Ketose
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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, because they can tautomerize into aldoses via an enediol intermediate, and the resulting aldehyde group can be oxidised, for example in the Tollens' test or Benedict's test. Ketoses that are bound into glycosides, for example in the case of the fructose moiety of sucrose, are nonreducing sugars. Examples of ketoses All ketoses listed here are 2-ketoses, in other words, the carbonyl group is on the second carbon atom from the end: * Trioses: dihydroxyacetone * Tetroses: erythrulose * Pentoses: ribulose, xylulose * Hexoses: fructose, psicose, sorbose, tagatose * Heptoses: sedoheptulose * Octoses: D-''manno''-octulose (the basis for KDO) * Nonose A nonose is a monosaccharide with nine carbons. Nonoses types Depending on ...
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Monosaccharide
Monosaccharides (from Greek '' monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. They are usually colorless, water-soluble, and crystalline solids. Contrary to their name (sugars), only some monosaccharides have a sweet taste. Most monosaccharides have the formula (though not all molecules with this formula are monosaccharides). Examples of monosaccharides include glucose (dextrose), fructose (levulose), and galactose. Monosaccharides are the building blocks of disaccharides (such as sucrose and lactose) and polysaccharides (such as cellulose and starch). The table sugar used in everyday vernacular is itself a disaccharide sucrose comprising one molecule of each of the two monosaccharides D-glucose and D-fructose. Each carbon atom that supports a hydroxyl group is chiral, except those at the end of the chain. This gives rise to a number of isomeric for ...
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Aldose
An aldose is a monosaccharide (a simple sugar) with a carbon backbone chain with a carbonyl group on the endmost carbon atom, making it an aldehyde, and hydroxyl groups connected to all the other carbon atoms. Aldoses can be distinguished from ketoses, which have the carbonyl group away from the end of the molecule, and are therefore ketones. Structure Like most carbohydrates, simple aldoses have the general chemical formula C''n''(H2O)''n''. Because formaldehyde (n=1) and glycolaldehyde (n=2) are not generally considered to be carbohydrates, the simplest possible aldose is the triose glyceraldehyde, which only contains three carbon atoms. Because they have at least one asymmetric carbon center, all aldoses exhibit stereoisomerism. Aldoses can exist in either a - form or - form. The determination is made based on the chirality of the asymmetric carbon furthest from the aldehyde end, namely the second-last carbon in the chain. Aldoses with alcohol groups on the right of the Fi ...
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Reducing Sugar
A reducing sugar is any sugar that is capable of acting as a reducing agent. 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 monosaccharides are reducing sugars, along with some disaccharides, some oligosaccharides, and some polysaccharides. The monosaccharides can be divided into two groups: the aldoses, which have an aldehyde group, and the ketoses, which have a ketone group. Ketoses must first tautomerize 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 glycosidic bonds between their anomeric carbons and thus cannot convert to an open-chain form with an al ...
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Hexose
In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol. Hexoses exist in two forms, open-chain or cyclic, that easily convert into each other in aqueous solutions. The open-chain form of a hexose, which usually is favored in solutions, has the general structure H–(CHOH)''n''−1–C(=O)–(CHOH)4−''n''–H, where ''n'' is 1, 2, or 3. Namely, five of the carbons have one hydroxyl functional group (–OH) each, connected by a single bond, and one has an oxo group (=O), forming a carbonyl group (C=O). The remaining bonds of the carbon atoms are satisfied by seven hydrogen atoms. The carbons are commonly numbered 1 to 6 starting at the end closest to the carbonyl. Hexoses are extremely important in biochemistry, both as isolated molecules (such as glucose and fructose) and as building blocks of other compounds such as starch, cellulose, and glycosides. Hex ...
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Ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considered reta ...
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Heptose
A heptose is a monosaccharide with seven carbon atoms. They have either an aldehyde functional group in position 1 (aldoheptoses) or a ketone functional group in position 2, 3 or 4 (ketoheptoses). Ketoheptoses have 4 chiral centers, whereas aldoheptoses have 5. Examples There are few examples of seven-carbon sugars in nature, among which are: * sedoheptulose or D-''altro''-heptulose (a ketose), an intermediate in the Calvin cycle and in lipid A biosynthesis * mannoheptulose (a ketose), found in avocado The avocado (''Persea americana'') is a medium-sized, evergreen tree in the laurel family (Lauraceae). It is native to Americas, the Americas and was first domesticated by Mesoamerica, Mesoamerican tribes more than 5,000 years ago. Pre-Columb ...es * L-''glycero''-D-''manno''-heptose (an aldose), a late intermediate in lipid A biosynthesis. References {{Biochem-stub ...
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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 solution to detect the presence of reducing sugars. The presence of other reducing substances also gives a positive result.Collins Edexcel International GCSEBiology, Student Book () p.42-43 Such tests that use this reagent are called the Benedict's tests. A positive test with Benedict's reagent is shown by a color change from clear blue to brick-red with a precipitate. Generally, Benedict's test detects the presence of aldehydes, alpha-hydroxy-ketones, and hemiacetals, including those that occur in certain ketoses. Thus, although the ketose fructose is not strictly a reducing sugar, it is an alpha-hydroxy-ketone and gives a positive test because the base in the reagent converts it into the aldoses glucose and mannose. Oxidation of the r ...
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Pentose
In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is , and their molecular weight is 150.13 g/mol.-Ribose
. PubChem compound webpage, accessed on 2010-02-06.
Pentoses are very important in . is a constituent of , and the related molecule, , is a constituent of
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Ribulose
Ribulose is a ketopentose — a monosaccharide containing five carbon atoms, and including a ketone functional group. It has chemical formula . Two enantiomers are possible, -ribulose (-erythro-pentulose) and -ribulose (-erythro-pentulose). -Ribulose is the diastereomer of -xylulose. Ribulose sugars are composed in the pentose phosphate pathway from arabinose. They are important in the formation of many bioactive substances. For example, -ribulose is an intermediate in the fungal pathway for -arabitol production. Also, as the 1,5-bisphosphate, -ribulose combines with carbon dioxide at the start of the photosynthesis process in green plants (carbon dioxide trap). Ribulose has the same stereochemistry at carbons 3 and 4 as the five-carbon aldoses ribose and arabinose Arabinose is an aldopentose – a monosaccharide containing five carbon atoms, and including an aldehyde (CHO) functional group. For biosynthetic reasons, most saccharides are almost always more abundant ...
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Dihydroxyacetone
Dihydroxyacetone (; DHA), also known as glycerone, is a simple saccharide (a triose) with formula . DHA is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, and by the fermentation of glycerin. Chemistry DHA is a hygroscopic white crystalline powder. It has a sweet cooling taste and a characteristic odor. It is the simplest of all ketoses and has no chiral center or optical activity. The normal form is a dimer (2,5-bis(hydroxymethyl)-1,4-dioxane-2,5-diol) which is slowly soluble in one part water and 15 parts ethanol. When freshly prepared, it reverts rapidly to the monomer in solution. : The monomer is very soluble in water, ethanol, diethyl ether, acetone and toluene. DHA may be prepared, along with glyceraldehyde, by the mild oxidation of glycerol, for example with hydrogen peroxide and a ferrous salt as catalyst. It can also be prepared in high yield and selectivity at ro ...
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Erythrulose
D-Erythrulose (also known as erythrulose) is a tetrose carbohydrate with the chemical formula C4 H8 O4. It has one ketone group and so is part of the ketose family. It is used in some self-tanning cosmetics, in general, combined with dihydroxyacetone (DHA). Erythrulose/DHA reacts with the amino acids in the proteins of the first layers of skin (the stratum corneum and epidermis). One of the pathways involves free radicals at one of the steps of the Maillard reaction, distantly related to the browning effect when a cut apple slice is exposed to oxygen. The other pathway is the conventional Maillard reaction; both pathways are involved in the browning during food preparation and storage. This is not a stain or dye, but rather a chemical reaction that produces a color change on all treated skin. It does not involve the underlying skin pigmentation nor does it require exposure to ultraviolet light to initiate the color change. However, the 'tan' produced by erythrulose/DHA only ha ...
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Sorbose
Sorbose is a ketose belonging to the group of sugars known as monosaccharides. It has a sweetness that is equivalent to sucrose (table sugar). The commercial production of vitamin C (ascorbic acid Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits and vegetables, also sold as a dietary supplement and as a topical 'serum' ingredient to treat melasma (dark pigment spots) a ...) often begins with sorbose. L-Sorbose is the configuration of the naturally occurring sugar. References {{ketone-stub Ketohexoses ...
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