25.1: Classification of Carbohydrates

Objectives

After completing this section, you should be able to

1. classify a specific carbohydrate as being a monosaccharide, disaccharide, trisaccharide, etc., given the structure of the carbohydrate or sufficient information about its structure.
2. classify a monosaccharide according to the number of carbon atoms present and whether it contains an aldehyde or ketone group.

Key Terms

Make certain that you can define, and use in context, the key terms below.

• aldose
• disaccharide
• ketose
• monosaccharide (simple sugar)
• polysaccharide

What Are Carbohydrates?

The most abundant biomolecules on earth are carbohydrates. From a chemical viewpoint, carbohydrates are primarily a combination of carbon and water, and many of them have the empirical formula (CH₂O)_n, where n is the number of repeated units. This view represents these molecules simply as “hydrated” carbon atom chains in which water molecules attach to each carbon atom, leading to the term “carbohydrates.” Although all carbohydrates contain carbon, hydrogen, and oxygen, there are some that also contain nitrogen, phosphorus, and/or sulfur. Carbohydrates have myriad different functions. They are abundant in terrestrial ecosystems, many forms of which we use as food sources. These molecules are also vital parts of macromolecular structures that store and transmit genetic information (i.e., DNA and RNA). They are the basis of biological polymers that impart strength to various structural components of organisms (e.g., cellulose and chitin), and they are the primary source of energy storage in the form of starch and glycogen.

Monosaccharides

In biochemistry, carbohydrates are often called saccharides, from the Greek sakcharon, meaning sugar, although not all the saccharides are sweet. The simplest carbohydrates are called monosaccharides, or simple sugars. They are the building blocks (monomers) for the synthesis of polymers or complex carbohydrates, as will be discussed further in this section. Monosaccharides are classified based on the number of carbons in the molecule. General categories are identified using a prefix that indicates the number of carbons and the suffix –ose, which indicates a saccharide; for example, triose (three carbons), tetrose (four carbons), pentose (five carbons), and hexose (six carbons). The hexose D-glucose is the most abundant monosaccharide in nature. Other very common and abundant hexose monosaccharides are galactose, used to make the disaccharide milk sugar lactose, and the fruit sugar fructose.

A second comparison can be made when looking at glucose, galactose, and fructose. All three are hexoses; however, there is a major structural difference between glucose and galactose versus fructose: the carbon that contains the carbonyl (C=O). In glucose and galactose, the carbonyl group is on the C₁ carbon, forming an aldehyde group. In fructose, the carbonyl group is on the C₂ carbon, forming a ketone group. The former sugars are called aldoses based on the aldehyde group that is formed; the latter is designated as a ketose based on the ketone group. Again, this difference gives fructose different chemical and structural properties from those of the related aldoses, glucose, and galactose, even though fructose, glucose, and galactose all have the same chemical composition: C₆H₁₂O₆.

Complex Carbohydrates

The simple sugars form the foundation of more complex carbohydrates. The cyclic forms of two sugars can be linked together by means of a condensation reaction to form a disaccharide. Multiple sugars can be linked to form polysaccharides.

Disaccharides

Two monosaccharide molecules may chemically bond to form a disaccharide. The name given to the covalent bond between the two monosaccharides is a glycosidic bond. Glycosidic bonds form between hydroxyl groups of the two saccharide molecules, an example of the dehydration synthesis described later in this chapter.

Common disaccharides are the grain sugar maltose, made of two glucose molecules; the milk sugar lactose, made of one galactose and one glucose molecule; and the table sugar sucrose, made of one glucose and one fructose molecule.

nosaccharide—OH+HO—monosaccharide⟶monosaccharide—O—monosaccharidedisaccharide

Polysaccharides

Polysaccharides, also called glycans, are large polymers composed of hundreds of monosaccharide monomers. Unlike mono- and disaccharides, polysaccharides are not sweet and, in general, they are not soluble in water. Like disaccharides, the monomeric units of polysaccharides are linked together by glycosidic bonds.

Polysaccharides are very diverse in their structure. Three of the most biologically important polysaccharides—starch, glycogen, and cellulose—are all composed of repetitive glucose units, although they differ in their structure. Cellulose consists of a linear chain of glucose molecules and is a common structural component of cell walls in plants and other organisms. Glycogen and starch are branched polymers; glycogen is the primary energy-storage molecule in animals and bacteria, whereas plants primarily store energy in starch. The orientation of the glycosidic linkages in these three polymers is different as well and, as a consequence, linear and branched macromolecules have different properties.

Summary

Complexity Simple Carbohydrates monosaccharides Complex Carbohydrates disaccharides, oligosaccharides & polysaccharides

Size Tetrose C4 sugars Pentose C5 sugars Hexose C6 sugars Heptose C7 sugars etc.

C=O Function Aldose sugars having an aldehyde function or an acetal equivalent. Ketose sugars having a ketone function or an acetal equivalent.

Exercise \(\PageIndex{1}\)

1) Classify each of the following sugars.

a)

b)

c)

d)

Answer

a) Aldoterose

b) Ketopentose

c) Ketohexose

d) Aldopentose

Contributors and Attributions

• William Reusch, Professor Emeritus (Michigan State U.), Virtual Textbook of Organic Chemistry

• Nina Parker, (Shenandoah University), Mark Schneegurt (Wichita State University), Anh-Hue Thi Tu (Georgia Southwestern State University), Philip Lister (Central New Mexico Community College), and Brian M. Forster (Saint Joseph’s University) with many contributing authors. Original content via Openstax (CC BY 4.0; Access for free at https://openstax.org/books/microbiology/pages/1-introduction)