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Stryer Chapter 9 Carbohydrates

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Chapter 9 Carbohydrates

1. Draw the D and L-form of aldoses and ketoses that have three, four and six carbon atoms, Identify the stereocenter and the position that defines the sugar as being either the D or the L form. pecifically know the structures of glucose, fructose, glyceraldehyde, dihydroxyacetone.

!. "e able to identify constitutional isomers, enantiomers, epimers, diastereoisomers, anomers and stereoisomers.

#. "e able to cyli$e aldoses and ketoses given the fisher pro%ection diagrams into & and ' ring structures.

(. )now the reaction of monosaccharides* redox reactions

&. )now the derivatives of monosaccharides* e.g. sugar phosphates +, - ./012 - /,# +,! ./012, -3 /111-, -3 1-41#5!'. List disaccharides of importance* maltose, lactose and sucrose. "e able to identify the different linkages. 6altose* disaccharide obtained by en$yme-cataly$ed hydrolysis of starch, consists of two D-glucopyranoses %oined by a 1,(7-beta-glycoside bond. It7s a reducing sugar because the anomeric carbons on the right-hand sugar are part of a hemiacetal. 6altose is digested without difficulty and is fermented readily. Lactose* occurs naturally in both human and cow7s milk. 8idely used in baking and in commercial infant-milk formulas. It7s a reducing sugar and exhibits mutarotation and is a 1,(7-beta-linked glycoside. Lactose contains two different monosaccharide units and the acidic hydrolysis of lactose yields 1 e9uiv of Dglucose and 1 e9uiv of D-galactose: the two are %oined by a beta-glycoside bond between /1 of galactose and /( of glucose. ucrose* a flexible structure that7s the most abundant pure organic chemical in the world and the one most widely known to nonchemists. ;ields 1 e9uiv of glucose and 1 e9uiv of fructose on acidic hydrolysis. <his 1*1 mixture of glucose and fructose is often referred to as invert sugar, since the sign of optical rotation changes .inverts2 during the hydrolysis from sucrose .=alpha>D 0 ?''.&degrees2 to a glucose fructose mixture .=alpha>D 0 -!!.@degrees2. +ot a reducing sugar and doesn7t exhibit mutarotation. Aacts imply that sucrose has no hemiacetal linkages and that glucose and fructose must both be glycosides. <his can happen only if the

two sugars are %oined by a glycoside link between /1 of glucose and /! of fructose. B. "e able to identify the differences between polysaccharides* starch, amylopectin, cellulose, glycogen. tarch* produced in plants as a way of storing energy and exists in two forms amylose and amylopectin. ,elical chain of glucose monomers, which are bonded by glycosidic linkages. C storage polysaccharide in plant cells, we can obtain starch from potatoes. Cmylopectin* is a branched polymer of alpha-glucose and is completely insoluble in water.

/ellulose* made exclusively by molecules of beta-glucose. /ellulose is the constituent of the cell walls in plant cells. "ecause of humans do not produce en$ymes which hydroly$e the cellulose, we cannot use it as a primary energy source .we cannot digest cellulose2. Dlycogen* the storage polysaccharide in animals. It7s also known as Eanimal starchF because of its similitude with amylopectin molecules, but glycogen is more branched than amylopectin. "esides, glycogen molecules are tighter than amylopectin molecules. ,umans can use glycogen as an energy source by hydrolysis of the polymer using specific en$ymes .organic substances that accelerate or retard the biochemical reactions2. G. "e able to recogni$e glycoproteins and their importance in blood groups. Cll blood groups have a deoxy sugar. <ype C* +-acetylgalactosamine <ype "* alpha-D-galactose <ype C"* both <ype 1* neither

H. "e able to recogni$e the important functions of carbohydrates ource of energy paring protein for tissue building and repairing Aat oxidation Iole in gastro-intestinal functions - lactose promotes the growth of certain desirable bacteria in the small intestine, which brings about the synthesis of certain "-complex vitamins. It also enhances the absorption of calcium. /ellulose provides fiber and bulk which helps in the stimulation of the peristaltic movements of the gastroinl tract. Important Terms and Comparisons 6onosaccharides, disaccharides and 1ligosaccharides Cldoses and ketoses Jpimers and epimeri$ation /hiral molecule Cnomeric /arbon atoms ,emiacetal and acetal Ieducing and +on-reducing sugar D and L -monosaccharides Aisher pro%ection and ,aworth structures Dlycosidic bond Auranose and pyranose Clpha and beta linkages

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