CARBOHYDRATES PART I
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1 CARBYDRATES PART I 1
2 CARBYDRATES Empirical formula: C x ( 2 ) y 2
3 CARBYDRATES- WERE ARE TEY? In solid parts of: plants, up to 80% animals, does not exceed 2% In plants: mainly as a storage material (starch) building material (celulose) In animals: source of energy building material: Skeleton of invertebrates and mushrooms (chitinous protective polysacharide substance) Structural function in vertebrates (glycosoaminoglycans) [ Invertebrates animal without skeleton ] 3
4 CARBYDRATES CLASSIFICATIN Monosaccharides simple sugars with multiple groups. ccarbohydrates which can not be divided to other carbohydrates components Disaccharides 2 monosaccharides covalently linked. During hydrolysis they are degrade to two compounds of monosaccharide, for example: maltose, saccharose ligosaccharides a few monosaccharide covalently linked. during hydrolysis they are degrade to 3 to 10 units of monosaccharide e.g. :maltotrioza Polisaccharides polymers consisting of chains of monosaccharide or disaccharide units. During hydrolysis they are degrade to over 10 molecules of monosaccharides, e.g.: starch, glycogen. 4
5 PYSICAL PRPERTIES F MNSACARIDES CLRLESS, DURLESS USUALLY TASTE SWEET VERY WELL SLUBLE IN WATER EXIBIT RTARY PLARIZATIN CEMICALLY NEUTRAL (N ACIDITY R BASISITY) 5
6 MNSACCARIDES - NMENCLATURE Monosaccharides containing: aldehyde group are called - aldose ketone group are called - ketose Aldoses (e.g., glucose) have an aldehyde group at one end. Ketoses (e.g., fructose) have a ketone group, usually at C2. C C C C C C 2 D-glucose C 2 C C C C C 2 D-fructose 6
7 TYPE F MNSACARIDES ISMERISMS 1. Configuration of D and L isomers 2. ptical isomerism 3. Piranoses and furanoses ring forms 4. Anomers a and b 5. Epimers 6. Isomers 7
8 CNFIGURATIN D and L Molecules of glyceric aldehyde are enantiomers. Stereoisomers are isomeric molecules that have the same molecular formula and sequence of bonded atoms (constitution), but which differ only in the three-dimensional orientations of their atoms in space. Enantiomers are also called mirror images. Glyceric aldehyde is a configuration standard for all optically active compounds. If certain compound can be transformed to one of glyceric aldehyde isomers then this compound belongs to D or L. D or L does not depend on rotary polarization. 8
9 ISMERS D and L L-glyceric aldehyde 1 C 2 C 3 C 2 D-glyceric aldehyde 1 C 2 C 3 C 2 D and L symbols determine sugars configuration. Reference is glyceric aldehyde. 1 C 2 C 3 C 4 C 5 C 6 C 2 L-glucose 1 C 2 C 3 C 4 C 5 C 6 C 2 D-glucose 9
10 TYPE L ISMERS L-iduronic acid Fucose L-fucose-1,6-N-acethyloglucosamine Animals and plants are mostly using D isomers of monosaccharides. Monosacharides form L-group are not able to replace those from D group because L-saccharides are not a substrates for chiral enzymes. Exceptions examples are L-iduronic acid and Fucose. a-d-fukoza b-l-fukoza 10
11 PTICAL ISMERISM F MNSACARIDES Amount of enantiomers pairs depends on active centers quantities. C *C *C *C *C C 2 For 4 centers the amount of enantiomers and diastereoisomers are 2 4 =16 11
12 FAMILY F D-aldose D-(+)- aldehyd glicerynowy D-(-)-ryboza D-(-)-arabinoza D-(-)-ksyloza D-(-)-liksoza 12
13 emiacetal & hemiketal formation An aldehyde can react with an alcohol to form a hemiacetal. A ketone can react with an alcohol to form a hemiketal. C R R C R' + R' R' C aldehyde alcohol hemiacetal + R R "R "R C ketone alcohol hemiketal R' 13
14 Pentoses and hexoses can cycles, as the ketone or aldehyde reacts with a distal. Glucose forms an intra-molecular hemiacetal, as the C1 aldehyde & C5 group reacts, to form a 6-membered pyranose ring, named after pyran. C1 is a new center. pyran 4 6C Alfa a-d-glucose α-d-glucopyranoses glukopiranoses C C C C C C 2 D-glucose (linear form) 6 C β-d glucopyranoses b-d-glucose Diastereoisomers = anomers = they differ from each other with configuration at C1 atom only, and have different physical properties 14
15 1 C 2 2 C C C C C 2 2 C D-fructose (linear) a-d-fructofuranose 1 C 2 2 Fructose forms either: 6-membered pyranose ring, by reaction of the C2 keto group with the on C6, or a 5-membered furanose ring, by reaction of the C2 keto group with the on C5. 15
16 4 6 5 C a-d-glucose α D-glukopiranoses C 2 b-d-glucose β-d glucopiranoses Cyclization of glucose produces a new asymmetric center at C1. This two stereoisomers are called anomers, a & b. aworth projections represent the cyclic sugars as having essentially planar rings, with the at the anomeric C1: a ( below the ring) b ( above the ring). 16
17 ß D glucose, boat configuration ß-D- glucose chair configuration a-d-glucopyranose b-d-glucopyranose Because of the tetrahedral nature of carbon bonds, pyranose sugars actually have a "chair" or "boat" configuration, depending on the sugar. The above representation reflects the chair configuration of the glucopyranose ring more accurately than the aworth projection. 17
18 Mutarotation Mutarotation it is a transformation of one anomeric form into another. Intermediate form is a chain form of monosaccharides. In D-glucose solution there is more b-d-glucopyranoses. All its groups get the most energetically beneficial equatorial position. 18
19 Monosaccharide epimers Epimers: C n aldoza endiol C n ketoza epimeryczna C n aldoza diasteroisomers which differ from each other with one position Different than at C-1 in aldose Different than at C-2 in ketose Different than at last asymmetric carbon atom Pair of epimers: glucose and mannose 19
20 Glucose epimers intermediate 20
21 Chemical properties of monosacharides Reductive properties only when free aldehyde or ketone group in saccharides molecule is present. In alkali environment Saccharides have reductive properties and ring can be opened In acidic environment saccharides are in cyclic form and there is no C = group. Saccharides oxidizes to acids, while reduces other substances e.g.: glucose oxidizes to gluconic acid 21
22 Chemical properties of monosacharides Acid inflence on saccharides all saccharides with amount of atoms more than 4 in molecule when heated with strong acids are undergo dehydration and cyclization BASE INFLUENCE N SACCARIDES in base environment reductive saccharides get enolization sazone creating - saccharides with phenyl hydrazine are creating yellow, not soluble in water dihydrasones called osazone. 22
23 sazone formation Phenyl hydrazyne D-glocose D-glucose osazone Glucose or mannose or fructose Epimers have joint osazone 23
24 Sugar derivatives C 2 C C C C 2 D-ribitol C C C C C C 2 D-gluconic acid C C C C C C D-glucuronic acid sugar alcohol no aldehyde or ketone group; e.g., ribitol. sugar acid - the aldehyde group at C1, or at C6, is oxidized to a carboxylic acid; e.g., gluconic acid, glucuronic acid. 24
25 Sugar derivatives C 2 C 2 N 2 N C C 3 a-d-glucosamine a-d-n-acetylglucosamine amino sugar - an amino group substitutes for hydroxyl group. An example is glucosamine. The amino group may be acetylated, as in N-acetylglucosamine. 25
26 3 C C N R C R = C C C 2 N-acetylneuraminate (sialic acid) N-acetylneuraminate (N-acetylneuraminic acid, also called sialic acid) is often found as a terminal residue of oligosaccharide chains of glycoproteins. Sialic acid imparts negative charge to glycoproteins, because its carboxyl group tends to dissociate proton at physiological p, as shown here. 26
27 Glycosidic Bonds The anomeric hydroxyl and a hydroxyl of another sugar or some other compound can join together, splitting out water to form a glycosidic bond: R- + -R' R--R' + 2 E.g., methanol reacts with the anomeric in glucose to form methyl glucoside (methyl-glucopyranose). + C 3-2 a-d-glucopyranose methanol C 3 methyl-a-d-glucopyranose 27
28 Glycosidic Bonds Glycosidic anomers 28
29 CARBYDRATES PART II 29
30 DISACCARIDES Disaccharides consisting of two monosacharides, and connected by glycoside bond are called -glycosides. The most important are: saccharose (present in honey, fruits), lactose (present in milk), maltose (product of enzymatic hydrolysis of starch), cellobiose (product of cellulose hydrolysis). 30
31 Disaccharides: Maltose, a cleavage (split) product of starch (e.g., amylose), is a disaccharide with an a(1 4) glycosidic link between C1 - C4 of two glucoses. It is the a anomer (C1 points down) C C Cellobiose, a product of cellulose breakdown, b anomer ( on C1 points up). The b(1 4) glycosidic linkage is represented as a zig-zag, but one glucose is actually flipped over, relative to the other maltose 4 cellobiose C C
32 ther disaccharides include: Sucrose, common table sugar, has a glycosidic bond linking the anomeric hydroxyls of glucose & fructose. Because the configuration at the anomeric C of glucose is a ( points down from ring), the linkage is a(12). The full name of sucrose is a-d-glucopyranosyl-(12)-b-dfructopyranose.) Lactose, milk sugar, is composed of galactose & glucose, with b(14) linkage from the anomeric of galactose. Its full name is b-d-galactopyranosyl-(1 4)-a-D-glucopyranose 32
33 C 2 6C 2 C amylose C 2 C 2 Polysaccharides: Plants store glucose as amylose or amylopectin, glucose polymers, collectively called starch. Glucose storage in polymeric form minimizes osmotic effects. Amylose is a glucose polymer with a(14) linkages. The end of the polysaccharide with an anomeric C1 not involved in a glycosidic bond is called the reducing end. 33
34 C 2 C 2 1 amylopectin C 2 C 2 6C C 2 C Amylopectin is a glucose polymer with mainly a(14) linkages, but it also has branches formed by a(16) linkages. Branches are generally longer than shown above. The branches produce a compact structure and provide multiple chain ends at which enzymatic cleavage can occur. 34
35 C 2 C 2 C 2 1 C 2 6C glycogen C 2 C Glycogen, the glucose storage polymer in animals, is similar in structure to amylopectin, but glycogen has more a(16) branches. The highly branched structure permits rapid glucose release from glycogen stores, e.g., in muscle during exercise. The ability to rapidly mobilize glucose is more essential to animals than to plants. 35
36 GLYCGEN omoglycan (in animals) high molecular weight storage material, built from: α-amylose, amylopectine stored in liver plays similar role as starch in plants. 36
37 C 2 6C 2 C 2 C cellulose C 2 Cellulose, a major constituent of plant cell walls, consists of long linear chains of glucose with b(14) linkages. Every other glucose is flipped over, due to b linkages. This promotes intra-chain and inter-chain -bonds and van der Waals interactions, that cause cellulose chains to be straight & rigid, and pack with a crystalline arrangement in thick bundles - microfibrils. Celulose has high mechanical strength Chemically resistant. Insoluble in water. Main component of cell walls. Schematic of arrangement of cellulose chains in a microfibril. 37
38 D-glucuronate 6C hyaluronate 1 C NCC 3 N-acetyl-D-glucosamine Glycosaminoglycans (mucopolysaccharides) are linear polymers of repeating disaccharides. Can be covalently bond to a protein to form protoglycans. The constituent monosaccharides tend to be modified with: acidic groups, amino groups, sulfated hydroxyl groups,etc. Glycosaminoglycans tend to be negatively charged because of the acidic groups presence. It is important component of connective tissues. Some examples of glycosaminoglycan uses in nature include heparin as an anticoagulant, hyaluronan as a component in the synovial fluid lubricant in body joints, and chondroitins, which can be found in connective tissues, cartilage, and tendons. 38
39 omoglycans 1,4--glycoside-bond 1,6--glycoside bond 39
40 omoglycans - starch Main storage material for plants. Is consisting of amylopectin and amylose: Amylopectin, insoluble in water α-1,4- i α-1,6-glycoside bonds Amylose soluble in water 40
41 4 D-glucuronate 6 C hyaluronate C NCC 3 1 N-acetyl-D-glucosamine yaluronate (hyaluronan) is a glycosaminoglycan with a repeating disaccharide consisting of two glucose derivatives, glucuronate (glucuronic acid) and N-acetyl-glucosamine. 41
42 core protein heparan sulfate glycosaminoglycan transmembrane a-helix cytosol Proteoglycans are glycosaminoglycans that are covalently linked to serine residues of specific core proteins. The glycosaminoglycan chain is synthesized by sequential addition of sugar residues to the core protein. 42
43 iduronate-2-sulfate N-sulfo-glucosamine-6-sulfate C 2 S 3 C S 3 NS 3 heparin or heparan sulfate - examples of residues eparan sulfate is initially synthesized on a membrane-embedded core protein as a polymer of alternating N-acetylglucosamine and glucuronate residues. Later, in segments of the polymer, glucuronate residues may be converted to the sulfated sugar iduronic acid, while N-acetylglucosamine residues may be deacetylated and/or sulfated. 43
44 eparin, a soluble glycosaminoglycan found in granules of mast cells, has a structure similar to that of heparan sulfates, but is more highly sulfated. When released into the blood, it inhibits clot (coagulated) formation by interacting with the protein antithrombin. PDB 1RID eparin has an extended helical conformation. heparin: (IDS-SGN) 5 Charge repulsion by many negatively charged groups may contribute to this conformation. eparin shown has 10 residues, alternating IDS (iduronate-2-sulfate) and SGN (N-sulfo-glucosamine-6-sulfate). 44
45 Proteins involved in signaling & adhesion at the cell surface recognize & bind heparan sulfate chains. E.g., binding of some growth factors (small proteins) to cell surface receptors is enhanced by their binding also to heparan sulfates. iduronate-2-sulfate N-sulfo-glucosamine-6-sulfate C 2 S 3 C S 3 NS 3 heparin or heparan sulfate - examples of residues 45
46 ligosaccharides that are covalently attached to proteins or to membrane lipids may be linear or branched chains. Glycosidic bond C 2 C 2 N C C 3 b-d-n-acetylglucosamine C N C serine residue -linked oligosaccharide chains of glycoproteins vary in complexity. They link to a protein via a glycosidic bond between a sugar residue and a serine or threonine. -linked oligosaccharides have roles in recognition, interaction, and enzyme regulation. 46
47 C 2 N N C C 3 N-acetylglucosamine Initial sugar in N-linked glycoprotein oligosaccharide N C C 2 C C N C C N C C R R Asn X Ser or Thr N-linked oligosaccharides of glycoproteins tend to be complex and branched. First N-acetylglucosamine is linked to a protein via the sidechain N of an asparagine residue in a particular 3-amino acid sequence. 47
48 APPY LIDAYS and a New
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