Carbohydrates ‘Carbon-Hydrates’ (CHOs)

• group of molecules that contain carbon, hydrogen, and

oxygen in a 1:2:1 ratio; general formula (CH2O)n

• eg. glucose C6H12O6 (CH2O)6

• but sucrose is C12H22O11 ???

types:
• mono saccharides - simple sugars sucrose
• monomer = monosaccharide
• dimer = disaccharide
• trimer = trisaccharide …. oligosaccharide

• oligo saccharides - (oligo = few) small chains

• attached to proteins - glycoproteins
• attached to lipids  glycolipids
• poly saccharides  very long sugar chains 2
 Function of Carbohydrates
structural
• eg ribose / deoxyribose part of nucleic acid monomer
• cellulose, chitin, peptidoglycan

cell-cell recognition
• all animal cells are covered with a ‘sugar coating’ (glycocalyx)
consisting of membrane proteins covalently bonded to
oligosaccharides
outside

inside of cell
energy storage
• α-1,4 –linkages of starch and glycogen are readily hydrolyzed to
release stored energy
3
 Recall

Condensation
Reaction – making Hydrolysis –
the chain breaking the
chain

4
Typical Structural Features of Sugar Monomers
• carbonyl group (either ketone or aldehyde)
• lots of -OH groups

• vary in length of carbon skeleton (C3, C5, C6, …) triose,

• What would you call a four carbon sugar?? pentose,
hexose
• isomeric forms (glucose, fructose, galactose)
• identical chemical groups arranged differently

aldose ketose

both of these are ‘trioses’ (3 carbons)

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• monosaccharides often form rings in solution
 Isomers – same atoms, different arrangements
fructose glucose galactose
H H H
H C OH C O C O
C O structural H C OH stereo- H COH
isomer isomer
HO C H HO C H HO C H
H C OH H C OH HO C H
H C OH H C OH H C OH
H C OH H C OH H C OH
H H H

• structural isomer – identical groups but bonded to different carbons

• stereo (optical) isomer – identical groups bonded to same carbons
but in different orientations, requires chiral centre (central carbon with
4 chemcially different attachments)

• 16different aldo-hexose structures possible, and 8 keto-hexoses all

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with formula C6H12O6
 Does arrangement of hydroxyl groups make
a big difference in biological function?
Yes as fuel:
• glucose is main source of chemical energy for cellular respiration
• galactose must first be converted to glucose before it can be used as fuel

as sweeteners:
glucose + fructose = sucrose (table sugar)
glucose + galactose = lactose (milk sugar)

fructose glucose galactose

H H H
H C OH C O C O
C O structural H C OH stereo- H C
OH
isomer isomer
HO C H HO C H HO C H
H C OH H C OH HO C H
H C OH H C OH H C OH
H C OH H C OH H C OH
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H H H
 Formation of Ring Structures: eg Glucose
α-glucose

glucose, linear

oxygen from C5 bonds to C1

β-glucose
• C1 is anomeric carbon
• carbonyl group converted to hydroxyl
• hydroxyl can be below plane of molecule (same as hydroxyl on
C2) or above (opposite to –OH on C2), form two different 8
ANOMERS
 CH2OH

HO
OH OH α

OH
 CH2OH

O OH
β
C

HO
OH

OH
Formation of disaccharides by condensation reactions.
• monomers are linked when C1 of one monosaccharide binds to a
C on another – often C4
• geometry of bond different depending on
• whether OH group of C1 is in α or β position
• which C of other sugar is involved in linkage
C1, α

C4
α-glucose α-glucose maltose, α-1,4 glycosidic bond
C1, β

C4
β-galactose β-glucose lactose, β-1,4 glycosidic bond
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(glucose has flipped over)
 Polymerization to build Polysaccharides
starch glycogen

amylose

+
amylopectin

• both are storage forms for energy

• starch – plants; glycogen – animals
• both consist of α-glucose monomers linked by α-1,4 bonds
• both coil into a helix (due to geometry of linkages)

• starch is mixture of unbranched amylose (α-1,4 ) and

branched amylopectin (α-1,4 and α-1,6 )
• glycogen is highly branched (α-1,4 and α-1,6 ) 12
Structural Polysaccharide in Plants: Cellulose
• polymer of β-glucose, joined by β-1,4 linkages
• each glucose is flipped relative to adjacent ones
• allows for H-bonding between adjacent strands
• extremely stable
• most abundant organic molecule on earth

parallel strands joined by H-bonds

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 What is the biological significance of how
monosaccharides are linked?
• α-1-4 linkages (and α-1-6) of starch and glycogen readily
hydrolyzed

• β-1-4 linkages in structural polysaccharides very

resistant to enzymatic degradation

for example:
• enzymes that digest cellulose (cellulases) produced
only by certain classes of bacteria, fungi and protozoa

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 How do glycosidic bonds differ from peptide
and phosphodiester bonds?
in common:
• condensation reactions, covalent bonds

different:
• peptide and phosphodiester bonds always occur at the
same position within their monomers
• each sugar monomer has several hydroxyl groups,
and geometry of glycosidic bonds is highly variable

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 Lipids
• group of carbon-containing compounds that are largely
non-polar / hydrophobic
• significant proportion of a given lipid molecule is
hydrocarbon
• the only macromolecule that is not a polymer

major groups of lipids in cells:

• fats / oils, triglycerides
energy
• energy storage
• weight for weight contain 6x as much energy as glucose

• sterols
• cholesterol – membrane component Signaling/membranes
• steroids - hormones

• phospholipids membranes
• major component of biological membranes 19
Fats (Triacylglycerols, Triglycerides)

fatty acid (carboxylic acid with long hydrocarbon ‘tail’)

Panel 2-4
20
ester linkages

21
Fatty Acids: Saturated versus Unsaturated

Panel 2-4 22
 Unsaturated Fats:
cis versus trans

All three are C18 fatty acids

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 Phospholipids – basic plan

Polar
Head
Group

phospholipid diacyl glycerol

Panel 2-4

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Panel 2-4 Other Lipids

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 Lipid Structures

bilayers
Panel 2-4

Fig. 2-21 26
 Lipid Bilayer:
Universal Structure for all Biological Membranes
• two closely apposed sheets of
lipids, studded with proteins
• lipids serve as permeability
barrier
• proteins perform most of the
functions
• carbohydrates (sugars)
attached to protein and lipids
in a non-random manner
Fig 11-4

composition varies with:

• type of organism (prokaryote vs animal vs plant vs …)
• type of cell within organism (muscle, liver, sperm, egg, …)
• type of membrane within cell (plasma membrane, Golgi, ER)
• inner versus outer layer
• different patches or ‘domains’ within a particular membrane
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 Model Phospholipid: Phosphatidyl choline

Fig 11-6
phospholipids are amphipathic
 their most important feature with respect to biology28
 All membrane lipids are amphipathic.

Fig 11-11

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Fig 11-7
 Lipid bilayers form spontaneously.
• hydrophobic molecules would exclude
water, clustering together to minimize
energy cost of organizing water
molecules
• form large droplets or surface film

• amphipathic molecules are subject to

conflicting forces
• solved by formation of bilayer
• energetically most favourable 
stable, spontaneous

• lipid bilayers are …

• closed – no free edges
• self-sealing
• important feature for cell fusion,
budding, locomotion
Fig 11-12

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