Biochem Prelim

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LESSON 1: INTRODUCTION TO BIOCHEMISTRY

CELL STRUCTURE AND FUNCTIONS

Frederick Gowland Hopkins

“A cell has history; its stucture is inherited, it grows, divides, and, as in the
embryo of higher animals, the products of division differentiate on complex
lines. Living cells, moreover transmit all that is involved in their complex
heredity.”

Basic Structure of a Cell

 1665 – Robert Hooke used a microscope to examine a thin slice cork


(dead plant cells)
o what he saw looked like small boxes
o responsible for naming cells
o cells – looked like small rooms that monks
lived in

 1673 – Anton van Leeuwenhoek


o Dutch microscope maker
o First to view organism (living things)
o Used simple, handheld microscope to view pond
water & scrapings from his teeth

Beginning of the Cell Theory

 1838 – Matthias Schleiden


o Concluded that all plants were made of cells
o Cofounder of cell theory
 1839 – Theodore Schwann
o All animals were made of cells
o Cofounded cell theory
 1855 – Rudolph Virchow
o Cells dividing under the microscope
o All cells come from other pre-existing cells by cell division

Cell Theory

 All living things are made of cells


 Cells are the basic unit of structure and function in an organism
 Organism – basic unit of life
 Cell division - cells come from the reproduction of existing cells

Discoveries since the Cell Theory

Prokaryotes – The First Cells

 Lack a nucleus or membrane-bound


organelles
 Bacteria
 Simplest type of cell
 Single, circular chromosome
 Nucleoid region (center) contains DNA
 Surrounded by cell membrane & cell wall
(peptidoglycan)
 Ribosomes (no membrane) in their cytoplasm to make proteins
Eukaryotes

 Have nucleus
 Protists, fungi, plants, and animals
 Complex type of cells

3 basic cell structures:

 Nucleus
 Cell membrane
 Cytoplasm w/organelles

Two types of Eukaryotic


Cells
Other Eukaryotic Cells – fungal cell, protozoa

The Organelles

 Microscopic
 Various functions
 Found in cytoplasm
 May/may not be membrane bound

Cell Membrane or Plasma


Membrane

 Double layer of
phospholipids and
proteins
 Surrounds outside of
ALL cells
 Controls what enters/leaves the cell
 Living layer

Phospholipids

 Head –
o Glycerol, Phosphate
o Hydrophilic (attract water)
 Tails = fatty acids; hydrophobic
 Bilayer – tails point INWARD toward each other
 Move laterally to allow small molecules to enter (O2, CO2 & H2O)
The Cell Membrane is Fluid

Molecules in cell membranes are constantly


moving and changing.

Physiological temp = cell membranes are


fluid
Cooler temp = gel-like

Membrane is a fluid mosaic in which


transmembrane proteins can move laterally in
the lipid bilayer.

Cell Membrane Proteins

 Help move large molecules


 Aid in cell recognition
 Peripheral proteins – attached on the
surface (inner/outer)
 Integral proteins – embedded through the
membrane

Cell Membrane (Plants)

 Against the cell wall


 Pushes out against the cell wall to:
Maintain cell shape
 Outside the cell membrane
 Nonliving
 Supports & protects cell
 Plants, fungi & bacteria

Cell Wall of Plants


Cell

wall of fungal and bacterial cell

Cytoplasm of a Cell

 Jelly-like
substance
 A medium for chemical reactions to take place
 Contains organelle (carry out specific jobs)
 Fluid and ogranelles that are outside the nucles (all the contents for prokaryotes)
 Removes waste material
 Helps in cell respiration
 Converts glucose = energy

Cytosol – liquid portion of cytoplasm

 Where many chemical reactions occur

The Nucleus

 Controls normal activities of the cell


 DNA in chromosomes
 Bounded by a nuclear envelope (membrane) w/pores
 Largest organelle

Chromosomes – fixed; carry genes


genes control cell characteristics.

Nuclear Envelope

 Double membrane
surrounding nucleus
 Nuclear membrane
 Contains nuclear pores (for
materials to enter/leave nucleus)

Inside The Nucleus

 DNA – hereditary material of the cell; spread


out
o appears as chromatin in non-dividing
cells
o Condensed & wrapped around proteins
o Form as chromosomes in dividing cells
o Genes that make up the DNA molecule code for different proteins

Nucleolus

 Inside nucleus
 Disappears when cell divides
 Makes ribosomes that make proteins

The Cytoskeleton

 Dynamic structure
 Microfilaments and microtubules can
depolymerise and repolymerise very easily
The Cytoskeleton

Functions:

 Scaffold creating and


supporting cell shape
 Molecular roads for
intracellular
transport of
materials
 Framework for whole cell movement & cell division
 Structure and support
 Intracellular support
 Contractility and Motility
 Spatial organization

Centrioles

 Animal cells
 Paired structures near nucleus
 Made of bundle of microtubules
 Appear during cell division forming mitotic
spindle
 Pull chromosome pairs apart to opposite ends
of the cell

Mitochondrion (Mitochondria)

 Powerhouse of the cell


 Generate cellular energy (ATP) adenosine
triphosphate
 More active cells, more mitochondria
 Plants & animal cells
 Site of cellular respiration (burning glucose)
 surrounded by double membrane
 own DNA
 Cristae – folded inner membrane; increases surface
area for more chemical reactions
 Matrix – interior
Endoplasmic Reticulum (ER)

 Network of hollow membrane tubules


 Connects to nuclear envelope & cell
membrane
 Synthesis of products & transport

Rough ER

 Ribosomes on its surface


 Makes membrane proteins; proteins for export out of cell
 Ribosomes – make proteins
 Protein threaded into the interior of the Rough ER to be modified and transported

Smooth ER

 Lacks ribosomes
 Lipid metabolism, carbohydrate metabolism, detoxification
 Abundant in mammalian liver and gonad cells
 Synthesizes phospholipids (secreted by testes, ovaries, skin oil glands)

Ribosomes

 Proteins and rRNA


 Protein factories
 Join amino acids to make proteins through
protein synthesis

Structure of Ribosomes

 Not bounded by membrane


 Prokaryotic ribosomes are smaller and less dense than Eukaryotic
 Two subunits –
o Each consists of ribosomal RNA
 mRNA binding site
o 3 tRNA binding sites
 A: aminoacyl – tRNA
 P: Peptidyl – tRNA
 E: exit
Golgi Apparatus/Golgi Bodies

 flattened sacs
 shipping side (cis face) & a receiving
side (trans face)
 Receive proteins made by ER
 Transport vesicles with modified
proteins pinch off the ends
 Modify, sort, package molecules from ER for storage or transport out of cell

Lysosome

 Digestive enzymes
 Break down
 Destroyer; Apoptosis – cell death
 Release enzymes to break down &
recycle cell parts

Lysosome Digestion

 Phagocytosis – cells take in food


 Lysosomes digest the food, gets rid of the wastes

Endomembrane System

(1) Rough ER - makes/packages proteins


transport vesicles
(2) Golgi apparatus – modifies and repackages materials
secretory vesicles fuse w/membrane → incoming vesicle
(3) Lysosome: digests food particles
transport vesicles
(4) Smooth ER – makes lipids/stores ions

Cilia and Flagella

Flagella – to the right, wave-line


movement; ex: sperm;
Cilia – to the left, wavy (balloon in a newly
opened store)

 Moves cells, fluids/small particles


across cell surface

Diff:

Cilia are slender protuberances that project from much larger cell body.
Flagella is a lash-like appendage that protrudes from the cell body.
Vacuoles

 Fluid-filled sacks for storage


 Small/absent in animal cells
 Plant cells have a large central vacuole
 In plants
o Stores cell sap
o Storage of sugars, proteins, minerals, lipids, wastes, salts, water and
enzymes

Chloroplasts (Plants only)

 double membrane
 DNA
 Green pigment chlorophyll

Function

 Responsible for photosynthesis


 Found only in organisms containing chlorophyll (producers)
 Use energy from sunlight to make own food (glucose)
o Energy from sun stored in chemical bonds of sugars

Cell type

 Eukaryotic, plant

Stroma – appropriate enzymes and a suitable pH for calvin cycle

Thylakoid – ETC & ATP synthase for photophosphorylation

Granum – flat membrane stacks increase SA/Vol ratio and small internal volumes
quickly accumulate ions

Lamella – connects & separates thylakoid stacks (grana)

Double membrane – endosymbiosis (independent origin0


Prokaryotic Cell Parts

Prokaryotes

 microscopic single-celled organism


 neither a distinct nucleus with a membrane nor other specialized organelles.
 Bacteria and Archaea.
 started just over 4 billion years ago, feeding off the early carbon dioxide, carbon
monoxide, steam, nitrogen, hydrogen, and ammonia atmosphere.

Bacteria shapes

 Spheres (Cocci)
 Rods (Bacilli
 Spirals

Classification

 Old 5 Kingdom system


o Monera, protists, plants, fungi, animals
 New 3 Domain system
o Prokaryote: Bacteria
o Prokaryote: Archaebacteria
o Eukaryotes
 Protists
 Plants
 Fungi
 Animals
Lesson 2: Properties of Water and the Basic Concepts of Biochemistry of Cells

 Cells are composed of water, inorganic ions, and carbon-containing (organic)


molecules.
 Water is the most abundant molecule in cells (70% or more of total cell mass)
 Hydrogen, oxygen, nitrogen, carbon, phosphorus, and sulfur normally make
up more than 99% of the mass of living cells
o When combined, produces organic molecules
o initially utilized in the synthesis of a small number of building blocks
 used in the construction of a vast array of vital macromolecules.

Glycolysis

 Phase 1 – Sugar activation


o Glucose to fructose-1,6-bisphosphate
o 2 ATP to 2 ADP (adenotriphosphate; adenosine diphosphate)
 Phase 2 – Sugar cleavage
o Exchange between dihydroxyacetone phosphate and glyceraldehyde
phosphate
 Phase 3 – Sugar oxidation and formation of ATP
o dihydroxyacetone phosphate (4 ADP – 4 ATP)
o glyceraldehyde phosphate (2 NAD++2 NADH+H+)
 produces 2 pyruvic acid
 dihydroxyacetone phosphate goes to Krebs cycle (aerobic
pathway)
 glyceraldehyde phosphate
o 2 NADH+H+ -- 2 NAD+
 2 Lactic acid
Organic molecules – contain both C and H; contain other elements as well

 Hydrocarbon – C & H only


 simple to extremely
complex

Importance of Organic Compound

 build all units of all living matter: carbohydrates, proteins, fats


 all foods are organic compounds
 Dead organisms - converted to fossil fuels like peat, coal and petroleum
 Petroleum - source of fuel and starting material for plastics, fabrics and
industrial chemicals

Photosynthesis - reaction that makes carbon a part of our food.

Water

 Inorganic, transparent, tasteless, odorless and near colorless chemical


substance
 Earth’s hydrosphere; fluids of all known living things
 Vital for all forms of life
 60-90% of an organism; universal solvent
 No calories or organic nutrients
Importance of water

 Assimilation of food and digestive leading processes


 Carries nutrients and oxygen
 Removes waste products through blood and lymphatic system
 Lubrication
 Eliminates impurities in the skin
 Replace liquid that we lose through
breathing, perspiration and digestion
 Perspiration – regulate body temperature
 Protective cushion for the brain and spinal
cord

Water

 Simple molecular structure; one oxygen


and two hydrogen
 Each hydrogen atom is covalently bonded to the oxygen (shared pair of
electrons
 Ability of ions and other molecules to dissolve in water due to polarity

Properties of water

 Cohesion – hydrogen bonds hold water molecules


 High specific heat – hydrogen absorb heat; minimizing temp changes
 High heat of vaporization – hydrogen bonds are broken
 Lower density of ice – molecules in an ice crystal are spaced relatively because
of hydrogen bonding
 Solubility – polar water molecules are attracted to ions/polar compounds
making them soluble

Carbon-based Molecules

 Organic chemistry – study of carbon compounds

Carbon is a versatile atom;

 Can share electrons w/other


atoms to form four covalent
bonds

Hydrocarbons

 Simplest; contain only carbon


and hydrogen atoms
Carbon use it bonds to:

 Attach to other carbons


 Form an endless diveristy of carbon skeletons
o Skeletons – can be arranged in rings
 Vary in length
 Unbranched/branched
 Double bonds that vary in location

Large Hydrocarbons

 Main molecules in the gasoline we burn in our cars


 Fat hydrocarbons – provide energy

Shape of Organic Molecules

 Has unique three-dimensional shape


o Shape determines its function in an organism

Functional group – specific group of atoms/bonds within a compound responsible for


the characteristic chemical reactions of that compound

 Behave similar, undergo similar reactions regardless of the compound

Types of functional groups:

Groups of atoms that give properties to the compounds to which they attach
 Examples: (O-H); ketone, alcohol, aldehyde, organic acid
Polymers

 Macromolecules
 Built from monomers
 Examples: carbohydrates, nucleic acids, lipids, proteins

Condensation – linking monomers /


Dehydration synthesis – removing water
molecule

o Joins two sugar monomers to


make double sugar

Breaking down polymers

 Hydrolysis – breakdown macromolecules by adding a molecule of water

Macromolecules in Organism

Four categories: Carbohydrates, Lipids, Proteins, Nucleic Acids

 Carbohydrates
o Small sugar molecules in softdrinks
o Long starch molecules in pasta/potatoes

Monosaccharides (C6H12O6)

o Simple sugars
o Glucose, fructose & galactose (milk sugar)
 Glucose found in sports drinks
 Fructose found in fruits
 Honey contains both
 -ose = sugar
o Same chemical, different structural formulas
o Cellular fuel

Isomers
o Glucose and fructose
 Structures are diff but chemical formulas are same

Rings

 Aqueous solutions
 Monosaccharides form ring structures

Disaccharides (examples are digestible)

 Double sugar
 Joining two monosaccharides
 Condensation – removing water molecule
 Glycosidic bond
 Ex: sucrose (table sugar), lactose (milk sugar), maltose (grain sugar)
o sucrose (table sugar) – glucose + fructose
o maltose (grain sugar) – 2 glucose molecules
o lactose (milk sugar) – galactose + glucose

Polysaccharides

 complex carbohydrates
 many sugar monomers linked together
 polymers of monosaccharide chain
 examples: starch, glycogen, cellulose
o starch – plant stores this for energy;
 potatoes and grains
o glycogen – excess sugar in animals;
 similar structure to starch because they are both glucose monomers
o cellulose – most abundant organic compound;
 cable-like fibrils in tough walls that encloses plants
 major component of wood
 dietary fiber

Dietary Cellulose

 animals cannot derive nutrition from fiber


o have bacteria in digestive tract that breakdown cellulose

Sugars in Water

 simple sugars and double sugars are soluble


o -OH groups make them hydrophilic

Lipids

 Hydrophobic
 Do not mix with water
 Fats, waxes, steroids, oils

Function of Lipids

 Store energy
 Insulate body
 Cushion/protect organs

Types of Fatty Acids

 Saturated fatty acids – max hydrogens bonded to the carbons (all single bonds
between carbons)
o Single bonds
 Unsaturated fatty acids – less than max hydrogens bonded to the carbons
o Unsaturated

Triglyceride

 Monomer of lipids
 Glycerol & 3 fatty acid chains
o Glycerol forms backbone of the fat
o Ex: organic alcohol (-OL)

Fats in Organisms

 Solids (butter, margarine & shortening)


 Animal fats have hig proportion of saturated fatty acids
 Plant oils – low saturated fatty acids
o Exist as liquids (oil)

Fats

 Triglyceride (glycerol and 3 fatty acids chains)


 Condensation links fatty acids to glycerol

Lipid and Cell Membranes

 Cell membranes = phospholipids


o Phospholipids – head (polar); phosphate
 2 tails – hydrophobic

Steroids

 Carbon skeleton bent to form 4 fused rings


 Cholesterol; body produces steroids
 Estrogen and testosterone

Synthetic Anabolic Steroids

 Variants of testosterone
 Build up muscles quickly
 Pose serious health risks

Proteins

 Polymers made of
amino acids
(monomers)
 20 different amino acids
linked in diff orders
 Used to build cells
 Act as hormones & enzymes
 Do much of work

20 Acid Monomers

 Essential amino acids – cannot be made by the body; must come from food
o Histidine
o Isoleucine
o Leucine
o Lysine
o Methionine
o Phenylalanine
o Threonine
o Tryptophan
o Valine
 Non-essential amino acids – bodies produce;
o Alanine
o Arginine
o Asparagine
o Aspartic acid
o Cysteine
o Glutamic acid
o Glutamine
o Glycine
o Proline
o Serine
o Tyrosine

Structure of Amino Acids

 Central carbon w/4 things bonded to it


 Peptide bonds
o Amino group – NH2
o Carboxyl group – COOH
o Hydrogen
o Side group – R
 Amino and carboxyl

Proteins as Enzymes

 Biological catalysts
 Thousands

Enzymes – control rate of


chemical reactions by
weakening bonds, lowering
amount of activation energy

Enzymes

 Globular proteins
 Folded conformation ---- active site
 Specific for only one type of substrate
 Reusable
 Active site changes shape
 Induced fit

Primary
protein
structure

polypeptide
 Specific sequence of amino acids in a protein

Secondary protein structure

 Protein chains coil/fold


 Polypeptides join together

Tertiary protein structure

 R groups interact

In the watery environment of a cell, proteins become globular in their


quaternary structure
Denaturating proteins

 Changes in temp & pH unfold (denature) a protein = not working

Changing Amino Acid Sequence

 Sickle-cell disease – substitution of one amino acid for another in hemoglobin

Other Important
Proteins

 Insulin – controls
blood sugar level
o Causes liver to
uptake & store
excess sugar (Glycogen)
 Cell membrane contains proteins
 Receptor proteins – recognize cells

Nucleic Acid

 Store hereditary information


 Contain information for making all proteins
 DNA & RNA
 Polymers of nucleotides
o Nucleic acid monomer

Bases

 each nucleotide has


o adenine (A)
o guanine (G)
o thymine (T)
o cytosine (C)

Nucleotide Monomers

 joined by sugars &


phosphates on the
sides
 long chains called DNA

DNA – deoxyribonucleic acid

 Two strands join to form a double helix


RNA – ribonucleic acid

 Ribose sugar has an extra -OH (hydroxyl)


 Uracil base

ATP – Cellular
Energy

 used by cells for


energy
 adenosine
triphosphate
 nucleotide
with 3 phosphate
groups
 energy is
stored in the chemical bonds of ATP
 last 2 phosphate bonds – high energy
 breaking last phosphate bond releases energy for cellular work;
o produces ADP & free phosphate
 ADP can rejoin to the free phosphate to make more ATP
Lesson 3: A review on Organic Chemistry

 Carbohydrates – one od the major compound in biochemistry


 Biochemical compounds – make up cells / other structures of organisms and
carry out life processes.
 Carbon -
basis of
all

biochemical compounds
 Polymers – most biochemicals are large molecules
o Repeated units of monomers
 Most organic compounds are covalent compounds
 Not part of organic chemistry – carbonate ions & bicarbonate ions
 Hydrocarbons - simplest organic compounds
o (Alkanes) Saturated hydrocarbons - have only single bonds / appear
as a chain (which can be a straight chain or can have branches)
 Meth - means one carbon atom;
o methane is an alkane with one carbon atom
 Eth- means two carbon atoms;
o ethane is an alkane with two carbon atoms.
 Prop- means three carbon atoms;
o propane is an alkane with three carbon atoms.

Basic Concepts of Organic Chemistry

 Organic Chemistry - study of carbon & carbon compounds


o Organic compounds - primary constituents of all living organisms.
o Carbon is able to form 4 covalent bonds (4 valence electrons) with other
carbon or other elements.

II. Characteristics of Organic Compounds

 They are nonpolar compounds – they do


not dissolve in polar solvents like Water.
 They have low melting points – due to
weak intermolecular forces.
 They react slower than ionic compounds – due to strong covalent bonds
between atoms.

Structural Formulas -

 Carbon is found in the center


 The short line – represents a pair of electrons.
 Carbon has 4 bonding sites.

1. Methane: CH4

2. Chloroform: CHCl3

3. Ethane: C2H6

Type of Bonds

 Single Bond – single covalent bond in which


they share 1 pair of electrons. (2 e-)
 Double Bond – carbon atoms may share 2 pairs of
electrons to form a double bond.
 Triple Bond – carbon atoms may share 3 pairs of
electrons to form a triple bond.

Types of Compounds

 Saturated Compound – carbon atoms are


bonded by SINGLE bonds.
o Ex: 1. Methane: CH4
 Unsaturated Compound – carbon atoms
have double or triple bonds.
o Ex: ethene: C2H4

Homologous Series of Hydrocarbons


 As size of molecule increases the
boiling and freezing points increase.
 Hydrocarbons - organic
compounds consist of only
Carbon and Hydrogen atoms.

Alkanes – simplest hydrocarbon

- Contain only hydrogen and carbon


- Only have single bonds
o Single, Saturated
hydrocarbons
o Formula: CnH2n+2

Naming Organic Compounds

 Organic compounds are named


according to the IUPAC
(international union of pure &
applied chemistry) system of
nomenclature

Alkanes – end in ane Alkenes – end in ene Alkynes – end in yne

Alkenes – unsaturated hydrocarbons; one double


bond (C=C)

 Formula: CnH2n
 Also called ethylene series (IUPAC name is ethene)

ISOMERS: Molecules have


the same molecular
formula, but have different
structural formulas.

Alkynes – unsaturated hydrocarbons / 1 triple bond

 Acetylene series
 Formula – CnH2n-2

Alkyl groups – one less hydrogen than corresponding alkane

 CH3 is methyl – one less H than methane


(CH4)
 C2H5 is ethyl – less H than ethane
 C3H7 is propyl -

Benzene – cyclic unsaturated hydrocarbons

 Formula – CnH2n-6
 C6H6 – simplest

IUPAC Naming Branched Hydrocarbon Chains

 Hydrocarbons can not / can be straight

1. Find the longest continuous chain of carbons


a. -Ane - Bonds in the chain of carbons are single bonds
b. Heptane - 7 continuous carbons
2. Number the carbons in the main sequence starting with the end that will give the
attached groups the smallest number
a. Chain is numbered from right to left because there is a subconstituent
closest to the right

3. Add numbers to the names of the groups


to identify positions on the chain
a. These numbers become prefixes to the parent chain
b. Example – 2-methyl, 3-methyl, 4-
ethyl
4. Use prefixes to indicate the appearance of a
group more than once in the structure.
a. Di – twice, tri – three times, tetra – four times
penta – five times
b. 2 methyl (CH3) groups - dimethyl

5. List the alykl groups in order


a. Ex: dimethyl
6. Use punctuation
a. Commas to separate numbers
b. Hyphens to separate numbers
w/words

Name of the compound: 2,3-dimethyl-


4-ethyl heptane

ANOTHER EXAMPLE

STEP 1 – 6 carbons =
hex; all single bonds = -
ane; HEXANE

STEP 2 – numbering
from right to left

STEP 3 – 2,4
DIMETHYL HEXANE

When naming w/a double/triple bond – start w/carbons closest to the bond

Other organic compounds

Functional groups – specific groupings of atoms that give characteristic properties to


organic compounds
 Halides – halogens
o F (fluoro-)
o Cl (chloro-)
o Br (bromo-)
o I (Iodo-)

Halides

 Formed when any halogen replaces an H


atom in an alkane
 Functional group – F, Cl, Br, I

 Drop the “ine” and add


“o”

Alcohols

 one or more hydrogens


placed with an -OH group
 Hydroxyl = -OH
 General formula = R-OH
o R – rest of the molecule

Monohydroxyl Alcohols – one -OH


IUPAC naming of alcohols

 Replace e with ol

Organic acids – have functional groups

 R-COOH

IUPAC naming of Organic Acids

 Replace e with -oic


 HCOOH – methanoic acid

Aldehydes – functional group -CHO

IUPAC naming of Aldehydes

 Replace e with al
 First member – methanal
o Aka formaldehyde
 Used to preserve biological samples

Ketones – functional group R-CO-R

 E with -one
 Simplest – propanone
o IUPAC name is propanone but
common name – acetone

Ethers – two primary alcohols are treated


w/dehydrating agent

 Water is removed and 2 alcohols are


joined together by an oxygen
bridge
 Diethyl ether – general anesthetic
 Dimethyl ether – CH3 -O- CH3

Esters – R-CO-O-R

 Between an organic acid and alcohol


 Have strong fragrant aromas: banana, wintergreen & oranges

IUPAC naming of Esters

Amines - -N-

 Ammonia = NH3

 IUPAC naming
o Replace final -e with -amine

Amides –

 End of carbon chain


 Final -e, add “amide”
Lesson 4: Carbohydrates and Its Classes

 Carbohydrates - sugars, starches and fibers found in fruits, grains, vegetables


and milk products.
o one of the basic food groups
o important to a healthy diet.
carbohydrate (/kɑːrboʊˈhaɪdreɪt/) - biomolecule consisting of carbon (C),
hydrogen (H) and oxygen (O) atoms,
o hydrogen–oxygen atom ratio of 2:1 (as in water)
o empirical formula - Cm(H2O)n (where m may be different from n).
o polyhydroxy aldehydes or ketones - broken down to form such
compounds.
o Examples of carbohydrates - starch, fiber, sugars, and structural
materials such as cellulose.
o Term carbohydrate - origin in a misinterpretation of the molecular
formulas of many of these substances.
 For example, because its formula is C6H12O6, glucose was once
thought to be a “carbon hydrate” with the structure C6·6H2O.

Photosynthesis - Green plants are capable of synthesizing glucose (C6H12O6) from


carbon dioxide (CO2)
and water (H2O) using
solar energy

6CO2 + 6H20 +
(energy) → C6H12O6 +
6O2 Carbon dioxide +
water + energy from light produces glucose and oxygen; (The 686 kcal come from
solar energy.)

Plants

 use the glucose for energy or convert it to larger carbohydrates,


o starch or cellulose.
 Starch provides energy for later use; nourishment for a plant’s
seeds
 Cellulose - structural material of plants.

Carbohydrates - needed for synthesis of nucleic acids and many proteins and
lipids.

Animals cannot synthesize carbohydrates from carbon dioxide and water

 dependent on the plant kingdom to provide these vital compounds.


 carbohydrates not only for food (about 60%–65% by mass of the average diet)
but also for clothing (cotton, linen, rayon), shelter (wood), fuel (wood), and paper
(wood).
 Monosaccharide – simplest carbo
o Cannot be hydrolyzed to produce smaller carbo
 Prefixes are used to indicate the number of such units in the chains.
 Disaccharide - two monosaccharide units
 Trisaccharide - three units
 Polysaccharides - chains with many monosaccharide units
o higher saccharides that can be hydrolyzed back to their constituent
monosaccharides.

Compounds that cannot


be hydrolyzed
will not react with water to form two or more smaller compounds.

Writing Structural Formulas and Naming Carbohydrates

Carbohydrates - group of naturally occurring carbonyl compounds (aldehydes or


ketones) that also contain several hydroxyl groups.

 derivatives which produce such compounds on hydrolysis.


 most abundant organic molecules
 “saccharides”
 “sugars” - soluble in water and sweet in taste

Structure of Carbohydrates

 Carbohydrates consist of carbon, hydrogen, and oxygen.


 general empirical structure - (CH2O)n.
 organic compounds organized in the form of aldehydes or ketones with
multiple hydroxyl groups coming off the carbon chain.
 Monosaccharides (simple sugars) - building blocks of all carbohydrates
o polyhydroxy aldehyde (aldose) or a polyhydroxy ketone (ketose).

The carbohydrates can be structurally represented in any of the three forms:


 Open chain structure.
 Hemi-acetal structure.
 Haworth structure.

Open chain structure – long straight-chain form of carbohydrates


Hemi-acetal structure –1st carbon of the glucose condenses with the -OH
group of the 5th carbon to form a ring structure.
Haworth structure –the presence of the pyranose ring structure.

Properties of Carbohydrates

Physical Properties of Carbohydrates

 Stereoisomerism –shaving the same structural formula but they differ in


spatial configuration.
o Example: Glucose has two isomers with respect to the penultimate carbon
atom. They are D-glucose and L-glucose.
 Optical Activity –rotation of plane-polarized light forming (+) glucose and (-)
glucose.
 Diastereo isomers – configurational changes with regard to C2, C3, or C4 in
glucose.
o Example: Mannose, galactose.
 Annomerism – spatial configuration with respect to the first carbon atom in
aldoses and second carbon atom in ketoses.

Chemical Properties of Carbohydrates


Osazone formation
 Osazone - carbohydrate derivatives when sugars are reacted with an
excess of phenylhydrazine.
o eg. Glucosazone
 Benedict’s test - Reducing sugars when heated in the presence of an alkali
o Enediols - powerful reducing species
o When Benedict’s reagent solution and reducing sugars are heated
together, the solution changes its color to orange-red/ brick red.
 Oxidation - Monosaccharides are reducing sugars if their carbonyl groups
oxidize to give carboxylic acids.
o In Benedict’s test, D-glucose is oxidized to D-gluconic acid thus, glucose is
considered a reducing sugar.

 Reduction to alcohols - The C=O groups in open-chain forms of


carbohydrates can be reduced to alcohols by sodium borohydride, NaBH4, or
catalytic hydrogenation (H2, Ni, EtOH/H2O). The products are known as
o “alditols” – product of reduced sodium borohydride or catalytic
hydrogenation

Properties of Monosaccharides
 sweet taste (fructose is sweetest; 73% sweeter than sucrose).
 solids at room temperature.
 extremely soluble in water
o Despite high molecular weights, the presence of large numbers of OH
groups make the monosaccharides much more water-soluble than most
molecules of similar MW.
 Glucose can dissolve in minute amounts of water to make a syrup (1 g / 1 ml
H2O).

Classification of Carbohydrates (Types of Carbohydrates)

The simple carbohydrates include single sugars (monosaccharides) and


polymers, oligosaccharides, and polysaccharides.

 Monosaccharides
o Simplest group of carbohydrates
o simple sugars since they cannot be further hydrolyzed.
o Colorless, crystalline solid
o soluble in water and insoluble in a non-polar solvent.
o possesses a free aldehyde or ketone group.
o general formula - Cn(H2O) or CnH2nOn.
o classified according to the number of carbon atoms
 basis of the functional group present.
The monosaccharides thus with 3,4,5,6,7… carbons are called trioses, tetroses,
pentoses, hexoses, heptoses, etc., and also as aldoses or ketoses depending
upon whether they contain aldehyde or ketone group.

Examples: Glucose, Fructose, Erythrulose, Ribulose.

 Oligosaccharides
o compound sugars that yield 2 to 10 molecules of the same or different
monosaccharides on hydrolysis.
o glycosidic linkage – join monosaccharide units
o further classified as disaccharide, trisaccharide, tetrasaccharide etc.
o Disaccharide - Oligosaccharides yielding 2 molecules of
monosaccharides on hydrolysis
o Trisaccharides/tetrasaccharides – 3 or 4 monosaccharides
o general formula (disaccharides) - Cn(H2O)n-
o trisaccharides - Cn(H2O)n-2
Examples: Disaccharides - sucrose, lactose, maltose, etc.
Trisaccharides - Raffinose, Rabinose.

 Polysaccharides
o “glycans”.
o more than 10 monosaccharide units and can be hundreds of sugar units
in length.
o more than 10 molecules of monosaccharides on hydrolysis.
o differ from each other in the identity of their recurring monosaccharide
units, in the length of their chains, in the types of bond linking units
and in the degree of branching.
o primarily concerned with two important functions ie.
 Structural functions and the storage of energy.
Homopolysaccharidese - monosaccharides of the same type
 starch, glycogen, cellulose, pectin.
heteropolysaccharides - monosaccharides of different types.
 Hyaluronic acid, Chondroitin.

Functions
 Carbohydrates - widely distributed molecules in plant and animal tissues.
 In plants and arthropods, carbohydrates form the skeletal structures,
o food reserves in plants and animals.
o important energy source required for various metabolic activities,
o the energy is derived by oxidation.

Major Functions
 carbohydrates as accessible energy to fuel cellular reactions.
 most abundant dietary source of energy (4kcal/gram) for all living beings.
 Glycolysis/kreb’s cycle – breakdown of glucose to yield ATP
 energy stores, fuels, and metabolic intermediates. 
 stored as glycogen in animals and starch in plants.
 Stored carbohydrates act as an energy source
 form structural and protective components, like in the cell wall of plants and
microorganisms.
 Structural elements in the cell walls of bacteria (peptidoglycan or murein),
plants (cellulose) and animals (chitin). 
 intermediates in the biosynthesis of fats and proteins.  
 aid in the regulation of nerve tissue
 energy source for the brain. 
 associated with lipids and proteins to form surface antigens, receptor
molecules, vitamins, and antibiotics. 
 structural framework of RNA and DNA (ribonucleic acid and deoxyribonucleic
acid).
 linked carbohydrates are important in cell-cell communication and in
interactions between cells and other elements in the cellular environment.
 In animals - constituent of connective tissues.
 Carbohydrates that are rich in fiber content help to prevent constipation. 
 the modulation of the immune system.

Aldohexoses
 subclass of the hexoses
 in the linear form, have carbonyl at carbon 1, forming an aldehyde derivative
with structure [H–C(=O)–(CHOH)5–H.]
 glucose

In linear form, aldohexose has four chiral centres,


 16 possible aldohexose stereoisomers
 8 pairs of enantiomers.
 The linear forms of the eight d-aldohexoses, in the Fischer projection, are:
 Of these d-isomers, all except d-altrose occur in living organisms, three are
common
o d-glucose, d-galactose, and d-mannose.
 l-isomers - generally absent in living organisms;
o l-altrose - isolated from strains of the bacterium Butyrivibrio
fibrisolvens.
chemist Emil Fischer - devised the following mnemonic device for remembering the
order given above, which corresponds to the configurations about the chiral centers
when ordered as a 3-bit binary string:
All altruists gladly make gum in gallon tanks
allose, altrose, glucose, mannose, gulose, idose, galactose, talose.
 Fischer projections of the d-aldohexoses can be identified with the 3-digit binary
numbers from 0 to 7,
o 000, 001, 010, 011, 100, 101, 110, 111.
o The three bits, from left to right, indicate the position of the hydroxyls
on carbons 4, 3, and 2, respectively:
 to the right if the bit value is 0, and to the left if the value is 1.

The Fischer diagrams of the eight l-aldohexoses are the mirror images of the
corresponding d-isomers;

with all hydoxyls reversed, including the one on carbon 5.

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