BME2106 - Introduction to

Cellular and Biomolecular

Engineering
Carbohydrates and Fatty Acids What other nutrients beside proteins?

Dr. Bee Luan KHOO

blkhoo@um.cityu.edu.hk
Room no 6720

Department of Biomedical Engineering

BME2106 - Introduction to Cellular and Biomolecular Engineering BME, City University of Hong Kong

What’s the difference?

 Simple carbohydrates are in foods such as table sugar and syrups.
What’s the difference?
Complex carbohydrates contain longer chains of sugar molecules than simple
carbohydrates.

As complex carbohydrates have longer chains, they take longer to break down and
provide more lasting energy in the body than simple carbohydrates.

https://integracareclinics.com/

• Complex carbohydrates are rich in essential nutrients

• “Sugar rush“?

• Carbohydrates, whether simple or complex, do not produce immediate

elevations in mood or activity levels, highlighting the importance of
balanced nutrition and moderation in dietary choices.
CLASSIFICATION OF CARBOHYDRATES CLASSIFICATION OF CARBOHYDRATES
 Simple carbohydrates – monosaccharides (single sugar)
 Complex carbohydrates – contain two or more monosaccharides
 Monosaccharides are classified according to the number of carbons:
linked together
Triose, Tetroses, Pentoses, Hexoses, Heptoses 3
1) Disaccharides – two monosaccharides linked together

2) Polysaccharides – more than 10 monosaccharides linked

together

Trioses consist of three carbon atoms, tetroses have four, pentoses contain
five, hexoses comprise six, and heptoses contain seven carbon atoms.

CLASSIFICATION OF CARBOHYDRATES CARBOHYDRATES

 Are polyhydroxy aldehydes – called aldoses (e.g. D-glucose)
 Are polyhydroxy ketones - called ketoses (e.g. as D-fructose)
 Have chemical formula of Cn(H2O)n

Disaccharides, oligosaccharides, and polysaccharides can be

broken down to monosaccharides by hydrolysis.

 Monosaccharides are classified according to the number of carbons:

Triose, Tetroses, Pentoses, Hexoses, Heptoses 3

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 CARBOHYDRATES Simple Carbohydrates
 Are important constituents of all living organisms Monosaccharides. The 3 monosaccharides are: glucose, fructose and
 Are important structural components of cells galactose.
fructose has a five member ring,
 Serve as major source of metabolic energy
glucose and galactose have 6 member rings.
 Are represented by wedge-and-dash structures or by Fischer
projections the only structural difference between glucose and galactose is the position of
the alcohol (OH) group

https://www.mbi.nus.edu.sg/mbinfo/cytosk
eleton-dyna mics/

Simple Carbohydrates Simple Carbohydrates

Glucose and galactose are stereoisomers (have atoms bonded • Fructose is a structural isomer of glucose and galactose,
together in the same order, but differently arranged in space).
They differ in their stereochemistry at carbon 4. • Glucose is noted for its greater stability compared to galactose,
less prone to the formation of nonspecific glycoconjugates.
STEREOCHEMISTRY STEREOCHEMISTRY
 An asymmetric center – tetrahedral atom bonded to four different groups  An asymmetric center – tetrahedral atom bonded to four different groups

 Asymmetric non-superimposable stereoisomers, like glucose and

fructose, share the same molecular formula yet differing in their
spatial atom arrangements

 A compound with one asymmetric center can exist as two

stereoisomers, and they are non-superimposable mirror images.

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STEREOCHEMISTRY STEREOCHEMISTRY

The ability of enantiomers to interact differently with plane-

polarized light, known as optical activity, has profound implications
in fields such as pharmaceuticals and biochemistry, influencing
drug efficacy and molecular recognition.

 Molecules that are non-superimposable mirror-images of each other

called enantiomers. Each member of a pair of enantiomers is chiral. 4

https://www.youtube.com/watch?v=q-YhdLDbe5o
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STEREOCHEMISTRY
 Whether a 5- or a 6-membered-ring is formed depends on the
Chiral nature of molecules greatly influences molecular recognition, relative stabilities.
impacting specific interactions between molecules based on their
 D-Ribose – an aldose that forms 5-membered ring hemiacetals:
complementary shapes and chemical properties.

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• Pyranoses and furanoses represent two distinct types of cyclic

monosaccharides, characterized by their six-membered and five-
CHAIR CONFORMATION OF ALDOHEXOSE
membered cyclic structures respectively, with oxygen atoms  Large substituents are more stable in the equatorial position because
positioned at opposite ends of the ring. there is less steric strain at that position.

• Despite their structural differences, pyranoses and furanoses

share the same molecular formula but exhibit unique
arrangements of atoms, highlighting their status as isomers.
 6-membered-ring sugars – pyranoses
 5-membered-ring sugars – furanoses
 In -D-glucose, the axial positions are all occupied by hydrogens,
which require little space and experience little steric strain. It is more
stable than -D-glucose.

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Example of the impact of steric Example of the impact of steric
hindrance hindrance
• Hemoglobin's quaternary structure comprises two alpha and two beta
subunits, while myoglobin features a tertiary structure

• Factors such as steric accessibility, hydrogen bonding, and local polarity

are believed to influence the rate of heme iron autooxidation

• These factors collectively affect the rate at which heme iron molecules
react with oxygen molecules

Disaccharide
• sugar formed when two monosaccharides
are joined by glycosidic linkage.
• Like monosaccharides, disaccharides are
simple sugars soluble in water.

Disaccharides
 Disaccharide
• sucrose, lactose, and maltose.
• one of the four chemical groupings of
carbohydrates.

DISACCHARIDES - CONTAIN TWO MONOSACCHARIDE SUBUNITS HOOKED EXAMPLES OF

TOGETHER BY AN ACETAL LINKAGE
DISACCHARIDES
 Two sugar molecules can be 1. Maltose – is obtained from the hydrolysis of starch
joined via a glycosidic bond - contains two D-glucose subunits
between an anomeric carbon
and a hydroxyl carbon.

 The disaccharide formed

upon condensation of two
glucose molecules via 1  4
bond is called maltose.

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EXAMPLES OF EXAMPLES OF
DISACCHARIDES DISACCHARIDES
1. Maltose – is obtained from the hydrolysis of starch
- contains two D-glucose subunits 2. Cellobiose – is obtained from the hydrolysis of cellulose
- contains two D-glucose subunits

• Maltose occurs naturally during the breakdown of starch

and glycogen, albeit in limited quantities. It is
subsequently metabolized into glucose through
enzymatic hydrolysis, facilitated by enzymes like
maltase.

https://www.youtube.com/watch?v=UVeoXYJlBtI

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3. Lactose – is a disaccharide found in milk

EXAMPLES OF - contains one D-galactose and one D-glucose
DISACCHARIDES
2. Cellobiose – is obtained from the hydrolysis of cellulose
- contains two D-glucose subunits

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3. Lactose 4. Sucrose – most common disaccharide, known as table sugar
• Lactose intolerance, resulting from a deficiency in the enzyme - contains one D-glucose and one D-fructose
lactase, affects many adults and some children, leading to the
inability to digest lactose and subsequent gastrointestinal discomfort.

• Galactosemia, a genetic disorder caused by the absence of an

enzyme required to convert galactose to glucose, poses a more
severe health concern, underscoring the importance of understanding
lactose metabolism and its implications for human health.

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POLYSACCHARIDES - CONTAIN AT LEAST 10 MONOSACCHARIDE SUBUNITS Polysaccharides

JOINED TOGETHER BY AN GLYCOSIDIC LINKAGES

1. Starch – is the major component of flour, potatoes, rice, beans,

• most abundant carbohydrate in food. corn, and peas
• long chain polymeric carbohydrates composed of - is a mixture of two different polysaccharides
monosaccharide units bound together by glycosidic linkages. (~20% amylose and ~80% amylopectin)
• react with water using amylase enzymes as catalyst, which D-glucose unit
produces constituent sugars.

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- Contains up to 106 glucose units

 Polysaccharides
1. Starch –
The branched structure of amylopectin enables efficient enzymatic access to
glucose units, facilitating rapid energy release during metabolism, thus serving
as a vital energy reserve in plants and a dietary staple for humans.
While amylose forms a smaller portion of starch with its linear arrangement,
amylopectin predominates with its complex branching pattern, contributing to
the effective storage of glucose in plant sources such as grains, potatoes, and
legumes.
• Amylase enzymes catalyze the breakdown of starch into sugars.
• Starch is a mixture of amylose and amylopectin polysaccharide
non reducing end of polymer = without a free
polymers. anomeric carbofor redox reactions
• β-Amylase, which works from the non-reducing end of the
polymer, hydrolyzes the second α-(1→4) glycosidic bond to
produce the two-glucose sugar maltose.
• primarily produced in the pancreas and salivary glands,

Upon digestion, starch undergoes enzymatic hydrolysis, breaking down into

glucose molecules, essential for sustaining human metabolism and physiological
functions.

Branching in amylopectin:

2. Cellulose – structural material of higher plants

- contains unbranched chains of D-glucose

All mammals have the enzyme (-glucosidase) that hydrolyzes the -1,4’-glycosidic
linkages that join glucose units in amylose, amylopectin, and glycogen, but they do
not have the enzyme (-glucosidase) that hydrolyzes -1,4’-glycosidic linkages.
Therefore, mammals cannot obtain the glucose they need by eating cellulose.

3. Chitin – structural component of the shells of lobsters, crabs, and

shrimps

43 They are?
 STRUCTURES AND ROLES OF SOME POLYSACCHARIDES NATURALLY OCCURRING PRODUCTS
DERIVED FROM CARBOHYDRATES
 Deoxy sugars – one of the OH groups is replaced by a hydrogen.
e.g. 2-Deoxyribose: missing the oxygen at the C-2 position

Sugar component of Sugar component of

ribonucleic acid (DNA) deoxyribonucleic acid (DNA)

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NATURALLY OCCURRING PRODUCTS GLYCOPROTEINS

DERIVED FROM CARBOHYDRATES
 Heparin – natural anticoagulant that is released for blood clotting
– polysaccharide made up of glucosamine, glucuronic acid,
and iduronic acid subunits
 They are proteins that bonded to oligosaccharides.
 Oligosaccharides are linked to the surface of the cell by the reaction of an
OH or an NH2 group of a cell-membrane protein.
 The oligosaccharide chains on the cell surface enable the cells to recognize
and interact with other cells and with invading viruses and bacteria.

• Prescribed for medical conditions or procedures predisposing to blood clot

formation, heparin functions by inhibiting specific enzymes.

• Heparin administration routes include intravenous, subcutaneous, or

topical

• May lead to adverse effects like bleeding, bruising, or skin rash,

necessitating adherence to prescribed dosages and close medical
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supervision.
GLYCOPROTEINS GLYCOLIPIDS
 A lipid with covalently bound oligosaccharide
 Different types of glycoproteins:
 Parts of plant and animal cell membranes.
(1) Structural proteins such as collagen
 In vertebrates, ganglioside carbohydrate composition determines
(2) Proteins found in mucous secretions, immunoglobulins, stimulating
hormones
blood groups. https://www.youtube.com/watch?v=xfZhb6lmxjk
(3) Blood plasma proteins

• Oligosaccharides, consisting of short chains of monosaccharides

linked by glycosidic bonds, are key components of glycoproteins
and glycolipids,

• also serve as biomarkers and are increasingly explored for

therapeutic applications

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GLYCOLIPIDS GLYCOLIPIDS
 In gram-negative bacteria,  In gram-negative bacteria, lipopolysaccharides cover the
lipopolysaccharides cover the peptidoglycan layer.
peptidoglycan layer.

Bacterial lipopolysaccharides 37 37

Bacterial lipopolysaccharides
 WHAT ARE LIPIDS?
 A lipid is any component of plant or animal tissue that is insoluble
in water but soluble in non-polar solvents.
 Lipids, are classified on the basis of a physical property, their
solubilities – rather than basis of their structures.
 Lipids include fats and oils (triglycerides 三酸甘油酯), cholesterol,
sex hormones, some vitamins (A, D, E, and K), and components
of cell membranes called phospholipids.

WHAT ARE LIPIDS? WHAT ARE FATTY ACIDS?

 Lipids include fats and oils (triglycerides 三酸甘油酯), cholesterol, sex
hormones, some vitamins (A, D, E, and K), and components of cell
membranes called phospholipids.  Fatty acids, one major group of
lipids, are carboxylic acids with
 The distinction between polar and nonpolar solvents lies in their ability long hydrocarbon chains.
to dissolve different types of compounds: polar solvents dissolve polar  Fatty acids can be saturated with
molecules due to their unequal electron distribution, whereas nonpolar hydrogen (and therefore have no
solvents dissolve nonpolar molecules where electrons are shared equally carbon-carbon double bond) or
or cancel out polar bonds. unsaturated (and have carbon-
carbon double bonds).
 Fatty acids with more than one
double bond are called
polyunsaturated fatty acids.

double bond = unsaturated

no double bond = saturated
2 -> affect the packing of the molecule

3
 WHAT ARE FATTY ACIDS?

• Fatty acids serve dual roles as energy reservoirs and

integral constituents of cellular membranes, signalling, metabolism

• Examples of fatty acids encompass saturated varieties

like palmitic acid and stearic acid, as well as unsaturated
counterparts such as oleic acid and linoleic acid,

unsaturated ( High good LDL low bad LDL) > saturated > trans-fat
cis rare occur in natural. body dont have enyzyme in breaking down the cis fat
cis fat has the H-atom on the same side of the carbohydrate chain so it bends the chain
3
trans fat has the H-atom on the opposite side of the chain so it’s a straight line.

 Fatty acids serve as a concentrated food reserve in cells.

 Fatty acids are stored in the cytoplasm of many cells in
the form of droplets of triacylglycerol molecules
(compounds made of three fatty acid chains joined to a
glycerol molecule).
 APPROXIMATE PERCENTAGE OF FATTY
ACID IN SOME COMMON FATS AND OILS

 Triacylglycerols are less soluble in water than fatty acids due to the lack
of charged carboxylate group.
 Triacylglycerols that are solids or semisolids at room temperature are
called fats. Most fats are obtained from animals and are composed
largely of saturated fatty acids. • Omega-3 fatty acids are polyunsaturated fatty acids that offer significant
 Liquid triacylglycerols are called oils. Oils come from plant products advantages for heart health.
such as corn, soybeans, olives, and peanuts. They are composed 6 • These essential fatty acids are abundant in certain fish species like 7
primarily of unsaturated fatty acids. salmon and mackerel, as well as in plant-based sources such as
plant oil is more healthy as
it contains more
flaxseed and walnuts.
unsaturated fatty acids

APPROXIMATE PERCENTAGE OF FATTY TRANS FAT

ACID IN SOME COMMON FATS AND OILS • Trans fats, classified as unsaturated fats, are formed through a process
called hydrogenation, where hydrogen is added to oils to convert them
• Omega-3 fatty acids play pivotal roles in cell membrane structure and from liquid to semi-solid form.
function

• Research has reported a reduction of the risk of coronary artery

disease, heart attacks, strokes, and other cardiovascular conditions.

• Contribute to the modulation of cholesterol and triglyceride levels

unsaturated fat
not much hydrogen for them to bind

7 https://www.youtube.com/watch?v=brs2nMubr84 8
 TRANS FAT
it is mostly found in the processed food but is not good for the health
• Food manufacturers commonly utilize
hydrogenation to enhance the shelf life
and texture of various food products,
particularly fried foods and bakery items
that incorporate hydrogenated
vegetable oils.

• While trans fats are predominantly

found in processed foods, they occur
naturally in low levels in dairy products
such as whole milk and butter, as well
as in the fat of sheep and cattle.

8 8

need balanced level of LDL( throughout the blood) and HDL(blood to liver)

STRUCTURAL LIPIDS IN STRUCTURAL LIPIDS IN

MEMBRANES MEMBRANES
 They contain polar head groups and nonpolar tails (usually  The properties of head groups determine the surface properties
attached fatty acids) of membranes
 Diversification can come from:  Different organisms have different membrane lipid head group
 modifying a different backbone compositions
 changing the fatty acids  Different tissues have different membrane lipid head group
compositions
 modifying the head groups

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WHAT ARE PHOSPHOLIPIDS?
 Fatty acids are important components of cell membranes that are
composed largely of phospholipids.
 Phospholipids are the lipids that contain a phosphate group.
Phosphoacylglycerols are similar to triacylglycerol except that a
terminal OH group is esterified with phosphoric acid rather than with
a fatty acid, forming a phosphatidic acid.
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WHAT ARE PHOSPHOLIPIDS?
• The hydrophobic tails of phospholipids form a nonpolar region
within the bilayer, providing insulation against water-soluble
substances and contributing to membrane stability.
• Conversely, the hydrophilic heads of phospholipids interact with the
aqueous environments inside and outside the cell, enabling
communication and transport processes essential for cellular
function and homeostasis.
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WHAT ARE PHOSPHOLIPIDS?
• The phospholipid bilayer, the fundamental structure of cell
membranes, consists of two layers of phospholipids arranged with
their hydrophobic tails oriented inward and hydrophilic heads facing
outward. This bilayer formation creates a barrier between the
internal and external environments of the cell, facilitating cellular
functions while maintaining membrane integrity.
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 Phosphatidic acids are the simplest phosphoacylglycerols and are
present only in small amounts in membranes.
 The most common phosphoacylglycerols in membranes have a
second phosphate ester linkage – they are phosphodiesters.
major component of
most eukaryotic cell
membranes
 The most commonly used alcohol to form second ester group are
ethanolamine, choline and serine.
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  Phosphoacylglycerols form membranes by arranging themselves
in a lipid bilayer. The polar heads of the phosphoacylglycerols are
on both surfaces of the bilayer, and the fatty acid chains form the
interior of the bilayer.
 The fluidity of a membrane – the ease with which its lipid
molecules move within the membrane – is controlled by the
fatty acid components of the phosphoacylglycerols.
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https://www.youtube.com/watch?v=qBCVVszQQNs
• The length of the fatty acid tails in phospholipids
also impacts membrane fluidity, with longer tails
promoting greater interactions between lipid
molecules and reducing overall fluidity. Conversely,
shorter tails enhance fluidity by decreasing
intermolecular interactions within the membrane.
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• Temperature is a significant factor influencing
membrane fluidity, with higher temperatures
increasing fluidity as lipid molecules gain kinetic
energy and move more freely.
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• At low temperatures, phospholipids tend to cluster together, restricting
fluidity. However, cholesterol molecules interspersed within the
phospholipid bilayer disrupt these clusters, enhancing fluidity by
reducing intermolecular interactions.
• Conversely, at high temperatures, phospholipids are more spaced out,
resulting in increased fluidity. Here, cholesterol plays a different role,
pulling phospholipids closer together to counteract excessive
fluidity by strengthening intermolecular forces.
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• The degree of saturation of fatty acid tails impact the arrangement and
interactions between phospholipid molecules.
• Saturated fatty acid tails lack double bonds and exhibit a straight, orderly
arrangement, maximizing interactions between adjacent tails and
consequently reducing membrane fluidity.
• In contrast, unsaturated fatty acid tails contain double bonds, resulting in
a crooked, kinked structure that increases the distance between tails.
WHAT ARE SPHINGOLIPIDS?
• Most common types of sphingolipids are sphingomyelins and
cerebrosides
• While phospholipids dominate the composition of cellular membranes,
sphingolipids are primarily found in nervous tissue, serving as key
structural components and regulatory molecules in cellular signaling
pathways.
• Sphingolipids exert significant influence on cellular processes such as
cell cycle regulation, apoptosis, and differentiation, highlighting their
crucial role in maintaining cellular homeostasis and functionality.
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WHAT ARE SPHINGOLIPIDS?
 Sphingolipids are another kind of lipid found in membranes and
they are the major lipid components in the myelin sheaths of nerve
fibers.
 They contain an amino alcohol called sphingosine
instead of glycerol. The amino group of sphingosine
is bonded to the acyl group of a fatty acid.
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WHAT ARE PROSTAGLANDINS?
 Prostaglandins are found in all body tissues and are responsible for
regulating a variety of physiology responses, such as inflammation,
blood pressure, blood clotting, fever, pain, the induction of labor,
and the sleep-wake cycle.
 Unlike most hormones, the prostaglandins are not secreted from a
gland to be carried in the bloodstream and work on specific areas
around the body. Instead, they are made by a chemical reaction at
the site where they are needed and can be made in nearly all the
organs in the body. Prostaglandins are part of the body’s way of
dealing with injury and illness.
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WHAT ARE PROSTAGLANDINS?
 All prostaglandins have a five-membered ring with a
seven-carbon carboxylic acid substituents and an eight-
carbon hydrocarbon substituents. The two substituents
are trans to each other.
 Prostaglandins are classified using the formula PGX,
where X designates the functional groups of the
compound’s five-membered ring.
WHAT ARE PROSTAGLANDINS?
• Dietary factors, such as the consumption of fatty foods, can influence
prostaglandin levels, potentially exacerbating symptoms like
menstrual cramping.
• Conversely, lifestyle practices like exercise, particularly low-impact
activities such as yoga and swimming, can mitigate prostaglandin-
related discomfort by enhancing blood flow and endorphin release.
• Apart from dietary and lifestyle factors, stress-related hormones like
adrenaline and cortisol also impact prostaglandin synthesis

Adrenaline makes the heart beat faster, causes blood pressure

to go up and gives you more energy.

Cortisol, the primary stress hormone, increases sugar, also

called glucose, in the bloodstream, enhances the brain's use of
glucose and increases the availability of substances in the
16 body that repair tissues. 16

REFERENCES
1. P. Y. Bruice, Organic Chemistry, Pearson Education, New
Jersey, 5th ed., 2007.
2. A. Bruce, D. Bray, K. Hopkin, A. Johnson, J. Lewis,
M. Raff, K. Roberts and P. Walter, Essential Cell Biology,
Garland Science, 2nd ed., New York, 2004.
3. For the information of trans fat:
http://www.cfs.gov.hk/english/faq/faq_13.html
4. For the information of vitamins (Webpage of National
Institutes of Health): http://ods.od.nih.gov/
5. David L Nelson, Michael M. Cox, Lehninger Principles of
Biochemistry, Freeman, 6th ed., 2013.
6. 1. P. Y. Bruice, Organic Chemistry, Pearson Education, New
Jersey, 5th ed., 2007 (Chapter 5 and 21).

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