ENGINEERING

BIOLOGY:
CARBOHYDRATES
Richa Sharma
Class IV

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“Carbo” “hydrate”
• The
name suggests that the molecule contains CARBON and HYDRA (or
WATER). CH2O monomer and (CH2O)n polymer
• The name “carbohydrate” is a little misleading, though, because
carbohydrates do not consist of carbon atoms bonded to water molecules.
Instead, they are made up of a carbonyl group (C=O), several hydroxyl
groups (-OH), along with multiple carbon–hydrogen bonds (C-H).
• Carbohydrates = sugars = saccharides
• The monomers called monosaccharides (literally, “one-sugar”), small
polymers called oligosaccharides (“few-sugars”), and the large polymers
called polysaccharides (“many-sugars”).
• The value of n can vary from 3, for the smallest sugar, to well over a 1000 for
some of the large polymers.
• Recall
that proteins and nucleic acids could satisfy three of the five
fundamental characteristics of life: information, replication, and evolution.
Carbohydrates play an important role in a fourth characteristic—energy.
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 Monosaccharides
• Sugars are fundamental to life. They provide chemical energy in cells and
furnish some of the molecular building blocks required for the synthesis of
larger, more complex compounds.
• Monosaccharides were important during chemical evolution, early in
Earth’s history, too e.g. ribose.
• Allmonosaccharides may have same basic formula. But then how do they
differ?
• 1. These two sugars share the same molecular formula (C3H6O3), their
molecular structures are different. The carbonyl group that serves as one
of monosaccharides’
distinguishing features can be
found either at the end of the
molecule, forming an aldehyde
sugar (an aldose), or within the
carbon chain, forming a ketone
sugar (a ketose). 3
 Variation among monosaccharides
• 2. The number of carbon atoms present also varies among
monosaccharides. By convention, the carbons in a monosaccharide are
numbered consecutively, starting with the end nearest the carbonyl group.
Three-carbon sugar = trioses. Ribose has five carbons = pentose; glucose six
carbon sugar = hexose.
• 3. Monosaccharides can vary in the spatial arrangement of their atoms.
This is a key point: Because the
structures of glucose and
galactose differ, their functions
differ. In cells, glucose is both
a source of carbon atoms that
are used to construct other
molecules and of chemical
energy that sustains life. But
galactose cannot do that. Simple
difference = enormous change. 4
• 4. It’s actually rare for sugars
consisting of five or more carbons
Variation in same
to exist in linear form. In aqueous
solution they spontaneously form
monosaccharide
ring structures when the carbonyl
group bonds to a carbon with a
hydroxyl group.
• When the ring structure is formed
in sugars, the position of the
newly formed C-1 hydroxyl
group will be fixed in one of two
possible orientations: below or
above the plane of the ring. So
there are two possible forms of
glucose: α-glucose and
β-glucose.
Glucose: C-1 carbon forms a bond with the oxygen
• The two forms exist in atom of the C-5 hydroxyl. The hydrogen displaced
equilibrium, but β-glucose is more from the C-5 hydroxyl is transferred to the C-1
common because it is slightly carbonyl (preserves the number of atoms and
more stable than α-glucose. hydroxyls between the ring and linear forms) 5
 Monosaccharides by chemical evolution?
• The presence of a carbonyl group along with multiple polar hydroxyl groups means
that even the simplest sugars have many reactive and hydrophilic functional
groups. Based on this observation, it’s not surprising that sugars are polar molecules
that form hydrogen bonds with water and are easily dissolved in aqueous solutions.
• Tosummarize, many distinct monosaccharides exist because so many aspects of
their structure are variable: aldose or ketose placement of the carbonyl group, the
number of carbons, and the different arrangements of hydroxyl groups in space. Ring
forms of the same molecule also have alternative forms. These variations give each
monosaccharide a unique structure and function.
• Laboratory simulations have shown that most monosaccharides are readily
synthesized under conditions that mimic those predicted for early Earth. For
example, when formaldehyde (CH2O) molecules are heated in solution, they react
with one another to form almost all the possible types of pentoses and hexoses.
These reactions may have occurred in the hot water released from undersea
volcanoes and hydrothermal vents.
• In addition, researchers have discovered the three-carbon ketose (Slide 3) along with
a wide array of compounds closely related to sugars, on a meteorite that struck
Murchison, Australia, in 1969. Based on these observations, investigators suspect
that sugars are synthesized on dust particles and other debris in interstellar space
and could have rained down onto Earth as the planet was forming.
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Polymerization of monosaccharide
• Monosaccharides polymerize when a condensation reaction occurs between
two hydroxyl groups, resulting in a covalent bond called a glycosidic linkage.
The inverse reaction, hydrolysis, cleaves these linkages.
• Glycosidiclinkages hold monomers together, just like the peptide bonds and
phosphodiester linkages do for proteins and nucleic acids. There is an
important difference, however. Peptide bonds and phosphodiester linkages
form between the same locations in their monomers, giving proteins and
nucleic acids a standard backbone structure, but this is not the case for
carbohydrates. Because glycosidic linkages form between hydroxyl
groups, and because every monosaccharide contains at least two
hydroxyls, the location and geometry of glycosidic linkages can vary
widely among oligosaccharides and polysaccharides.
• Similarto proteins and nucleic acids, the structure and function of larger
carbohydrates depends on the types of monomers involved and how they
are linked together
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 Variation in simplest polymer – a disaccharide

• Maltose = Glucose + Glucose and is abundant in the starter liquid used to brew beer.
• Lactose = Glucose + Galactose, an important sugar in milk
• Maltose and lactose illustrate two of the most common glycosidic linkages, called the
α-1,4-glycosidic linkage and the β-1,4-glycosidic linkage. The numbers refer to the
carbons on either side of the linkage, between the C-1 and C-4 carbons. Their geometry
is different: α and β refer to the contrasting orientations of the C-1 hydroxyls—on
opposite sides of the plane of the glucose rings.
• Functionalconsequence : enzymes used to hydrolyze maltose will not cleave lactose.
Lactose is digested by lactase—an enzyme that many humans stop secreting after
childhood. Without lactase, adults may become lactose intolerant and suffer intestinal
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discomfort if they consume dairy products.
 Starch and glycogen - storage

• Starch consists entirely of α-glucose joined by glycosidic linkages. Most of these

linkages are between C-1 and C-4, and the angle of these bonds causes the chain of
glucose residues to coil into a helix. starch is made up of two types of polymers. One is
an unbranched molecule called amylose, which contains only α-1,4-glycosidic
linkages. The other is a branched molecule called amylopectin. Branching occurs when
a glycosidic linkage forms between a C-1 carbon and a C-6 carbon (an α-1,6 linkage). In
amylopectin, branching occurs at about one out of every 30 glucose residues.
• Glycogen performs the same storage role in animals that starch performs in plants
(liver and muscle in humans). Almost identical to starch in structure. However, a branch
occurs in about 1 out of every 10 glucose subunits
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 Cellulose - structure

• Allcells are enclosed by a membrane, and the cells of most organisms are also
surrounded by a protective layer of material called a cell wall. In plants, bacteria, fungi,
and many other groups, the cell wall is composed primarily of one or more
polysaccharides.
• In plants, the major component of the cell wall is cellulose.
Cellulose is a polymer made
from β-glucose monomers joined by β-1,4-glycosidic linkages. The geometry of the
linkage is such that each glucose residue in the chain is flipped in relation to the
adjacent residue. The flipped orientation is important because (1) it generates a linear
molecule, rather than the helix seen in starch; and (2) it permits multiple hydrogen
bonds to form between adjacent, parallel strands of cellulose. As a result, cellulose
forms long, parallel strands that are joined by hydrogen bonds. The interacting 10
cellulose
fibres are strong and give the cell structural support.
Chitin - structure

• Chitin is a polysaccharide that stiffens the cell walls of fungi. It’s also found in a few
types of protists and in many animals. It is, for example, the most important
component of the external skeletons of insects and crustaceans.
• Chitin is similar to cellulose, but instead of consisting of glucose residues, the
monosaccharide involved is one called N-acetylglucosamine (abbreviated as NAG).
These NAG monomers are joined by β-1,4-glycosidic linkages. As in cellulose, the
geometry of these bonds results in every other residue being flipped in orientation.
The NAG subunits in chitin also form hydrogen bonds between adjacent strands to
produce a stiff protective armour.
• Cellulose is the most abundant organic compound on Earth today, and chitin is
probably the second most abundant by weight
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 Peptidoglycan - structure

• Mostbacteria, like all plants and fungi, have cell walls. The primary structural
component of bacterial cell walls consists of a polysaccharide called peptidoglycan.
• Peptidoglycan is the most complex of the polysaccharides discussed so far. It has a
long backbone formed by NAG and N-acetylmuramic acid (NAM) that alternate with
each other and are linked by β-1,4-glycosidic linkages.
• Inaddition, a short chain of amino acids is attached at the C-3 carbon of NAM. When
molecules of peptidoglycan align, peptide bonds link the amino acid chains on adjacent
strands. These links serve the same purpose as the hydrogen bonds between the
parallel strands of cellulose and chitin in the cell walls of other organisms.
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Role in chemical evolution
• Despite their current importance to life, polysaccharides probably played
little to no role in the origin of life.
• No plausible mechanism exists for the polymerization of monosaccharides
under conditions that prevailed early in Earth’s history. In cells and in
laboratory experiments, the glycosidic linkages form only with the aid of
protein enzymes. No enzyme-like RNAs are known to catalyze these
reactions.
• To date, no polysaccharide has been discovered that can catalyze
polymerization reactions. Even though polysaccharides contain reactive
hydroxyl and carbonyl groups, they lack the structural and chemical
complexity that makes proteins, and RNA, effective catalysts.
• The monomers in polysaccharides are not capable of complementary base
pairing. Unlike nucleic acids, polysaccharides cannot serve as templates for
their own replication.
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 Function 1: Structure
• To appreciate why cellulose, chitin, and peptidoglycan are effective structural
molecules, recall that they form long strands and that bonds can form between
adjacent strands. In the cell walls of plants, for example, a collection of about 80
cellulose molecules are cross-linked by hydrogen bonding to produce a tough
fiber. These cellulose fibers, in turn, crisscross to form a tough sheet that is able
to withstand pulling and pushing forces—what an engineer would call tension
and compression
• Inaddition to being tough, structural carbohydrates are durable. a few
organisms have enzymes capable of digesting cellulose, chitin, or
peptidoglycan. These fibers tend to be insoluble due to the strong interactions
between strands consisting of β-1,4- glycosidic linkages. The exclusion of water
within these fibers makes their hydrolysis more difficult so they are resistant to
degradation and decay.
• Ironically, the fact that cellulose is indigestible makes it extremely important for
digestive health. The cellulose that you ingest when you eat plants—what
biologists call dietary fiber— forms a porous mass that absorbs and retains
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water. This improves bowel movement, digestion and excretion.
Function 2: Cell Identity
The variety in the types of monosaccharides
and how they can be linked together makes
it possible for an enormous number of unique
carbohydrates e.g. Unique molecules:
Glycolipid = Polysaccharide + Lipids
Glycoproteins = Polysaccharides + Proteins
Each cell type and each species can display a
unique identity

• Structural polymers tend to be repetitive, made up of only one or two types of

monosaccharides. Some polysaccharides exhibit enormous structural diversity,
because their component monomers—and the linkages between them—vary a
lot. As a result, they are capable of displaying information to other cells through
their structure. More specifically, polysaccharides act as an identification badge
on the outer surface of the plasma membrane that surrounds a cell.
• Glycolipids and glycoproteins are key molecules in what biologists call cell–cell
recognition and cell–cell signalling. Each cell in your body has carbohydrates on
its surface that identify it as part of your body. Blood groups, different tissues,
recognition of egg by sperm. 15
Function 3: Energy storage
• Recall that the essence of chemical evolution was energy transformations. For
example, it was proposed that the energy in sunlight may have been converted into
chemical energy and stored in bonds of molecules such as formaldehyde (CH2O).
• This same type of transformation from light energy to chemical energy occurs in cells
today, cells produce sugars. For example, plants harvest the energy in sunlight and
store it in the bonds of carbohydrates by the process known as photosynthesis.
• Photosynthesis entails a complex set of reactions that can be summarized most
simply : CO2 + H2O + sunlight → (CH2O)n + O2

1. The electrons in the C=O bonds of carbon

dioxide, so low potential energy.
2. The electrons involved in the C-H bonds of
carbohydrates are shared equally , so high
potential energy.
3. Same for carbon–carbon (C-C) bonds, high
potential energy.
Carbohydrates store much more chemical
energy than carbon dioxide does. 16
 Breakdown of stored energy
• Recall that the potential energy in bonds is released when they are broken and new,
stronger bonds are formed.
• Starch and glycogen are efficient energy-storage molecules because they polymerize
via α-glycosidic linkages instead of the β-glycosidic linkages observed in the structural
polysaccharides. The α-linkages in storage polysaccharides are readily hydrolyzed to
release glucose, while the structural polysaccharides resist enzymatic degradation.
• The most important enzyme involved in catalyzing the hydrolysis of α-glycosidic
linkages in glycogen molecules is a protein called phosphorylase. Many of your cells
contain phosphorylase, so they can break down glycogen to provide glucose on
demand. The glucose subunits are processed in reactions that result in the production
of chemical energy that can be used in the cell.
• When a cell needs energy, reactions break down glucose and capture some of the
released energy through synthesis of the nucleotide adenosine triphosphate (ATP).
More specifically, the energy that’s released when sugars are processed is used to
synthesize ATP from a precursor called adenosine diphosphate (ADP) plus a free
inorganic phosphate (Pi) molecule. The overall reaction can be written as follows:

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Function 4: Substrate for synthesizing
more-complex molecules
Function 5: Building blocks

• Recall that RNA contains the five-carbon sugar ribose (C5H10O5) and DNA
contains the modified sugar deoxyribose (C5H10O4). The nucleotides that
make up these polymers consist of the ribose or deoxyribose sugar, a
phosphate group, and a nitrogenous base. The sugar itself acts as a subunit
of each of these monomers.
• Sugars frequently furnish the raw “carbon skeletons” that are used as
building blocks in the synthesis of important molecules. Your cells are using
sugars right now, for example, as a starting point for the synthesis of amino
acids.

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• For use of ATP by cells as energy units, a selectively permeable
membrane barrier is required.
• Lipids are needed to build these membranes

• Role they played in the evolution of the first cell.

Next?
Lipids, membranes, first cells

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