Chapter 1

D. Amino Sugars

Amino sugars are generally known as monosaccharide carbohydrate sugars that have replaced an -NH2 amine group
with the 2'-carbon hydroxyl substituent. The most abundant amino sugar is one of the oldest and most abundant
organic compounds on Earth. More than 60 amino sugars are known, many of them having been isolated and
identified only recently as components of antibiotics. Examples of amino sugars include:
 N-Acetylglucosamine
 Galactosamine
 Glucosamine
 Sialic acid
Galactosamine, for example, is one of eight essential amino
acids that function in cell to cell interaction. Though research
on galactosamine has just begun, research has shown that it
may help those with joint inflammations. Lacking in
galactosamine may even be one of the factors related to heart
disease. Also, it may also function as a toxin leading to liver
failure. In addition, galactosamine may also function as one of
the sugars composing the follicle stimulating hormone (FSH)
and the luteinizing hormone (LH), both of which are needed in
the reproductive processes of the human body. Sources of
galactosamine include bovine (which includes both cattle and
oxen), red1 algae and shark meat.
Glucosamine, contrary to galactosamine is a very popular and
relatively well-known amino sugar that our bodies use to
produce glycoconjugates like glycosylated lipids and proteins.
Glucosamine has a structural role in composing the hard
exoskeleton of chitins, such as a variety of arachnids,
crustaceans, and insects. Our bodies can obtain glucosamine
from external sources such as the fermentation of different
grains, like wheat and rice and barley, and like galactosamine, from bovine and shark. As far as its effect on bodily
functions, glucosamine's precursor, glucosaminoglycans are major segments involved in joint cartilage, and thus can
help in the treatment of osteoporosis, or osteoarthritis.
Sialic Acid is a very important sugar amine necessary to our bodies' mental and physical well being. Without sialic
acid, our bodies would deteriorate in both aspects. For example, children found lacking in this particular sugar
amine have been known to be adversely affected in their development, growth and in the pigmentation of their hair
and skin. In a study done by Bing Wang et al., improved sialic acid concentrations in infants proved to improve their
synaptogenesis and their neurological development. However, although sialic acid may serve to help us, it may also
be the culprit that allows different viruses to enter. Sialic acid is normally found on the surfaces of cell membranes,
it is not only responsible for fluid uptake to its negatively charged regions, but it also has the ability to recognize and
bind to proteins on certain viruses, such as Hemagglutinin which is found on the cell surface of the Influenza virus.
Thus, once the two bind together, it opens a door for the virus to enter into the cell and spread to other parts of the
body, causing injurious repercussions.
'N-Acetyl-d-glucosamine' is the main component of the polysaccharide in chitin, the substance that makes up the
tough outer skeleton of arthropods and insects.

https://en.m.wikibooks.org/wiki/Structural_Biochemistry/Carbohydrates/Carbohydrate_Derivatives

D. Physical Properties of Monosaccharides

Monosaccharides such as glucose and fructose are crystalline solids at room temperature, but they are quite soluble
in water, each molecule having several OH groups that readily engage in hydrogen bonding. Monosaccharides have
a characteristic sweet taste. The sweetness of different carbohydrates can be compared using sucrose as the "100
sweetness parameter". Fructose is the sweetest of all sugars, approximately 73% more sweet than table sugar
(sucrose).

https://chem.libretexts.org/Courses/Brevard_College/CHE_301_Biochemistry/02%3A_Carbohydrates/
2.05%3A_Physical_properties_of_monosaccharides

WHAT ARE THE CYCLIC STRUCTURES OF MONOSACCHARIDES

OVERVIEW

Monosaccharides so far is represented as linear molecules, but many of them also adopt cyclic structures.
Commonly, the cyclic forms of sugars are depicted using a convention first suggested by Walter N. Haworth, an
English chemist. The molecules are drawn as planar hexagons with a darkened edge representing the side facing
toward the viewer.

A. HAWORTH PROJECTION

Haworth projection is a common way of writing a structural formula of sugars (monosaccharides and
disaccharides) with an unpretentious three-dimensional perspective. This type of illustration is mostly
used in organic chemistry, especially biochemistry. Haworth projection differs from Fischer
projection in that it represents the carbohydrate in its cyclical form. It retains the essential aspects of
the molecule, such as the orientation of the hydrogen (H) and hydroxyl (OH) attachments.

Monosaccharides are a 4-, 5- or 6-membered ring structures and have several stereocenters. In order to
distinguish between types of monosaccharides (e.g., glucose and fructose), it is essential to have a
simple way to draw the sugar molecules while keeping the orientation of the hydroxyl groups.
Haworth projection has become the standard in organic chemistry for stereochemical carbohydrate
illustrations.

The Howarth projection has been named after the British chemist and Nobel laureate Norman
Haworth. His 1929 publication of The Constitution of Sugar has become a classic.

https://www.chemistrylearner.com/haworth-projection.html
27.3 WHAT ARE THE PRINCIPAL COMPOUNDS OF THE COMMON METABOLIC PATHWAY?

OVERVIEW

Metabolic pathways refer to the sequence of enzyme catalyzed reactions that lead to the conversion of a substance
into a final product. Metabolic cycles encompass a series of reactions in which the substrate is continuously
reformed and the intermediate metabolites are continuously regenerated. Substances that enter the cycle are known
as feeders of the cycle, while the molecules that leave the cycle are called products.

The common metabolic pathway has two parts: the citric cycle (also called the tricarboxylic acid cycle or the Krebs
Cycle) and the electron transport chain and phosphorylation, together called the oxidative phosphorylation pathway.

KEY TERMS

 The citric acid cycle, or Krebs cycle, is a series of chemical reactions used by all aerobic organisms to
generate energy through the oxidization of acetate—derived from carbohydrates, fats, and proteins—into
carbon dioxide. In addition, the cycle provides precursors including certain amino acids as well as the
reducing agent NADH that is used in numerous biochemical reactions.
 The electron transport chain is a series of electron transporters embedded in the inner mitochondrial
membrane that shuttles electrons from NADH and FADH2 to molecular oxygen. In the process, protons are
pumped from the mitochondrial matrix to the intermembrane space, and oxygen is reduced to form water.
 Phosphorylation is the addition of a phosphoryl (PO3) group to a molecule. In biological systems, this
reaction is vital for the cellular storage and transfer of free energy using energy carrier molecules.
Adenosine 5’-triphosphate (ATP), the most abundant energy carrier molecule, has two high-energy
phosphate-phosphate bonds that can be broken to release free energy when the cell needs it to power
various cellular processes.
 During oxidative phosphorylation, energy released during the oxidation of nutrients by enzymes is used to
drive energy-requiring phosphorylation reactions (i.e. oxidation and phosphorylation are coupled). Energy
is captured as electrons are transferred from electron donors to electron acceptors, such as oxygen, in a
series of reduction-oxidation (redox) reactions. This energy is ultimately used to power an ATP-
synthesizing enzyme called ATP synthase through a process called electron transport. Oxidative
phosphorylation is highly efficient, but only occurs under aerobic conditions.

https://courses.lumenlearning.com/boundless-microbiology/chapter/the-citric-acid-krebs-cycle/

https://courses.lumenlearning.com/wm-biology1/chapter/reading-electron-transport-chain/

https://www.sigmaaldrich.com/PH/en/technical-documents/technical-article/protein-biology/protein-
labeling-and-modification/phosphorylation

Chapter 8 (Final Term)

A. Agents for Storage of Energy and Transfer of Phosphate Groups

The most important of these agents are three rather than complex compounds: adenosine monophosphate
(AMP), adenosine diphosphate (ADP), and adenosine triphosphate (ATP). All of these molecules contain
the heterocyclic amine adenine and the sugar D-ribose joined together a β-N glycosidic bond forming
adenosine.
Adenosine triphosphate, or ATP, is the principal molecule for storing and transferring energy in cells. It is
often referred to as the energy currency of the cell and can be compared to storing money in a bank. ATP can be
used to store energy for future reactions or be withdrawn to pay for reactions when energy is required by the
cell. Animals store the energy obtained from the breakdown of food as ATP. Likewise, plants capture and store
the energy they derive from light during photosynthesis in ATP molecules. ATP is a nucleotide consisting of an
adenine base attached to a ribose sugar, which is attached to three phosphate groups. These three phosphate
groups are linked to one another by two high-energy bonds called phosphoric anhydride bonds. When one
phosphate group is removed by breaking a phosphoric anhydride bond in a process called hydrolysis, energy is
released, and ATP is converted to adenosine diphosphate (ADP). Likewise, energy is also released when a
phosphate is removed from ADP to form adenosine monophosphate (AMP). This free energy can be
transferred to other molecules to make unfavourable reactions in a cell favourable. AMP can then be recycled
into ADP or ATP by forming new phosphoric anhydride bonds to store energy once again. In the cell, AMP,
ADP, and ATP are constantly interconverted as they participate in biological reactions.

https://www.nature.com/scitable/definition/atp-318/

B. Agents for Transfer of Electrons in Biological Oxidation-Reduction Reactions

In metabolism, many redox reactions are involved. Redox reactions require that electrons can be transferred or
removed to either reduce or oxidize a particular substrate or molecule. Therefore, we need intermediates
capable of undergoing electron transfer. These are the coenzymes NAD/NADH and FAD/FADH2. These
coenzymes can exist in their oxidized (NAD+ and FAD) or reduced forms (NADH and FADH2). NADPH is a
close derivatives of NADH that also acts as a redox couple.

NAD+ and NADP+ are derivatives of nicotinic acid or nicotinamide. They intervene in biological redox
reactions.
 Figure: NAD is a derivative of nicotinic acid or nicotinamide. NADP+ contains an additional phosphate group

Both NAD+ and NADP+ can undergo two electron redox steps, in which a hydride is transferred from an organic
molecule to the NAD+ or NADP+, with the electrons flowing to the positively charged nitrogen of NAD+ which
serves as an electron sink. All NAD+/NADH reactions in the body involve 2 electron transfers. The products of
these reactions is indicated ad NADH or NADPH, respectively. 
The main difference between NADH and NADPH is that NADH is mainly involved in catabolic reactions, such
as respiration,  whereas NADPH is involved in anabolic reactions, such as photosynthesis. 

FAD (or flavin mononucleotide-FMN) and its reduction product, FADH2, are derivatives of riboflavin, and
can also undergo redox reactions:

Figure: derivatives of riboflavin

FAD/FADH2 differ from NAD+/NADH since they are bound tightly to enyzmes which use them. This is
because FADH2 is susceptible to reaction with dioxygen while NADH is not. FAD/FADH2 is another redox
pair that intervene in redox processes in biological systems

Figure: FAD/FADH2 electrons transfers. 

FAD/FADH2 are tightly bound to enzymes so as to control the nature of the oxidizing/reducing agent that interacts
with them. (i.e. so dioxygen in the cell won't react with them in the cytoplasm.). FAD is usually involved in the
oxidation of saturated carbon chains to form double bonds: 

https://chem.libretexts.org/Courses/Brevard_College/CHE_301_Biochemistry/07%3A_Nutrition/
7.08%3A_The_Chemistry_of_NAD_and_FAD

C. Agent for Transfer of Acetyl Groups

The final principal compound in the common catabolic pathway is coenzyme A, which is acetyl (CH3CO-)
transporting molecule.

Coenzyme A, a helper molecule, is a nonprotein chemical substance needed for the activation of some enzymes, the
proteins that catalyze or activate important chemical reactions within the body. It is naturally synthesized from
pantothenic acid or vitamin B5, a vitamin found naturally in food sources such as meat, vegetables, legumes and
milk, wrote Jeremy M. Berg and colleagues in "Biochemistry." Coenzyme A and its derivatives can also be
successfully produced in chemical laboratories.

coenzyme A is the helper molecule that facilitates the oxidation pathway. This process results in the production of
acetyl-coenzyme A, an important chemical substance used for the initiation of fatty acid production within the living
cell. Without this much-needed process, there is no production of fatty acids, the compounds that maintain the
integrity of the cell membrane, the protective covering of each living cell.
Energy Production

Coenzyme A, in the form of acetyl-coenzyme A, initiates the Krebs cycle, a chemical process within the body that
results in the production of carbon dioxide and adenosine triphosphate, according to the Charles E. Ophardt's
"Virtual Chembook." published online by Elmhurst College. ATP is an important, energy-rich compound that
provides fuel and energy needed for the synthesis of protein and deoxyribonucleic acid, the genetic code needed for
cell replication in the body.

https://www.livestrong.com/article/271006-the-functions-of-coenzyme-a/

SUMMARY OF TOPIC REPORT

Submitted by:

Marielle A. Villanueva BSA-AgEd II