Bioc 460 - Dr.

Miesfeld Fall 2008

Cellulose is a biofuel
Lecture 31 - Carbohydrate Structure

Key Concepts
- Review of monosaccharide and disaccharide structures
- Structures of common complex carbohydrates
- Carbohydrates are often covalently attached to polypeptides

Key Questions about carbohydrate structure and function:

Describe three ways in which carbohydrates contribute to cell structure and function.

Biochemical Applications:
Pigs and chickens cannot digest raffinose series oligosaccharides that are present
in soybean-based feed because they lack the enzyme α-galactosidase. To
prevent dietary problems associated with the inability to digest these
oligosaccharides, soybean feed is pre-treated with a commercially-produced α-
galactosidase enzyme. This same α-galactosidase enzyme preparation (isolated
from a fungus) is marketed commercially as a dietary product for humans called
BeanoTM. Raffinose oligosaccharides are found in many types of vegetables, e.g.,
beans, broccoli, and cabbage, which helps make Beano a multimillion dollar product.

Review of monosaccharide and disaccharide structures

Carbohydrates are the most abundant biomolecules on planet earth, primarily because they are
the major structural element of plants in the form of cellulose, a repeating unit of glucose found in
plant cell walls. The word "carbohydrate" comes from the term carbon hydrate which describes the
empirical formula for carbohydrates, (CH2O)n, in which n > 3. However, as we saw in the Calvin
cycle, carbon hydration is not an accurate description for carbohydrate biosynthesis since the
formation of glyceraldehyde-3-phosphate (GAP) is the result of enzymatic reactions catalyzing CO2
fixation, not hydration. We can divide carbohydrates into three major groups based on their basic
structures; 1) simple sugars consisting of monosaccharides and disaccharides that function as
metabolic intermediates in energy conversion pathways, 2) complex carbohydrates consisting of
oligosaccharides (several monosaccharide units) or polysaccharides (many monosaccharide units)
that serve structural roles, or function as storage forms of glucose, and 3) glycoconjugates
consisting of carbohydrate units, often modified forms of glucose, that are covalently linked to
proteins giving rise to glycoproteins, or attached to lipids Figure 1.
forming glycolipids.
Simple sugars are defined as monosaccharides and
disaccharides. The word saccharide comes from the Greek
word sakcharon which means sugar. Glucose is the most
plentiful monosaccharide in nature and has the molecular
formula of C6H12O6. Glucose is a polyhydroxy aldehyde,
while fructose, which has the same molecular formula as
glucose, is a polyhydroxy ketose. The chemical structure of
glucose is shown in figure 1 using either Fisher projections
that have flattened bond angles to represent linear
monosaccharides, or Haworth perspectives which are used to
illustrate the cyclic structure of monosaccharides. Glucose
can also be drawn using a conformational formula in which
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glucose is represented by either the "boat" or "chair" conformations to reflect the nonplanar
structure of pyranose rings.
Simple sugars are sweet to the taste and found in many types of fruits and vegetables, they
are also used commercially as Figure 2.
additives to enhance the flavor of
processed foods and beverages.
The sensation of sweetness is the
result of ligand activation of G
protein-coupled receptors
expressed on the surface of
gustatory cells (taste cells in the
tongue). The G protein-coupled
receptors in these cells bind
sugars with differential affinities
based on their chemical structure.
Sugar binding to taste receptors
stimulates a neuronal signal that is
transmitted to the brain. Human
taste tests can be used to
measure the relative sweetness of
simple sugars and artificial
sweeteners (figure 2). For
example, fructose, which is found
in high concentrations in many
types of fruit, is perceived to be about three times sweeter than glucose and two times sweeter
than the disaccharide sucrose (table sugar). Honey is a natural product made by honeybees that
consists of a mixture of glucose and fructose. Interestingly, it has been known for centuries that
honey contains antibiotic properties which is why honey can be stored at room temperature without
becoming contaminated. Figure 2 also shows the structure of the artificial sweetener Sucralose
which is a chlorinated sucrose molecule that is marketed under the brand name of SplendaTM.
Sucralose is currently the sweetest compound available commercially and is an amazing 600 times
sweeter than sucrose because of its differential binding properties to taste receptor proteins on the
tongue. Another artificial sweetener, aspartame, marketed as NutraSweet®, is not a carbohydrate
at all, but rather a dipeptide derivative of aspartate and phenylalanine.
Monosaccharides have either an aldehyde group at the
Figure 3.
end of the molecule, such as glucose, or a ketone group on
the second carbon as in fructose (figure 3). Aldehyde-
containing monosaccharides are called aldoses and ketone-
containing monosaccharides are called ketoses. All
monosaccharides have a CH2OH group on the end of the
carbon chain opposite the aldehyde or ketone group, and
each of the carbons in the middle have OH groups and
function as chiral centers. The carbonyl atom (C=O) is either
at the end of the carbon chain (aldose) or on the second
carbon (ketose). The name of the monosaccharide reflects
the number of carbons in the chain, for example, an aldose
with three carbons is a triose, four carbons a tetrose, five
carbons a pentose, and six carbons a hexose.

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The smallest monosaccharide is glyceraldehyde, a Figure 4.

triose sugar with one chiral center. A carbon chiral center is
an atom with four different functional groups. Chiral
compounds lack a plane of symmetry and exist as two optical
isomers, also called enantimers. Enantimers exist in nature
as either right handed (D form) or left-handed (L form) and
differentially reflect polarized light. The structures D-
glyceraldehyde and L-glyceraldehyde are shown in figure 4
where it can be seen that these two isomers of
glyceraldehyde are mirror images of each other. By
convention, when the hydroxyl group in the chiral carbon is on
the right side of a Fisher projection, it is the D isomer, and
when it is on the left side, it is the L isomer.
Monosaccharides of five, six or seven carbons are
often more stable in aqueous solution as cyclic structures
than they are as open chains. Cyclic monosaccharides form
spontaneously through a covalent linkage of the carbonyl carbon with a hydroxyl group in the
carbon backbone. This bond is the result of a reaction between an alcohol group and an aldehyde
group of an aldose sugar to form a hemiacetal, or between an alcohol group and the ketone group
of a ketose sugar to form a hemiketal. Figure 5 illustrates the cyclization reaction that occurs
when the C-5 hydroxyl group of D-glucose attacks the oxygen atom of the C-1 aldehyde group to
form a cyclic hemiacetal. In this conformation, the C-1 carbon of D-glucose becomes the new
chiral center, and as such, cyclic forms of glucose exists as either β-D-glucose with the hydroxyl
group at C-1 above the plane of the ring, or as α-D-glucose with the hydroxyl group below the
plane of the ring. Crystalline glucose exists in the cyclic α-D-glucose form, but once it is dissolved
in an aqueous solution, an equilibrium is established
Figure 5.
between the α-D-glucose and β-D-glucose
conformations at a ratio of about 40:60 for α-D-
glucose:β-D-glucose. A very small amount of the
monosaccharide is found in the open chain conformation
(<0.05%).
The hemiacetal C-1 carbon of cyclic D-glucose is
called an anomeric carbon, and β-D-glucose and α-D-
glucose are referred to as anomers because they only
differ at the anomeric carbon. Cyclic conformations of
hexose sugars are called pyranoses because the six-
membered ring is similar to a pyran compound.
Therefore cyclic forms of glucose are sometimes called
α-D-glucopyranose and β-D-glucopyranose. Ketoses
such as fructose can also form cyclic structures, but
because the carbonyl is in the C-2 position of the open
chain, the ring that forms contains only five carbons.
These sugars are furanoses because they resemble a
furan. Cyclic conformations of fructose are called α-D-
fructofuranose and β-D-fructofuranose. Note that
pyranose rings are much more stable in solution than
furanose rings.

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Disaccharide Figure 6.
sugars are formed by a
condensation reaction
between two
monosaccharides. The
covalent linkage is called
an O-glycosidic bond
and represents the
formation of an acetal
from a hemiacetal and an alcohol. The glycosidic bond in the disaccharide maltose is called an α1-
4 linkage because the anomeric carbon is in the α conformation (figure 6). The glucose molecule
on the right retains the hemiacetal structure at its C-1 anomeric carbon and can convert to the
aldehyde open chain form in a reaction involving the reduction of Cu2+ to form Cu+. Using this
functional definition (the reduction of Cu2+), the glucose on the right is designated as the reducing
end of the disaccharide molecule because it can participate in a reduction reaction. In contrast,
the glucose on the left represents the nonreducing Figure 7.
end because the C-1 carbon is part of the α1-4 linkage
and cannot form the open chain structure in a Cu2+
reduction reaction. Since maltose contains one
reducing end it is called a reducing sugar.
Disaccharides can contain different monosaccharide
units connected through α or β glycosidic bonds
involving ring carbons, and therefore, it is convenient to
name disaccharides using a descriptive nomenclature.
Using standard conventions, the disaccharide is
named by first listing the nonreducing monosaccharide
on the left, followed by the glycosidic linkage between
the two monosaccharides, and then the
monosaccharide on the right. With this shorthand
nomenclature, maltose can be described as a Glc(α1-
4)Glc disaccharide in which the abbreviation "Glc" is
used for glucose.
Figure 7 shows the structures of three common
disaccharides found in nature; 1) lactose, also called
milk sugar, which contains a β1-4 glycosidic bond
linking a galactose (Gal) to a glucose to form Gal(β1-
4)Glc, 2) sucrose, made in plants and used as table
sugar in its crystalline form, contains fructose (Fru)
linked to glucose through the two anomeric carbons to
form Glu(α1-β2)Fru, and 3) trehalose, a glucose
disaccharide made in insects, contains a glycosidic
bond between the two anomeric carbons to form the disaccharide Glc(α1-α1)Glc. Importantly, of
these three disaccharides, only lactose is a reducing sugar, because like maltose, it contains a free
anomeric carbon that can interconvert the hemiacetal to an aldehyde. Both sucrose and trehalose
are nonreducing sugars because they lack a reducing end.

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Structures of common complex carbohydrates

The most abundant carbohydrate molecules found in nature are actually large complex structures
consisting of mixtures of monosaccharide derivatives.
Carbohydrates consisting of several monosaccharides Figure 8.
are called oligosaccharides, a designation that could
also include disaccharides, whereas, carbohydrates with
~10 or more monosaccharide units are called
polysaccharides. Polysaccharides can either be
homopolymeric (same repeating monosaccharide unit)
or heteropolymeric (mixture of monosaccharides). We
will first look at several oligosaccharides that share a
common structure consisting of galactose units linked to
sucrose, and then briefly describe the structure and
function of the four major polysaccharides in nature;
cellulose, chitin, starch, and glycogen.
Figure 8 shows three representative
oligosaccharides found in many types of plants; the
trisaccharide raffinose, the tetrasaccharide stachyose
and the pentasaccharide verbascose. All three of these
oligosaccharides contain 1-3 galactose units covalently
attached to sucrose. These three oligosaccharides are
sometimes called the raffinose series oligosaccharides
because they are structurally related and produced by a
set of enzymes that are found in similar types of plants.
Humans and non-ruminating animals such as pigs and
poultry cannot digest these galacto-oligosaccharides because they lack the necessary α-
galactosidase enzyme needed to hydrolyze the α1-6 glycosidic bond. Eating foods high in
raffinose series oligosaccharides can lead to gastrointestinal discomfort (flatulence) because the
undigested carbohydrates end up in the lower intestine
where bacteria, which do contain α-galactosidase, ferment Figure 9.
the compounds to produce methane, carbon dioxide and
hydrogen gases. The product BeanoTM is a commercial
preparation of α-galactosidase that can be taken as a pill
to aid in digestion of these oligosaccharides resulting in
the release of free galactose. Sucrose is further
metabolized to glucose and fructose by the enzyme
sucrase found in the small intestine.
The most abundant polysaccharide on earth is
cellulose, a homopolymeric molecule consisting of
thousands of repeating glucose units connected by β1-4
glycosidic bonds. Cellulose provides plants with a rigid
cell wall consisting of layers of cellulose fibers that are
held together by hydrogen bonds. Figure 9 shows the
structure of the repeating Glc(β1-4)Glc unit in cellulose,
called cellobiose, and a diagram depicting hydrogen
bonding within and between cellulose strands. Most
animals lack the enzyme cellulase which is required to
hydrolyze the β1-4 glycosidic bonds in cellulose.
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Therefore, plant material high in cellulose fiber is considered "roughage" in the diet because it
passes through the digestive system without being degraded. Some animals have evolved
symbiotic relationships with microorganisms that inhabit their digestive tracts and secrete cellulase.
Ruminating herbivores (plant eating organisms) such as cows and goats have an unusual stomach
that permits them to regurgitate their food and thereby maximize mechanical and enzymatic
breakdown of cellulose with the help of bacteria. The released glucose is absorbed by the
intestine and used as the primary source of metabolic energy for the animal. Termites and moths
also depend on the help of symbiotic microorganisms to help digest cellulose in their diets which
can unfortunately include houses and sweaters.
Another abundant linear polysaccharide in nature is chitin, the structural component of
invertebrate exoskeletons found in insects and crustaceans. As seen in figure 10, chitin consists of
repeating N-acetylglucosamine units (NAG, also abbreviated Figure 10.
GlcNAc) linked by a β1-4 glycosidic bond. The only difference
between glucose and N-acetylglucosamine is the replacement of
the C-2 hydroxyl with an acetylated amino group. Chitin, like
cellulose, provides the organism with an excellent biomaterial for
building a strong body frame by virtue of hydrogen bonding
contacts within and between polysaccharide strands. Moreover,
because of the β1-4 glycosidic bond, chitin can only be used as a
source of carbohydrate fuel by microorganisms that contain the
enzyme chitinase. It is estimated that over 1012 metric tons of
cellulose and chitin are synthesized each year by plants and
invertebrates.
Plants and animals store glucose in the form of very large
polysaccharide glucose homopolymers that contain both α1-4 and
α1-6 glycosidic bonds. The glucose homopolymer produced in
plants is called starch, while the glucose homopolymer produced in animal cells is called
glycogen. Plants synthesize two forms of starch, amylose, a linear polysaccharide containing
about ~100 glucose units linked by α1-4 glycosidic bonds, and amylopectin, a branched
polysaccharide containing ~100,000 glucose units connected by α1-4 and α1-6 glycosidic bonds.
About 20% of starch is in the linear
Figure 11.
amylose form and the rest is
amylopectin. Amylose can form
stable left-handed helical structures
as a result of intramolecular
hydrogen bonding (figure 11). Each
turn of the helix contains six glucose
molecules to allow efficient packing
of the glucose polymer within starch
granules. The presence of α1-6
bonds in amylopectin (and
glycogen) creates branch points that
greatly increase the number of free
ends in the homopolymeric
molecule. Unlike cellulose and
chitin, starch is a terrific dietary
source of glucose for animals because it can be readily hydrolyzed by the enzyme α-amylase
which cleaves α1-4 glycosidic bonds.
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Both amylopectin and glycogen contain the same α1-4 and α1-6 glycosidic bonds, however,
glycogen which is the carbohydrate energy store
Figure 12.
for animals, is much more highly branched and
contains up to 106 glucose units per granule. As
shown in figure 12, amylopectin contains a branch
point about once every 25 glucose units forming a
sort of tree branch arrangement, whereas,
glycogen has a branch point every ~10 glucose
residues resulting in a much more compact
spiraling macromolecule. Since glucose units can
only be added and removed from the non-
reducing ends of amylopectin and glycogen, the
more branch points there are, the more ends that
are available for glucose retrieval and storage. A
second difference between the macromolecular
structures of amylopectin and glycogen is that
amylopectin contains one free glucose at the
reducing end of the "tree branch," whereas,
glycogen lacks a free reducing end. This is
because the glucose residue at the center of the
glycogen "spiral" is covalently linked to a protein called glycogenin.

Carbohydrates are often covalently attached to polypeptides

The simplest type of protein glycoconjugate is a glycoprotein which consists of a small number of
carbohydrate units (oligosaccharides)
covalently attached to a core protein. Figure 13.
Oligosaccharide modification of proteins
takes place within the lumen of the
endoplasmic reticulum compartment of the
cell. A second general type of protein
glycoconjugate is one in which the majority
of the macromolecule consists of
carbohydrate units with only a small
contribution coming from protein. Two
classes of glycoconjugates are
proteoglycans which are found in the
extracellular matrix and serve as the "gel"
around tissues and in joints, and
peptidoglycans which form the cell wall of
bacteria.

Glycoproteins
Many types of membrane-bound proteins,
and most secreted proteins, are
glycoproteins containing covalently linked
carbohydrate residues that serve as high
affinity binding sites for extracellular
proteins (figure 13). The best

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characterized of these glycoprotein interactions are Figure 14.

in the immune system where receptors on certain
types of immune cells bind to glycoproteins on the
surface of target cells. In fact, viruses and bacteria
exploit these glycoprotein binding sites on immune
cells to gain entry into the cells, or to kill the cells
though the binding of high affinity toxins. Figure 14
shows the molecular structure of the extracellular
portion of the human CD2 protein that is expressed
on the surface of T cells. This glycoprotein
contains five sugar residues (two N-
acetylglucosamines and three mannoses) that are
covalently linked to an asparagine residue in Figure 15.
the CD2 polypeptide. Protein glycosylation is
highly specific and requires the activity of
glycosylating enzymes called
glycosyltransferases.
As shown in figure 15, carbohydrate
linkage to glycoproteins occurs through either
the amide nitrogen atom of asparagine (N-
linked oligosaccharides), or through the
oxygen atom of serine or threonine residues
(O-linked oligosaccharides). Most all N-
linked glycoproteins have a pentasaccharide
core consisting of an N-linked N-
acetylglucosamine (NAG), followed by a
second NAG residue linked to three mannose
residues as seen in the CD2 protein.
Additional carbohydrate residues are often
attached to these the branched mannose sugars to generate a variety of glycoprotein structures. It
has been found that glycosyltransferases that attach the N-linked NAG residue to asparagine
recognize the tripeptide Asn-X-Ser/Thr in the protein sequence where X is any amino acid except
proline. O-linked glycoproteins often contain a Figure 16.
mannose sugar linked directly to a threonine
or serine residue (figure 15).
Genetic differences in the expression
and activity of glycosyltransferases accounts
for immunological incompatibility between
individuals. One of the best examples of this
is the biochemical basis for the A, B and O
blood groups in humans. As illustrated in
figure 16, all three blood groups have a
common core oligosaccharide linked to protein
or lipid molecules on the surface of red blood
cells. This oligosaccharide, called the H
antigen, is further modified by the A/B
glycosyltransferase (α1-3-N-
acetylgalactosaminyltransferase) enzyme.
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Individuals who express the A variant of this glycosyltransferase are able to add an extra GalNAc
residue to the terminal galactose of the pentasaccharide, whereas, individuals with the B variant
add an extra galactose residue in this same
position. The A and B variants of the Figure 17.
glycosyltransferase enzyme differ by four amino
acids that function to specify the carbohydrate
substrate used in the glycosylation reaction. A third
type of A/B glycosyltransferase, the O variant, is a
nonfunctional mutant form of the enzyme.
Individuals with the O variant contain unmodified
forms of the H antigen oligosaccharide on the
surface of their red blood cells.

Proteoglycans
An important class of polysaccharides found in
connective tissue and the extracellular matrix are
the glycosaminoglycans. These unbranched
polysaccharide chains consists of repeating
disaccharide units made up of modified
monosaccharides, one of which is either a
derivative of NAG or GalNAc. The largest
glycosaminoglycan is hyaluronic acid which has
up to 50,000 disaccharide units of D-glucoronic
acid linked to NAG through a β1-3 glycosidic bond
as shown in figure 17. The disaccharides in
hyaluronic acid are themselves linked together
through β1-4 glycosidic bonds. Hyaluronic acid is
highly hydrated and functions as a lubricant in joints
(synovial fluid) and is also found in the vitreous
humor of the eye (clear gel inside the eyeball).
Other glycosaminoglycans include keratan sulfate,
chondroiton 4-sulfate and heparin, each of which
are negatively charged polysaccharides containing
anionic sulfhydral and carboxyl groups on the
disaccharide repeating unit. Heparin is an example
of highly sulfated glycosaminoglycan that is present
in granules of special cells in the circulatory system
called mast cells. Release of heparin from mast cells prevents blood clotting by the binding of the
negatively-charged heparin to proteins that initiate the clotting cascade. Purified heparin is used
as an anti-coagulant in clinical laboratories
Figure 18.
that need to store and process blood
products. Figure 18 shows the molecular
structure of a portion of heparin where the
high density of sulfate groups in the
repeating disaccharide can be seen as
yellow atoms.

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Glycosaminoglycans are covalently or noncovalently linked to proteins to form

glycoconjugates called proteoglycans. Some types of proteoglycans are membrane bound
proteins with glycosaminoglycans attached to the extracellular domain of the protein as shown in
figure 19. In this example, a modified version of heparin, called heparin sulfate, is covalently
attached to the protein along with the glycosaminoglycan chondroiton sulfate.
Glycosaminoglycans are often attached to membrane proteins via a trisaccharide linker that has
an O-linked glycosidic bond to a serine or threonine residue in the protein. The glycosaminoglycan
portion of proteoglycans serve as binding sites for a variety of extracellular molecules, primarily
Figure 19.

proteins in the extracellular matrix, but also receptors on other cells. Proteoglycans can be
secreted directly into the extracellular matrix where they form large aggregates, often associated
with hyaluronic acid. Proteins noncovalently attached to hyaluronic acid serve as anchors for
covalently bound oligosaccharides and glycosaminoglycans. The glycosaminoglycans keratan
sulfate and chondroiton sulfate can be covalently attached to the core protein through an
oligosaccharide linker that is O-linked to the core protein at a serine or threonine residue.

Peptidoglycans
Bacterial cell walls are rigid structures that give Figure 20.
bacteria their shape and serve as the physical
boundary for bacterial membranes, thereby
protecting the cell from osmotic pressure and lysis.
The bacterial cell wall consists of multiple strands of
a linear polysaccharide made up of repeating units
of a β1-4 linked disaccharide containing NAG and
N-acetylmuramic acid (NAM). These NAG-NAM
polysaccharide strands are tethered together by
peptide linkages to form a type of glycoconjugate
called a peptidoglycan. The structure of the
peptidoglycan cell wall in the bacteria strain
Staphylococcus aureus is shown in figure 20.
Tetrapeptide linkers consisting of both L and D amino acid stereoisomers connect NAM residues in
adjacent strands. In S. aureus, the NAG-NAM strands are interconnected by pentaglycine bridges
which further strengthens the proteoglycan structure.

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Based on differences in the higher order organization of the NAG-NAM polysaccharide

strands and on the presence or absence of an outer membrane, bacteria can be divided into two
groups, 1) gram-positive bacteria which have a thick peptidoglycan cell wall (250 Å) but no outer
membrane, and 2) gram-negative bacteria which have a thin peptidoglycan cell wall (25 Å)
surrounded by a protective outer membrane called a capsule (figure 21). The terms gram-positive
and gram-negative refer to a laboratory assay Figure 21.
first described in 1884 by Christian Gram, a
Danish bacteriologist, who developed a simple
test to differentiate between non-pathogenic
bacteria (gram-positive), and the pathogenic
bacteria Klebsiella pneumonia (gram-negative)
which causes clinical pneumonia. The
biochemical basis for the Gram test is the
differential ability of heat-treated bacteria to
retain an indicator dye (crystal violet) after
washing the cells with ethanol or acetone.
Gram-positive bacteria, which lack an outer
membrane, are color-stained by this procedure,
whereas, gram-negative bacteria remain
colorless because the dye cannot penetrate the
outer cell membrane.
The Scottish bacteriologist Alexander Fleming discovered the antibiotic penicillin in 1929
when he noticed that a mold on one of
his Staphylococcus aureus bacterial Figure 22.
plates was killing the bacteria. The mold
was identified as Penicillium notatum and
the antibacterial agent it secreted was
named penicillin (figure 22). Penicillin
inhibits bacterial enzymes called
transpeptidases that are required for
peptidoglycan synthesis, and thereby kills
bacteria that depend on high rates of cell
wall synthesis for cell division. Since
animal cells don't have a cell wall or
transpeptidase, penicillin is an ideal
antibiotic because it is highly selective for
its bacterial target and has few side effects. Some bacteria are resistant to penicillin because they
produce an enzyme called β-lactamase that hydrolyzes the β lactam ring in penicillin to inactivate
it. This type of penicillin-resistance has been overcome by developing synthetic compounds such
as methicillin that block transpeptidase activity without being
substrates for β-lactamase. However, because of the wide-spread Figure 23.
use of methicillin, particularly in hospitals where bacterial infections
are treated aggressively, a methicillin-resistant strain of S. aureus,
called MRSA, has emerged that expresses a variant form of the
transpeptidase enzyme. This transpeptidase does not recognize
methicillin as a substrate and it is ineffective in blocking
peptidoglycan synthesis and bacteria survive. A MRSA infection can
be very serious because it is resistant to treatment (figure 23).
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ANSWER TO KEY QUESTIons about carbohydrate structure and function:

Describe three ways in which carbohydrates contribute to cell structure and function.

Carbohydrates contribute to cell structure and function in three major ways; 1) highly-branched
glucose polymers in the form of starch and glycogen particles function to store metabolic energy
for the cell, 2) modified carbohydrate residues serve as intercellular signaling moieties when
covalently-linked to cell surface glycoproteins, 3) bacterial and plant cell walls consist of cross-
linked carbohydrates that form a strong structural barrier preventing cell lysis due to osmotic
stress. Branchpoints in glucose polymers contained in plant and animal cells provide a means to
generate large numbers of free ends (non-reducing ends) that are subject to rapid degradation and
synthesis through highly-regulated enzymatic processes. Many types of complex intercellular
signaling interactions are mediated by glycoproteins which consists of a small number of
carbohydrate units (oligosaccharides) covalently attached to proteins. Glycoproteins are either
inserted into the plasma membrane where they function as extracellular signaling molecules
(ligands or receptors), or they are secreted. Plant cell walls contain large amounts of cellulose
consisting of glucose polymers with β1-4 glycosidic bonds, whereas, bacterial cell walls contain
multiple strands of a linear polysaccharide tethered together by peptide linkages to form a
glycoconjugate called a peptidoglycan.

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