Product Code Database
A reducing sugar is any sugar that is capable of acting as a reducing agent. (2025). 9781118083505, Wiley. ISBN 9781118083505 In an alkaline solution, a reducing sugar forms some aldehyde or ketone, which allows it to act as a reducing agent, for example in Benedict's reagent. In such a reaction, the sugar becomes a carboxylic acid.
All are reducing sugars, along with some , some , and some . The monosaccharides can be divided into two groups: the , which have an aldehyde group, and the , which have a ketone group. Ketoses must first tautomerization to aldoses before they can act as reducing sugars. The common dietary monosaccharides galactose, glucose and fructose are all reducing sugars.
Disaccharides are formed from two monosaccharides and can be classified as either reducing or nonreducing. Nonreducing disaccharides like sucrose and trehalose have between their and thus cannot convert to an open-chain form with an aldehyde group; they are stuck in the cyclic form. Reducing disaccharides like lactose and maltose have only one of their two anomeric carbons involved in the glycosidic bond, while the other is free and can convert to an open-chain form with an aldehyde group.
The aldehyde functional group allows the sugar to act as a reducing agent, for example, in the Tollens' test or Benedict's test. The cyclic hemiacetal forms of can open to reveal an aldehyde, and certain ketoses can undergo tautomerization to become aldoses. However, , including those found in polysaccharide linkages, cannot easily become free aldehydes.
Reducing sugars react with amino acids in the Maillard reaction, a series of reactions that occurs while cooking food at high temperatures and that is important in determining the flavor of food. Also, the levels of reducing sugars in wine, juice, and sugarcane are indicative of the quality of these food products.
A sugar is classified as a reducing sugar only if it has an open-chain form with an aldehyde group or a free hemiacetal group. (2025). 9780840068583, Cengage Learning. ISBN 9780840068583
Similarly, most polysaccharides have only one reducing end.
Many , like cellobiose, lactose, and maltose, also have a reducing form, as one of the two units may have an open-chain form with an aldehyde group.
In glucose such as starch and starch-derivatives like corn syrup, maltodextrin and dextrin the macromolecule begins with a reducing sugar, a free aldehyde. When starch has been partially hydrolysis the chains have been split and hence it contains more reducing sugars per gram. The percentage of reducing sugars present in these starch derivatives is called dextrose equivalent (DE).
Glycogen is a highly branched polymer of glucose that serves as the main form of carbohydrate storage in animals. It is a reducing sugar with only one reducing end, no matter how large the glycogen molecule is or how many branches it has (note, however, that the unique reducing end is usually covalently linked to glycogenin and will therefore not be reducing). Each branch ends in a nonreducing sugar residue. When glycogen is broken down to be used as an energy source, glucose units are removed one at a time from the nonreducing ends by enzymes.
3,5-dinitrosalicylic acid is another test reagent, one that allows quantitative detection. It reacts with a reducing sugar to form 3-amino-5-nitrosalicylic acid, which can be measured by spectrophotometry to determine the amount of reducing sugar that was present.
Some sugars, such as sucrose, do not react with any of the reducing-sugar test solutions. However, a non-reducing sugar can be hydrolyzed using dilute hydrochloric acid. After hydrolysis and neutralization of the acid, the product may be a reducing sugar that gives normal reactions with the test solutions.
All carbohydrates are converted to aldehydes and respond positively in Molisch's test. But the test has a faster rate when it comes to monosaccharides.
(2025). 9780471756149, John Wiley & Sons. ISBN 9780471756149 However, sucrose and trehalose, in which the anomeric carbon atoms of the two units are linked together, are nonreducing disaccharides since neither of the rings is capable of opening.
Characterization
Several qualitative tests are used to detect the presence of reducing sugars. Two of them use solutions of cupric ions: Benedict's reagent (Cu2+ in aqueous sodium citrate) and Fehling's solution (Cu2+ in aqueous sodium tartrate). (2025). 9780471756149, John Wiley & Sons. ISBN 9780471756149 The reducing sugar reduces the copper ions in these test solutions to copper(I), which then forms a brick red copper(I) oxide precipitate. Reducing sugars can also be detected with the addition of Tollen's reagent, which consist of silver ions (Ag+) in aqueous ammonia. When Tollen's reagent is added to an aldehyde, it precipitates silver metal, often forming a silver mirror on clean glassware.
Importance in medicine
Fehling's solution was used for many years as a diagnostic test for diabetes, a disease in which blood glucose levels are dangerously elevated by a failure to produce enough insulin (type 1 diabetes) or by an inability to respond to insulin (type 2 diabetes). Measuring the amount of oxidizing agent (in this case, Fehling's solution) reduced by glucose makes it possible to determine the concentration of glucose in the blood or urine. This then enables the right amount of insulin to be injected to bring blood glucose levels back into the normal range.
Importance in food chemistry
Maillard reaction
The carbonyl groups of reducing sugars react with the amino groups of amino acids in the Maillard reaction, a complex series of reactions that occurs when cooking food. Maillard reaction products (MRPs) are diverse; some are beneficial to human health, while others are toxic. However, the overall effect of the Maillard reaction is to decrease the nutritional value of food. One example of a toxic product of the Maillard reaction is acrylamide, a neurotoxin and possible carcinogen that is formed from free asparagine and reducing sugars when cooking starchy foods at high temperatures (above 120 °C). However, evidence from epidemiological studies suggest that dietary acrylamide is unlikely to raise the risk of people developing cancer.
Food quality
The level of reducing sugars in wine, juice, and sugarcane are indicative of the quality of these food products, and monitoring the levels of reducing sugars during food production has improved market quality. The conventional method for doing so is the Lane-Eynon method, which involves titrating the reducing sugar with copper(II) in Fehling's solution in the presence of methylene blue, a common redox indicator. However, it is inaccurate, expensive, and sensitive to impurities.
|
|
