The most important pentoses include xylose, found combined as xylan in woody materials; arabinose from coniferous trees; ribose, a component of ribonucleic acids and several vitamins; and deoxyribose, a component of deoxyribonucleic acid. Among the most important aldohexoses are glucose, mannose, and galactose; fructose is a ketohexose. Several derivatives of monosaccharides are important. Ascorbic acid (vitamin C) is derived from glucose. Important sugar alcohols (alditols), formed by the reduction of (i.
e. , addition of hydrogen to) a monosaccharide, include sorbitol (glucitol) from glucose and mannitol from mannose; both are used as sweetening agents. Glycosides derived from monosaccharides are widespread in nature, especially in plants. Amino sugars (i. e.
, sugars in which one or two hydroxyl groups are replaced with an amino group, -NH2) occur as components of glycolipids and in the chitin of arthropods. carbohydrateClasses of carbohydrates Monosaccharides Sources The most common naturally occurring monosaccharides are D-glucose, D-mannose, D-fructose, and D-galactose among the hexoses, and D-xylose and L-arabinose among the pentoses. In a special sense, D-ribose and 2-deoxy-D-ribose are ubiquitous because they form the carbohydrate component of ribonucleic acid (RNA) and deoxyribonucleic acid (DNA), respectively; these sugars are present in all cells as components of nucleic acids. Sources of some of the naturally occurring monosaccharides are listed in Table 2.
D-xylose, found in most plants in the form of a polysaccharide called xylan, is prepared from corncobs, cottonseed hulls, or straw by chemical breakdown of xylan. D-galactose, a common constituent of both oligosaccharides and polysaccharides, also occurs in carbohydrate-containing lipids, called glycolipids, which are found in the brain and other nervous tissues of most animals. Galactose is generally prepared by acid hydrolysis (breakdown involving water) of lactose, which is composed of galactose and glucose. Since the biosynthesis of galactose in animals occurs through intermediate compounds derived directly from glucose, animals do not require galactose in the diet. In fact, in most human populations (Caucasoid peoples being the major exception) the majority of people do not retain the ability to manufacture the enzyme necessary to metabolize galactose after they reach the age of four, and many individuals possess a hereditary defect known as galactosemia and never have the ability to metabolize galactose.
D-glucose (from the Greek word glykys, meaning “sweet”), the naturally occurring form, is found in fruits, honey, blood, and, under abnormal conditions, in urine. It is also a constituent of the two most common naturally found disaccharides, sucrose and lactose, as well as the exclusive structural unit of the polysaccharides cellulose, starch, and glycogen. Generally, D-glucose is prepared from either potato starch or cornstarch. D-fructose, a ketohexose, is one of the constituents of the disaccharide sucrose and is also found in uncombined form in honey, apples, and tomatoes. Fructose, generally considered the sweetest monosaccharide, is prepared by sucrose hydrolysis and is metabolized by man.
Chemical reactions The reactions of the monosaccharides can be conveniently subdivided into those associated with the aldehydo or keto group and those associated with the hydroxyl groups. The relative ease with which sugars containing a free or potentially free aldehydo or keto group can be oxidized to form products has been known for a considerable time and once was the basis for the detection of these so-called reducing sugars in a variety of sources. For many years, analyses of blood glucose and urinary glucose were carried out by a procedure involving the use of an alkaline copper compound. Because the reaction has undesirable features–extensive destruction of carbohydrate structure occurs, and the reaction is not very specific (i.e., sugars other than glucose give similar results) and does not result in the formation of readily identifiable products–blood and urinary glucose now are analyzed