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0.2 Biological macromolecules: carbohydrates  (Page 2/13)

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The molecular structures of the linear forms of glucose, galactose, and fructose are shown. Glucose and galactose are both aldoses with a carbonyl group (carbon double-bonded to oxygen) at one end of the molecule. A hydroxyl (OH) group is attached to each of the other residues. In glucose, the hydroxyl group attached to the second carbon is on the left side of the molecular structure and all other hydroxyl groups are on the right. In galactose, the hydroxyl groups attached to the third and fourth carbons are on the left, and the hydroxyl groups attached to the second, fifth and sixth carbon are on the right. Frucose is a ketose with C doubled bonded to O at the second carbon. All other carbons have hydroxyl groups associated with them. The hydroxyl group associated with the third carbon is on the left, and all the other hydroxyl groups are on the right.
Glucose, galactose, and fructose are all hexoses. They are structural isomers, meaning they have the same chemical formula (C 6 H 12 O 6 ) but a different arrangement of atoms.

What kind of sugars are these, aldose or ketose?

Glucose, galactose, and fructose are isomeric monosaccharides (hexoses), meaning they have the same chemical formula but have slightly different structures. Glucose and galactose are aldoses, and fructose is a ketose.

Monosaccharides can exist as a linear chain or as ring-shaped molecules; in aqueous solutions they are usually found in ring forms ( [link] ). Glucose in a ring form can have two different arrangements of the hydroxyl group (OH) around the anomeric carbon (carbon 1 that becomes asymmetric in the process of ring formation). If the hydroxyl group is below carbon number 1 in the sugar, it is said to be in the alpha ( α ) position, and if it is above the plane, it is said to be in the beta ( β ) position.

The conversion of glucose between linear and ring forms is shown. The glucose ring has five carbons and an oxygen. In alpha glucose, the first hydroxyl group is locked in a down position, and in beta glucose, the ring is locked in an up position. Structures for ring forms of ribose and fructose are also shown. Both sugars have a ring with four carbons and an oxygen.
Five and six carbon monosaccharides exist in equilibrium between linear and ring forms. When the ring forms, the side chain it closes on is locked into an α or β position. Fructose and ribose also form rings, although they form five-membered rings as opposed to the six-membered ring of glucose.

Disaccharides

Disaccharides (di- = “two”) form when two monosaccharides undergo a dehydration reaction (also known as a condensation reaction or dehydration synthesis). During this process, the hydroxyl group of one monosaccharide combines with the hydrogen of another monosaccharide, releasing a molecule of water and forming a covalent bond. A covalent bond formed between a carbohydrate molecule and another molecule (in this case, between two monosaccharides) is known as a glycosidic bond    ( [link] ). Glycosidic bonds (also called glycosidic linkages) can be of the alpha or the beta type.

The formation of sucrose from glucose and fructose is shown. In sucrose, the number one carbon of the glucose ring is connected to the number two carbon of fructose via an oxygen.
Sucrose is formed when a monomer of glucose and a monomer of fructose are joined in a dehydration reaction to form a glycosidic bond. In the process, a water molecule is lost. By convention, the carbon atoms in a monosaccharide are numbered from the terminal carbon closest to the carbonyl group. In sucrose, a glycosidic linkage is formed between carbon 1 in glucose and carbon 2 in fructose.

Common disaccharides include lactose, maltose, and sucrose ( [link] ). Lactose is a disaccharide consisting of the monomers glucose and galactose. It is found naturally in milk. Maltose, or malt sugar, is a disaccharide formed by a dehydration reaction between two glucose molecules. The most common disaccharide is sucrose, or table sugar, which is composed of the monomers glucose and fructose.

The chemical structures of maltose, lactose, and sucrose are shown. Both maltose and lactose are made from two glucose monomers joined together in ring form. In maltose, the oxygen in the glycosidic bond points downward. In lactose, the oxygen in the glycosidic bond points upward. Sucrose is made from glucose and fructose monomers. The oxygen in the glycosidic bond points downward.
Common disaccharides include maltose (grain sugar), lactose (milk sugar), and sucrose (table sugar).

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.
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Source:  OpenStax, Biological macromolecules (gpc). OpenStax CNX. Feb 26, 2014 Download for free at http://cnx.org/content/col11584/1.5
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