CHO Chemistry Zatona Foundation Med Robot PDF

CHO Chemistry Definition : organic substances composed of carbon , hydrogen and oxygen. CHO → dietary calories, Energy storage and cell membrane components. Classification of carbohydrates Monosaccharides Oligosaccharides Polysaccharides...

CHO Chemistry Definition : organic substances composed of carbon , hydrogen and oxygen. CHO → dietary calories, Energy storage and cell membrane components. Classification of carbohydrates Monosaccharides Oligosaccharides Polysaccharides D-Glucose D-Mannose D-galactose D-Fructose “ glycans” - These are the 2-10 More than 10 simplest building monosaccharide monosaccharide Aldo-hexose Keto-hexose units units units - Can’t be 2 Disaccharides hydrolyzed into 3 Trisaccharides Ring structure of Monosaccharides simpler form - Monosaccharides of 5 or more Carbon atoms are present in Ring forms. - Ring formation involves condensation between carbonyl group “C1 in aldoses & C2 in ketoses” with one of the Alcohol groups (OH) present on the same Classification of Monosaccharides sugar, usually the sub terminal one. According to the According to the Characteristic carbonyl - The carbonyl Carbon atom in cyclic form will be Number group called the Anomeric carbon, and it can exist as α or of carbon Atoms β isomers or Anomers. Aldosugars Ketosugars - In Haworth configuration, all the groups to the “ glycans” Right of C are oriented down& all the groups to the Trioses (3 C) - Contain aldehyde - Contain ketone left of C are oriented up EXCEPT those around C5 Tetroses (4 C) group (- CHO) group (C = O) “ pre last one ” the reverse orientation occurs. Pentoses (5 C) - As Glucose, - Fructose Hexoses (6 C) Ribose, Heptoses (7 C) Glyceraldehyde. Aldo Triose Keto triose Aldo pentose Keto Pentose Glucose α-D- Glucopyranose α- D- Glucose D- Glyceraldehyde Di Hydroxy Acetone D-Ribose D-Ribulose ( open chain ) α- D- Glucose  Epimers : - Two Monosaccharides differ only in the configuration around one specific carbon atom ( not the Anomeric ). - D-glucose & D-Mannose Epimers with respect to C2 - D-glucose & D-galactose Epimers with respect to C4 Aldose - Ketose isomers : - Two Monosaccharides have the same molecular formulae, but differ in their functional groups. Fructose α-D-Fructo-furanose - One has Aldehyde group & the other has Ketone group. α- D- Fructose ( open chain ) α- D- Fructose E.g.: Glucose & Fructose α and β anomers : Asymmetric Carbon atom - Isomers of Monosaccharides that differ from each Anomeric carbon : other only in configuration around the Anomeric carbon. The new - It is a carbon atom attached to four different atoms or groups. asymmetric carbon - Any compound having asymmetric carbon atom(s) will possess : - If OH on the Right (down) of the Anomeric α. atom obtained in - Isomers : Compounds with the same molecular weight & same percentage - If OH on the left (up) of the Anomeric β Ring structure composition, but differ in their physical and chemical properties. Important types of isomerism 1. D-glucose and D-mannose are epimers at C2 2. D-glucose and D-galactose are epimers at C4 D&L Aldose – Ketose 3. D-glucose and L-glucose are mirror image to each other isomers Epimers α and β anomers isomers 4. Number of asymmetric carbon atoms at aldehyde containing sugar = number of carbon atoms – 2 5. Number of asymmetric carbon atoms at ketone containing sugar = D & L isomers : number of carbon atoms – 3 - Two isomers one of them is the mirror image of the other. 6. Di-hydroxy acetone = No asymmetric carbon atoms as it is ketotriose - Differ according to sub terminal OH. 7. 2 Monosaccharides that differ from each other in 1 carbon not the anomeric … epimers - Right → D & Left → L. 8. 2 Monosaccharides that differ from each other in 1 carbon which is the - Most of Monosaccharides in mammals are of the D-configuration. anomeric …. Alpha and Beta anomers 9. 2 Monosaccharides that differ from each other in Functional group … aldose ketose isomers 10. 2 Monosaccharides that differ from each other around the Functional group …. Alpha and Beta anomers D- Glucose L- Glucose  3. Deoxy sugars : Monosaccharides of biological Importance OH has been replaced by H, Pentoses e.g. D-Ribose → 2-Deoxy D- Ribose D- Ribose - RNA , NAD+ , NADP+ , ATP, GTP 4. Amino sugars : OH at carbon 2 is replaced by Amino group NH2. 2-Deoxy Ribose - DNA -The Amino group may or may not be acetylated. Hexoses e.g.: D-glucose - Blood sugar and utilized by cells. D-glucose → D-glucosamine - called dextrose as it is dextrorotatory. D-galactose → D-galactosamine D- Fructose - In semen for sperm nutrition. 5. Amino sugar Acids : - called Levulose as it is Levorotatory. 9 carbons Amino sugar derivatives = 6C Amino sugar + 3C acid. D- galactose - In Mucopolysaccharides & galactolipids - The Amino group is usually acetylated. Derivatives of Monosaccharides - Mannosamine + Pyruvic Acid = Neuraminic Acid. - Mannosamine + Pyruvic Acid + Acetyl group = N-Acetyl Neuraminic Acid Sugar alcohol glycosides = NANA = Sialic Acid. Amino sugar Sugar acid - Sialic Acid is present in glycolipids (Gangliosides) acid Amino sugar Deoxy sugars 6. Glycosides : Compounds formed from condensation between: 1. Sugar Acid : Oxidation products of Monosaccharides. a. Sugar + another sugar→ Disaccharides & higher oligosaccharides. b. Sugar & A/glycone ( non sugar ) Uronic acid L-Ascorbic acid = vitamin C - Nucleosides = Pentose + Nitrogenous Base - Obtained by oxidation of These are components of nucleotides & nucleic acids ( DNA & RNA ) last carbon as D-glucuronic - Sugar + Protein as in glycoproteins and proteoglycans Acid Naturally occurring sugar - Sugar + Lipids as in glycolipids - D-glucose → D-glucuronic Acid Glycosidic Bonds : Acid → in polysaccharides - These are bonds that link sugars. and detoxification - Formed by Glycosyl Transferases enzymes. - They may be O-Glycosidic bonds as in ( Disaccharides ). 2. Sugar Alcohols : Reduction products of Monosaccharides. - They may be N-Glycosidic bonds as in ( Nucleosides ). Naturally occurring sugar Alcohol→ Myoinositol = inositol , cyclic sugar Alcohol and enters in formation of Phosphatidyl Inositol. Ribose Mannose Fructose glucose galactose Ribitol mannitol sorbitol galactitol Diuretic in hypertension to help the body produce more urine in cases of hypertension and oedema Relieves constipation Disaccharides Maltose Lactose Sucrose Chemical units α-D-glucose + α-D-glucose β-D-galactose + α-D-glucose α-D-glucose+β-D-fructose Bonds α–1-4 glucosidic bond Β-1-4 galactosidic bond - α-1-2 glucosidic bond - β 2,1 fructosidic bond Free anomeric Has free anomeric Has free anomeric No free anomeric - α and β - Reducing sugar - Osazone Formation Sources - action of amylase on starch Milk only - cane & Honey - Germinating cereals and malt - beet - Table sugar 1. milk sugar….. Lactose 2. Cane sugar … Sucrose 3. Glycosidic bond in maltose …. α–1-4 glucosidic bond 4. Glycosidic bond in Lactose …. Β-1-4 galactosidic bond 5. Glycosidic bond in Sucrose …. α-1-2 glucosidic bond , β 2,1 fructosidic bond 6. Maltose , Lactose …. Free anomeric 7. Maltose , lactose … osazone formation , reducing sugar , α and β 8. Sucrose … no free anomeric , no reducing sugar , no osazone 9. Maltose = glucose + glucose 10. Lactose = galactose + glucose 11. Sucrose = glucose + fructose 12. Glucose … α , galactose / fructose … β  Polysaccharides Homopolysaccharides “Simple” Homopolysaccharides “Simple” Heteropolysaccharides “mixed” Contain one type of monosaccharide units. G G G G G G Contain one type of Contain more than one Type of monosaccharide units. monosaccharide units Glucosans Starch ,Glycogen , Cellulose Glucosans Starch ,Glycogen , Cellulose Starch Fructosans Inulin Galactosans Agar Agar G G D-glucose G G units Acidic Neutral G G G G “ mucopolysaccharides = Glycosaminoglycans = GAGs ” Sugars + Amino sugars Sugar + Amino sugar +/- Uronic G G G G G G G G G G G G Acid +/- Sulfate G G No Uronic or Sulfuric Acids G G Sulfate free Sulfated e.g. : G G Human Blood group substances G G e.g.: - Chondroitin Amylopectin sulfate Complete hydrolysis By : ( 80% ) 1) Acid → Glucose units Amylose α-1,6 - Dermatan Glucosidic - outer part sulfate 2) Amylase → Maltose units ( 20% ) α-1,4 e.g.: + dextrins Bonds.. - branched - Keratan - Inner part Glucosidic Hyaluronic sulfate branching - straight chain Bonds Acid - Heparan point sulfate - Heparin ( Anti- Coagulant ) major source Storage form of of CHO for CHO in plants Animals  GAG Sugar Amino Sugar Uronic Sulfate Function Glycogen Acid Storage form of major source of Chondroitin N-Acetyl D- Glucuronic ✅ Bone CHO in plants Sulfate galactosamine acid Cartilage CHO for …. starch Animals …. starch Keratan galactose N-Acetyl D- ❌ ✅ cartilage Structural Sulfate glucosamine Loose CT polysaccharide , Storage form of Cornea present in CHO in animal ( transparent ) plants … cellulose …. glycogen Heparan D- D- ✅ cell Sulfate glucosamine glucuronic membrane disulphate acid receptors - Storage form of CHO in Animals, mainly in liver & sulfate or Cell-cell Muscles. L-iduronic interaction acid Control cell - Its structure is similar to Amylopectin, but it is highly sulfate differentiation Branched & highly Compact “ so it contains α-1,4 and α-1,6 control tissue “. morphogenesis Cellulose and homeostasis Dermatan N-Acetyl D- D- ✅ Blood β-1,4 Glucosidic Bond Sulfate galactosamine glucuronic vessels G G G G G sulfate acid and heart valves L-iduronic skin acid Sclera Cellulase enzyme Not digested Hyaluronic N-Acetyl D- Glucuronic ❌ Synovial fluid G Acid glucosamine acid Lubricant Shock absorber - Structural polysaccharide , present in plants. Loose CT - Linear polymer of D-glucose units connected by β-1,4 Glucosidic Bond. - Not digested in humans due to absence of cellulase enzyme. - It stimulates Intestinal peristalsis → prevents constipation and forms the main Bulk of stools. 1. D-glucuronic acid … L-iduronic acid …. Epimers at C5 2. D-glucuronic acid … L-glucuronic acid … D,L isomers 3- D-glucuronic acid.. sugar acid … oxidation of last carbon of D-glucose D-glucose D-glucuronic acid L-iduronic acid L-glucuronic acid  Proteoglycans Glyco-protein - CHO … 1-70% - CHO … 95% Proteoglycan - Protein … 30-99% monomer = aggrecan = GAGs + core protein Core protein… covalent Covalent Bond Hyaluronic Backbone = with GAGs …. Link acid polypeptide Non-covalent with protein … = protein link Protein non-covalent Oligosaccharides. low CHO and diverse NH2 OH as : 1. N-Acetyl amino sugar ( N-Acetyl - Marco molecules of ECM or cell surface containing up to 95% CHO N-linked O-linked glucosamine or N-Acetyl galactosamine). - The basic proteoglycan unit is called Aggrecan or proteoglycan 2. Hexoses (Mannose and galactose). Monomer. Asparagine serine , therionine 3. L-Fucose ( 6-deoxy-L-galactose ). - It contains long strand of Hyaluronic Acid attached non-covalently to 4. Sialic Acid ( N-Acetyl Neuraminic Acid ) link proteins. - Link proteins are attached non-covalently to core proteins. - Core proteins are attached covalently to GAGs by O-glycosidic bonds Functions of glycoproteins : between Xylose sugar and OH of serine. - membrane bound glycoproteins - Proteoglycan Monomer = Core protein + Attached GAGs. - cell surface recognition - Aggregation of proteoglycan monomers within collagen meshwork , - cell surface antigenicity ( as blood group antigens ) adding structural Rigidity to matrix. - components of ECM and Mucin of GIT and urogenital tracts - GAGs in proteoglycans are polyanions (-) and can bind greatly with - Almost all globular plasma proteins ( except albumin ) polycations (+) like Na+ & K+ which attract H2O by osmotic pressure - immunoglobulin G ( IgG ) contains < 4 % CHO into ECM  َ َّ ْ ‫تقف‬ ‫إعت ْم وكد ِفإن مضيت فال‬ ‫ز‬ 1. Reduction of Monosaccharides yields ….. Sugar alcohols 2. Ascorbic acid is an example of ….. Sugar acid ُ ُ ْ ْ‫ر‬ 3. A polysaccharide indigestible by man is …. Cellulose ‫وثابر فالنجاح محقق‬ ‫وأصت‬.. 4. Glucuronic acid is produced from ….. oxidation of last carbon atom 5. Inulin is a simple polysaccharide built up of ….. fructose 6. The richest site for fructose in the body is … seminal fluid Telegram chat 7. Dextrose … glucose … aldohexose …. Dextro-rotatory 8. Levulose …. Fructose …. Ketohexose …. Levo-rotatory 9. The glycosidic linkage seen in lactose ….. Beta 1,4 10. The glycosidic linkage seen in maltose ….. Alpha 1,4 11. The glycosidic linkage seen in Sucrose ….. Alpha 1,2 or beta 2,1 12. The only sulfate free GAG is … Hyaluronic acid 13. Polysaccharide acts an anti-couagulant … heparin 14. Storage CHO in plants …. Starch 15. Storage CHO in animals …. Glycogen … in liver and muscles Wafeeden Group 16. Structural CHO in plants …. Cellulose 17. Structural CHO in animals …. GAGs 18. The only Uronic acid free GAG is … keratan sulfate 19. The major GAG present in cartilage is … chondroitin sulfate 20. Important for corneal transparency …. Keratan sulfate 21. GAG that is important for maintenance of shape of sclera … Dermatan sulfate 22. The major component of proteoglycans is usually … CHO 23. The major component of Glycoproteins is usually …. Protein 24. Can form osazone … maltose , lactose I Med academy app 25. Cant form osazone … sucrose 26. Non-Digestable Sugar … cellulose 27. A branched component of starch is …. amylopectin