This document is a chapter from a general chemistry textbook titled "Chemistry of the Living State" that discusses the key biomolecules (lipids, carbohydrates, proteins, nucleic acids) that make up living matter and their structures and roles in metabolism. It covers the basics of how these biomolecules are broken down and built up to fuel cellular processes and provides information on DNA replication and protein synthesis.

1. Philip Dutton
University of Windsor, Canada
N9B 3P4
Prentice-Hall © 2002
General Chemistry
Principles and Modern Applications
Petrucci • Harwood • Herring
8th
Edition
Chapter 28: Chemistry of the Living State

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Contents
28-1 Chemical Structure of Living Matter: An Overview
28-2 Lipids
28-3 Carbohydrates
28-4 Proteins
28-5 Aspects of Metabolism
28-6 Nucleic Acids
Focus On Protein Synthesis and the Genetic Code

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29-1 Chemical Structure of Living Matter:
An Overview

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Cellular Organization

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28-2 Lipids

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Table 29.1 Some Common Fatty Acids

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Saponification

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Fats and Oils
• Both are triglycerides.
– Differ in the nature of the acid components attached.
– Both are colorless, odorless and tasteless.
• Flavors and aromas come from organic impurites.
• Fats.
– Predominantly saturated fatty acids.
– Normally solid at room temperature
• Oils.
– Predominantly unsaturated fatty acids.
– Liquids at room temperature.

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Butter

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Table 28.2 Some Common Fats and Oils

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“Calorie-Free” Fats

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Phospholipids

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Phospholipids

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28-3 Carbohydrates
• Hydrates of carbon: Cx(H2O)y.
• Monosaccharides.
– The simplest carbohydrates.
• Oligosaccharides.
– Two to ten monosaccharides attached together.
• Polysaccharides.
– Starch and cellulose.

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Glyceraldehyde

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Absolute Configuration
• R and S system of nomenclature.
• Optical rotation of plane
polarized light.
– Dextrorotatory (+) or
levorotatory (-).
• Fischer Projection formulas
• Fischer D,L-convention.

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Fischer Projections of Glyceraldehyde

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Enantiomeric Relationships in the
Aldotetroses

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Diastereomeric Relationships

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Monosaccharides
• Sixteen possible aldohexoses.
– Three occur widely.
• D-glucose, D-mannose and D-galactose.
• Predominantly in the cyclic form.
• Reducing sugars.
– Reduce Cu2+
to Cu2O and form a brick red precipitate.
– Fehling’s solution (tartrate) or Benedict’s solution (citrate).

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Ring Closure in Glucose

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α- and β-D-glucose

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Some Common Disaccharides

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Two Common Polysaccharides

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Photosynthesis
• Plants convert carbon dioxide and water into
carbohydrates via photosynthesis.
– 100 sequential steps convert six moles of CO2 to one
mole of glucose.
– Carbon-14 radiolabelling helped to identify individual
steps.
• Conversion of solar energy to chemical energy.
– Light reactions.
• Synthesis of carbohydrates.
– Dark reactions.

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Biomass
• Any living matter.
• Raw material can be used as fuel directly or can be
converted into other forms of liquid or solid
materials.
– Usually by fermentation.
• Decomposition in the absence of air through the
action of a microorganism.

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28-4 Proteins

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Zwitterionic Form of an Amino Acid

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Table 28-3 Some Common Amino Acids

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Peptides

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A tripeptide
Gly-Ala-Ser
N-terminal C-terminal

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Sequencing

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Amino Acid Sequence in Beef Insulin

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Structure of Proteins: α-Helix

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Structure of Proteins: β-Sheet

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Linkages Contributing to Tertiary
Structure

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Four Levels of Protein Structure

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RuBisCo

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28-5 Aspects of Metabolism
• Metabolism.
• The life process.
– Catabolism.
• Substances are broken down.
– Anabolism.
• Substances are built up.

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Carbohydrate Metabolism

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Metabolism
• Lipid metabolism.
– Uptake of fats through walls of intestine.
– Glycerol converted to glyceraldehyde-3-phosphate.
– Fatty acids are oxidized by β–oxidation.
• Protein metabolism.
– Stomach:
• HCl and pepsin hydrolize 10% of peptide bonds.
– Intestine:
• Trypsin and chymotrypsin cleave peptide fragments
further.

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Energy Relationships in Metabolism

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Enzymes
E + S  ES → E + P

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Sucrase Mechanism
→
→

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Sucrase Mechanism
→

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Carboxypeptidase

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Active Site of Carboxypeptidase

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28-6 Nucleic Acids
• DNA
– Deoxyribonucleic acid.
• Chromasomes.
– Double stranded DNA rod-like structures.
• Genes.
– Specific locations on chromasomes that code for
specific traits.

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Nucleic Acids
• RNA
– Ribonucleic acid
• Contains ribose instead of deoxyribose.
• Generally single stranded.

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Components of DNA and RNA

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RNA Single Strand

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DNA Double Helix

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DNA Replication

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Focus On Protein Synthesis and the
Genetic Code

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Protein Synthesis

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Chapter 28 Questions
Develop problem solving skills and base your strategy not
on solutions to specific problems but on understanding.
Choose a variety of problems from the text as examples.
Practice good techniques and get coaching from people who
have been here before.