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Subject Code CHEM 3 Chemistry 3

Module Code 5.0 Biomolecules II
Lesson Code 5.6 Review of Nucleic Acids: Structure and Functions (Part I)
Time Frame 30 minutes

TA ATA
Components Tasks
(mins) (mins)
Target At the end of this module, you are expected to:
• distinguish between a purine and a pyrimidine; and
• explain the differences among nucleoside, nucleotide and 1
nucleic acids.

Hook Among the most fundamental characteristics of living organisms

that sets them apart from non-living ones is their ability to
reproduce while passing on their traits to succeeding generations
(Cooper, 2000). As you have learned from Biology 2 back when
you were in Grade 10, the genetic; hence, hereditary information
of living organisms that determine their structure and function are
stored and transmitted in biomolecules called nucleic acids. These
include deoxyribonucleic acid (DNA) and ribonucleic acid
(RNA).

Recalling from stock knowledge, tell whether these statements are

TRUE or FALSE. (Non-graded)

_______ a) Nucleic acids are macromolecules.

5
_______ b) Like carbohydrates and proteins, nucleic acids are
polymers.
_______ c) Nucleic acids are acidic because their structural
components – adenine, guanine, cytosine, guanine,
and thymine or uracil – are acidic.

Though James Watson and Francis Crick have been widely

credited for deciphering the three-dimensional structure of DNA
for which they, along with Maurice Wilkins, have been awarded
the Nobel Prize in Physiology and Medicine in 1962, it is also
worthwhile to recognize how several other scientists contributed
towards this significant feat. In this learning guide, we shall review
the primary structure of nucleic acids in greater detail.

Ignite A touch of history and the basic structure of nucleic acids

The first systematic chemical studies on cell nuclei were made by

Johannes Friedrich Miescher, a Swiss physician and biologist.
In 1968, he was able to isolate a phosphorous-containing
substance from pus cells (leukocytes) obtained from fresh surgical
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bandages (Dahm, 2005; Pray, 2008; and Nelson and Cox, 2017).
He named named the substance ‘nuclein’ which he further found
to be composed of a protein component which was basic and an
acidic component, now known as DNA (Pray, 2008; and Nelson
and Cox, 2017); hence, the term, nucleic acid.

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Albrecht Kossel, a German biochemist, discovered the existence

of the nitrogenous bases that were produced along with large
quantities of phosphates and a carbohydrate from the hydrolysis
of nucleic acids (Frixione and Ruiz-Zamarripa, 2019). This was
one of the reasons that won him the Nobel Prize in Physiology and
Medicine in 1910 (Nobel Media AB, 2021). These bases all have
nitrogen- or amine-containing heterocylic rings. These are
classified into purines (adenine and guanine) and pyrimidines
(cytosine, thymine in DNA, and uracil in RNA) shown in Figure
1.

Figure 1. Structures of purine and pyrimidine bases in nucleic

acids. (Image adapted from McMurry, 2008).

Recall that heterocycles refer to those that contain atoms other the
C such as N, O, or S in the ring structure. Notice that purines are
made up of two fused heterocycles while pyrimidines only have
one. The slight variations in the chemical structures of these
nitrogenous bases have a great impact in how they are paired in
the nucleic acids which will be described in the succeeding texts.

Meanwhile, Phoebus Levene, a Russian physician and biochemist

discovered that the sugar in nucleic acids is a pentose (or
furanose). In DNA, it is 2-deoxyribose which has no –OH group
at C2’ (Pray, 2008) while in RNA, the sugar is ribose (Figure 2).

Figure 2. Structures of sugars in nucleic acids: ribose in RNA

and 2-deoxyribose in DNA. (Image adapted from McMurry,
2008).

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Levene was also the one who proposed the order of the three
components in a nucleotide: phosphate – sugar – base (Figure 3).
A nucleoside, on the other hand, is merely composed of the sugar
and the base; that is, without the phosphate group. Levene, along
with other scientists, proposed that nucleic acids of higher
structural order could be built from nucleotides (Frixione and
Ruiz-Zamarripa, 2019).

Figure 3. Structures of a nucleotide versus a nucleoside. (Image

adapted from Nelson & Cox, 2017).

Recall that in DNA, the deoxyribonucleotides are composed only

of the bases: adenine, cytosine, guanine, and thymine. In RNA,
thymine is replaced with uracil with the ribose sugar in
ribonucleotides. Figures 4 and 5 show the different structures of
nucleotides.

Figure 4. Structures of deoxyribonucleotides in DNA with their

names and symbols. (Image from McMurry, 2011)

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Figure 5. Structures of ribonucleotides in RNA with their names

and symbols. (Image from McMurry, 2011)

Alexander Todd, a British Nobel Laureate, did much work on the

synthesis of nucleotides and is credited for the structural
understanding of the sugar-phosphate backbone of nucleic acids
(Shampo, Kyle, and Steensma, 2012). In DNA and RNA,
nucleotides are covalently bonded by phosphodiester bonds (or
phosphate-group bridges). These linkages have the structure:
R’O – (PO2–) – OR” where R’ represents the sugars connected to
the phosphate group, one of which at its 3’ hydroxyl group and the
other at its 5’ hydroxyl group. The end that contains the ‘free’
phosphate group is the 5’ end while the other end with a free 3’
hydroxyl group is the 3’ end as depicted in Figure 6.

Figure 6. Structure of the sugar-phosphate backbone of nucleic

acids. (Image from McMurry, 2011)

A chain of nucleotides is called a polynucleotide chain which is

the primary structure of nucleic acids. (McMurry, 2011; Nelson
and Cox, 2017).

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Navigate It is time to test how much you’ve learned. 😊

Answer the following questions and submit your answer sheet in

accordance to the instructions of your teacher. This is a Graded
Formative Assessment.

Part I. Study the features of the given structures and choose which
one/s is/are described. Write the corresponding letters of your
answers. (1 point per correct letter/answer)
O
B OH OH
A HO
O C HO
O
NH

NH O OH OH
O OH

O NH

N
D NH E HO
O
N O

NH N NH 2
NH2
OH
O N
O
F N
NH G HO P O N O
O
N OH
HO N NH2
O
OH O H
7

OH NH2
NH2
N N
H N N I
O HO N N
N O
HO P O N
O
OH
O OH OH
OH HO P O OH
O
OH
J
OH

___________ 1) purine
___________ 2) pyrimidine
___________ 3) sugar in DNA
___________ 4) sugar in RNA
___________ 5) nucleotide which contains a purine found in DNA
___________ 6) nucleoside which contains a purine found in RNA
___________ 7) pyrimidine-containing deoxyribonucleoside
___________ 8) purine-containing ribonucleotide

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Part II. Refer to the following information.

Extensive studies on the relative composition of bases in different

samples were conducted by Erwin Chargaff (Austro-Hungarian-
born American biochemist) and his team (Pray, 2008; and Nelson
and Cox, 2017). Figure 7 shows an image of one of Chargaff’s
data tables in studying salmon sperm DNA.

Figure 7. Image of Chargaff’s data on the base composition of

salmon sperm DNA. (Retrieved from
https://www.jbc.org/article/S0021-9258(18)55924-X/pdf).

Tell whether the following inferences about Chargaff’s Data are

CORRECT or INCORRECT. (1 point each)
___________ 1) Salmon sperm DNA essentially contains a
significantly greater percentage of purines than
pyrimidines.
___________ 2) The ratio of guanine to cytosine is 1:1 and the ratio
of adenine to thymine is also 1:1.
___________ 3) In DNA, guanine pairs with cytosine while
adenine pairs with thymine.
___________ 4) DNA is a double helix.

Nucleotides are the repeating units or monomers of nucleic acids.

It is composed of a phosphate group, a pentose sugar (ribose in
RNA and 2-deoxyribose in DNA), and a nitrogenous base which
could be a purine or a pyrimidine. Purines include adenine and
Knot
guanine with two fused rings both of which are present in DNA
3
and RNA. Pyrimidines with 6-membered heterocyclic ring
include cytosine (present in both DNA and RNA), thymine
(present only in DNA), and uracil (present only in RNA).
Nucleosides are composed only of a sugar and a nitrogenous base.

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Nucleotides are covalently bonded together by phosphodiester

linkages in a polynucleotide chain that makes up the primary
structure of nucleic acids. Being composed of monomers and a
large number of atoms, nucleic acids are thus classified as
macromolecules and natural polymers.
a suggested time allocation set by the teacher
b actual time spent by the student (for information purposes only)

Answer Key

HOOK
a) TRUE. Macromolecules are defined as those containing a large number of atoms and these
include nucleic acids along with carbohydrates and proteins as well as synthetic polymers.
b) TRUE. Nucleic acids are polymers since they are composed of repeating units called
nucleotides.
c) FALSE. The components mentioned (adenine, guanine, cytosine, thymine, and uracil) are, in
fact, basic. What makes nucleic acids acidic is their phosphate component which is protonated
in the presence of water. As such, they behave like phosphoric acid.
References:

Cooper G.M. (2000) The Cell: A Molecular Approach. 2nd edition. Sunderland (MA): Sinauer
Associates. Heredity, Genes, and DNA. Available from:
https://www.ncbi.nlm.nih.gov/books/NBK9944/
Chargaff, E., Lipshitz, R., Green, C. & Hodes, M.E. (1951) The Composition of the
Desoxyribonucleic Acid of Salmon Sperm. J. Biol. Chem. Retrieved on May 16, 2021 from
https://www.jbc.org/article/S0021-9258(18)55924-X/pdf
Dahm, R. (2004) Friedrich Miescher and the discovery of DNA. Developmental Biology, 278,
doi:10.1016/j.ydbio.2004.11.028
Frixione, E., & Ruiz-Zamarripa, L. (2019) The “scientific catastrophe” in nucleic acids research that
boosted molecular biology. J. Biol. Chem. 294(7), 2249–2255. DOI
10.1074/jbc.CL119.007397
Macmurry, J. (2011) Fundamentals of Organic Chemistry, 7th ed. Brooks/Cole: California.
Nelson, D.L.; and Cox, M.M. (2017) Lehninger Principles of Biochemistry, 7th ed. W. H. Freeman
and Company: New York.
Nobel Media AB (2021) Albrecht Kossel – Facts. NobelPrize.org. Retrieved on May 16, 2021 from
https://www.nobelprize.org/prizes/medicine/1910/kossel/facts/
Nobel Media AB (2021) The Nobel Prize in Physiology or Medicine 1962. NobelPrize.org. Retrieved
on May 16, 2021 from https://www.nobelprize.org/prizes/medicine/1962/summary/
Pray, L. (2008) Discovery of DNA structure and function: Watson and Crick. Nature Education
1(1):100
Shampo, M.A., Kyle, R.A., & Steensma, D.P. (2012). Alexander Todd - British Nobel Laureate.
Mayo Clinic, Proc. 87(3) : e19. doi:10.1016/j.mayocp.2011.12.009

Prepared by: GENALYN ALICE R. VILORIA Reviewed by: MELBA C. PATACSIL

Position: Special Science Teacher V Position: Special Science Teacher V
Campus: PSHS-CVC Campus: PSHS-CARC
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