CARBOHYDRATES

By:
Dr. I. O. Otemuyiwa
Dept of Chemistry
Obafemi Awolowo University, Ile-Ife, Nigeria

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Carbohydrates are polyhydroxy aldehydes or ketones, or substances that yield such compounds on hydrolysis. Most
substances of this class have empirical formulas suggesting that they are carbon "hydrates," in which the ratio of
C : H : O is 1: 2 : 1. For example, the empirical formula of glucose is C6H12O6, which can also be written (CH2O)6 or
C6(H2O)6. Although many common carbohydrates conform to the empirical formula (CH2O)n, others do not; some
carbohydrates also contain nitrogen, phosphorus, or sulfur
There are three major size classes of carbohydrates: monosaccharides, oligosaccharides, and polysaccharides (the word
"saccharide" is derived from the Greek sakkharon, meaning "sugar").
Monosaccharides, or simple sugars, consist of a single polyhydroxy aldehyde or ketone unit. The most abundant
monosaccharide in nature is the six carbon sugar D-glucose.

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Monosaccharides
Monosaccharides are colorless, crystalline solids that are freely soluble in water but insoluble in nonpolar
solvents. Most have a sweet taste. The backbone of monosaccharides is an unbranched carbon chain in which all
the carbon atoms are linked by single bonds. One of the carbon atoms is double-bonded to an oxygen atom to
form a carbonyl group; each of the other carbon atoms has a hydroxyl group. If the carbonyl group is at an end of
the carbon chain, the monosaccharide is an aldehyde and is called an aldose; if the carbonyl group is at any other
position, the monosaccharide is a ketone and is called a ketose. The simplest monosaccharides are the two
three-carbon trioses: glyceraldehyde, an aldose, and dihydroxyacetone, a ketose.
Monosaccharides with four, five, six, and seven carbon atoms in their backbones are called, respectively,
tetroses, pentoses, hexoses, and heptoses. There are aldoses and ketoses of each of these chain lengths:
aldotetroses and ketotetroses, aldopentoses and ketopentoses, and so on.

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Reactions of Monosaccharides

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Ester and Ether Formation

The -OH groups on a monosaccharide can be readily converted to esters and ethers. Esterification can be done with
an acid chloride or acid anhydride, while treatment with an alkyl halide leads to the ether

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Summary of reactions

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Formation of glycosides
The hydroxyl group that is attached to the anomeric carbon atom (i.e., the carbon containing the aldehyde or keto
group) of carbohydrates in solution has unusual reactivity, and derivatives, called glycosides, can be formed;
glycosides formed from glucose are called glucosides. It is not possible for equilibration between the α- and
β-anomers of a glycoside in solution (i.e., mutarotation) to occur. The reaction by which a glycoside is formed
involves the hydroxyl group (―OH) of the anomeric carbon atom (numbered 1) of both α and β forms
of D-glucose—α and β forms of D-glucose are shown in equilibrium in the reaction sequence—and the hydroxyl
group of an alcohol (methyl alcohol in the reaction sequence); methyl α-D-glucosides and β-D-glucosides are
formed as products, as is water.

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 Disaccharides
Disaccharides are a specialized type of glycoside in which the anomeric hydroxyl group of one sugar has
combined with the hydroxyl group of a second sugar with the elimination of the elements of water.
Sucrose, or common table sugar, its world production had amounted to more than 170 million tons annually. The
unusual type of linkage between the two anomeric hydroxyl groups of glucose and fructose means that neither a
free aldehyde group (on the glucose moiety) nor a free keto group (on the fructose moiety) is available to react
unless the linkage between the monosaccharides is destroyed; for this reason, sucrose is known as a
nonreducing sugar.

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Maltose, or malt sugar, is a disaccharide formed by a dehydration reaction between two glucose molecules.

Lactose is a disaccharide consisting of the monomers glucose and galactose.

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 Polysaccharides
A long chain of monosaccharides linked by glycosidic bonds is known as a polysaccharide (poly– = “many”). The
chain may be branched or unbranched, and it may contain different types of monosaccharides. The molecular
weight may be 100,000 daltons or more depending on the number of monomers joined. Starch, glycogen,
cellulose, and chitin are primary examples of polysaccharides.
Starch is the stored form of sugars in plants and is made up of a mixture of amylose and amylopectin (both
polymers of glucose).
Starch is made up of glucose monomers that are joined by α 1-4 or α 1-6 glycosidic bonds. The numbers 1-4 and
1-6 refer to the carbon number of the two residues that have joined to form the bond. As illustrated in Figure below
amylose is starch formed by unbranched chains of glucose monomers (only α 1-4 linkages), whereas amylopectin
is a branched polysaccharide (α 1-6 linkages at the branch points)

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Cellulose is the most abundant natural biopolymer. The cell wall of plants is mostly made of cellulose; this
provides structural support to the cell. Wood and paper are mostly cellulosic in nature. Cellulose is made up of
glucose monomers that are linked by β 1-4 glycosidic bonds
As shown in Figure below, every other glucose monomer in cellulose is flipped over, and the monomers are
packed tightly as extended long chains. This gives cellulose its rigidity and high tensile strength—which is so
important to plant cells. While the β 1-4 linkage cannot be broken down by human digestive enzymes, herbivores
such as cows, koalas, buffalos, and horses are able, with the help of the specialized flora in their stomach, to
digest plant material that is rich in cellulose and use it as a food source.

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Thank you

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