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1C Intro

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Chemicals of life include carbohydrates, lipids, proteins and nucleic acid.

The general objective is to relate structure-functions of these in biological processes at the molecular,
cellular and organismal level. Their Metabolism will be discussed at the end of the chapter.

Activity 1:
A. knowing the group to which these elements belong, distribute the total outer electrons following the
Octet rule concept.
1. Carbon
2. Hydrogen
3. Nitrogen
4. Oxygen, the most abundant element in human body, (61% of a person’s mass)
5. Sulfur
6. Phosphorus

B. Following the Lewis concept (dots/two dots replaced with a dash line), draw the structure of the
following substances. Electrons (both bonding and non-bonding electrons) must be shown.
1. ammonia
2. carbon dioxide
3. NO2
4. ethanaldehyde
5. propanoic acid

The six elements are key building blocks of the chemicals found in living thingsC,H,N,O,S,P
The first four are the most essential elements found in our body: C, H, N, O
Oxygen, the most abundant element in human body,(61% of a person’s mass) . Others(0.85%) in human
body are sulfur, phosphorus, sodium, chlorine and magnesium.

Major organic biochemicals: carbohydrates, lipids, proteins, nucleic acid


CARBOHYDRATES(saccharides) are polyhydroxyaldehydes or polyhydroxyketones or compounds that
can be hydrolyzed to or derived from polyhydroxyaldehydes or polyhydroxyketones.

Biological functions of carbohydrates:


1. For energy storage in animals and plants: glucose, starch, glycogen
2. As supportive structures in plants(cellulose) and crustaceans(chitin)
3. As component of the nucleic acids.

Monosaccharides, the simplest carbohydrates have general formula of (CH2O)n:


Classification based on the carbonyl group.
1.aldoses contain an aldehyde(-CHO) group at the end of the chain and is numbered C1.
This Photo by Unknown Author is licensed under CC BY-SA glyceraldehyde

In D-glyceraldehyde, C2 is the Chiral carbon. The substituents to this carbon are different. The -OH
attached to this chiral carbon is connected on the right. The letter D stands for dextrorotatory, that is,
rotation is to the right when subjected to plane polarized light.
2.Ketoses contain the keto (C = 0) group. In all naturally occurring ketoses, the
keto carbon is next to the terminal carbon, therefore, it is

numbered C2.
Classification based on the number of carbon atoms:trioses, tetroses, pentoses
and hexoses.
Aldoses: aldotrioses, aldotetroses, aldopentoses, aldohexoses
Ketoses: Ketotrioses, ketotetroses, ketopentoses, ketohexoses
aldohexose: six carbon monossacharide with an aldehyde group

Formation of cyclic hemiacetal Structures of glucose: α-D-glucose and β-D-glucose


The position of -OH in C-1 determines alpha(__________) or Beta(___________).
Why 36% α-D-glucose and 64% β-D-glucose?

Formation of cyclic hemiacetal structure of D-fructose


C-2, the hemiketal carbon, has two different carbon substituents and two different oxygen substituents.
C-2 corresponds to the carbonyl carbon of the open-chain form.

Properties
1.most common monosaccharides are colorless, crystalline solids, soluble in
water and have a sweet taste. These are quite stable and are not hydrolyzed.
They sizzle when heated and give off a distinction odor. They are optionally
active
*Ribose is an aldopentose
*glucose is aldohexose
*fructose is a ketohexose

2. slightly soluble in alcohol and insoluble in nonpolar solvents like ethers and hydrocarbons.
3. Monosaccharides undergo mutarotation, the interconversion of α- and β-anomers in aqueous
solution

How many chiral carbons are there in the aldoses and hexoses in the attached pictures above.

DISACCHARIDES are glycosides formed from two molecules of monosaccharide by dehydration between
OH substituents. The monosaccharides may be the same or different.

Important disaccharides:
1.Maltose(also called malt sugar, corn sugar) is produced from partial hydrolysis of starch. It is found in
processed corn syrup and germinating grains. Hydrolysis of maltose yields two glucose units
This Photo by Unknown Author is licensed under CC BY-SA-NC

Draw the structure of β-D-maltose.

2. lactose(also called milk sugar) is a disaccharide found in mammalian milk, consist of glucose and
galactose where C-1 of galactose and C-4 of glucose are involve in the β-1,4 linkage.

This Photo by Unknown Author is licensed under CC BY-SA

3.sucrose(table sugar) is a disaccharide of glucose and fructose, where C-1 of α-D-glucose and C-2 of β-
D-fructose are involve in the 1,2-linkage.
This Photo by Unknown Author is licensed under CC BY-SA

Note: pyranose( 6 sided ring) and furanose(5 sided ring)

4.cellobiose is a disaccharide obtained by partial hydrolysis of cellulose. There is β-1,4 -linkage between
glucose.

This Photo by Unknown Author is licensed under CC BY

Comparison of the structures of the disaccharides show that sucrose linkage occur between the
hemiacetal OH of glucose and the hemiketal OH of fructose. Sucrose, therefore, has no hemiacetal or
hemiketal group. Maltose, cellobiose and lactose , on the other hand have hemiacetal groups, hence
they undergo mutarotation.

Polysaccharides
1. Cellulose is linear polymer of glucose in β-1,4 linkage. Cellulose constitutes 40-50% of wood and
90% of cotton.
2. Amylose is linear polymer with glucose in α-1,4 linkage
3. Amylopectin is a branched polymer of glucose in α-1,4 linkage and branching in in α-1,6 linkage
4. Glycogen is more highly branched compared to amylopectin.

This Photo by Unknown Author is licensed under CC BY-NC

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