Chemistry of carbohydrates final
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CARBOHYDRATE CHEMISTRYDR ROHINI C SANE
PROFESSOR
DEPARTMENT OF BIOCHEMISTRY
DR D Y PATIL MEDICAL COLLEGE
EBENE
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CARBOHYDRATE CHEMISTRY
• Definition :Polyhydroxy aldehydes or ketones
• Empirical formula : (CH2O) n----Hydrates of carbon
• C2H4O2---ACETIC ACID---NOT CARBOHTRATE
• C3H6O3 ---LACTIC ACID ---NOT CARBOHTRATE
PHYSICAL PROPERTIES
• SWEET TASTE
• WATER SOLUBLE
• SMELL OF BURNT SUGAR ON BURNING
• CRYSTALLINE
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CARBOHYDRATE CHEMISTRYFUNCTIONS
ENERGY –4KCAL/GM
PRECURSORS OF ORGANIC COMPOUNDS—FAT ,AMINO ACIDS
STORAGE FORM OF ENERGY –GLYCOGEN
STRUCTURAL COMPONENTS OF MEMBRANE
STRUCTURAL COMPONENTS OF CELLULOSE,EXOSKELETON,CELL WALL OF MICRO-ORGANISMS
INDUSTRIAL—PAPER, TEXTILE
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CLASSIFICATION OF CARBOHYDRATES• Monosaccharides –ONE SAKCHARON---SUGAR
• BASED ON FUNCTIONAL GROUPS
• ALDOSES— CHO
• KETOSES— C=O
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DISACCHARIDES =C n(H2O)n-1• α GLUCOSE + α GLUCOSE = MALTOSE
• α GLUCOSE + β FRUCTOSE = SUCROSE
• β GLUCOSE + β GALACTOSE = LACTOSE
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α D GLUCOSYL (1 4) α D GLUCOSE
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β- D galactosyl (14) β- D glucose
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α D glucosyl (12 ) β D fructose
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C6H12O6 +C6H12O6 ---- >C12H22O11 +H20
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MALTOSE LACTOSE SUCROSE
GLUCOSE (1)+GLUCOSE 4 GALACTOSE 1+ GLUCOSE 4 GLUCOSE 1 + FRUCTOSE 2
PANCREATIC AMYLASE INTESTINAL LACTASE SUCRASE
GLYCOSIDIC BONDGLUCOSE α (1--->4)
β GAL(1---4) β GLUCOSE α GLUCOSE (1- 2)β FRUCTOSE
REDUCING SUGAR REDUCING SUGAR NON REDUCING SUGAR
SUNFLOWER SHAPED OSAZONES LADY POWDER PUFF OSAZONES NO OSAZONES
SOURCE –DIGESTION OF STARCH MILK SUGAR CANE SUGAR,BEET SUGAR
DISACCHARIDES ---CRYSTALLINE, WATER SOLUBLE ,SWEET TASTE ,FORM OSAZONES (EXCEPT SUCROSE )
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POLYSACCHRIDESHIGH MOLECULAR WEIGHTTASTE LESSCOLLOIDAL
STARCH ,CELLULOSE ,GLYCOGENHETEROGLYCANS
HEPARIN,CHONDROTIN SULPHATEHYALURONIC ACIDDERMATAN SULPHATEKERATAN SULPHATE
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AMYLOSE AMYLOPECTIN
MOLECULAR WIGHT > 400000 MOLECULAR WIGHT 1 MILLION
SOLUBLE IN HOT WATER INSOLUBLE IN HOT WATER
200- 1000 UNITS α(1 4)LINKAGE 1000 UNITS IN α(1 4)& α(1 6)LINKAGE
INNER LINEAR OUTER PORTION BRANCHED
STARCH ,CELLULOSE , GLYCOGEN ---GLYCANS----POLYMERS OF GLUCOSEINULIN ---FRUCTOSANCELLULOSE ---PAPER
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STARCH • HYDROLYSIS- WITH ACIDS –END PRODUCT –GLUCOSE
• HYDROLYSIS- WITH ENZYMES –END PRODUCT –MALTOSE(HYDROLYSIS WITH MALTASE YEILDS GLUCOSE )
• STARCH + IODINE> BLUE
• AMYLODEXTRINS >VIOLET
• ERYTHRODEXTRINS -RED
• ACRODEXTRINS > >COLORLESS
• MALTOSE –COLORLESS
• NO BRANCHING IN PROTEINS & NUCLEIC ACIDS
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STARCH CELLULOSE GLYCOGEN INULIN
ORIGIN PLANT PLANT ANIMAL PLANT
HOMOPOLYSACCHARIDE OF
GLUCOSE GLUCOSE GLUCOSE FRUCTOSE
GLYCOSIDIC BONDS α(1--->4 )&α(1--->6 ) β (1--->4 ) α(1--->4 )&α(1--->6 )INTENSE BRANCHING
FATE CAN BE DIGESTED CANNOT BE DIGESTED LIVER GLYCOGEN-GLYCOGENOLYSIS ….>>GLUCOSEMUSCLES GLYCOGEN-GLYCOGENOLYSIS ….>>GLUCOSE 6 P(GLYCOLYSIS)
CANNOT BE DIGESTED
ENZYME INVOLVED IN METABOLISM
α AMYLASE CELLULASE GLYCOGEN PHOSPORYLASE
NOT METABOLISED
END PRODUCT OF ENZYME ACTION
MALTOSE β GLUCOSE GLUCOSE/GLUCOSE 6 P
FUNCTION DIETARY SOURCEFOR ANIMALS
PLANT CELLWALL STORAGE FOERM OF CABOHYDRATES IN LIVER,MUSCLES
Used for measuring GLOMERULAR FILTRATION RATE (GFR )
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CELLULOSE• NOT DIGESTED IN HUMAN BODY
• WITHIODINE RED COLOR
• UNBRANCHED
• CONSTIUENT OF COTTON (90%),WOOD (50%),HAY (40%)
• MAJOR CONSTITUENT OF FIBRE
• SOURCES ---FRUITS ,LEAFY VEGETABLES,WHOLE WHEAT LEGUME, RICE BRAN
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ADVANTAGES OF DIETARY FIBRES(CELLULOSE ,HEMICELLULOSE ,LIGNIN,PECTINS)
IMPROVES GLUCOSE TOLERANCE(DIMINISHED RATE OF ABSORPTION OF GLUCOSE )
DECREASED ABSORPTION OF CHOLESTEROL FROM INTESTINE >>>>REDUCE PLASMA
CHOLESTEROL LEVELS
FIBRES BIND WITH BILE SALTS & REDUCE ENTERO HEATIC CIRCULATION >>>DEGRADATION
OF CHOLESTEROL TOBILE SALTS & ITS DISPOSAL FROM BODY IS INCREASED
PREVENTS CONSTIPATION (INCREASING BULK OF FAECES BY ABSORBING WATER )
ELEMINATES BACERIAL TOXINS (ADSORPTION OF TOXIC COMPOUNDS )
LOWER INCIDENCE OF GIT CANCER
SATIETY VALUE –SENSETION OF STOMATCH FULLNESS , SATIETY WITHOUT CONSUMPTION
OF EXCESS CALORIES
ADVERSE EFFECTS OF FIBRE
DIGESTION & ABSORPTION OF PROTEINS ARE ADVERSLY AFFECTED
INTESTINAL ABSORPTION OF MINERALS CALCIUM ,MAGNESIUM ,PHOSPHOROUS
DECREASED
INTESTINAL BACTERIA FERMENT FIBRES CAUSING FLATULANCE
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DEXTRINS
• BREAKDOWN PRODUCTS OF STARCH (WITH ACIDS OR ENZYMES)
• STARCH +IODINE (ADSORPTION -BLUE COLOR )
• AMYLODEXTRIN –(VIOLET COLOR)
• ERYTHRODEXTRINS (RED COLOR)
• ACHRODEXTRINS (NO COLOR )
• MALTOSE (NO COLOR )
• GLUCOSE (NO COLOR )
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DEXTRANS• HOMOPOLYSACCHARIDE
• SYNTHESIZED BY YEAST & BACTERIA
• LINEAR CHAIN α(16 )GLYCOSIDIC LINKAGE
• BRANCHING 1,2
1,3
1,4 GLYCOSIDIC LINKAGES
INTRAVENOUS ADMISTRATION AS PLASMA SUBSTITUTE DURING BLEEDING ,DIARRHOEA,SURGERY ,ACCIDENTS (DONOT GO OUT OF VASCULAR TISSUE THEREFORE TREATMENT OF HYPOVOLUMIC SHOCKS)
DENTAL PLAQUES
INDUSTRY ----SEPHADEX (CROSS LINKED DEXTRANS)
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• DEXTRINS –PARTIALLY DIGESTED PRODUCTS OF STARCH
• DEXTRAN---HYPOVOLUMIC SHOCKS
• DEXTROSE –BEDSIDE MEDICINE
• CHITIN –STRUCTURAL POLYSACCHARIDE FOUND IN EXOSKELETONS OF INVERTEBRATES
• N- acetyl D-glucosamine
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AGAR• SEA WEED
• HETEROPOLYSACCHARIDE –SULPHATED GALACTOSE/GLUCOSE/OTHER SUGARS
• DISSOLVES IN WATER (SET ON COOLING )
• BACTERIA DONOT UTILIZE AGAR –THEREFORE CULTURE MEDIUM
• USED IN IMMUNO-DIFFUSION ,IMMUNO-ELECTROPHORESIS
• TRATMENT OF CONSTIPATION (INCREASE BULK OF FAECES)
• AGAROSE –PRODUCED BY BACTERIA WHEN GROWN ON SUCROSE MEDIUM –(GALACTOSE+3,6 ANHYDROGALACTOSE )
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Heteropolysaccharides
• GLYCOSAMINOGLYCANS(GAG )/MUCOPOLYSACCHARIDES/HETEROGLYCANS
• REPEATING ALTERNATE UNITS OF SULPHATED AMINOSUGARS & URONIC ACID
• RICH IN SULPHATES ,CARBOXYL GROUPS = ACIDIC MUCOPOLYSACCHARIDES
• Mucoproteins =proteoglycans (95% carbohydrates +5% proteins )
• Occurrence ---1.extra cellular spaces in tissue
• 2 cartilage ,skin ,blood vessels ,tendon,ground tissue in connective tissue
• Presence of charged groups-attracts water ---viscous solution
•
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Heteropolysaccharides
Functions Of Hyaluronic acid
• present in synovial fluid, ground tissue in connective tissue
• Lubricant & shock absorbent
• Gel around ovum
• Enzyme hyaluronidase is present in acrosome of spem,snake venoms ,insect venoms ,bacteria
Functions Of HEPARIN
• Anticoagulant –inactivates anti-thrombin III,FACTOR IX, FACTOR X
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HETEROPOLYSACCHARIDE
OCCURRENCE FUNCTIONS CHEMICAL COMPONENTS
Hyaluronic acid synovial fluid, ground tissue in connective
tissue,SORROUNDINGOVUM ,
LUBRICANTS ,SHOCK ABSORBANT
Repeating Disaccharide units of (D -GLUCORONIC ACID ,
N ACETYL GLUCOSAMINE )
Chondroitin-6- sulphate Bone,cartilage,tendon,heart
valves ,cornea
LUBRICANTS ,SHOCK ABSORBANT
D -GLUCORONIC ACID ,N acetyl Galactosamine -4- sulphate
HEPARIN Anticoagulant –activates antithrombinIII,FACTOR IX, FACTOR X
N-sulpho D glucosamine -6 sulphate & gluconate -2 sulphate
Dermatan sulphate skin LUBRICANTS ,SHOCK ABSORBANT
L-induronic acid N acetyl galactosamine
Keratan sulphate Keratin of hair LUBRICANTS ,SHOCK ABSORBANT
D-galactosamineN ACETYL GLUCOSAMINE 6 sulphate
D GLUCORONIC ACID BY INVERSION GIVES L
INDURONIC ACID
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• Gum acacia –Gal+ Arabinose +glucoronic acid
• Pectins –galactose +uronic acid (citrous fruits ,apples )
Mucopolysaccridoses
Deposition of muco-polysaccharides in lysosomes of various tissues
Mental retardation
Skeletal deformties
Corneal opacity
Urinary excretion of particular mucopolysaccharide
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Mucopolysaccridoses
Type of mcopolysaccridosis
Enzyme defect manifestation
Hurler’s syndrome Induronidase Accumulation of Dermatan sulphate &heparin
sulphate in tissue & excretion in urine
Hunter’s syndrome Induronate sulphtase Accumulation of Dermatan sulphate &heparin
sulphate in tissue & excretion in urine
Marquio syndrome GalactosidaseGalactosamine
sulphtase
Accumulation excretion of keratan sulphate &
chondroitin sulphate in urine
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Glycoproteins• Carbohydrates ( 1-90%)+proteins = glycoproteins • 4% carbohydrate content mucoproteins• CARBOHYDRATES are mannose, galactose ,xylose,l-fucose +Nacetyl
glucosamine+ Nacetyl galactosamine• Enzymes • Hormones • Transport proteins • RBC blood group antigens (N ACETYL GALACTOSAMINE +GALACTOSE+
FUCOSE ,SIALIC ACID+GLYCOLIPID• Structural proteins• ANTI -FREEZE PROTEINS FROM ANTARTIC FISHES LOWER FREEZING OF
PLASMA AT LOW TEMP (ALA—ALA—THR ___GAL____(1-3 )Nacetylgalactosamine
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Reactions of Monosaccharides
• Tauto-merization –shifting of carbon atom from one carbon to another
• Glucose/fructose /mannose ---undergo tautomerization when placed in alkaline medium to form enendiol (intermediate of highly reducing agent )
• Benedict's test
• Sugar -alkaline medium enendiol
• CuSO4 -CUPRIC CU2+Cu+2 Cu (OH)Cu2O(YELLOW PPT)+2H2O
• BENEDICT’S test -- CuSO4& Na corbonate ,Na –citrate--+reducing monosaccharides /disaccharides
• Barfoed’s test---copper acetate /acetic acid + monosaccharides /-vedisaccharides
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Dehydration • Glucose /fructose /lactose /maltose + conc H2SO4 FURFURAL
• FURFURAL + PHENOLIC COMPOUND COLOR COMPLEX
• PHENOLIC COMPOUND---
PHENOLIC COMPOUND-
COLOR TEST APPLICATION
ALPHA NAPHTOL VIOLET MOLISCH’S GROUP TEST FOR CARBOHYDRATES
RECERCINOL CHERRY RED SELIWAOFF’S KETOSES (FRUCTOSE /SUCROSE+VE)
ALPHA NAPHTOL VIOLET RAPID FURFURAL KETOSES (FRUCTOSE /SUCROSE+VE)
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OSAZONE FORMATION• GLUCOSE /FRUCTOSE/LACTOSE /MALTOSE –REDUCING SUGAR WITH
FREE ALDEHYDE GROUP FORM OSAZONES ( YELLOW CRYSTALLINE SUBSTANCE WITH SPECIFIC SHAPE
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OSAZONE FORMATION• The reaction is stepwise;
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DERIVATIVES OF MONOSACCHARIDES
SUGAR ACIDS
• GLUCOSE (C1 )-> GLUCONIC ACID
• GLUCOSE (C6 )-> GLUCORONIC ACID
• GALACTOSE > MUCIC ACID
SUGAR ALCOHOL
GLUCOSE SORBITOL
MANNOSE MANNITOL
GALACTOSE DULCITOL
RIBOSE RIBITOL
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DERIVATIVES OF MONOSACCHARIDES
ALDITOLS
• MONOSACCHARIDES ---POLY HYDROXY ALCOHOL
• GLYCEROL (COMPONENT OF TG )
• MYO-INISITOL(SECONDARY MESSENGER )
• RIBITOL (FLAVIN )
• XYLITOL(SWEETENER)
AMINO SUGARS
• OH OF SUGAR AMINO SUGAR
• GLUCOSE GLUCOSAMINE
FORMATION OF ESTERS –GLUCOSE ESTERIFICATION GLUCOSE -6 P
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DERIVATIVES OF MONOSACCHARIDESAmino Sugar on acetylation acetylated amino sugar
• Glucosamine N-acetyl Glucosamine
• N acetyl mannose + pyruvic acid N- acetyl neuraminic acid (NANA)—COMPONENTOF GLYCOPROTEIN/GLYCOLIPID
• NANA +NANA –DERIVATIVES SIALIC ACID
DEOXY RIBOSE SUGAR
SUGAR DE-OXYSUGAR (CHOH –O =CH2 )—DEOXY RIBOSE –DNA
CH2OH CH3
RHAMNOSE /L-FUCOSE POLYSACCHARIDE
ASCORBIC ACID –VITAMIN C –DERIVED FROM GLUCOSE IN LOWER ANIMALS
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OPTICAL ACTIVITY
• COMPOUND WITH ASYMMETRICAL CARBON ATOMS –PLANE OF POLARIZED LIGHT TOWARDS LEFT (LAEVO ROTATORY )/RIGHT(DEXTRO-ROTATORY )
• CHARACTERISTIC FEATURE OF COMPOUND WITH ASYMMETRICAL CARBON ATOM
• D(+) ,D (-) ,L(+) ,L (-)
• RECEMIC MIXTURE (NO OPTICAL ROTATION )
• DETRO ROTATORY + LAEVO ROTATORY = ZERO OPTICAL ROTATION
• (-Xο
)+ (+Xο
)= 0
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EPIMERS
• Monosaccharides which differ in configuration
around one specific C-atom are called epimers of
one another
• C-2 epimers
• glucose and mannose
• C-4 epimers
• glucose and galactose
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H C O
H C OH
HO C H
H C OH
H C OH
CH2OH
D-GLUCOSE
H C O
HO C H
HO C H
H C OH
H C OH
CH2OH
D-MANNOSE
CARBON-2 EPIMERS
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CARBON-4 EPIMERS
H C O
H C OH
HO C H
H C OH
H C OH
CH2OH
D-GLUCOSE
H C O
H C OH
HO C H
HO C H
H C OH
CH2OH
D-GALACTOSE
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STEREOISOMERS OF MONASACCHARIDES • SAME STRUCTURAL FORMULA DIFFER IN THEIR SPACIAL
ARRANGEMENT/ CONFIGURATION
• Asymmetrical carbon atoms –attached to four different groups
• Number of possible isomers of given compound 2 n (n =number of asymmetric carbon atoms within molecule )
• Glucose 4 asymmetric carbon atoms –2 4 =16 isomers
• D-Glucose –OH GROUP on penultimate carbon atoms is on right side
• L- Glucose –OH GROUP on penultimate carbon atoms is on LEFT side
• Glyceraldehyde is simplest reference carbohydrate -D & L ISOMERS USED FOR COMPARISION
• Naturally occurring monosaccharide in mammalian tissue –D configuration
• Enzymes present to metabolise D isomer =dextro -rotatory
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• ANOMERIC CARBON ATOM
The carbon atom which is part of the carbonyl group
Alpha(α) and Beta(β) anomers differ from each other
only in respect to configuration around anomeric
carbon atom.
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ISOMERISM IN SUGARS
• Isomers/Stereo-isomers: Compounds having the
same chemical formulae but differing in the
arrangement of their atoms in space and having
different physical properties are called isomers.
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Mutarotation
• Alpha ,beta have diffirent optical activity
• GLUCOSE CRYSTALLIZED FROM WATER & ALCOHOLALPHA D –GLUCOSE(+112.2ο ))
• GLUCOSE CRYSTALLIZED FROM WATER ABOVE 98ο & PYRIDINEBETA D GLUCOSE (+18.8 ο )
• In aqueous solution the beta form of D glucose is more stable & predominant
• Definition –change in the specific optical rotation representing the interconversion of alpha & beta form of D glucose to specific equilibrium mixture.( 52.7% ).This conversion takes place through straight chain /linear form.
• Inter conversion is faster in alkaline form.
• equilibrium mixture-has 63% of beta form,36% of alpha form& 1% 0pen chain form.
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MUTAROTATION OF FRUCTOSE
• PYRANOSE (SIX MEMBER RING ) FUNAROSE (FIVE MEMBER RING )
• CHAIR & BOAT CONFIRMATION OF FRUCTOSE
BOAT CHAIR
(LESS STABLE ) (MORE STABLE )
AXIAL EQUATORIAL ARRANGEMENT
PARALLEL HEAVY GROUPS PERPENDICULAR HEAVY GROUPS
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INVERSION OF SUGARSUCROSE (+66.5
ο)+ SUCRASE /HCL α D-GLUCOPYRINOSE (+52.5
ο)
+
β D-FRUCTO FUNAROSE (-92 ο
)
DEXTRO –ROTATORY (SUCROSE ) LAEVO ROTATORY HYDROLYSATE (-39.5)
NON- REDUCING (BENEDICT’S NEGATIVE ) REDUCING (BENEDICT’S POSITIVE)
• SUCROSE –INVERT SUGAR ,SUCRASE –INVERTASE
• SWEETNER
• MAJOR CARBOHYDRATE– PHOTOSYNTHESIS
• STORAGE & TRANSPORT FORM IN PLANTS ,ROOTS ,TUBERS
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OXIDATION OF MONOSACCHARIDES • Oxidation –CHO COOH (MILD OXIDATION/BROMINE )
• GLUCOSEGLUCONIC ACID (C1 )
• GLUCOSE GLUCORONIC ACID (C6)
• GLUCOSE GLUCOSACCHARIC ACID ( C1,C6)WITH STRONG ACIDS HNO3
• FUNCTION OF GLUCORONIC ACID (C6)---DETOXIFICATION ,SYNTHSESIS OF MUCOPOLYSACCHARIDES
• GALACTOSE MUCIC ACID –DIAGNOSIS OF GALACTOSE INTOLERENCE
ESTIMATION OF GLUCOSE BY GOD –POD METHOD
• GLUCOSE GLUCONIC ACID +H2O2
• H2O2 -POD H20 +(O)
• CHROMOGENIC SUB+(O)-COLOR COMPLEX
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REDUCTION OF MONOSACCHARIDES
• CHO CH2OH ALCOHOLS (WITH SODIUM AMALGAM)
• GLUCOSE SORBITOL
• GALACTOSE DULCITOL
• MANNOSE MANNITOL
• FRUCTOSE MANNITOL & SORBITOL
• RIBOSE RIBITOL
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Glycosides
• Hemiacetal +R2OH OH
R 1 -- C -- H
OR2• HEMI ACETAL HYDROXY GROUP OF ANOMERIC CARBON OR HEMIKATAL
HYDROXY GROUP OF ANOMERIC CARBON+
• HYDROXY GROUP OF ANOTHER CARBOHYDRATE OR NON CARBOHYDRATE CARBOHYDRATE + CARBOHYDRATE ---GLYCOSIDE (LINKING WITH
GLYCOSIDIC BOND)• HEMI ACETAL HYDROXY GROUP OF GLUCOSE + HYDROXY GROUP OF
ANOTHER GLUCOSE-MALTOSE• OH FROM ANOMERIC CARBON –GLYCOSIDES /GLUCOSIDES/GALACTOSIDESOF MONOSACCHARRIDESCARBOHYDRATE +NON CARBOHYDRATES (AGLYCAN)GLYCOSIDES OH FROM ANOMERIC CARBON + OH OF METHANOL /ETHANOL/STEROL(AGLYCAN)
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Physiologically important Glycosides • Glucovanilin----vanilla flavor
• Cardiac glycosides –muscle contraction
• digitoxin & digoxin—pumping of heart
• Streptomycin—antibiotic for tuberculosis
• ERYTHROMYCIN—DIMETHYL AMINO SUGARS • Quabain – inhibitors of Na+k+ ATPase
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SUGAR AGLYCAN GLYCOSIDE FUNCTION
GLUCOSE PHLORETIN PHLORIZIN(ROSE BARK ) RENAL DAMAGE
GALACTOSE & XYLOSE DIGITOGENINE DIGITONIN CARDIAC STIMULANT
GLUCOSE INDOXYL PLANT INDICAN STAIN
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Pentose sugars
• RIBOSE –RNA /ATP/NAD
• RIBULOSE HMP SHUNT INTERMEDIATE
• ARABINOSECHERRIES
• XYLOSEPROTEOGLYCANS
• XYLULOSEURONIC ACID PATHWAY
Aminated sugar
N acetyl Glucosamine—Hyaluronic acid
• Nacetyl Galactosamine---chondroitoin sulphate
• Glycoprotein –carbohydrate (< 10% )+ protein
• Mucoprotein =mucopolysaccharides (>10%)+protein
• Mucopolysaccharidesuronic acid + amino sugar
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