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A reducing sugar is any sugar that is capable of acting as a
reducing agent In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are commonly reducing agents include the Earth me ...
. In an alkaline solution, a reducing sugar forms some
aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
or ketone, which allows it to act as a reducing agent, for example in
Benedict's reagent Benedict's reagent (often called Benedict's qualitative solution or Benedict's solution) is a chemical reagent and complex mixture of sodium carbonate, sodium citrate, and copper(II) sulfate pentahydrate. It is often used in place of Fehling's ...
. In such a reaction, the sugar becomes a carboxylic acid. All monosaccharides are reducing sugars, along with some
disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, la ...
s, some
oligosaccharide An oligosaccharide (/ˌɑlɪgoʊˈsækəˌɹaɪd/; from the Greek ὀλίγος ''olígos'', "a few", and σάκχαρ ''sácchar'', "sugar") is a saccharide polymer containing a small number (typically two to ten) of monosaccharides (simple sug ...
s, and some polysaccharides. The monosaccharides can be divided into two groups: the aldoses, which have an aldehyde group, and the
ketose A ketose is a monosaccharide containing one ketone group per molecule. The simplest ketose is dihydroxyacetone, which has only three carbon atoms. It is the only ketose with no optical activity. All monosaccharide ketoses are reducing sugars, be ...
s, which have a ketone group. Ketoses must first tautomerize to aldoses before they can act as reducing sugars. The common dietary monosaccharides
galactose Galactose (, '' galacto-'' + ''-ose'', "milk sugar"), sometimes abbreviated Gal, is a monosaccharide sugar that is about as sweet as glucose, and about 65% as sweet as sucrose. It is an aldohexose and a C-4 epimer of glucose. A galactose molecu ...
,
glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, u ...
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 Trehalose (from Turkish '' tıgala'' – a sugar derived from insect cocoons + -ose) is a sugar consisting of two molecules of glucose. It is also known as mycose or tremalose. Some bacteria, fungi, plants and invertebrate animals synthesize it ...
have
glycosidic bond A glycosidic bond or glycosidic linkage is a type of covalent bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate. A glycosidic bond is formed between the hemiacetal or hemiketal group ...
s between their anomeric carbons 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 Benedict's reagent (often called Benedict's qualitative solution or Benedict's solution) is a chemical reagent and complex mixture of sodium carbonate, sodium citrate, and copper(II) sulfate pentahydrate. It is often used in place of Fehling's ...
. The cyclic
hemiacetal A hemiacetal or a hemiketal has the general formula R1R2C(OH)OR, where R1 or R2 is hydrogen or an organic substituent. They generally result from the addition of an alcohol to an aldehyde or a ketone, although the latter are sometimes called hemi ...
forms of aldoses can open to reveal an aldehyde, and certain ketoses can undergo tautomerization to become aldoses. However,
acetal In organic chemistry, an acetal is a functional group with the connectivity . Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R' groups must be organic fragments n ...
s, including those found in polysaccharide linkages, cannot easily become free aldehydes. Reducing sugars react with amino acids in the
Maillard reaction The Maillard reaction ( ; ) is a chemical reaction between Amino acid, amino acids and Reducing sugar, reducing sugars that gives browned food its distinctive flavor. Searing, Seared steaks, fried dumplings, cookies and other kinds of biscuits, b ...
, 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.


Terminology


Oxidation-reduction

A ''reducing sugar'' is one that ''reduces'' another
compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with defensive struc ...
and is itself ''
oxidized Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...
''; that is, the
carbonyl In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containi ...
carbon of the sugar is oxidized to a
carboxyl In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
group. A sugar is classified as a reducing sugar only if it has an open-chain form with an aldehyde group or a free
hemiacetal A hemiacetal or a hemiketal has the general formula R1R2C(OH)OR, where R1 or R2 is hydrogen or an organic substituent. They generally result from the addition of an alcohol to an aldehyde or a ketone, although the latter are sometimes called hemi ...
group.


Aldoses and ketoses

Monosaccharides which contain an aldehyde group are known as aldoses, and those with a ketone group are known as
ketoses A ketose is a monosaccharide containing one ketone group per molecule. The simplest ketose is dihydroxyacetone, which has only three carbon atoms. It is the only ketose with no optical activity. All monosaccharide ketoses are reducing sugars, be ...
. The aldehyde can be oxidized via a
redox reaction Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
in which another compound is reduced. Thus, aldoses are reducing sugars. Sugars with ketone groups in their open chain form are capable of isomerizing via a series of tautomeric shifts to produce an aldehyde group in solution. Therefore, ketones like fructose are considered reducing sugars but it is the isomer containing an aldehyde group which is reducing since ketones cannot be oxidized without decomposition of the sugar. This type of isomerization is catalyzed by the base present in solutions which test for the presence of reducing sugars.


Reducing end

Disaccharides consist of two monosaccharides and may be either reducing or nonreducing. Even a reducing disaccharide will only have one reducing end, as disaccharides are held together by glycosidic bonds, which consist of at least one anomeric carbon. With one anomeric carbon unable to convert to the open-chain form, only the free anomeric carbon is available to reduce another compound, and it is called the ''reducing end'' of the disaccharide. A nonreducing disaccharide is that which has both anomeric carbons tied up in the glycosidic bond. Similarly, most polysaccharides have only one reducing end.


Examples

All monosaccharides are reducing sugars because they either have an aldehyde group (if they are aldoses) or can tautomerize in solution to form an aldehyde group (if they are ketoses). This includes common monosaccharides like
galactose Galactose (, '' galacto-'' + ''-ose'', "milk sugar"), sometimes abbreviated Gal, is a monosaccharide sugar that is about as sweet as glucose, and about 65% as sweet as sucrose. It is an aldohexose and a C-4 epimer of glucose. A galactose molecu ...
,
glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, u ...
,
glyceraldehyde Glyceraldehyde (glyceral) is a triose monosaccharide with chemical formula C3 H6 O3. It is the simplest of all common aldoses. It is a sweet, colorless, crystalline solid that is an intermediate compound in carbohydrate metabolism. The word comes ...
, fructose,
ribose Ribose is a simple sugar and carbohydrate with molecular formula C5H10O5 and the linear-form composition H−(C=O)−(CHOH)4−H. The naturally-occurring form, , is a component of the ribonucleotides from which RNA is built, and so this compo ...
, and
xylose Xylose ( grc, ξύλον, , "wood") is a sugar first isolated from wood, and named for it. Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional g ...
. Many
disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, la ...
s, 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. However, sucrose and
trehalose Trehalose (from Turkish '' tıgala'' – a sugar derived from insect cocoons + -ose) is a sugar consisting of two molecules of glucose. It is also known as mycose or tremalose. Some bacteria, fungi, plants and invertebrate animals synthesize it ...
, in which the anomeric carbons of the two units are linked together, are nonreducing disaccharides since neither of the rings is capable of opening. In glucose
polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
s such as starch and starch- derivatives like
glucose syrup Glucose syrup, also known as confectioner's glucose, is a syrup made from the hydrolysis of starch. Glucose is a sugar. Maize (corn) is commonly used as the source of the starch in the US, in which case the syrup is called " corn syrup", but glu ...
,
maltodextrin Maltodextrin is a polysaccharide that is used as a food ingredient. It is produced from vegetable starch by partial hydrolysis and is usually found as a white hygroscopic spray-dried powder. Maltodextrin is easily digestible, being absorbed as ...
and
dextrin Dextrins are a group of low-molecular-weight carbohydrates produced by the hydrolysis of starch and glycogen. Dextrins are mixtures of polymers of D-glucose units linked by α-(1→4) or α-(1→6) glycosidic bonds. Dextrins can be produced from ...
the macromolecule begins with a reducing sugar, a free aldehyde. When starch has been partially hydrolyzed 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 Glycogenin is an enzyme involved in converting glucose to glycogen. It acts as a primer, by polymerizing the first few glucose molecules, after which other enzymes take over. It is a homodimer of 37-kDa subunits and is classified as a glycosyltr ...
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.


Characterization

Several qualitative tests are used to detect the presence of reducing sugars. Two of them use solutions of copper(II) ions:
Benedict's reagent Benedict's reagent (often called Benedict's qualitative solution or Benedict's solution) is a chemical reagent and complex mixture of sodium carbonate, sodium citrate, and copper(II) sulfate pentahydrate. It is often used in place of Fehling's ...
(Cu2+ in aqueous sodium citrate) and
Fehling's solution In organic chemistry, Fehling's solution is a chemical reagent used to differentiate between water-soluble carbohydrate and ketone () functional groups, and as a test for reducing sugars and non-reducing sugars, supplementary to the Tollens' reag ...
(Cu2+ in aqueous sodium tartrate). The reducing sugar reduces the copper(II) ions in these test solutions to copper(I), which then forms a brick red
copper(I) oxide Copper(I) oxide or cuprous oxide is the inorganic compound with the formula Cu2O. It is one of the principal oxides of copper, the other being or copper(II) oxide or cupric oxide (CuO). This red-coloured solid is a component of some antifoulin ...
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. 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 Spectrophotometry is a branch of electromagnetic spectroscopy concerned with the quantitative measurement of the reflection or transmission properties of a material as a function of wavelength. Spectrophotometry uses photometers, known as sp ...
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 Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...
. 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.


Importance in medicine

Fehling's solution In organic chemistry, Fehling's solution is a chemical reagent used to differentiate between water-soluble carbohydrate and ketone () functional groups, and as a test for reducing sugars and non-reducing sugars, supplementary to the Tollens' reag ...
was used for many years as a diagnostic test for
diabetes Diabetes, also known as diabetes mellitus, is a group of metabolic disorders characterized by a high blood sugar level ( hyperglycemia) over a prolonged period of time. Symptoms often include frequent urination, increased thirst and increased ...
, 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 The Maillard reaction ( ; ) is a chemical reaction between Amino acid, amino acids and Reducing sugar, reducing sugars that gives browned food its distinctive flavor. Searing, Seared steaks, fried dumplings, cookies and other kinds of biscuits, b ...
, 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 Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted primary ...
, a neurotoxin and possible
carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...
that is formed from free
asparagine Asparagine (symbol Asn or N) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form under biological conditions), an α-carboxylic acid group (which is in the depro ...
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 A redox indicator (also called an oxidation-reduction indicator) is an indicator which undergoes a definite color change at a specific electrode potential. The requirement for fast and reversible color change means that the oxidation-reduction e ...
. However, it is inaccurate, expensive, and sensitive to impurities.


References

{{DEFAULTSORT:Reducing Sugar Carbohydrate chemistry Biomolecules Carbohydrates