Monosaccharides (from Greek monos: single, sacchar: sugar), also called simple sugars, are a class of organic compounds usually with the formula (CH2O)x. By definition they have two or more carbon-carbon bonds. More specifically, they are classified as polyhydroxy aldehydes or polyhydroxy ketones with the respective formulas H-[CHOH]n-CHO or H-[CHOH]m-CO-[CHOH]n-H respectively. Monosaccharides can be classified by the number x of carbon atoms they contain: triose (3), tetrose (4), pentose (5), hexose (6), heptose (7), and so on. They are colorless, water-soluble, and crystalline organic solids. Most monosaccharides have a sweet taste. Examples of monosaccharides include glucose (dextrose), fructose (levulose), and galactose. Monosaccharides are the building blocks of disaccharides (such as sucrose, lactose and maltose) and polysaccharides (such as cellulose and starch). The table sugar used in everyday vernacular is a disaccharide sucrose derived from the condensation of one molecule of each of the monosaccharides D-glucose and D-fructose. The monosaccharide glucose plays a pivotal role in metabolism, where chemical energy is extracted through glycolysis and the citric acid cycle to provide energy to living organisms. Maltose is the dehydration condensate of two glucose molecules.
Structure and nomenclature
Each carbon atom that supports a hydroxyl group is chiral, except those at the end of the chain. Saccharides of a given formula can exist as a number of isomeric forms. Each form has distinct properties, especially in a biological context. In addition to the many possible isomers for a given formula, each saccharide can exist in at least one cyclic form. The combination of these factors - many "chiral centers" and the chain-ring equilibria - gives rise to particularly complicated chemistry. With few exceptions (e.g., deoxyribose), monosaccharides have the chemical formula (CH2O)x, where conventionally x ≥ 3. Glucose, used as an energy source and for the synthesis of starch, glycogen and cellulose, is a hexose. Ribose and deoxyribose (in RNA and DNA, respectively) are pentose sugars. Examples of heptoses include the ketoses mannoheptulose and sedoheptulose. Monosaccharides with eight or more carbons are rarely observed as they are quite unstable. In aqueous solutions monosaccharides exist as rings if they have more than four carbons.
Linear-chain monosaccharides Simple monosaccharides have a linear and unbranched carbon skeleton with one carbonyl (C=O) functional group amid a linear chain of carbon atoms each of which has a hydroxyl (OH) group attached to it. Therefore, the molecular structure of a simple monosaccharide can be written as H(CHOH)n(C=O)(CHOH)mH, where n + 1 + m = x; so that its elemental formula is CxH2xOx. By convention, the carbon atoms are numbered from 1 to x along the backbone, starting from the end that is closest to the C=O group. Monosaccharides are the simplest units of carbohydrates and the simplest form of sugar. If the carbonyl is at position 1 (that is, n or m is zero), the molecule begins with a formyl group H(C=O)− and is technically an aldehyde. In that case, the compound is termed an aldose. Otherwise, the molecule has a ketone group, a carbonyl −(C=O)− between two carbons; then it is formally a ketone, and is termed a ketose. Ketoses of biological interest usually have the carbonyl at position 2. The various classifications above can be combined, resulting in names such as "aldohexose" and "ketotriose". A more general nomenclature for open-chain monosaccharides combines a Greek prefix to indicate the number of carbons (tri-, tetr-, pent-, hex-, etc.) with the suffixes "-ose" for aldoses and "-ulose" for ketoses. In the latter case, if the carbonyl is not at position 2, its position is then indicated by a numeric infix. So, for example, H(C=O)(CHOH)4H is pentose, H(CHOH)(C=O)(CHOH)3H is pentulose, and H(CHOH)2(C=O)(CHOH)2H is pent-3-ulose.
… excerpt ends here. Continue reading the full article.






