Chemical Composition of the Body 33
Carbohydrates and lipids are similar in many ways. Both
groups of molecules consist primarily of the atoms carbon,
hydrogen, and oxygen, and both serve as major sources of
energy in the body (accounting for most of the calories con-
sumed in food). Carbohydrates and lipids differ, however, in
some important aspects of their chemical structures and physi-
cal properties. Such differences significantly affect the func-
tions of these molecules in the body.
Carbohydrates
Carbohydrates are organic molecules that contain car-
bon, hydrogen, and oxygen in the ratio described by their
name— carbo (carbon) and hydrate (water, H 2 O). The gen-
eral formula for a carbohydrate molecule is thus C n H 2 n O n ;
the molecule contains twice as many hydrogen atoms as car-
bon or oxygen atoms (the number of each is indicated by the
subscript n ).
Monosaccharides, Disaccharides, and
Polysaccharides
Carbohydrates include simple sugars, or monosaccharides,
and longer molecules that contain a number of monosaccha-
rides joined together. The suffix - ose denotes a sugar mol-
ecule; the term hexose, for example, refers to a six-carbon
monosaccharide with the formula C 6 H 12 O 6. This formula
is adequate for some purposes, but it does not distinguish
between related hexose sugars, which are structural isomers
of each other. The structural isomers glucose, galactose,
and fructose, for example, are monosaccharides that have
the same ratio of atoms arranged in slightly different ways
( fig. 2.14 ).
2.2 Carbohydrates and Lipids
Carbohydrates are a class of organic molecules that includes
monosaccharides, disaccharides, and polysaccharides. All
of these molecules are based on a characteristic ratio of
carbon, hydrogen, and oxygen atoms. Lipids constitute a
category of diverse organic molecules that share the physi-
cal property of being nonpolar, and thus insoluble in water.
with such molecules in a stereo-specific way in chemical reac-
tions—cannot combine with the “wrong” stereoisomer. The
enzymes of all cells (human and others) can combine only with
L-amino acids and D-sugars, for example. The opposite stereo-
isomers (D-amino acids and L-sugars) cannot be used by any
enzyme in metabolism.
CLINICAL APPLICATION
In the mid-twentieth century, the drug thalidomide was
widely used by pregnant women to treat morning sickness
until scientists realized that it caused birth defects; it was
banned in 1961. These teratogenic effects were produced
by only one of its enantiomers, but because tho enantio-
mers rapidly interconvert in the body, no form of thalido-
mide is safe for pregnant women. However, thalidomide
has a number of beneficial effects that make it useful for
the treatment of a variety of cancers, particularly multiple
myeloma, as well as other diseases, including AIDS and
leprosy.
Clinical Investigation CLUES
Brian was concerned that the interconvorsion of thalido-
mide enantiomers (to form a racemic mixture of the two)
in his body would have negative effects.
- What are the enantiomers of monosaccharides and
amino acids? - What danger does thalidomide pose, and would this
affect Brian?
| CHECKPOINTS
- List the components of an atom and explain how
they are organized. Explain why different atoms are
able to form characteristic numbers of chemical
bonds. - Describe the nature of nonpolar and polar covalent
bonds, ionic bonds, and hydrogen bonds. Why are
ions and polar molecules soluble in water?
3a. Define the terms acidic, basic, acid, and base. Also
define pH and describe the relationship between pH
and the H^1 concentration of a solution.
3b. Using chemical equations, explain how bicarbonate
ion and carbonic acid function as a buffer pair. - Explain how carbon atoms can bond with each other
and with atoms of hydrogen, oxygen, and nitrogen.
LEARNING OUTCOMES
After studying this section, you should be able to:
- Identify the different types of carbohydrates and
lipids, and give examples of each type. - Explain how dehydration synthesis and hydrolysis
reactions occur in carbohydrates and triglycerides. - Describe the nature of phospholipids and
prostaglandins.