Carbohydrates

Carbohydrates are the most abundant class of compounds in the biological world, making up more than 50% of the dry weight of the earths biomass. Carbohydrates are important constituents of all living organisms, and have a variety of different functions. The most abundant carbohydrate in nature is D-glucose. Cells of organisms oxidize D-glucose in the first of a series of processes that provide them with energy. When animals have more D-glucose than they need for energy, they convert excess D-glucose into a polymer called glycogen. When an animal needs energy glycogen is broken into individual D-glucose molecules. Plants convert excess D-glucose into a polymer known as starch. The major structural component of plants, cellulose is another polymer of D-glucose. Chitin, a carbohydrate similar to cellulose, makes up the exoskeletons of crustaceans, insects and other arthropods. Animals obtain glucose by eating plants (or other food that contains D-glucose). Plants form glucose by photosynthesis. The terms carbohydrate (hydrate of carbon, Cn(H2O)n), saccharide and sugar are used interchangeably. Saccharide comes from the word sugar in Greek (sakcharon) and Latin (saccharum). There are two classes of carbohydrates – simple carbohydrates and complex carbohydrates. Simple carbohydrates are monosaccharides (single sugars), whereas complex carbohydrates contain two or more sugar subunits linked together. Disaccharides are complex carbohydrates with two sugar subunits linked together. Monosaccharides A monosaccharide can be a polyhydroxy aldehyde or a polyhydroxy ketone. Polyhydroxy aldehydes are called aldoses (‘ose’ is the suffix for a sugar), while polyhydroxy ketones are called ketoses. Monosaccharides with three carbons are called trioses, those with four carbons tetroses, five carbons pentoses and six carbons hexoses. A six carbon polyhydroxy aldehyde such as D-glucose is an aldohexose, whereas a six carbon polyhydroxy ketone, such as D-fructose is a ketohexose. The smallest aldose, and the only one whose name does not end in ‘ose’ is glyceraldehyde, an aldotriose. Glyceraldehyde has a chiral carbon and exists as a pair of enantiomers. We usually show the stereochemistry of sugars using Fisher projections. Emil Fischer studied carbohydrates in the late 19th century and he named the dextrorotatory stereoisomer of glyceraldehyde, D-glyceraldehyde. D-Glyceraldehyde turned out to be (R)-(+)-glyceraldehyde.
O H H OH CH2OH O HO H H CH2OH

D-glyceraldehyde (R)-(+)-glyceraldehyde

L-glyceraldehyde (S)-(-)-glyceraldehyde

D and L notations are often used to describe the configurations of carbohydrates and amino acids, so we need to understand what they signify. In Fisher projects, the carbonyl is always placed at the top or in the case of ketoses as close to the top as possible. From the structure of galactose below you can see that it has four chiral carbons. If the OH group attached to the bottom-most chiral centre (the second carbon up from the bottom) is on the right, the compound is a D-sugar. If the OH group is on the left the compound is an L-sugar. Almost all sugars found in nature are D-sugars. Notice that the mirror image of a D-sugar is an L-sugar.
O H HO HO H H OH H H OH CH2OH O HO H H HO H H OH OH H CH2OH

D-galactose

L-galactose mirror image of D-galactose

D and L, like R and S, indicate the configuration of a chiral centre, but they do not indicate whether the compound rotates the plane of polarized light to the right (+) or to the left (-).

An easy way to learn their structures is to memorize the structure of D-glucose and then remember that D-mannose is a C-2 epimer and D-galactose is a C-4 epimer. D-mannose and D-galactose are the most common aldohexoses in biological systems. . D-ribose and D-arabinose are C-2 epimers. Configurations of the Ketoses Naturally occurring ketoses have the ketone group at carbon-2. D-glucose. a ketose has only half as many stereoisomers as an aldose with the same number of carbon atoms. Configurations of D-aldoses Aldotriose H H O OH CH2OH D-Glyceraldehyde or (R)-2.Figure 1. A ketose has one fewer chiral carbons than does an aldose with the same number of carbon atoms. Sugars such as D-glucose and D-galactose are diastereomers because they are stereoisomers that are not enantiomers. Therefore.3-dihydroxypropanal Aldotetroses H H H O OH OH CH2OH H HO H O H OH CH2OH D-Erythrose Aldopentoses H H H H O OH OH OH CH2OH H HO H H O H OH OH CH2OH H H HO H O OH H OH CH2OH D-Threose H HO HO H O H H OH CH2OH D-Ribose Aldohexoses H H H H H O OH OH OH OH CH2OH H HO H H H O H OH OH OH CH2OH H H HO H H D-Arabinose O OH H OH OH CH2OH H HO HO H H O H H OH OH CH2OH H H H HO H D-Xylose O OH OH H OH CH2OH H HO H HO H O H OH H OH CH2OH H H HO HO H O OH H H OH CH2OH D-Lyxose H HO HO HO H O H H H OH CH2OH D-Allose D-Altrose D-Glucose D-Mannose D-Gulose D-Idose D-Galactose D-Talose Diastereomers that differ in configuration at one chiral centre are called epimers.

Configurations of D-ketoses Ketotriose CH2OH O CH2OH 1. . Anomers are two sugars that differ in configuration at the hemiacetal carbon (the carbonyl carbon). like epimers. it is β-D-glucose. If the OH group bonded to the new chiral centre is on the right. Anomers. glucose rapidly establishes an equilibrium (catalyzed by acid or base) with the open chain aldehyde and the α and β anomer. are a particular kind of diastereomer. The aldehyde carbon has become a chiral centre in the hemiacetal. If the stereochemistry of the hemiacetal (or hemiacetal in glycosides) carbon is S. The C-5 alcohol group reacts intramolecularly with the aldehyde group forming a six-membered ring hemiacetal. the sugar is called the αanomer and if it is R. the β-anomer. In solution. The three forms have different physical properties and different specific rotations. There is an open chain form which we have just described and two cyclic forms α-D-glucose and β-D-glucose. it is α-D-glucose. if the OH group is on the left. This is called the anomeric carbon (Ano is Greek for upper – anomers differ in configuration at the uppermost chiral center.Figure 2. α-D-glucose and β-D-glucose are called anomers.3-Dihydroxypropanone Ketotetrose CH2OH O H OH CH2OH D-Erythrulose Ketopentoses CH2OH O H H OH OH CH2OH HO H CH2OH O H OH CH2OH D-Ribulose Ketohexoses CH2OH O H H H OH OH OH CH2OH HO H H CH2OH O H OH OH CH2OH H HO H CH2OH O OH H OH CH2OH D-Xylulose CH2OH O HO HO H H H OH CH2OH D-Psicose D-Fructose D-Sorbose D-Tagatose Hemiacetal Formation D-Glucose exists in three different forms.

2° to +52. Consequently. with the anomeric carbon (C1) on the right-hand side and the primary alcohol group drawn up from the left-hand corner (C5).or a six-membered ring.002% aldehyde) the specific rotation is +52. The anomeric carbon is on the right-hand side and the primary alcohol group is drawn up from the back left-hand corner. In a Haworth projection of a D-pyranose. where pyranose indicates that the sugar exists as a six-membered ring hemiacetal. the compound is β-D-fructose. These names come from the pyran and furan rings.H HOH2C HO HO OH H O OH H HO H H O HOH2C OH H OH OH CH2OH HO HO OH OH O H β-D-glucopyranose β-anomer (63%) open-chain aldehyde (0. it will exist predominately as a cyclic hemiacetal in solution. α-Dglucose is called α-D-glucopyranose.7°. the six-membered ring is represented as being flat and is viewed edge on. the compound is α-D-fructose. Groups on the left in a Fisher projection are up in a Haworth projection. up. .7°. When equilibrium is reached. A slow change in optical rotation to an equilibrium value is known as mutarotation. If an aldose can form a five. Groups on the right in a Fisher projection are down in a Haworth projection. Six-membered ring sugars are called pyranoses and five-membered ring sugars are called furanoses.002%) α-D-glucopyranose α-anomer (37%) When crystals of pure α-D-glucose are dissolved in water. D-fructose forms a five-membered ring hemiketal as a consequence of the C5 OH group reacting with the ketone.or six-membered ring is formed depends on their relative stabilities. β-D-glucopyranose O HO H HO H H CH2OH H OH H OH HO H H H CH2OH H OH OH β-D-ribofuranose O Fisher projections CH2OH O OH OH OH OH OH OH CH2OH O OH Haworth projections Groups on the right are down and on the left. Ketoses also exist predominantly in cyclic forms. 37% α-D-glucose and 0.7° to +52. Fisher projections are not effective at showing cyclic sugars and so we use Haworth projections. the specific rotation gradually changes from +18. These sugars can also be called αD-fructofuranose and β-D-fructofuranose. The ring oxygen is always placed in the back right-hand corner of the ring. Whether a five. the specific rotation gradually changes from +112. (63% β-D-glucose.7°. in water the hemiacetal opens to form the aldehyde. The Haworth projection of a D-furanose is viewed edge on with the ring oxygen away from the viewer. if the OH group is on the left. When crystals of pure β-D-glucose are dissolved in water. which can then recyclize to form both α-D-glucose and β-D-glucose. If the new chiral centre has the new OH group on the right in a Fisher projection. Notice that in fructose the anomeric carbon is at C2 and not C1 as in the aldoses. This change in rotation occurs because.

CH2OH CH2OH CH2OH O OH OH HO CH2OH OH H H O H OH OH CH2OH HO H H O H OH OH CH2OH HO OH OH CH2OH OH O β-D-fructofuranose (32%) open-chain ketone of fructose β-D-fructopyranose (68%) . while the furanose form predominates when the sugar is in a disaccharide. The pyranose form predominates in the monosaccharide. Haworth projections are useful because they allow us to see easily whether the OH groups on the ring are cis or trans to each other. up. As five-membered rings are close to planar. β-D-fructofuranose O HO HO H H CH2OH CH2OH H OH HO HO H H H2C CH2OH H OH OH β-D-fructopyranose O Fisher projections CH2OH OH OH O O OH OH OH OH CH2OH CH2OH OH Haworth projections Remember groups on the right are down and on the left. However Haworth projections do not show the chair conformations that are important for the six-membered pyranose rings. furanoses are represented well by Haworth projections.CH2OH O HO H H H OH OH CH2OH HO HO H H CH2OH O H OH CH2OH HOH2C HO H H CH2OH OH H OH O HO HO H H CH2OH CH2OH H OH O D-fructose α-D-fructofuranose β-D-fructofuranose Remember the α-anomer is S and β-anomer is R D-Fructose can also form a six-membered ring by using the C6 OH group.

to draw β-L-gulose. Therefore. first draw β-D-gulose (gulose differs from glucose at C3 and C4. if you want to draw α-D-mannose. H H HO H H O OH H OH OH CH2OH HO HO HOH2C O OH OH H HO HO H H O H H OH OH CH2OH HO HO OH HOH2C OH O D-glucose D-mannose To draw an L-pyranose. Why is there more β-D-glucose than α-D-glucose in an aqueous solution at equilibrium? The OH group bonded to the anomeric carbon is in the equatorial position in β-D-glucose. You would put these two OH groups in axial positions instead. To convert a Haworth projection into a chair conformation. For example. For example. This means that β-D-glucose is the most stable of all the aldohexoses.Stability of Glucose Drawing glucose in its chair conformation shows why it is the most common aldohexose in nature. whereas it is in the axial position in α-D-glucose. Then draw the mirror image of β-D-gulose to get β-L-gulose. Because the OH group bonded to C4 is trans to the primary alcohol group (this is easily seen in the Haworth projection). so β-D-glucose predominates at equilibrium in an aqueous solution. β-D-glucopyranose O HO H HO H H CH2OH H OH H OH OH OH OH CH2OH O OH HO HO HOH2C O OH OH Fisher projection Haworth projection chair conformation As you move around the ring. OH HOH2C O OH OH OH HO HO OH O OH CH2OH β-D-gulose β-L-gulose . The C3 OH group is trans to the C4 OH group. β-D-glucose is more stable than α-D-glucose. it is easy to draw the chair conformation of any other pyranose. so the C3 OH group is also in the equatorial position. which require little space and therefore experience little steric strain. you would put all the OH groups in equatorial positions except the OH groups at C2 (because mannose is a C2 epimer of glucose) and at C1 (because it is the α-anomer). the C4 OH group is also in the equatorial position. you will find that all the OH substituents in β-D-glucose are in equatorial positions. start by placing the ring oxygen at the back right-hand corner and the primary alcohol group in the equatorial position (this is the largest of the substituents). So it is not surprising that it is the most prevalent aldohexose in nature. No other aldohexose exists in such a strain-free conformation. so the OH groups at these positions are in axial positions). and then draw its mirror image. If you remember that all the OH groups in β-D-glucose are in equatorial positions. draw the D-pyranose first. The axial positions are all occupied by hydrogens.

. so that part of the molecule is planar. Glycosides are named by replacing the ‘e’ ending of the sugar’s name with ‘ide’.Glycoside formation Aldehydes react with an alcohol to form a hemiacetal and the hemiacetal can then react with another alcohol to form a acetal. D-glucose forms more of the α-glycoside than the β-glycoside. the acetal is called a pyranoside or furanoside. The lone-pair electrons of the anomeric substituent have repulsive interactions with the lone-pair electrons of the ring oxygen if the anomeric substituent is in the β-position. Notice that the mechanism is the same as the mechanism for acetal formation. 66%) Notice that the reaction of a single anomer with an alcohol leads to the formation of both the α. The mechanism explains why. HOH2C O O OH OH OH O 3-Oxo-α-ionol 9-O-β-D-glucopyranoside – an important aroma precursor in chardonnay grapes The Anomeric Effect We have seen that β-D-glucose is more stable than α-D-glucose because there is more room for a substituent in the equatorial position.and β-glycosides. What is responsible for the anomeric effect? One clue is that all the substituents that prefer the axial position have lone-pair electrons on the atom bonded to the ring. (An oxocarbenium ion has a positive charge that is shared by a carbon and an oxygen. Thus the glycoside of glucose is a glucoside. we just saw that when glucose reacts with an alcohol to form a glucoside. The anomeric carbon in the resulting oxocarbenium ion is sp2 hybridized. when the alcohol comes in from the bottom of the plane. 33%) Methyl α-D-glucopyranoside (cyclic acetal. The preference for the axial position by certain substituents bonded to the anomeric carbon is called the anomeric effect. HOH2C HO HO OH HOH2C CH3OH OH HCl HO HO OH HOH2C O OCH3 HO HO OH OCH3 O O β-D-Glucopyranose (cyclic hemiacetal) Methyl β-D-glucopyranoside (cyclic acetal. the β-glycoside is formed. This means that the α-glucoside must be more stable than the β-glucoside. and a nonbonding pair of electrons on the ring oxygen helps expel a molecule of water. If the pyranose or furanose name is used. The reason for this is explained in the next section. However. The acetal (or ketal) of a sugar is called a glycoside. but not if it is in the αposition. the major product is the α-glucoside. attack from the top HOH2C HO HO O OH OH HOH2C HO HO O OH OH2 HOH2C HO HO O HOH2C OH H CH3OH HO HO O OH OCH3 H -H CH3OH HOH2C HO HO O OH OCH3 H -H H attack from the bottom Surprisingly. the α-glycoside is formed. The OH group bonded to the anomeric carbon becomes protonated in the acidic solution. Similarly the cyclic hemiacetal (or hemiketal) formed by a monosaccharide can react with an alcohol to form an acetal (or ketal).) When the alcohol comes in from the top of the plane.

when the hydrogen is replaced by an alkyl group. therefore. aldoses are easily oxidized to yield the corresponding carboxylic acids.HOH2C HO HO O OH O CH3 HOH2C HO HO O OH H3C O Apparently the attractive interaction of the hydrogen of the anomeric OH group of D-glucose with the lone-pair electrons of the ring oxygen decreases the importance of the anomeric effect. Maltose exists in both the α. It undergoes mutarotation and can be oxidized to a carboxylic acid by bromine water. It contains two D-glucose units. and lactose are disaccharides with α-1.4.4-glycoside linkage (or bond).or β. Maltose. Fructose is a reducing sugar because it undergoes two base-catalysed keto-enol tautomerizations that result in conversion to an aldohexose. The monosaccharides are joined by a glycoside linkage between the anomeric carbon of one monosaccharide and an −OH group of the other. depending on the configuration at the anomeric carbon atom. or Benedict’s reagent (Cu2+ in aqueous sodium citrate) to yield the oxidized sugar and a reduced metallic species. The most common glycoside linkage is between the 4-hydroxy group of one monosaccharide and the α.4-linkage. Reducing sugars Like other aldehydes. All three reagents serve as simple chemical tests for what are called reducing sugars – reducing because the sugar reduces the metal oxidizing reagent. CH2OH O HO H H H OH OH CH2OH NaOH / H2O keto-enol tautomerism H HO H H OH OH H OH OH CH2OH NaOH / H2O keto-enol tautomerism H H HO H H O OH H OH OH CH2OH D-fructose an enediol An aldohexose Disaccharides Disaccharides are dimers made up of two monosaccharide molecules.4. the anomeric effect decreases the stability of the β-position. . both in the pyranose form. One ring of maltose contains a carbonyl group that is still in a hemiacetal form. However. H H HO H H O OH H OH OH CH2OH H HO H H COOH OH H OH OH CH2OH All aldoses are reducing sugars because they contain a aldehyde carbonyl group.4-glycoside linkages.position of the anomeric carbon. so it is a reducing sugar. making β-D-glucose more stable than α-D-glucose. Maltose is the principal product of the acid. Glycosides are nonreducing because the acetal group is not hydrolysed to an aldehyde under basic conditions. The wavy bonds indicate unknown stereochemistry. Maltose. so α-glycosides are more stable than β-glycosides. reduces Fehlings solution and Tollens reagent. joined by an α-1. The monosaccharides may be either the same or different. Ketoses are only reducing if they can under-go keto-enol tautomerism to an aldehyde (e.or β-1. This carbonyl group can undergo the normal reactions of a carbonyl group of an aldose. Aldoses react with Tollens’ reagent (Ag+ in aqueous ammonia). fructose). This kind of a link is called an α-1.and β-anomeric forms.or enzyme-catalyzed hydrolysis of starch. cellobiose. Fehling’s reagent (Cu2+ in aqueous sodium tartrate).or β-1.g. called aldonic acids.

This means. Like maltose and cellobiose. so it cannot have a hemiacetal group. OH OH HO H OH α OH β O O HO H HO OH HO HO HO HO O O O O OH β OH β H OH α-Cellobiose 4-O-(β-D-glucopyranosyl)-α-D-glucopyranoside OH β-Cellobiose 4-O-(β-D-glucopyranosyl)-β-D-glucopyranoside H Lactose. It contains two D-glucose units joined by a β-1. The two are both in their pyranose forms. is a reducing sugar and undergoes mutarotation. It is obtained commercially from sugar beets and sugar cane. and exists as two anomers. hydrolysis of lactose forms one equivalent of glucose and one equivalent of galactose. lactose is a reducing sugar. Unlike maltose and cellobiose. a disaccharide that occurs in both human and cows milk. contains a β-1. . Like maltose.OH HO HO O α OH O HO H H OH HO HO OH O OH O HO α H H OH O HO H β HO OH O HO α H α-Maltose 4-O-(α-D-glucopyranosyl)-α-D-glucopyranoside β-Maltose 4-O-(α-D-glucopyranosyl)-β-D-glucopyranoside Cellobiose is a disaccharide that is obtained by the partial hydrolysis of cellulose. that the pyranose form of glucose and the furanose form of fructose are joined by an acetal link between the two anomeric carbons. cellobiose exists as two anomers.4-glycoside bond. Sucrose is not a reducing sugar.4-glycoside bond. OH OH OH HO H OH OH α OH β O O H OH HO HO HO HO O O O O OH β OH β H α-Lactose 4-O-(β-D-galactopyranosyl)-α-D-glucopyranoside OH OH β-Lactose 4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside H Sucrose (ordinary table sugar) is one of the most widespread carbohydrates in nature. so it is isomeric with maltose. and the β-glycoside bond joins the anomeric carbon of galactose with C4 of glucose. in turn. Hydrolysis of sucrose forms one equivalent of D-glucose and one equivalent of D-fructose. undergoes mutarotation.

Polysaccharides have two quite different roles in nature.4-linked polyglucose. Their different roles are due to the fact that two D-glucopyranose molecules can be joined by either β-1. D-fructose. Notice that every pyran ring in the chain is rotated 180° relative to the previous one. The most stable arrangement of D-glucopyranose molecules joined by β-1.or α-1. glucose is sometimes referred to as dextrose and fructose as levulose. Notice that every pyran ring in the straight chain is rotated by 180° relative to the previous one.4 bonds is a straight chain. [α]D = −20°. The equilibrium mixture of fructose isomers has a negative optical rotation. and sucrose. These extended chains pack tightly together because many hydrogen bonds form between the chains. Honey is largely a mixture of D-glucose. Polysaccharides Most carbohydrates in nature exist as high-molecular-weight polymers called polysaccharides. Based on the sign of their optical rotations. while others serve as structural units.4-glycoside bonds. The optical rotation of fructose is so highly negative that the 1:1 mixture of fructose and glucose formed on complete hydrolysis of sucrose is also levorotatory. Polysaccharides are formed by joining hundreds and thousands of monosaccharides by means of glycoside bonds. The reason the sugar inverts becomes apparent when we look at the optical rotations of glucose and fructose. Cellulose OH O HO O OH β H HO O A H OH β O OH O HO O O OH β H OH A.OH HO HO O OH O α H 1 2' 1' OH β O HO OH OH sucrose 2-O-(α-D-glucopyranosyl)-β-D-fructofuranoside Sucrose is dextrorotatory with [α]D = +66°.4. The remarkable fact is that the polysaccharides that function in these two ways both consist of 1. these chains are strong and chemically relatively inert. Lets first learn how a β-1. Honeybees have enzymes called invertases that catalyze the hydrolysis of sucrose to fructose and glucose. The dextrorotatory solution of pure (+)-sucrose becomes levorotatory during the hydrolysis reaction.4-linked polyglucose. Either acid. [α]D = 52°.4-glycoside bond affects the properties of a 1. as shown in Figure 3. Straight chains are the most stable arrangement of D-glucopyranose molecules that are joined together by β-1. [α]D = −92°. This solution is called invert sugar because the sign of optical rotation inverts during its preparation. while the equilibrium mixture of glucose isomers has a positive optical rotation. This results in an almost fully extended polysaccharide chain.4-glycoside bonds.or enzyme-catalyzed hydrolysis of (+)-sucrose produces an interesting phenomenon. As a result. . Some polysaccharides serve as a means of storing chemical energy. The most common monosaccharide present in polysaccharides is D-glucose. Figure 3.

B. Two D-glucopyranose units joined by an α-1. Cotton fiber and filter paper are almost entirely cellulose. A chain of D(+)-glucopyranose molecules joined by α-1. Cellulose is an example of a polysaccharide consisting of tightly packed extended chains of D-glucopyranose molecules joined by β-1.4glycoside bonds. Starch is the major source of carbohydrates in the human diet. It is estimated that branching occurs at one in every 20 to 25 glucopyranose molecules in the amylopectin chain. therefore. . The chains formed by D-glucopyranose molecules joined by β-1. Amylopectin. Cellulose is the most abundant of all polysaccharides. as shown in Figure 4. Amylopectin differs from amylose in that an occasional glucopyranose molecule in the polymer forms an additional αglycoside bond at C6. Amylose is a straight-chain polysaccharide made up entirely of D-glucopyranose molecules joined by α1. the chains of D-glucopyranose molecules joined by α-1.4 glycoside bonds. Instead of linear chains. It is the major constituent of cell membranes and other structural features of plants.4 bonds pack tightly together because many hydrogen bonds form between adjacent chains.4 glycoside bonds adopts a helical configuration. has a branched chain structure.4-linkage.B.4-glycoside bonds adopt a helical configuration. Starch O HO α H OH O α H OH O OH O HO O HO A. Starch is an example of a polysaccharide consisting of coiled chains of D-glucopyranose molecules joined by α-1.4-glycoside bonds. It is a mixture of about 20% amylose and 80% amylopectin. while wood is about 50% cellulose. Figure 4.

glycogen is a branched polymer of glucopyranose molecules joined by α-1.4g1ycoside bonds of cellulose. The extended linear chain of D-glucopyranose molecules joined by β-1. Between meals and during fasting. by a protozoan that synthesizes the enzyme cellulase. The coiled chain of D-glucopyranose molecules joined by α-1. on the other hand. so the excess is converted to glycogen and stored in the body.4-linkage B HO O O α H Glycogen is another example of a polysaccharide consisting of coiled chains of D-glucopyranose molecules joined by α1.4-glycoside bonds. Glycogen is used to store carbohydrates in animals. so we cannot use cellulose as a source of D-glucose.4-linkage HO O OH α H OH α-1.6-glycoside bonds. It is formed from D-(+)-glucose obtained by hydrolysis of starch in the food we eat.Figure 5.and α-1. The amount of glucose obtained in this way is often more that the body needs. is used in nature as an energy-storing polymer.4-linkage OH O OH HO α-1. Amylopectin O HO OH O α-1. Correlated with this difference in their functions is the widespread distribution of enzymes capable of hydrolyzing starch and glycogen and the very limited distribution of enzymes that hydrolyze cellulose. such as termites. the body hydrolyzes glycogen to glucose as it is needed. Like amylopectin.4. or in insects. . Humans do not have this enzyme.4-glyocoside bonds is used in nature for cell membranes and the structural features of plants and trees.4glycoside bonds. such as the cow. Cellulose is hydrolyzed in the gastrointestinal tract of herbivores. which hydrolyzes the β-1.6-linkage HO HO O α O α H O HO O H O α H OH O HO α-1.

4-glycosidic linkages. OH O HO NH O H O β HO O OH O NH O H β O HO NH O H OH O β O . in that it has an N-acetylamino group instead of an OH group at C2 of glucose.. It is the major structural component of the shells of crustaceans (e. lobster. Like cellulose.Chitin is a polysaccharide that is structurally similar to cellulose.g. It differs from cellulose. chitin has β-1. crabs and shrimps). the exoskeletons of insects and is a minor component of the cell wall of yeasts.