drug
Ibuprofen
Albuterol
Condition
Effective
Enantiomer
Ineffective
Enantiomer
Pain;
inflammation
Asthma
S-Ibuprofen
R-Ibuprofen
R-Albuterol
S-Albuterol
Слайд 34Concept 4.3: A few chemical groups are key to the functioning
Distinctive properties of organic molecules depend on the carbon skeleton and on the molecular components attached to it
A number of characteristic groups can replace the hydrogens attached to skeletons of organic molecules
Слайд 35The Chemical Groups Most Important in the Processes of Life
Functional groups
The number and arrangement of functional groups give each molecule its unique properties
Слайд 37The seven functional groups that are most important in the chemistry
Hydroxyl group
Carbonyl group
Carboxyl group
Amino group
Sulfhydryl group
Phosphate group
Methyl group
Слайд 38Figure 4.9-a
STRUCTURE
CHEMICAL
GROUP
Hydroxyl
NAME OF
COMPOUND
EXAMPLE
Ethanol
Alcohols (Their specific names
usually end in -ol.)
(may be written
Carbonyl
Ketones if the carbonyl group is
within a carbon skeleton
Aldehydes if the carbonyl group
is at the end of the carbon skeleton
Carboxyl
Acetic acid
Acetone
Propanal
Carboxylic acids, or organic acids
FUNCTIONAL
PROPERTIES
• Is polar as a result of the
electrons spending more time
near the electronegative oxygen
atom.
• Can form hydrogen bonds with
water molecules, helping dissolve
organic compounds such as
sugars.
• A ketone and an aldehyde may be
structural isomers with different
properties, as is the case for
acetone and propanal.
• Ketone and aldehyde groups are
also found in sugars, giving rise
to two major groups of sugars:
ketoses (containing ketone
groups) and aldoses (containing
aldehyde groups).
• Found in cells in the ionized form
with a charge of 1− and called a
carboxylate ion.
Nonionized
Ionized
• Acts as an acid; can donate an
H+ because the covalent bond
between oxygen and hydrogen
is so polar:
Слайд 39Figure 4.9-b
Amino
Sulfhydryl
Phosphate
Methyl
Methylated compounds
Organic phosphates
(may be
written HS—)
Thiols
Amines
Glycine
Cysteine
• Acts as a base; can
surrounding solution (water, in living
organisms):
Nonionized
Ionized
• Found in cells in the
ionized form with a
charge of 1+.
• Two sulfhydryl groups can
react, forming a covalent
bond. This “cross-linking”
helps stabilize protein
structure.
• Cross-linking of cysteines
in hair proteins maintains
the curliness or straightness
of hair. Straight hair can be
“permanently” curled by
shaping it around curlers
and then breaking and
re-forming the cross-linking
bonds.
• Contributes negative charge to
the molecule of which it is a part
(2– when at the end of a molecule,
as above; 1– when located
internally in a chain of
phosphates).
• Molecules containing phosphate
groups have the potential to react
with water, releasing energy.
• Arrangement of methyl
groups in male and female
sex hormones affects their
shape and function.
• Addition of a methyl group
to DNA, or to molecules
bound to DNA, affects the
expression of genes.
Glycerol phosphate
5-Methyl cytidine
Слайд 40Figure 4.9a
STRUCTURE
EXAMPLE
Alcohols
(Their specific
names usually
end in -ol.)
NAME OF
COMPOUND
FUNCTIONAL
PROPERTIES
(may be written
HO—)
Ethanol
• Is polar
of the electrons
spending more
time near the
electronegative
oxygen atom.
• Can form hydrogen
bonds with water
molecules, helping
dissolve organic
compounds such
as sugars.
Hydroxyl
Слайд 41Figure 4.9b
Carbonyl
STRUCTURE
EXAMPLE
Ketones if the carbonyl
group is within a
carbon skeleton
NAME OF
COMPOUND
FUNCTIONAL
PROPERTIES
Aldehydes if
group is at the end of the
carbon skeleton
A ketone and an
aldehyde may be
structural isomers
with different properties,
as is the case for
acetone and propanal.
Acetone
Propanal
Ketone and aldehyde
groups are also found
in sugars, giving rise
to two major groups
of sugars: ketoses
(containing ketone
groups) and aldoses
(containing aldehyde
groups).
Слайд 42Carboxyl
STRUCTURE
EXAMPLE
Carboxylic acids, or organic
acids
NAME OF
COMPOUND
FUNCTIONAL
PROPERTIES
Acetic acid
• Acts as an acid; can
donate an
covalent bond between
oxygen and hydrogen is so
polar:
• Found in cells in the ionized
form with a charge of 1– and
called a carboxylate ion.
Nonionized
Ionized
Figure 4.9c
Слайд 43Amino
Amines
Glycine
STRUCTURE
EXAMPLE
• Acts as a base; can
pick up an H+ from the
surrounding solution
(water,
organisms):
NAME OF
COMPOUND
FUNCTIONAL
PROPERTIES
• Found in cells in the
ionized form with a
charge of 1+.
Nonionized
Ionized
Figure 4.9d
Слайд 44Sulfhydryl
Thiols
(may be
written HS—)
STRUCTURE
EXAMPLE
• Two sulfhydryl groups can
react, forming a covalent
bond. This
helps stabilize protein
structure.
NAME OF
COMPOUND
FUNCTIONAL
PROPERTIES
• Cross-linking of cysteines
in hair proteins maintains
the curliness or straightness
of hair. Straight hair can be
“permanently” curled by
shaping it around curlers
and then breaking and
re-forming the cross-linking
bonds.
Cysteine
Figure 4.9e
Слайд 45Figure 4.9f
Phosphate
STRUCTURE
EXAMPLE
NAME OF
COMPOUND
FUNCTIONAL
PROPERTIES
Organic phosphates
Glycerol phosphate
• Contributes negative
charge to the molecule
of which it
(2– when at the end of
a molecule, as at left;
1– when located
internally in a chain of
phosphates).
• Molecules containing
phosphate groups have
the potential to react
with water, releasing
energy.
Слайд 46Figure 4.9g
Methyl
STRUCTURE
EXAMPLE
NAME OF
COMPOUND
FUNCTIONAL
PROPERTIES
Methylated compounds
5-Methyl cytidine
• Addition of a methyl group
to DNA, or
bound to DNA, affects the
expression of genes.
• Arrangement of methyl
groups in male and female
sex hormones affects their
shape and function.
Слайд 47ATP: An Important Source of Energy for Cellular Processes
One phosphate molecule,
ATP consists of an organic molecule called adenosine attached to a string of three phosphate groups
Слайд 50The Chemical Elements of Life: A Review
The versatility of carbon makes
Variation at the molecular level lies at the foundation of all biological diversity
