Dr. Nasim1 Carbohydrates AP Biochem. Dr. Nasim2 Monosaccharides (Single sugar residue) 3 C: Trioses 4 C: Tetroses 5 C: Pentoses 6 C: Hexoses

Dr. NasimDr. Nasim 11

CarbohydratesCarbohydrates

Dr. NasimDr. NasimAP BiochemAP Biochem


MonosaccharidesMonosaccharides (Single sugar residue) (Single sugar residue) 3 C: 3 C: TriosesTrioses4 C: 4 C: TetrosesTetroses5 C: 5 C: PentosesPentoses6 C: 6 C: HexosesHexoses6 C: 6 C: HexosesHexoses


MonosaccharidesMonosaccharides (Single sugar residue) (Single sugar residue) (Aldose)(Aldose) (ketose) (ketose) Glyceraldehydes Glyceraldehydes DHA - DHA - 3 C 3 C Erythrose Erythrose Erthrulose - 4 CErthrulose - 4 C Ribose Ribose Ribulose - 5 CRibulose - 5 C XyloseXylose XyluloseXylulose 5 C 5 C GlucoseGlucose Fructose - 6 C Fructose - 6 C


MonosaccharidesMonosaccharides

Aldoses: Aldoses: Those Monosaccharides which Those Monosaccharides which contain Aldehyde group. (H-C=O)contain Aldehyde group. (H-C=O)

Ketose: Ketose: Those Monosaccharides which Those Monosaccharides which contain keto group. (C=O)contain keto group. (C=O)


Anomeric carbon: Anomeric carbon: Aldoses & Ketose Aldoses & Ketose may cyclize to produce an Anomeric may cyclize to produce an Anomeric carbon.carbon.

Anomeric carbon contain reactive Anomeric carbon contain reactive hydroxyl group.hydroxyl group.




If the Reactive hydroxyl group is free (Not If the Reactive hydroxyl group is free (Not attached to any other molecule) then the attached to any other molecule) then the sugar is known as sugar is known as reducing sugarsreducing sugars..

Reactive hydroxyl group may attached Reactive hydroxyl group may attached covalently to another molecule.covalently to another molecule.

N-Glycosidic linkage: N-Glycosidic linkage: If the Reactive If the Reactive hydroxyl group is attached to–NH2 hydroxyl group is attached to–NH2 group.group.



O-Glycosidic linkage: If the Reactive O-Glycosidic linkage: If the Reactive hydroxyl group is attached to–OH group.hydroxyl group is attached to–OH group.

ISOMERS: If 2 compound have the same ISOMERS: If 2 compound have the same chemical formula. E.g. Fructose & chemical formula. E.g. Fructose & glucose are isomers of each other. glucose are isomers of each other.



Epimers: If 2 compound have the same Epimers: If 2 compound have the same chemical formula but the differ in chemical formula but the differ in configuration around 1 specific C atom.configuration around 1 specific C atom.

Galactose & glucose are C 4 Epimers of Galactose & glucose are C 4 Epimers of each other.each other.

Mannose & glucose are C 2 Epimers of Mannose & glucose are C 2 Epimers of each other. each other.



Enantiomers: If 2 compound are mirror image Enantiomers: If 2 compound are mirror image of each others. of each others.

E.g. L - Glucose & D – Glucose.E.g. L - Glucose & D – Glucose. The configuration of asymmetric carbon atom The configuration of asymmetric carbon atom

farthest from the aldehyde or keto group (with farthest from the aldehyde or keto group (with reference to D or L glyceraldehydes) reference to D or L glyceraldehydes) determines whether a monosaccharide is of D determines whether a monosaccharide is of D or L series.or L series.

In D form OH gp is on right side & vice versa in In D form OH gp is on right side & vice versa in left side.left side.


DisaccharidesDisaccharides(2 Monosaccharides (2 Monosaccharides

units)units)Sucrose = Glucose + FructoseSucrose = Glucose + Fructose((αα1-2 linkage)1-2 linkage)Lactose = Glucose + GalactoseLactose = Glucose + Galactose((ββ1-4 linkage)1-4 linkage)Maltose = Glucose + GlucoseMaltose = Glucose + Glucose((αα1-4 linkage)1-4 linkage)Iso-malotose = Iso-malotose = Glucose + Glucose (Glucose + Glucose (αα1-6)1-6)


OligosaccharidesOligosaccharides(3-10 Monosaccharides)(3-10 Monosaccharides) E.g. Maltotriose: Compose of 3 Glucose E.g. Maltotriose: Compose of 3 Glucose

residues. residues.


PolysaccharidesPolysaccharides(>10 Monosaccharides (>10 Monosaccharides

units)units)Homo PolysaccharidesHomo Polysaccharides

(contain same type of monosaccharides)(contain same type of monosaccharides)Glycogen which is also known as animal Glycogen which is also known as animal

starch.starch.Dextrin Dextrin DextranDextranCelluloseCellulose


PolysaccharidesPolysaccharides

Hetero PolysaccharidesHetero Polysaccharides(contain same type of monosaccharides (contain same type of monosaccharides

or different monosaccharides along with or different monosaccharides along with prosthetic groups)prosthetic groups)

Muco PolysaccharidesMuco PolysaccharidesMucilagesMucilagesHemicellulose Hemicellulose



Hetero PolysaccharidesHetero Polysaccharides Muco PolysaccharidesMuco PolysaccharidesHyaluronic acidHyaluronic acidHeparin Heparin Chondroitin sulphateChondroitin sulphateBlood group Polysaccharides.Blood group Polysaccharides.Serum mucoidsSerum mucoids



Hetero PolysaccharidesHetero Polysaccharides MucilagesMucilagesAgarAgarVegetableVegetablePectin Pectin



Glyceraldehydes: Glyceraldehydes: Reference sugarReference sugarAll sugars are derived from itAll sugars are derived from itD & L forms are refer to itD & L forms are refer to itDHADHAProduced from glucose in glycolysis & Produced from glucose in glycolysis &

also from glycerol which is produced in also from glycerol which is produced in break down of fatsbreak down of fats



Erythrose & ErthruloseErythrose & ErthruloseProduced from glucose in HMP shuntProduced from glucose in HMP shuntCan be converted to glucoseCan be converted to glucoseRiboseRiboseProduced from glucose in HMP shuntProduced from glucose in HMP shuntRibose component of RNARibose component of RNADeoxy-Ribose component of RNADeoxy-Ribose component of RNA



Ribulose, Xylose & XyluloseRibulose, Xylose & XyluloseProduced from glucose in HMP shuntProduced from glucose in HMP shunt



GlucoseGlucoseGrape sugarGrape sugarDextroseDextroseDextro-rotationDextro-rotationMost common source sucrose which is Most common source sucrose which is

table sugartable sugarMain source of energy for body & Main source of energy for body &

specially brain. specially brain.



Glucose (Cont.)Glucose (Cont.)FBS 60 – 100 mg/dlFBS 60 – 100 mg/dlRBS 100 – 160 mg/dlRBS 100 – 160 mg/dlOn reduction glucose forms alcohol e.g. On reduction glucose forms alcohol e.g.

SorbitolSorbitolOn oxidation sugar acidsOn oxidation sugar acidsGluconic acid If oxidation of C1 of Gluconic acid If oxidation of C1 of

glucoseglucose



Glucose (Cont.)Glucose (Cont.)Glucuronic acid If oxidation of C6 of Glucuronic acid If oxidation of C6 of

glucoseglucoseGlucaric acid If oxidation of C1& C6 of Glucaric acid If oxidation of C1& C6 of

glucoseglucoseGlucuronic acid is used for detoxification Glucuronic acid is used for detoxification

of various toxic substancesof various toxic substances



GalactoseGalactoseMain source Lactose which is milk sugarMain source Lactose which is milk sugarC 4 epimer of glucoseC 4 epimer of glucoseMannoseMannoseCan be converted to glucoseCan be converted to glucoseOn reduction forms Mannitol On reduction forms Mannitol



FructoseFructose Levulose.Levulose. Levo-rotation.Levo-rotation. Sweetest among all sugars.Sweetest among all sugars. Most common source Sucrose (table sugar).Most common source Sucrose (table sugar). Pure honey = Fructose only.Pure honey = Fructose only. Fructose Fructose Glucose. Glucose. Entry into cells is independent of Insulin.Entry into cells is independent of Insulin. Source of energy for sperms. Source of energy for sperms.


DisaccharidesDisaccharides

Maltose = Glucose + Glucose (Maltose = Glucose + Glucose (αα1-41-4))Fruit sugarFruit sugarReducing sugarReducing sugarProduced from starch by hydrolysis due Produced from starch by hydrolysis due

to salivary & pancreatic amylase. to salivary & pancreatic amylase. Hydrolyzed by MaltaseHydrolyzed by Maltase



Lactose = Glucose+ Galactose (Lactose = Glucose+ Galactose (ββ1-4) 1-4) Milk sugarMilk sugarReducing sugarReducing sugarHydrolyzed by LactaseHydrolyzed by Lactase



Sucrose = Glucose + Fructose (Sucrose = Glucose + Fructose (αα1-21-2))Cane sugarCane sugarTable sugarTable sugarNon-reducing sugarNon-reducing sugar Invert sugarInvert sugarHydrolyzed by Sucrase (Invertase) Hydrolyzed by Sucrase (Invertase)



Homo PolysaccharidesHomo PolysaccharidesGlycogenGlycogenStore from of GlucoseStore from of GlucosePresent mostly in Liver & Muscles.Present mostly in Liver & Muscles.Animal starchAnimal starchBranched structure (Tree like)Branched structure (Tree like)Less then 12 glucose residuesLess then 12 glucose residues



Homo PolysaccharidesHomo PolysaccharidesGlycogen (Cont.1)Glycogen (Cont.1)Within a chain (Within a chain (αα1-4) broken by 1-4) broken by

Phosphorylase enzyme.Phosphorylase enzyme.At branch point (At branch point (αα1-6) broken by de-1-6) broken by de-

branching enzyme.branching enzyme.Blood glucose levels are usually Blood glucose levels are usually

maintained by Liver glycogen stores.maintained by Liver glycogen stores.



Homo PolysaccharidesHomo PolysaccharidesStarchStarchMost of dietary carbohydrates are in this Most of dietary carbohydrates are in this

form.form.2 types2 typesAmylose (Straight chain)Amylose (Straight chain)Amylopectin (Branched structure) more Amylopectin (Branched structure) more

then 12 residues in each chain.then 12 residues in each chain.



Homo PolysaccharidesHomo PolysaccharidesStarch (Cont.)Starch (Cont.)Hydrolyzed by salivary & Pancreatic Hydrolyzed by salivary & Pancreatic

amylase into Maltose, Maltotriose & amylase into Maltose, Maltotriose & dextrins. dextrins.



Homo PolysaccharidesHomo PolysaccharidesDextrinsDextrins Intermediate product of hydrolysis of Intermediate product of hydrolysis of

starch.starch.E.g. Amylodextrins, Erythrodextrins & E.g. Amylodextrins, Erythrodextrins &

Achrodextrins. Achrodextrins.



Homo PolysaccharidesHomo PolysaccharidesDextransDextransHighly viscous.Highly viscous.Plasma expander.Plasma expander.CelluloseCelluloseCan’t be digested.Can’t be digested. Increase bulk of stool.Increase bulk of stool.




Hetero PolysaccharidesHetero PolysaccharidesMuco PolysaccharidesMuco PolysaccharidesAnimal originAnimal originMucoprotein & Mucin (when in Mucoprotein & Mucin (when in

combination with proteins)combination with proteins)



Hetero PolysaccharidesHetero PolysaccharidesMuco PolysaccharidesMuco PolysaccharidesSubtypes Subtypes Hyaluronic AcidHyaluronic Acid Chondroitin sulphateChondroitin sulphate HeparinHeparin Blood group PolysaccharidesBlood group Polysaccharides Serum mucoidsSerum mucoids


PolysaccharidesPolysaccharidesMuco PolysaccharidesMuco Polysaccharides

Hyaluronic Acid (Cementing agent)Hyaluronic Acid (Cementing agent) Present in skin, synovial fluid, seminal Present in skin, synovial fluid, seminal

fluid & vitreous humor.fluid & vitreous humor. FunctionsFunctions Prevents penetration of bacteria into skinPrevents penetration of bacteria into skin Lubrication of the jointsLubrication of the joints Helps in fertilization Helps in fertilization Hydrolyzed by Hyaluronidase Hydrolyzed by Hyaluronidase



Chondroitin sulphateChondroitin sulphate



HeparinHeparin



Blood group PolysaccharidesBlood group Polysaccharides



Serum mucoidsSerum mucoids



MucilagesMucilagesPlant originPlant originAgarAgarNon-digestibleNon-digestibleLaxative Laxative Culture mediaCulture media



Vegetable gumsVegetable gumsUsed in pharmaceutical industryUsed in pharmaceutical industryPectinsPectinsFor making jelliesFor making jelliesHemicelluloseHemicellulose


Asymmetric carbon atomAsymmetric carbon atom

Asymmetric carbon atom: The carbon atom to Asymmetric carbon atom: The carbon atom to which 4 different chemical groups are attached which 4 different chemical groups are attached & it can rotate plain polarized light to the right & it can rotate plain polarized light to the right or to the left.or to the left.

E.g. Open chain formula of Glucose contains 4 E.g. Open chain formula of Glucose contains 4 Asymmetric carbon atoms. (C2, 3, 4 & 5).Asymmetric carbon atoms. (C2, 3, 4 & 5).

E.g. Close chain formula of Glucose contains 5 E.g. Close chain formula of Glucose contains 5 Asymmetric carbon atoms. (C1, 2, 3, 4 & 5).Asymmetric carbon atoms. (C1, 2, 3, 4 & 5).


Optical IsomersOptical Isomers

Those sugars which rotates plain Those sugars which rotates plain polarized light to right are (d) sugars & polarized light to right are (d) sugars & which to left are (l) sugars. which to left are (l) sugars.

Racemic Mixture:Racemic Mixture: Such a solution which contains equal Such a solution which contains equal

amount of Levo & dextro-rotatory then amount of Levo & dextro-rotatory then rotation of light will be equal but in rotation of light will be equal but in opposite direction.opposite direction.


Ring StructureRing Structure

Hemiacetal ring: if the ring is formed by Hemiacetal ring: if the ring is formed by aldehyde gp.aldehyde gp.

Hemiketal ring: if the ring is formed by Hemiketal ring: if the ring is formed by keto gp.keto gp.

Pyranose Ring: 6 sided ring. O2 bridge Pyranose Ring: 6 sided ring. O2 bridge b/w C1 & C5.b/w C1 & C5.

Furanose Ring: 5 sided ring. O2 bridge Furanose Ring: 5 sided ring. O2 bridge b/w C1 & C4.b/w C1 & C4.


Anomeric carbonAnomeric carbon

C of Aldehyde or keto gp forming C of Aldehyde or keto gp forming hemiacetal or Hemiketal rings.hemiacetal or Hemiketal rings.

C1 in Aldo-sugars. E.g. glucoseC1 in Aldo-sugars. E.g. glucose C2 in keto sugars. E.g. fructose C2 in keto sugars. E.g. fructose


Mutarotation Mutarotation

The direction of plain polarized light in a The direction of plain polarized light in a freshly prepared glucose solution goes freshly prepared glucose solution goes on changing for some time before settling on changing for some time before settling to specific direction.to specific direction.

Reason: unfolding of ring structure to Reason: unfolding of ring structure to striaght chain in order to maintain striaght chain in order to maintain equilibrium b/w equilibrium b/w αα & & ββ forms of sugars. forms of sugars.


Phenomenon of Inversion Phenomenon of Inversion

Documents

Dr. Nasim1 Carbohydrates AP Biochem. Dr. Nasim2 Monosaccharides (Single sugar residue) 3 C: Trioses 4 C: Tetroses 5 C: Pentoses 6 C: Hexoses