Carbohydrates

Hassan Ebrahem
Dániel Borbély
 What are carbohydrates?
• Polyhydroxy compounds of aldehydes (aldose) or ketones (ketose)
• Cx(H2O)y
• Can be monomer (simple sugar), dimer (disaccharide) or polymer
(polysaccharide)
• Contain 3-7 carbon atoms (triose-heptose), mostly 5-6 in nature
• Important monomers: Glucose, Fructose, Ribose

Glucose Fructose Ribose

Monomers reacts with each other to from di- or polysaccharides with a
glycoside bond

Lactose Sucrose

Cellulose Starch
 Stereochemistry of carbohydrates

• Chiral carbon atoms  enantiomers (mirror images) and diastereomers

• A hexose can have 24 (16) stereoisomers
• Diastereomers have different names
• Enantiomers (mirror images) are called L or D,
• Most carbohydrates are D
• L, if the –OH on before the last carbon points to the right, D, if it points to the
left
 Fischer projection
• Find the carbon backbone, make it „turn” into a chain, and make the –H
and the –OH groups turn at the top

• The first C atom (on the top) should be the aldehyde group or closest to
the keto group, and the last C atom (on the bottom) should be the –CH2O
 Haworth projection
Cyclic form of
monosaccharides
• In crystal form, they are in
100% cyclic form, open
chain form only exist in
solution form (~0.02%)

• The carbonyl carbon atom

(6) and the last chiral
carbon can form together
a hemiacetal
 The anomeric carbon atom
• In solution the –OH group can be in α or β position on the anomeric C
• α, when the –OH group is not on the same side as the –CH2OH group
• β, when the –OH group is on the same side as the –CH2OH group

• In solution the β anomer is present in 64% and the α anomer is 36%

 Importance of Monosaccharides

• Most monosaccharide and disaccharides are sweet-tasting

• It is the final product of complex carbohydrate digestion and provides acetyl
groups for entry into the citric acid cycle as acetyl-CoA to be converted to
energy.
• in blood cell surfaces structures
• In both of DNA and RNA
• The extra amounts of carbohydrates are converted to glycogen and stored in
liver or muscles or converted to fats
 Important monosaccharides
• Produced by
photosynthesis
Part of :
• Blood sugar o Ribonucleic acid
o Coenzyme A
D-glucose o Second messenger cyclic
• Found in plant gums,
AMP
pectins and milk (lactose)
• Component of brain and D-ribose
nervous system tissue
• Part of the DNA
D-galactose
• Found in fruits and honey
(fruit sugar)
• Sweeter than sucrose
2-Deoxyribose
D-fructose
Why glucose is the most important form of
carbohydrates among other forms ?
 Carbohydrates in blood type

• Four blood types: A, B, AB and 0

• Different blood types have different oligosaccharides (sugar chains) on the
red blood cell
• AB blood has both chain on the
same cell
 Reactions of monosaccharides

• Monosaccharides that can be oxidised called reducing sugars

• The aldehyde group is oxidised to a carboxylic group
• Monosaccharides can be reduced by H2 in the present of Pt catalyst
• The aldehyde group is reduced, the result is a sugar alcohol
• On the anomeric carbon atom, bonds can be formed, turning the
hemiacetals to acetals
• Esters can be formed on the –OH groups
 Reducing sugars

• Oxidation of the aldehyde (-CHO) group to carboxylic (-COOH) group

• Only in the open chain form  only hemiacetals

• Keto group can be oxidised, because

it can undergo a rearrangement
 Benedict’s test

• Monosaccharides can be oxidised  test for the presence of

monosaccharides or other reducing sugars
• Cu2+ ions get reduced by the monosaccharides in basic solution to Cu+ ions
 Sugar alcohols

• Reduction of the aldehyde (-CHO) group to –CH2OH group

• With H2 and Pt catalyst
• Sugar-ose  Sugar-itol
• D-sorbitol, D-xylitol, D-mannitol are used as sweeteners, in larger amount
they can cause diarrhea
 Glycosides

• Reaction of –OH group on the anomeric carbon with an alcohol gives acetals
called glycosides
• Di- and polysaccharides are connected to each other with glycosidic bonds

• During digestion this glycosidic bonds get hydrolised

 Phosphate esters

• -PO32- group can form esters with the –OH groups of the carbohydrates
• During metabolism these esters are the reactants ot the products
• Glucose phosphate is formed first by the transfer of a -PO32- group of the ATP
 Important disaccharides
• Malt sugar
• In fermenting grains
• Hydrolised by maltase

Maltose Sucrose
• Table sugar
• Milk sugar • Produced from sugar
• In human milk (7%) beets and sugar cane
• Hydrolised by lactase • Hydrolised by sucrase
• Lack of lactase 
Lactose Lactose intolerance
 Important glucose based polysaccharides
Cellulose Amylose

• Most abundant polysaccharide • Found in plants, mostly in the

• Found in plants
• Humans do not digest, grazing
animals do
• Used to build houses, make
cardboards…
seeds (beans, potatoes, wheat,
rice…)
• Soluble in hot water
• Hydrolised by α-amylase in
animals
 Important glucose based polysaccharides
Amylopectin Glycogen

• Found in plants, mostly in the • Found in animals (animal starch)

seeds (beans, potatoes, wheat…)
• Insoluble in hot water
• Energy for the seeds
• α-1,4 bonds are hydrolised by α-
amylase in animals, α-1,4 bonds
are not
• Glucose storage in liver and
muscle cells
• Supplies glucose for blood sugar
• Larger than amylopectin (Up to
one million glucose in a
molecule)
 Bacterial cell walls

• Functions of the cell wall in bacterias: protection, giving shape

• The majority of bacterial cell walls are made of polymer of peptidoglycan,
sequence with modified sugars N-acetylglucosamin (NAG) or N-
acetylmuraminic acid (NAMA)

NAG NAMA
 Modified glucose
• Chaines of modified monosaccharides bind to proteins or lipids to form
glycoproteins or glycolipids to enchance their funtions
• Three common polimers:
• Hyaluronate: β-D-glucoronate and N-acetyl-β-D-glucosamine as a
repeating pair (found in joints and in the vitreous humor of the eye)
• Chondroitin: polymer of β-D-glucoronate and N-acetyl-β-D-glucosamine-6-
sulfate (found in tendons and cartilage)
• Heparin: polymer of β-D-glucoronate-2-sulfate and acetylsulfate-β-D-
glucosamine-6-sulfate (used as anticouagulant)
 Modified glucose

β-D-glucoronate β-D-glucosamin N-acetyl-β-D-glucosamin

Thank You for the attention
https://www.nutrientsreview.com/carbs/disaccharides-sucrose.html
https://www.bostoncheesecellar.com/post/2018/04/08/lactose-intolerance-explained
https://theory.labster.com/starch/
https://byjus.com/question-answer/glucose-and-mannose-are-anomers-diastereomersstereoisomersepimers/
The Sugar Lobby Bribed Scientists to Make It Seem Healthy -- Science of Us (thecut.com)
https://theory.labster.com/benedicts_procedure/
https://microbiologyinfo.com/benedicts-test-principle-composition-preparation-procedure-and-result-interpretation/
N-Acetylmuramic acid = 98 10597-89-4 (sigmaaldrich.com)
https://www.specsavers.co.za/post/health-and-wellbeign/the-dirt-on-sugar