The Republic of Iraq

University of Baghdad, College of Science,

Department of Biotechnology

penta sugars
A report submitted to the Department of Biological Products to obtain the final degree in
biochemistary

Supervisor

Dr. Ali Waleed Noaman

Preparation

‫مريم عكاب يوسف زغير‬

A2 ‫شعبة‬

2019/2020
 INTRODUCTION
Pentose: In chemistry, a pentose is a monosaccharide (simple sugar)
with five carbon atoms.(1)The chemical formula of all pentoses is C

5H10O5, and their molecular weight is 150.13 g/mol.

Pentoses are very important in biochemistry. Ribose is a constituent of

RNA, and the related molecule, deoxyribose, is a constituent of DNA.
Phosphorylated pentoses are important products of the pentose
phosphate pathway, most importantly ribose 5-phosphate (R5P),
which is used in the synthesis of nucleotides and nucleic acids, and
erythrose 4-phosphate (E4P), which is used in the synthesis of
aromatic amino acids.

Like some other monosaccharides, pentoses exist in two forms, open-

chain (linear) or closed-chain (cyclic), that easily convert into each
other in water solutions. The linear form of a pentose, which usually
exists only in solutions, has an open-chain backbone of five carbons.
Four of these carbons have one hydroxyl functional group (–OH) each,
connected by a single bond, and one has an oxygen atom connected by
a double bond (=O), forming a carbonyl group (C=O). The remaining
bonds of the carbon atoms are satisfied by six hydrogen atoms. Thus
the structure of the linear form is H–(CHOH)x–C(=O)–(CHOH)4-x–H,
where x is 0, 1, or 2.

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The term "pentose" sometimes is assumed to include deoxypentoses,
such as deoxyribose: compounds with general formula C5H10O5-y
that can be described as derived from pentoses by replacement of one
or more hydroxyl groups with hydrogen atoms.(2)

Classification
The aldopentoses are a subclass of the pentoses which, in the linear
form, have the carbonyl at carbon 1, forming an aldehyde derivative with
structure H–C(=O)–(CHOH)4–H. The most important example is
ribose. The ketopentoses have instead the carbonyl at positions 2 or 3,
forming a ketone derivative with structure H–CHOH–C(=O)–
(CHOH)3–H (2-ketopentose) or H–(CHOH)2–C(=O)–(CHOH)2–H (3-
ketopentose). The latter is not known to occur in nature and are difficult
to synthesize.

In the open form, there are 8 aldopentoses and 4 2-ketopentoses,

stereoisomers that differ in the spatial position of the hydroxyl groups.
These forms occur in pairs of optical isomers, generally labelled "d" or
"l" by conventional rules (independently of their optical activity).

▪ Aldopentoses
The aldopentoses have three chiral centers; therefore, eight (23) different
stereoisomers are possible.

Ribose is a constituent of RNA, and the related molecule, deoxyribose, is

a constituent of DNA. Phosphorylated pentoses are important products

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 of the pentose phosphate pathway, most importantly ribose 5-
phosphate (R5P), which is used in the synthesis of nucleotides and
nucleic acids, and erythrose 4-phosphate (E4P), which is used in the
synthesis of aromatic amino acids.

Pentose Sugars

There are two main types of monosaccharides in the synthesis of

nucleotides. The first type is the D-Ribose sugar which is found in
the nucleotides derived from the RNA, and the second type is the
deoxy ribose sugar and is found in the nucleotides derived from the
DNA , And here we notice the second difference between the DNA
molecule and the RNA molecule, and it is possible to distinguish
these two sugars from each other by making some color reactions of
the sugary compounds. This feature was adopted for the initial
detection and differentiation of RNA and DNA in tissues. Ribose
sugar, as it is known, reacts with the organic compound Orcinol in
the acidic environment of hydrochloric acid containing ferric
chloride (Fecl3), while the deoxyribose sugar interacts with the
organic compound diphenyl amine. In both cases, we obtain

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colored products, the intensity of which depends on the
concentration of the sugar substance.

The most important chemical characteristics of ribose and

deoxyribose diabetes depend on the hydroxyl groups with the
ability to form ester bonds (ester linkage) with phosphoric acid,
especially the hydroxyl groups at sites number three and number
five of the sugar compound.

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 ▪ Ketopentoses
The 2-ketopentoses have two chiral centers; therefore,
four (22) different stereoisomers are possible. The 3-
ketopentoses are rare.

Cyclic form
The closed or cyclic form of a pentose is created when the carbonyl
group interacts with an hydroxyl in another carbon, turning the
carbonyl into a hydroxyl and creating an ether bridge –O– between the
two carbons. This intramolecular reaction yields a cyclic molecule, with
a ring consisting of one oxygen atom and usually four carbon atoms; the
cyclic compounds are then called furanoses, for having the same rings as
the cyclic ether tetrahydrofuran.(2)

The closure turns the carboxyl carbon into a chiral center, which may
have any of two configurations, depending on the position of the new

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hydroxyl. Therefore, each linear form can produce two distinct closed
forms, identified by prefixes "α" and "β".

Properties

In the cell, pentoses have a higher metabolic stability than hexoses.

A polymer composed of pentose sugars is called a pentosan

Tests for pentoses

The most important tests for pentoses rely on converting the

pentose to furfural, which then reacts with a chromophore. In
Tollens’ test for pentoses (not to be confused with Tollens' silver-
mirror test for reducing sugars) the furfural ring reacts with
phloroglucinol to produce a colored compound;(3) in the aniline
acetate test with aniline acetate;(4) and in Bial's test, with orcinol.
(5) In each of these tests, pentoses react much more strongly and
quickly than hexoses.

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 referances

1- Merriam-Webster

2- Morrison, Robert Thornton; Boyd, Robert Neilson. Organic

Chemistry (2nd ed.). Allyn and Bacon. Library of Congress catalog 66-
25695

3-Oshitna, K., and Tollens, B., Ueber Spectral-reactionen des

Methylfurfurols. Ber. Dtsch. Chem. Ges. 34, 1425 (1901)

4- Seager, Spencer L.; Slabaugh, Michael R.; Hansen, Maren S. (2016-12-

05). Safety Scale Laboratory Experiments. Cengage Learning. p. 358.

5- Pavia, Donald L. (2005). Introduction to Organic Laboratory

Techniques: A Small Scale Approach. Cengage Learning. p. 447