Structure n Fx of Carb n Lipid
Carbohydrates – Carbon,hydrogen,oxygen (CHO)
• (CH2O)n - “hydrates of carbon”
- contain aldehyde or ketone functional groups
with one or more hydroxyl groups.
Membrane Carbohydrates : minor component
- occur as oligosaccharide that is covalently
bound to lipid and proteins to form glycolipids &
glycoprotein.
- Never as free form. Mostly – glucose, galactose,
mannose, N-acetyl glucosamine,fucose, sialic
acid
- Glycolyx – loose Carbbohydrate layer on outer
surface of cell
- For cell-cell recognition :
- Ability of a cell to distinguish neighboring cells
- Important organ n tissue devlepmonet
- Basis rejection of foreign cell by immune sys
Classification of CHO
 Monosaccharides – simple sugars
-glucose, fructose, galactose, ribose,
deoxyribose, glyceraldehydes, erythrose
 Disaccharides (2 Mono)
-Sucrose ,Lactose, Maltose
 3. Polysaccharides (> 10 Mono)
-Glycogen , Starch, Cellulose
 4.Oligosaccharides (3-10 Mono)
-Galactooligosaccharides , Human milk
oligosaccharides, Glycoproteins, Glycolipids
MONOSACCHARIDES
• Simplest , cannot be hydrolysed to smaller CHO
• Suffix ‘ose’ in sugar names
• Consists a linear chain of > 3 carbon atoms.
• One of C forms a carbonyl gp thru a
= bond with O.
• Other C of unmodified mono
contain OH gps
• OH gps are often locations of enzyme reactions
• General formula CnH2nOn
• Glucose, fructose, galactose, glyceryldehyde
MONOSACCHARIDES CLASSIFICATION BASED :
• Carbonyl gp: aldehyde
(aldose), ketone (ketose)
–functional gp
• Number of C atoms: 3
(trioses), 4 (tetroses), 5
(pentoses), 6 (hexoses)
• Example: glucose – aldohexose
(Based on functional gp and no of C atoms)
MONOSACCHARIDES STRUCTURE
1)D & L sugars
• Based on chiral nature
• Chiral : A carbon contains 4 different
chemical gps forms asymmetric centre
• Chirality (geometric property): 4 gps attached
to the asymmetric c atom can be arranged to
form 2 different isomers (molecules) that are
mirror image to each other (cannot be not
superimposed)
 Pairs of structures that are
mirror images of each other
(Enantiomers)
• Two molecules of the pair are designated as a D-
and L- sugar
• Designated of D & L is based on the orientation of
the asymmetrical carbon furthest from carbonyl
gp – position of hydroxyl gp
D sugar- have OH gp on the right
L sugar have OH gp on the left
• Majority of sugars in human are D-sugars
2) STEREOISOMERS & EPIMERS
• STEREOISOMERS : same chemical formula but
different orientiation / arrangement ie OH gp
• EPIMERS : Stereoisomers that differ in the
position of the OH gp at only one of their
asymmetric carbons.
• ie: D-glucose and D galactose are epimers of
each other at C4. D-mannose and D glucose are
epimers at C2.
3) RING STRUCTURES
i)Monosaccharides with 5 or more carbon exists
predominantly in ring form
• Less than 1 percent exists in the open-chain
(acyclic) form.
• Anomeric carbon at carbon 1 for aldose / carbon
2 for ketose.
ii)Monosaccharides exists in solution mainly in
ring structures.
• Carbonyl gp reacted with a OH gp in the same
molecule to form a five or six membered ring
• O that was on the OH gp is now part of the ring,
original carbonyl C which now contain OH gp has
become the anomeric C atom.
4) SUBSTITUTED SUGARS
• Sugars usually contain phosphate , amino, sulfate
or N-acetyl groups.
• Most of free mono within cells are
phosphorylated at terminal C (to prevent
transport out of the cells). ie glucose-6-
phosphate
• Amino sugars ie galactosamine & glucosamine
contain an amino gp instead of OH gp on one of
the C atom (usually carbon 2)
OXIDIZED & REDUCED SUGARS
• Sugars can be oxidized at aldehyde carbon to
form acid
– No longer sugar
– Ending on its name
changed from “ose” to
“onic acid” or “onate”
• Aldehyde reduced, all carbon contain hydroxyl
group reduced – polypol (e.g.: sorbitol)
• Sugar - if 1 hydroxyl group reduced and carbon
contains 1 H– deoxysugar (eg: deoxyribose)
DISACCHARIDES
• 2 mono joined by a covalent bond (O-glycosidic
bond) formed by dehydration process.
• Rxn results in the loss of hydrogen from one
monosaccharides and a OH gp from the other
• Example i) Sucrose (D-glucose and D fructose)
ii) Lactose – sugar in milk (D-galactose and D
glucose) ,iii) Maltose (?)
Lactose :
Galactose & glucose linked Through
β(1-> 4) bond formed bwn The β-OH
group of the anomeric carbon of
galactose And OH gp on C4 glucose.
POLYSACCHARIDES
• Contain 10-100 of monosaccharides
• Joined by glycosidic forms to form linear chains
or branched structures.
• The anomeric carbon of 1 unit joined to C4 or
C6 of the next unit
• Storage and structural roles
• Amylopectin (starch) - Structural
• Glycogen (storage form of glucose in human)
Polysaccharides classified into:
• Homopolysaccharides – composed of single
type of mono unit
• Heterepolysaccharides – contain 2 or more
types of mono
• Oligopolysaccharides- poly with small number
of mono
- starch :
• plant polysaccharides
• a mixture of amylose (linear chain of
glucose with a-1,4-glycosidic bonds)
• and amylopectin (a-1,4 and branch made up
of a-1,6 linkages)
- glycogen : (for storage)
• more branch points
• animal polysaccharides
• Similar in structure to amylopectin
- Cellulose – plant cell walls
 linear polymer of repeating cellobioses
(glucose-glucose in b-1,4 linkages)
OLIGOSACCHARIDES
• Contain from 3-10 monosaccharides linked
together
• Often attached to N- or O- glycosidic bonds to
protein to form glycoproteins.
• Glycolipids are lipid molecules bound to
oligosaccharides, generally present in the lipid
bilayer. Additionally, they can serve as
receptors for cellular recognition and cell
signaling. Eg: ABO blood Are marked by
oligosaccharides.
N-linked
• sugar molecule attached to non
carbohydrate at –NH2 group
O-linked
• sugar molecule attached to non
carbohydrate at –OH group
• All sugar – sugar glycosidic bonds are O-type
linkages.
 Saturated and unsaturated fatty acids with 18
carbon atoms.
 Polyunsaturated (with 2 or more double bonds;
PUFA) w
Oleic - 18:1Δ9 Δ9 – fatty acid
 Numbering system: Δ from the COOH end,
w – from the CH3 end (3,6,9)
LIPID
• Insoluble in water
• Soluble in nonpolar solvents, eg.:
methanol, chloroform
• Major biological functions:
• Component of biological membranes
(together with proteins)
• Lipids with hydrocarbon chain (fatty
acids) serve as energy stores
• Intra- and intercellular signaling events
(e.g IP3 and DAG as second messenger;
prostaglandins)
Lipids can be classified into:
• Simple lipids
a) Fats (oils) : Esters of fatty acids with
glycerol (TRIACYLGLYCEROLS)
b) Waxes :Esters of fatty acids with
higher molecular weight
monohydric Alcohols
• Complex lipids
Esters of fatty acids containing groups in
addition to an alcohol and a fatty acid
a) PHOSPHOLIPIDS
b) Glycolipids
• Precursor and derived lipids
a)FATTY ACIDS
b)STEROIDS
 Sterols - cholesterol
FATTY ACID
 Carboxylic acids with long-chain
hydrocarbon side groups
 Usually occur mainly as esters in natural
fats and oils
 Divided into saturated &Unsaturated
General rules for the structures of naturally
fatty acids:
1. Most fatty acids have an even number of
carbon atoms
2. The hydrocarbon chain is almost always
unbranched
3. Most carbon-carbon bonds are single;
however, acids may contain two or more
carbon-carbon double bonds
4. Double bonds are most often cis
5. For monounsaturated fatty acids, the
double bond is usually between carbons 9
and 10
6. The double bonds for polyunsaturated
fatty acids are not conjugated but are
separated by a methylene unit
a) Triacylglycerols (TAG)
• 3 fatty acids are esterified to a glycerol
• ester of fatty acids and glycerol
• Water insoluble
• Function as an energy
store (adipose tissues)
• Not a component of
cell membrane
• Non polar, very compact
• :. storage form of lipid.
• R1 = palmitate, R2= Oleate and R3=stearate
• TAG is major fat in the human diet
• Synthesis occur in liver, adipose tissue, small intestine
• TAG also found in skeletal muscle, cardiac muscle &
lactating mammary gland– for local consumption.
• In the body, TAG is the most abundant type of lipid
Function of TAG :
• Source of energy/ major storage form of fat
• Act as thermal insulation
• Main storage of fat in adipose tissue
• Different function with cholesterol
PHOSPHOLIPID
 Fatty acids
 Glycerol / sphingosine /
complex alcohol
 A phosphate
 An alcohol (X)
• Amphipathic in nature.
• hydrophilic head (a P group plus bases)
• a long hydrophorbic tail (hydrocarbons).
• Thus, are components of lipid bilayers.
• Other function of phospholipids:
• as a reservoir for intracellular 2ndmessengers
(phosphatidyl inositosol)
• Component of blood lipoprotein
• as components of lung surfactants.
• Source of polyunsaturated fatty acids (arachidonic
acids ie prostaglandin, thromboxanes)
• as components of bile with detergent properties
aiding solubilisation of cholesterol.
Important type of phospholipid:
i) Glycerophospholipids
• Consists of glycerol backbone
• Major component of blood lipoprotein, bile, lung
surfactant, source of PUFA ie arachidonic acids)
ii) Sphingophospholipids
• Consists of sphingosine backbone
• Forming myelin sheath surrounding nerves in CNS &
in signal transduction
EICOSANOIDS derived from the phospholipids
• Origin from polyunsaturatd fatty acids with 20C
• Derived from arachidonic acid
• Can be sub-divided into different groups:
Prostaglandins, prostacyclins , thromboxanes
leukotrienes
• Present in cells at very low concentrations and are
involved in the production of pain and fever,
regulation of blood pressure, blood coagulation, and
reproduction.
• Tend to act locally,close to the cells that produce them
CHOLESTEROL
• Steroid
• Very hydrophobic compound
• Major sterol in animal tissues
• Mostly Eukaryotic origin
• The characteristic of steroid
alcohol of animal tissues;
performs a number of
essential function in the body
• Transported in blood via lipoproteins
• Human: Obtain from food & synthesized de novo (major)
• Liver – central role in the regulation of the body’s cholesterol
homeostasis.
CHOLESTERYL ESTER (CE)
• Most plasma cholesterol is in esterified form of
cholesterol with fatty acids at C-3 (CE)
• > hydrophobic than FC
• Packaged in lipoprotein particle
• CE not found in cell membranes
CHOLESTROL FUNCTION
• Structural component of all cell membranes (Stabilizing)
• Precursors of bile acids, steroid hormones & Vitamin D
• Component of plasma lipoproteins sent to peripheral tissues
CHOLESTROL SYNTHESIS
• Liver – central role in the regulation of the body’s cholesterol
homeostasis.
• Source of hepatic cholesterol:
- Dietary cholesterol (from chylomicron remnants) - exogenous
- Cholesterol from extrahepatic tissue (VLDL & HDL)
-De novo synthesis (endogenous)