Chapter 11: Carbohydrates
Chapter 11: Carbohydrates
Chapter 11 Educational en a Fischer projection of a monosaccharide, classify it as either aldoses or ketoses.Given a Fischer projection of a monosaccharide, classify it by the number of carbons itcontains.Given a Fischer projection of a monosaccharide, identify it as a D-sugar or L-sugar.Given a Fischer projection of a monosaccharide, identify chiral carbons and determine thenumber of stereoisomers that are possible.Identify four common types of monosaccharide derivatives.Predict the products when a monosaccharide reacts with a reducing agent or withBenedict’s reagent.Define the term anomer and explain the difference between α and β anomers.Understand and describe mutarotation.Given its Haworth projection, identify a monosaccharide either a pyranose or a furanose.Identify the anomeric carbon in Haworth structures.Compare and contrast monosaccharides, disaccharides, oligosaccharides, andpolysaccharides.Given the structure of an oligosaccharide or polysaccharide, identify the glycosidic bond(s)and characterize the glycosidic linkage by the bonding pattern [for example: β(1 4)].Given the Haworth structures of two monosaccharides, be able to draw the disaccharidethat is formed when they are connected by a glycosidic bond.Understand the difference between homopolysaccharides and heteropolysaccharides.Compare and contrast the two components of starch.Compare and contrast amylopectin and glycogen.Identify acetal and hemiacetal bonding patterns in carbohydrates.
An Introduction to CarbohydratesCarbohydrates are quite abundant in nature. More than half of the carbon found inliving organisms is contained in carbohydrate molecules, most of which are containedin plants.The primary reason for such an abundance is that a carbohydrate is produced by a seriesof chemical reactions that we call photosynthesis.Energy from sunlight is used by plants to provide energy to drive the photosynthesisprocess. In the photosynthesis process, carbon dioxide and water are converted tooxygen gas and a carbohydrate called glucose.Plants can use glucose to produce the ATP molecules that are needed to do the worknecessary for life. Plants store excess glucose as starch, for later use.Animals obtain energy that is stored in starch by eating plants, or by eating animals thatate plants or had herbivores in their food-chain.Carbohydrates are also referred to as sugars or saccharides.
MonosaccharidesMonosaccharides are the smallest carbohydrates and serve as the building blocks oflarger carbohydrates. They are also referred to as simple sugars.Monosaccharides have the general chemical formula of Cn(H2O)n; where n (thenumber of carbon atoms ) can be three to seven.They are polyhydroxyl aldehydes or ketones: Monosaccharides contain either an aldehyde group or a ketone bonding pattern. Monosaccharides contain more than one hydroxyl (OH) group.
A monosaccharide that contains an aldehyde group is called an aldose.A monosaccharide that contains the ketone bonding pattern is called a ketose.general form of an aldosegeneral form of a ketoseNote that the group in the parenthesis can repeat.an aldose structure where X 3a ketose structure where X 3
Understanding CheckClassify each of the following monosaccharides as either an aldose or a ketose.
Monosaccharides can be classified according tothe number of carbons they contain.A monosaccharide may also be classified by both the number of carbons and whether itis an aldose or a ketose. This is done by using the prefix “aldo” for aldoses, or “keto” for ketoses, in front of“triose,” “tetrose,” “pentose,” “hexose,” or “heptose.” For example, an aldose that contains five carbons is an aldopentose.an aldopentose
Understanding CheckClassify each of the following monosaccharides using the prefix “aldo” for aldoses, or“keto” for ketose, in front of “ triose,” “tetrose,” “pentose,” “hexose,” or “heptose.”
Stereochemistry of MonosaccharidesExcept for the ketotriose, monosaccharides contain at least one chiral carbon.Recall, that a chiral carbon is a carbon that is surrounded by four different groups.Molecules with just one chiral carbon have a pair of geometric isomers calledenantiomers.Enantiomers have the same atomicconnections, but a different threedimensional arrangement of atoms,and are nonsuperimposable mirrorimages of each other.
If a molecule has more than one chiral carbon, then it will have more than one pair ofenantiomers.If a monosaccharide has n chiral carbons, then it will have 2n stereoisomers. For example, if amolecule has three chiral carbons, then it will have 23 (2 x 2 x 2) 8 stereoisomers (four pairsof enantiomers).Example: How many stereoisomers are possible for the monosaccharide shown below?Solution: Identify the number of chiral carbons, and then calculate the number of stereoisomers. There are four chiral carbons in this molecule. The chiral carbons are highlighted in thestructure below.HOHHHHHOCCCCCCHOHOHOHOHHRecall that a carbon is chiral if it is surrounded by four different groups; you must considerwhether each of the entire groups bonded to the carbon are different from each other. In thisexample, the left-most carbon is not chiral because it is bonded to two hydrogen atoms. Theright-most carbon is not chiral because it is only bonded to three groups.Since this monosaccharide structure has four chiral carbons, there are 24 (2 x 2 x 2 x 2) 16possible stereoisomers (eight pairs of enantiomers).
We found that there are 16 different molecules (stereoisomers) that share this molecular formulaand structural formula.Most of the physical properties of these 16 stereoisomers are quite similar; however, the way theyeach behave in biological systems can be very different.HOHHHHHOCCCCCCHOHOHOHOHH
Let’s consider the three dimensional arrangement of the atoms in the smallest monosaccharide,glyceraldehyde. Glyceraldehyde has only one chiral carbon.HOHHOCCCHOHHglyceraldehydeThe chiral carbon in the structuralformula is highlighted in red.the pair of glyceraldehyde enantiomers(nonsuperimposable mirror images)Since there is one chiral carbon in glyceraldehyde, then there are 2n 21 2 stereoisomers (onepair of enantiomers/nonsuperimposable mirror images).
In order for professionals in healthcare,engineering, and science fields to discuss anddepict the various monosaccharidestereoisomers, it is necessary to be able to drawtwo-dimensional (flat) structural formulas on apage or computer display, such that they stillcontain the three-dimensional informationparticular to each stereoisomer.In previous chapters, we used the wedge anddash system to retain the three-dimensionalinformation on a flat surface.wedge and dash representationsFor monosaccharides, Fischer projections are used for this purpose.
Fisher projections are related to an imaginary “shadow” that would be produced if a chiral carbon and itsfour bonded groups were placed in a particular orientation between a light source and a surface.In Fischer projections, chiral carbons are implied to be at the intersection of a vertical and horizontal line.Fischer’s choice of the particular orientation of the chiralcarbon and its four groups was arbitrary, any orientation couldhave been used; however, for consistency, one specificorientation needed to be chosen.The chosen orientation of a chiral carbon and the four groupsthat are bonded to it relative to the drawing surface/page in allFischer Projections is as follows:The bonds from the chiral carbon to the other carbon atomspoint at a downward angle, and their shadows form verticallines on the Fischer projection. In this model, these are the bonds from the chiral carbonto groups Y and W.The bonds from the chiral carbon to the non carbon groupspoint at an upward angle, and their shadows form horizontallines on the Fischer projection. In this model, these are the bonds from the chiral carbonto groups X and Z.XZCYstereoisomerWshadowFischerprojectionFor aldoses, the aldehyde group is positioned at the end of the molecule that is closest to the top of the page(position W).For ketoses, the carbonyl carbon is positioned as close as possible to the end molecule that is nearest the top ofthe page.
Let’s consider the Fischer projections for both of the glyceraldehyde stereoisomers.Recall that glyceraldehyde has one chiral carbon.Because the other two carbons in glyceraldehyde are not chiral, shorthand notation is used tosimplify the e aldehyde group isrepresented by “CHO.”
HHOH2CCCHOOHglyceraldehydeThe Fischer projections for the twoenantiomers of glyceraldehyde are:
The Fischer projections for the twoenantiomers of glyceraldehyde:We do not need to draw the bonds around the top orbottom carbon atoms because they are not chiral.Note that we draw the hydroxyl groups that are onthe left-hand side of Fischer projections as “HO.”
For monosaccharides with more than one chiral carbon, Fischer projections must be drawn (orinterpreted) by considering the orientation around each of the chiral carbons.This is done one chiral carbon at a time. As an example, let’s consider aldotetroses, whichcontain two chiral carbons:an aldotetroseSince aldotetroses each have two chiral carbons, there are 22 (2 x 2) 4 stereoisomers (twopairs of enantiomers).CHOCHOCHOHOHHOHHOHOHHOHHCH2OHCH2OHan enantiomer pair(mirror images)CHOHOHCH2OHOHHHHOCH2OHan enantiomer pair(mirror images)Note that the hydrogen (H) and the hydroxyl group (OH) positions are reversed on chiralcarbons for each particular enantiomer pair.
Implication of a Fischer ProjectionWedge and Dash RepresentationFischer ProjectionCHOHOHHOHCH2OH
Understanding CheckAn aldopentose contains three chiral carbons, and therefore there are 23 8 aldopentosestereoisomers. Draw Fischer projections of the eight stereoisomers.
D- and L- Designations for MonosaccharidesCarbohydrates are most often referred to by their common names, all of which use the “-ose”suffix. A common name is assigned to each pair of enantiomers.In order to differentiate the two individual monosaccharides of an enantiomer pair, ‘D-’ or ‘L-’designations are used with the common name. The ‘L-’ designation is used for the enantiomer in which the chiral carbon that is furthestfrom the top of the Fischer projection has its hydroxyl group on the left. The ‘D-’ designation is used for the other enantiomer of the L-erythrose(an enantiomer pair)HOHCH2OHCHOHHOOHHCH2OHD-threoseL-threose(an enantiomer pair)Monosaccharides with the L- designation are sometimes referred to as “L-sugars,” and thosewith the D- designation are sometimes referred to as “D-sugars.”
Monosaccharides are produced in living organisms by chemical reactions, some of which requireenzymes that can only produce one particular enantiomer.For example, the stereoisomer of glucose that is made in photosynthesis is D-glucose.Fischer projections for both of the glucose enantiomers are shown ucoseL-glucose(an enantiomer pair)Dashed boxes are shown around the chiral carbons and hydroxyl groups responsible for theD- and L- designations.The glucose enantiomer pair (D-glucose and L-glucose) are two of the sixteen aldohexosestereoisomers. There are seven more aldohexose enantiomer pairs that can be drawn by varying the positionsof the H and OH on each side of a Fischer projection. These seven other enantiomer pairs are differentiated from glucose, and each other, by theircommon names.
An example of a ketose is fructose. D-Fructose is one of our major dietary HCH2OHD-fructoseL-fructose(an enantiomer pair)
Understanding CheckClassify each of the eight stereoisomers shown below as either D- or L- HOHHOHHOHHOHCH2OHHOHCH2OHHOHHOHCH2OHHOHHOHOHHCH2OH
The Cyclic Forms of MonosaccharidesWhen monosaccharides that contain five to seven carbons are in aqueous solutions, they canundergo a reaction in which they rearrange their bonding pattern to form cyclic structures.It is a reversible reaction in which the open-chain form is interconverted with the cyclic form. Example: The cyclization rearrangement reaction is shown below for a D-glucose scher projection(open-chain form)C1 coseHaworth projection(cyclic form)The cyclic form is lower in energy and is therefore the predominant form. In most solutions, the equilibrium ratio of cyclic form to open-chain form is aboutone hundred to one.The side view structures of cyclic monosaccharides (above, right), are called Haworthprojections or Haworth structures. The carbon atoms that form the ring are not drawn explicitly, but are implied to occurwhere lines/bonds meet.
To help you understand the three-dimensional implications of Haworth projections, I havedrawn a ball-and-stick model that shows the actual geometry/bond angles of the cyclic form ofD-glucose, next to its Haworth Projection representation:ball-and-stick model(actual molecular geometry)Haworth projection I used large black dots at the ring-carbon positions in both structures. Each ring-carbon is bonded to two other ring-atoms and two other groups. Groups that are oriented upward relative to the ring-carbons are shaded green. Groups that are oriented downward from ring-carbons are shaded red.
The rearrangement/cyclization reaction of a monosaccharide is actually a form of thehemiacetal formation reaction that you learned about at the end of the previous chapter.Let’s take a moment to review that reaction.A hemiacetal is a molecule that contains both an OR group and OH group that are bonded to thesame carbon.general form of a hemiacetalAn aldehyde or a ketone will react with an alcohol to form a hemiacetal.The OR” from the alcohol forms a bond to the carbonyl-carbon of the aldehyde or ketone, the Hfrom the alcohol bonds to the carbonyl-oxygen, and the carbonyl group’s double bond is changedto a single bond.aldehyde or ketonealcoholhemiacetal
Now let’s think about how this reaction can occur for a monosaccharide.A hemiacetal is formed when a monosaccharide’s hydroxyl group reacts with its carbonyl e(cyclic form)6CH2OH5HWhen the OR bonding pattern occurs in this way, forminga ring, the molecule is referred to as a cyclic hemiacetal.OH2HD-glucose(open-chain form, drawn curved)D-glucose(open-chain form, drawn curved)H3OHNote that, beginning at carbon number 1 and moving counter-clockwise,as indicated by the red arrow, the OR bonding pattern is seen.OH4HCH2OH4OHOHHOHOH123HHOHD-glucose(cyclic form)ROHO1CH
An example of the cyclization of a ketose (fructose) is shown eFischer projection(open-chain form) ctoseHaworth projection(cyclic form)
The most common cyclic monosaccharide structures are five- and six-member rings.Cyclic monosaccharides with five-member rings are called furanoses, and those with sixmember rings are called pyranoses. These terms are often used as suffixes when naming cyclic monosaccharide structures. Examples:A six-member ringA five-member ringCH2OHHHOHOHHOHOHD-glucopyranose(a pyranose)OHHCH2OHOHOOHHCH2OHHHOHD-fructofuranose(a furanose)
The cyclization reaction is reversible; the cyclic form interconverts with the open-chain formwhen monosaccharides are in solution.Each time that the open-chain form is converted to the cyclic form, one of two cyclicenantiomers will be formed. Example: The cyclization of D-glucose.Rotation of the Aldehyde (open-chain form)HOHHO3HOH1C265HOHHO HOHHO3HOH6 CH2OHCH2OH5O4OD-glucose(open-chain form)6HC2HCaused by rotation around the bondbetween carbon 1 and carbon 2.1H3OHHOH4HCH2OHHOH12OHβ-D-glucopyranose(cyclic form)HEnantiomers(a cyclic enantiomer pair)5H4OHOHHO3HHH12OHα-D-glucopyranose(cyclic form)OH
Rotation of the Aldehyde open-chain form)5OOHHHHO3H1C265HOHHO HOHHO3HOH6 CH2OHCH2OH5O4OD-glucose(open-chain form)6HC2HCaused by rotation around the bondbetween carbon 1 and carbon 2.1H3OHHOH4HCH2OHHOH12OHβ-D-glucopyranose(cyclic form)HEnantiomers(a cyclic enantiomer pair)5H4OHOHHO3HHH12OHOHα-D-glucopyranose(cyclic form)In the open-chain form of D-glucose that is shown in top-left of the illustration above, thecarbonyl group (C O) is oriented upward from the ring; therefore, when the cyclic hemiacetal isformed (bottom, left), the new hydroxyl group (OH) will be oriented upward from carbonnumber 1. Free rotation occurs around single bonds in the open-chain form (as depicted in thebox in the top-middle of the illustration). Rotation around the bond between carbon number 1and carbon number 2 of the open-chain form causes the carbonyl group to, at times, be orienteddownward from the ring (as seen in the open-chain form in the top-right of the illustration). Inthis arrangement, when the cyclization reaction occurs, the cyclic hemiacetal is formed with thenew hydroxyl group (OH) oriented downward from carbon number 1 (as seen in the bottomright structure of the illustration).
The formation of either of two different cyclic structures, a cyclic enantiomer pair, is possiblebecause of the four different groups bonded to a chiral hemiacetal carbon (the carbon whichcontains an OH and an OR).This carbon is called the anomeric carbon.The cyclic enantiomers are almost identical; the only difference is that the bonding patternaround the anomeric carbons are mirror images.anomeric carbons6 CH62OHCH2OH5OH4HOHHO3HHOH12HEnantiomers(a cyclic enantiomer pair)OHβ-D-glucopyranose(cyclic form)5H4OHOHHO3HHH12OHOHα-D-glucopyranose(cyclic form)The sugar produced in photosynthesis, and almost all of the other monosaccharides found inplants and animals, are D-sugars. At some point in the history of Earth, nature showed apreference for D-sugars.For the remainder of this course, you will only see D-sugars.
It is easy to identify the anomeric carbon in a Haworth projection of a D-sugar; it is the ringcarbon to the right-hand side of the ring-oxygen.The two enantiomers that can be formed during the cyclization process are called anomers.They are classified, based on the orientation of the hydroxyl group (OH) on the anomericcarbon, as the α-anomer or the β-anomer. The α-anomer has the OH on the anomeric carbon oriented downward from the ring. The β-anomer has the OH on the anomeric carbon oriented upward from the ring.β-anomerα-anomeranomeric carbons6 clic yclic form)OH
H6CH2OH5OHOH4OHHO31HCH2HOHD-glucose(open-chain form)6 CH2OH5H4HOHHO3H6HOH1C 5H4HCH2OHOHHOH1OHOHD-glucose(open-chain form) β-anomerα-anomer6 HH12OHα-D-glucopyranose(cyclic form)β-D-glucopyranose(cyclic form)The conversion from α-anomer, to theopen-chain form, then to the β-anomer(and vice versa) is called mutarotation.OH
The formation of β-anomers or α-anomers also occurs, for the same reason, for ketoses. For example, the cyclization of D-fructose results in the formation of two possible anomers,as shown below.anomeric β-D-fructofuranose)H1 CH2OHOOH4HH23OHOHα-anomer(α-D-fructofuranose)
Understanding CheckFor the molecules shown below,a) Classify each of the molecules as either a pyranose or a furanose.b) Label the anomeric carbon.c) Classify each as either a β-anomer or an HOHOHCH2OHHOHOH
Alternative Methods for Drawing Cyclic Forms of H3H2H4HOOH32HH14OHHOHdrawn in the style thatI will use in this wn without hydrogenson ring-carbonsH14OHOH1OH6HOHdrawn using vertical linesfor bonds to ring-carbons.α-D-glucopyranoseHOCH2OH54HOHdrawn using wedge and dashnotation at the anomeric carbon.HOH1HOHdrawn using vertical linesfor bonds to ring-carbons.1OHOH6H62OH4HCH2OH56 CH1236HHOHHOHdrawn using wedge and dashnotation at the anomeric carbon.OHOHHOCH2OH5H4HOHdrawn in the style thatI will use in this course.6H1HCH2OH5OHOCH2OHO51OH32OHOHdrawn without hydrogenson ring-carbons
I would like you to be able to do the following on an examination:Given a Haworth projection of a D-monosaccharide:1. Identify the molecule as a pyranose or a furanose.1. Identify the anomeric carbon.1. Identify the molecule as the β-anomer or the α-anomer.1. Understand the definition of mutarotation.1. Understand how the three-dimensional arrangement of atoms in a monosaccharide (asseen in a ball-and-stick model) is implied by a Haworth projection.
Summary of Monosaccharides Stereochemistry
Monosaccharide Derivatives and ReactionsMonosaccharide derivatives are compounds that are derived from monosaccharides.I will introduce you to four classes of monosaccharide derivatives:1)2)3)4)Amino SugarsCarboxylic Acid SugarsAlcohol SugarsDeoxy Sugars
Amino SugarsIn an amino sugar, a hydroxyl group (OH) of a monosaccharide has been replaced by anamino group (NH2).An example of an amino sugar is D-glucosamine. D-Glucosamine is derived when thehydroxyl group on carbon number 2 of D-glucose is replaced by an amino pen-chain D-glucosamineα-D-glucosamineLike monosaccharides, amino sugars undergo mutarotation.O6C1CH2OH5H4HOHOHHO3HHHOH12NH2H 2HO3H4H56NH2HOHOH chain D-glucosamineα-D-glucosamineOH
D-Glucosamine of the larger monosaccharidecontaining polymers that make up the exoskeletonsof crustaceans (e.g. shrimp, lobster, crab) and otherarthropods.D-glucosamine is purified for commercial use byprocessing exoskeletons or other organic materialthat contains it. Although it has been deemed safefor human consumption and sold as a “dietarysupplement,” its actual effectiveness in thetreatment of any health/medical condition,according to the US National Institutes of Health,has not been established.
Carboxylic Acid SugarsIn a carboxylic acid sugar, an aldehyde group (CHO) of a monosaccharide has been replaced bya carboxyl group (COOH).This is done by a reaction that you have previously seen, oxidation of aldehydes to carboxylicacids. Example: D-glucose can be oxidized to produce D-gluconic acid:OOHCOHCHOHHOHHOHCH2OHD-glucose[O] HOHHOHHOHCH2OHD-gluconic acid
This oxidation of aldoses reaction was used for about 50 years in the measurement of blood sugarlevels.Stanley Benedict first discovered and published a method in whicha solution containing Cu2 ions acts as an oxidizing agent in theconversion of aldoses to carboxylic acid sugars.This solution is now referred to as Benedict’s reagent.It is used as a test for aldoses since it will oxidize the aldehydegroups but not the hydroxyl groups or the ketone bonding patterns.OOHCOHCHOHHOHHOHCH2OHD-glucose[O] HOHHOHHOHCH2OHD-gluconic acidStanley Benedict1884 - 1936
Cu2 ions appear clear-blue when in solution. If a sample that contains an aldose is placed in atest tube that contains hot Benedict's reagent, the Cu2 will be reduced to Cu1 . The Cu1 thenreacts with hydroxide to form a colored solid. As the aldose concentration in a sample increases,more of the colored solid is made and the color of the Benedict’s test goes from blue to green toorange to red to brown. When a color change is observed, we say that it is a “positive” test.aldose concentration (% w/v)Exception: Although fructose is a ketose (not an aldose), it gives a positive Benedict’s test result.Sugars that produce a color change in Benedict’s reagent are called “reducing sugars,” since theyreduce Cu2 to Cu1 .Because Benedict’s reagent is not specific for D-glucose, which is the important blood sugarspecies in diabetes monitoring, its use in most medical diagnostic work has been replaced byglucometers. Glucometers are much more specific in sensing only D-glucose since they arebased on a naturally-occurring enzyme which only catalyzes a reaction of D-glucose.
Understanding CheckDraw the Fischer projection of the carboxylic acid sugar that is formed when the aldehyde groupof D-ribose (shown below) is oxidized.OHCHOHHOHHOHCH2OHD-ribosea carboxylic acid sugar
Alcohol SugarsAlcohol sugars, sometimes called “sugar alcohols,” are derived when the carbonyl group (C O)of a monosaccharide is reduced to a hydroxyl (OH) group.This is done by a reaction that you have previously seen, reduction of aldehydes and ketones toalcohols.OHCH2OHC Example of the reduction of amonosaccharide (D-glucose) toform an alcohol sugar (sorbitol):HHOOHHHOHHOH[R] HHOOHHHOHHOHCH2OHCH2OHD-glucosesorbitol(an alcohol sugar)Alcohol sugars are used in the food and beverage industry as thickeners and sweeteners. Unlikesugars, alcohol sugars cannot be metabolized by oral bacteria, and therefore do not cause toothdecay. Unfortunately for chefs, alcohol sugars do not caramelize, as do natural sugars. Sorbitolcan be manufactured by the reduction of D-glucose and it also occurs naturally in pears, peaches,prunes, and apples. Sorbitol is used as a sugar substitute, mostly to replace natural sugars inorder to prevent tooth decay. It is not so effective as a dietary aid because it can be metabolizedby humans for energy. On a per gram basis, it provides 65% of the energy of natural sugars, yetis only 60% as sweet as table sugar (sucrose). Sorbitol is used in toothpaste, mouthwash, andchewing gum. It is also used, in greater quantities, as an orally or rectally administered laxative.
Alcohol Sugars Other examples of alcohol sugars are mannitol and OHCH2OHxylitolMannitol is used as a sweetener and has many applications in medicine. It is frequentlyused as a filler in the production of tablets of medicine.Xylitol is used as a sweetener in chewing gum. Like other alcohol sugars, it is unusable byoral bacteria. However, unlike the other alcohol sugars, xylitol aids in the recalcification ofteeth.
Understanding CheckDraw the Fischer projection of the alcohol sugar that is formed when D-ribose (shown below) isreduced.OHCHOHHOHHOHCH2OHD-ribose
Deoxy SugarsDeoxy sugars are derived when a hydroxyl group (OH) in a monosaccharide is replaced by ahydrogen atom. Example: D-2-deoxyribose (a deoxy sugar) is derived when the hydroxyl group oncarbon number 2 of D-ribose (a monosaccharide) is replaced by a hydrogen atom:OHOC1H2H3H4HC1OHOH OH5CH2OHD-ribose(a monosaccharide)H2H3H4HOHOH5CH2OHD-2-deoxyribose(a deoxy sugar)The “2” in D-2-deoxyribose indicates the carbon position where a hydrogen (H)replaces a hydroxyl group (OH) of the D-ribose monosaccharide.
Deoxy SugarsO5CH2OH4HH3OHC1HOH21OHH H2H3HH45HOHOH se(a oxyribose(a deoxy sugar)Like monosaccharides, deoxy sugars undergo mutarotation.D-2-deoxyribofuranose is one of the residues that make deoxyribonucleic acids (DNA).
Understanding CheckD-2-deoxyglucose is currently being used in the development of anticancer strategies.Using the Fischer projection of D-glucose (shown below) as the starting point, draw the Fischerprojection of seD-2-deoxyglucose
Table for the Review of Monosaccharide Derivatives
Understanding CheckIdentify each of the molecules shown below as either a monosaccharide, amino sugar, carboxylicacid sugar, alcohol sugar, or a deoxy .OOHHHHHOHHOHOHHOHHOHCH2OH
Carbohydrates can be classified into three major groups based on their size:1) monosaccharides2) oligosaccharides3) polysaccharidesOligosaccharidesOligosaccharides are molecules that are made when two to ten monosaccharides chemicallybond to each other.Molecules from particular organic families (such as monosaccharides) are referred to as“residues” when they bond together to form a large molecule.Oligosaccharides are often subcategorized by the number of monosaccharide residues that theycontain. For example, an oligosaccharide that is composed of two monosaccharide residues iscalled a disaccharide. Likewise, an oligosaccharide made from three monosaccharide residues is called atrisaccharide.
Let’s consider the bond formed betweentwo α-D-glucose monosaccharides.I will sometimes use large black dots atthe position of the anomeric carbons inorder to draw your attention to them.Step 1: An H atom is removed from thehydroxyl group (OH) that is bonded tothe anomeric carbon of the left-mostresidue, and an OH is removed fromany carbon in the right-most residue.The H and OH that were removed forma water molecule.Step 2: Draw a new bond from theoxygen (O) that remains on the anomericcarbon in the left-most residue to thecarbon from which the OH was removedin the right-most residue. This new bond is oriented in the samedirection as was the bond to OH thatwas removed.This method can be used to form a bond between any two sugar residues.The disaccharide that is formed in this example is called maltose.
Maltose is found in malt, which is purified from germinated grains. Brewers interrupt the barleygrain germination to obtain what is referred to as malted barley. Malted barley has a highconcentration o
Chapter 11 Educational Goals 1. Given a Fischer projectionof a monosaccharide, classify it as either aldosesorketoses. 2. Given a Fischer projectionof a monosaccharide, classify it by the number of carbons it contains. 3. Given a Fischer projectionof a monosaccharide, identify it as a D-sugaror L-sugar. 4. Given a Fischer projectionof a monosaccharide, identify chiral
Part One: Heir of Ash Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18 Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 Chapter 24 Chapter 25 Chapter 26 Chapter 27 Chapter 28 Chapter 29 Chapter 30 .
Complex Carbohydrates Include starches and some forms of fiber. About 50% of your diet should come from complex carbohydrates. Examples of foods containing complex carbohydrates include pasta, wheat, corn, vegetables, fruit, sweet potatoes, beans and grains. Simple carbohydrates Include sugars such as glucose, fructose and sucrose.
Chapter 22 -Carbohydrates Chem 306 Roper I. Carbohydrates - Overview A. Carbohydrates are a class of biomolecules which have a variety of functions. 1. energy 2. energy storage 3. structure 4. other functions! B. Chemically speaking carbohydrates are polyhydroxyaldehydes, polyhydroxyketones, or compounds that yield them after hydrolysis. CH
TO KILL A MOCKINGBIRD. Contents Dedication Epigraph Part One Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 Part Two Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18. Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 Chapter 24 Chapter 25 Chapter 26
Carbohydrates are, in fact, an essential part of our diet; grains, fruits, and vegetables are all natural sources of carbohydrates. Carbohydrates provide energy to the body, particularly through glucose, a simple sugar that is a component of starch and an ingredient in many staple foods. Carbohydrates also have other
Carbohydrates: Complex and Simple Complex Carbohydrates are also known as starches and fibers. Complex carbohydrates in the form of starches should be included in the diet and should make up the bulk of your daily calories. Complex carbohydrates in the form of fiber should be avoided. Simple carbohydrates are also known as sugars.
DEDICATION PART ONE Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 7 Chapter 8 Chapter 9 Chapter 10 Chapter 11 PART TWO Chapter 12 Chapter 13 Chapter 14 Chapter 15 Chapter 16 Chapter 17 Chapter 18 Chapter 19 Chapter 20 Chapter 21 Chapter 22 Chapter 23 .
Food Carbohydrates: Chemistry, Physical Properties, and Applications is intended as a comprehensive reference book for researchers, engineers, and other professionals who are interested in food carbohydrates. The layout and content of the book may be suitable as a reference or text book for advanced courses on food carbohydrates.
