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    5 views15 pages

    Carbohydrates

    Uploaded by

    Krizzia Oñate
    caarbs

    Copyright:

    © All Rights Reserved
    Download as PDF or read online from Scribd
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    of 15
    . 3 CHEMISTRY OF CARBOHYDRATES GTO : Understand the chemistry and properties of carbohydrates of biological significance. SBO:: 1. Define and classify carbohydrates, 2. Discuss the followi 21 Rane We A | 2.2. asymmetric carbon). 2.3” optical activity r ~ I. - 24. stereoisomers 2.8 epimers 2.6 anomers 3. Explain mutarotation 4. Recognize biological importance of the following groups of sugar derivatives. 4.1 neutral hexoses 42 sugar acids 43, amino sugars | 4.4. pentoses 45. deoxysugars \ 4.6. sugar alcohols 4.7. phosphate esters of sugars is ifferentiate the different oligosaccharides and polysaccharides according to: 5.1 repeating units 5.2 glycosidic tinkages 1, DEFINITION Carbohydrates — also known as saccharides, are, polyhydroxy! aldehydes or ketones and their derivatives with at least three carbon atoms that possess 2 carbonyl group. = most abundant organic molecules = represented by the simple stoichometric formula (CH:0)n hence used to be known as “hydrated carbon”. - Functions: provide significant fraction of the energy in the diet of most organisins | . storage form of energy in the/body; used as a primary cellular fuel serve as cell membrane components that mediate soine forms of intercellular communication serve as structural components of many organisms 2. CLASSIFICATION rates is based on their ability to be hydrolyzed to mber of carbon atoms, by the direction of rotation Classification of carbol jationships to the three-carbon sugar smaller compounds, by the a of polarized light, and by the'structural rel glyceraldehyde. 3.1 Monosaccharides are simple, mondineric sugars that can no longer be hydrolyzed to smaller molecules. They consist of a single polyhydroxy aldehyde or ketone unit. 2.11 They may be further classified, depending) n the number of carbon atoms present into: | - ‘Trioses: the smallest molecules composed|pf 3 carbon atoms. There arc two trioses, the glyceraidehyde (aldose) and the dihydroacetone (ketose), which have the same atomic composition but differ in the location of their hydrogen and double bonds (tautomers). = Tetroses: composed of 4 carbon atoms, (CH,0),, include threose, erythrose, and ketose 7 - Pentoses: of major biological importance consisting of 5 carbon atoms. Examples are ribose, xylose, arabinose and rhamnose - Hexoses: 6 carbon atoms like glucose, fructose, mannose and galactose 2.1.2 Depending on the kind of functional group present, monosaccharides can be classified into: . a. Aldoses-contain the aldehyde group, -(H)C=O b, Ketoses-possess the ketone group, -C=O ©. Derived monosaccharides contain functional groups other than carbonyl or hydroxyl ' 2.2. Disaccharides are group of carbohydrates which on hydrolysis yield two monosaccharides which may be the same, or different from each other. Examples are sucrose, lactose, maltose and isomaltose. They may’be distinguished from one another from: a. the two specific sugar monomers involved, and their stereoconfigurations b. the carbons involved in linkage c. the order of 2 monomer units, if they|are different kinds d. . anomeric configuration of the hydroxyl group on carbon I of each residue | 2.3. Oligosaccharides contain three to twelve units of monosaccharides joined in glycosidic linkage. Maltotriose and raffinose belong to this group. re than 12 monosaccharide units joined 2.4 Polysaccharides are polymers of moi : interest and importance in this group in long linear or branched chains. O are starch, glycagen and cellulose 33 3. MONOSACCHARIDES 3 32 33 These are polyhydroxyaldehydes and hydroxyketones derivatives eee the empirical perlaarans where ned oF ‘ns large number. A‘tharacteristic of the simple sugars is the presence of the carbonyl ketone group(-C=0), or the carbonyl aldehyde group (-CHO). - If the carbonyl group is at the end of the chain, the monosaccharide is an aldehyde derivative and called an aldose. The simplest aldose is glyceraldehyde or glycerose. - If the carbonyl group is at any other position, it is a ketone derivative and called a ketose, the simplest of which is dihydroxyacetone. Monosaccharides are represented using the. Fischer projection formulas given below: H-C=0 CHOH 1.C.0H oo | tion : cH.on Glyceraldehyde Dihydroxyacetone ‘The carbon atoms are identified by corresponding numbers, ‘with carbon 1 (C1) being the carbon of the carbonyl group (functional group) in glyceraldehyde and C2 in dihydroxyacetone. Isomerism {somers aré compounds that have the same structural or chemical formula but differ in spatial configuration. The presence of asymmetric carbon atoms to which four different groups or radicals are joined allows the formation of isomers. The number of possible isomers of a sugar depends upon the number of asymmetric carbon in the molecule, expressed as 2" where n is the number of asymmetric carbon. | 3.3.1 D and L configuration. If the OH group n the asymmetric carbon farthest from the carbonyl group points to the right (estro), the sugar is the D isomer. If the OH group i nts to the left (levo), it is the L isomer. ee =) | 2 of each other and are that occur in mammals The D and L tsomers are mirror im known 2s enantiomers. Most simple suga are of the D configuration. C=O HC=O I I H-C.O8 HOCH | | CHOU con D-Glycerakiehyde —_L-Glyceraldehyde 4 33.2, Epimers. These are isomers that differ Gnly in the confiyuration Around one specific carbon atom. Glucose and mannose are epimers with respect to carbon atom 2, while glucose and galactose epimers with respect to carbon 4. re 33.3 Optical actitny, When a beam of polarized light is allowed to pass through a solution of an optical isomer. it will be rotated cither to the Fight, dextrorotary'(+), or to the left, levorotary (-). D- and L- sugars are not necessarily d- or I-, respectively. 3.3.4 Cyclization of monosaccharides (the ring structure). Most monosaccharides with five or more carbon fitoms in the chains give these compounds the potential to form very stadle ring structures. Where the aldehyde or ketone group reacts ‘vith an alcohol group on the same sugar, they form a hemiacetal or ieemiketal ring, respectively. The hydrogen of the hydroxyl group on the penultimate carbon shifts to the carbonyl group with ihe formation of an osygen (O). If the resulting ring has six members (5 carbons und 1 oxygen), it is a Pyranose ring, and if five-membered (4 carbons and 1 oxygen), it is called a furanose ring. | r H-C=O0, HO-CH | HCOH | I | \ HCO HCO H.C.OH | | | : i. HOCH 9 HOCH HOCH i | HCOH HCO HCO I | ! HC HCO s c 1 | | \ CHOW CLOW ||CLOH «

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