Download (a) Structural isomers

LECTURE PRESENTATIONS
For CAMPBELL BIOLOGY, NINTH EDITION
Jane B. Reece, Lisa A. Urry, Michael L. Cain, Steven A. Wasserman, Peter V. Minorsky, Robert B. Jackson
Chapter 4
Carbon and the Molecular
Diversity of Life 碳與生命的分子
多樣
Lectures by
Erin Barley
Kathleen Fitzpatrick
© 2011 Pearson Education, Inc.
Overview: Carbon: The Backbone of Life
• Living organisms consist mostly of carbonbased compounds
• Carbon is unparalleled in its ability to form
large, complex, and diverse molecules
碳架構的有機分子豐富多樣的有機分子世界
• Proteins, DNA, carbohydrates, and other
molecules that distinguish living matter are all
composed of carbon compounds 豐富生命的
蛋白、核酸、碳氫子分等均為碳化合物
© 2011 Pearson Education, Inc.
Figure 4.1
Concept 4.1: Organic chemistry is the study
of carbon compounds
• Organic chemistry is the study of
compounds that contain carbon
有機化學乃以碳為主架構的化合物研究
• Organic compounds range from simple
molecules to colossal ones
• Most organic compounds contain
hydrogen atoms in addition to carbon
atoms 有機化合物結合許多氫原子於碳上
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• Vitalism 生機論, the idea that organic
compounds arise only in organisms, was
disproved when chemists synthesized
these compounds有機分子組成有機體
• Mechanism is the view that all natural
phenomena are governed by physical
and chemical laws 所有自然現象均有其
物理或化學法則
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Organic Molecules and the Origin of Life
on Earth
• Stanley Miller’s classic experiment
demonstrated the abiotic synthesis of
organic compounds無機化合物可以經
由化學反應組成有機分子
• Experiments support the idea that
abiotic synthesis of organic compounds,
perhaps near volcanoes, could have
been a stage in the origin of life 海底火
山可能是生命起源處
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Figure 4.2
EXPERIMENT
“Atmosphere”
CH4
Water vapor
Electrode
Condenser
Cooled “rain”
containing
organic
molecules
H2O
“sea”
Sample for chemical analysis
Cold
water
Concept 4.2: Carbon atoms can form diverse
molecules by bonding to four other atoms
• 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 電子特性決定分子
鍵結數目與型式
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The Formation of Bonds with Carbon
• With four valence electrons, carbon can form
four covalent bonds with a variety of atoms
• This ability makes large, complex molecules
possible 碳原子為有機分子骨架，組構大份子
• 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 雙鍵可使份子形成ㄧ平面
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Figure 4.3
Name and
Comment
Molecular
Formula
(a) Methane
CH4
(b) Ethane
C2H6
(c) Ethene
(ethylene)
C2H4
Structural
Formula
Ball-andStick Model
Space-Filling
Model
• The electron configuration of carbon
gives it covalent compatibility with many
different elements
• The valences of carbon and its most
frequent partners (hydrogen, oxygen, and
nitrogen) are the “building code” that
governs the architecture of living
molecules
• 碳原子可與許多其他原子結合形成許多有
機分子
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Figure 4.4
Hydrogen
(valence  1)
Oxygen
(valence  2)
Nitrogen
(valence  3)
Carbon
(valence  4)
• Carbon atoms can partner with atoms other
than hydrogen; for example:
– Carbon dioxide: CO2
– Urea: CO(NH2)2
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Figure 4.UN01
Urea
Molecular Diversity Arising from Carbon
Skeleton Variation
• Carbon chains form the skeletons of most
organic molecules
• Carbon chains vary in length and shape
碳為骨架的有機分子，可變化無窮的有機分子
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Figure 4.5
(c) Double bond position
(a) Length
Ethane
Propane
(b) Branching
Butane
1-Butene
2-Butene
(d) Presence of rings
2-Methylpropane
(isobutane)
Cyclohexane
Benzene
Figure 4.5a
(a) Length
Ethane
Propane
Figure 4.5b
(b) Branching
Butane
2-Methylpropane
(commonly called isobutane)
Figure 4.5c
(c) Double bond position
1-Butene
2-Butene
Figure 4.5d
(d) Presence of rings
Cyclohexane
Benzene
Hydrocarbons 碳氫化合物
• Hydrocarbons are organic molecules
consisting of only carbon and hydrogen
• Many organic molecules, such as fats,
have hydrocarbon components
• Hydrocarbons can undergo reactions that
release a large amount of energy碳氫化
合物蘊含大量能量
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Figure 4.6
Nucleus
Fat droplets
10 m
(a) Part of a human adipose cell
(b) A fat molecule
Isomers 異構物
• Isomers are compounds with the same
molecular formula but different structures
and properties
– 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
© 2011 Pearson Education, Inc.
Figure 4.7
(a) Structural isomers
直鏈
支鏈
(b) Cis-trans isomers
順式
反式
cis isomer: The two Xs
are on the same side.
trans isomer: The two Xs
are on opposite sides.
(c) Enantiomers
CO2H
CO2H
左旋
右旋
H
NH2
CH3
L isomer
NH2
H
CH3
D isomer
Figure 4.7a
(a) Structural isomers
Figure 4.7b
(b) Cis-trans isomers
cis isomer: The two Xs
are on the same side.
trans isomer: The two Xs
are on opposite sides.
Figure 4.7c
(c) Enantiomers
CO2H
H
CO2H
NH2
CH3
L isomer
NH2
H
CH3
D isomer
鏡像異構物活性不同
• Enantiomers are important in the
pharmaceutical industry
• Two enantiomers of a drug may have
different effects
• Usually only one isomer is biologically
active
• Differing effects of enantiomers
demonstrate that organisms are sensitive
to even subtle variations in molecules
© 2011 Pearson Education, Inc.
Figure 4.8
Drug
Condition
Ibuprofen
Pain;
inflammation
Albuterol
Effective
Enantiomer
Ineffective
Enantiomer
S-Ibuprofen
R-Ibuprofen
R-Albuterol
S-Albuterol
Asthma
Fig. 4-UN9
L-dopa
D-dopa
Concept 4.3: A few chemical groups are key
to the functioning of biological molecules
• 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
• ㄧ群小分有子機分子提供生物活性
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The Chemical Groups Most Important in
the Processes of Life
• Functional groups are the components
of organic molecules that are most
commonly involved in chemical reactions
The number and arrangement of functional
groups give each molecule its unique
properties
官能基是化學分子進行化學反應處
亦提供分子特性
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Figure 4.UN02
Estradiol
Testosterone
• The seven functional groups that are most
important in the chemistry of life:
– Hydroxyl group 羥基
– Carbonyl group 羰基
– Carboxyl group 羧基
– Amino group 氨基
– Sulfhydryl group 硫氫基
– Phosphate group 磷酸基
– Methyl group 甲基
© 2011 Pearson Education, Inc.
Figure 4.9-a
CHEMICAL
GROUP
Hydroxyl
Carbonyl
Carboxyl
STRUCTURE
(may be written HO—)
NAME OF
COMPOUND
Alcohols (Their specific names
usually end in -ol.)
Ketones if the carbonyl group is
within a carbon skeleton
Carboxylic acids, or organic acids
Aldehydes if the carbonyl group
is at the end of the carbon skeleton
EXAMPLE
Ethanol
Acetone
Acetic acid
Propanal
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).
• Acts as an acid; can donate an
H+ because the covalent bond
between oxygen and hydrogen
is so polar:
Nonionized
Ionized
• Found in cells in the ionized form
with a charge of 1 and called a
carboxylate ion.
Figure 4.9-b
Amino
Sulfhydryl
Phosphate
Methyl
(may be
written HS—)
Amines
Organic phosphates
Thiols
Cysteine
Glycine
• Acts as a base; can
pick up an H+ from the
surrounding solution
(water, in living
organisms):
Nonionized
Ionized
• Found in cells in the
ionized form with a
charge of 1+.
Glycerol phosphate
• Two sulfhydryl groups can
react, forming a covalent
bond. This “cross-linking”
helps stabilize protein
structure.
• 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).
• 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.
• Molecules containing phosphate
groups have the potential to react
with water, releasing energy.
Methylated compounds
5-Methyl cytidine
• Addition of a methyl group
to DNA, or to molecules
bound to DNA, affects the
expression of genes.
• Arrangement of methyl
groups in male and female
sex hormones affects their
shape and function.
Figure 4.9a
Hydroxyl
STRUCTURE
(may be written
HO—)
EXAMPLE
Ethanol
Alcohols
(Their specific
names usually
end in -ol.)
NAME OF
COMPOUND
• Is polar as a result
of the electrons
spending more
time near the
electronegative
oxygen atom.
FUNCTIONAL
PROPERTIES
• Can form hydrogen
bonds with water
molecules, helping
dissolve organic
compounds such
as sugars.
Figure 4.9b
Carbonyl
STRUCTURE
Ketones if the carbonyl
group is within a
carbon skeleton
NAME OF
COMPOUND
Aldehydes if the carbonyl
group is at the end of the
carbon skeleton
EXAMPLE
Acetone
Propanal
• 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).
FUNCTIONAL
PROPERTIES
Figure 4.9c
Carboxyl
STRUCTURE
Carboxylic acids, or organic
acids
NAME OF
COMPOUND
EXAMPLE
• Acts as an acid; can
FUNCTIONAL
PROPERTIES
donate an H+ because the
covalent bond between
oxygen and hydrogen is so
polar:
Acetic acid
Nonionized
Ionized
• Found in cells in the ionized
form with a charge of 1– and
called a carboxylate ion.
Figure 4.9d
Amino
STRUCTURE
Amines
NAME OF
COMPOUND
EXAMPLE
•
FUNCTIONAL
PROPERTIES
Acts as a base; can
pick up an H+ from the
surrounding solution
(water, in living
organisms):
Glycine
Nonionized
•
Ionized
Found in cells in the
ionized form with a
charge of 1.
Figure 4.9e
Sulfhydryl
STRUCTURE
Thiols
NAME OF
COMPOUND
•
Two sulfhydryl groups can
react, forming a covalent
bond. This “cross-linking”
helps stabilize protein
structure.
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.
(may be
written HS—)
EXAMPLE
Cysteine
Figure 4.9f
Phosphate
STRUCTURE
Organic phosphates
EXAMPLE
•
FUNCTIONAL
Contributes negative
charge to the molecule PROPERTIES
of which it is a part
(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.
Glycerol phosphate
NAME OF
COMPOUND
Figure 4.9g
Methyl
STRUCTURE
Methylated compounds
EXAMPLE
•
Addition of a methyl group FUNCTIONAL
PROPERTIES
to DNA, or to molecules
bound to DNA, affects the
expression of genes.
•
Arrangement of methyl
groups in male and female
sex hormones affects their
shape and function.
5-Methyl cytidine
NAME OF
COMPOUND
ATP: An Important Source of Energy for
Cellular Processes
• One phosphate molecule, adenosine
triphosphate (ATP), is the primary
energy-transferring molecule in the cell
• ATP consists of an organic molecule
called adenosine attached to a string of
three phosphate groups
• 能量載體
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Figure 4. UN04
Adenosine
Figure 4. UN05
Reacts
with H2O
Adenosine
Adenosine
ATP
Inorganic
phosphate
ADP
Energy
The Chemical Elements of Life: A Review
• The versatility of carbon makes possible
the great diversity of organic molecules
• Variation at the molecular level lies at the
foundation of all biological diversity
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