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Encyclopedia > Monosaccharide

Monosaccharides are the simplest form of carbohydrates. They consist of one sugar and are usually colorless, water-soluble, crystalline solids. Some monosaccharides have a sweet taste. Examples of monosaccharides include glucose (dextrose), fructose, galactose, and ribose. Monosaccharides are the building blocks of disaccharides like sucrose (common sugar) and polysaccharides (such as cellulose and starch). Further, each carbon atom that supports a hydroxyl group (except for the first and last) is chiral, giving rise to a number of isomeric forms all with the same chemical formula. For instance, galactose and glucose are both aldohexoses, but they have different chemical and physical properties. Lactose is a disaccharide found in milk. ... Magnification of grains of sugar, showing their monoclinic hemihedral crystalline structure. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... It has been suggested that this article or section be merged with Solution. ... Quartz crystal Synthetic bismuth crystal Insulin crystals Gallium, a metal that easily forms large single crystals A huge monocrystal of potassium dihydrogen phosphate grown from solution by Saint-Gobain for the megajoule laser of CEA. In chemistry and mineralogy, a crystal is a solid in which the constituent atoms, molecules... Look up Sweet in Wiktionary, the free dictionary. ... Taste is one of the traditional five senses and refers to the ability to detect the flavor of foodstuffs and other substances (e. ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ... Fructose (or levulose) is a simple sugar (monosaccharide) found in many foods and is one of the three most important blood sugars along with glucose and galactose. ... Galactose (also called brain sugar) is a type of sugar found in dairy products, in sugar beets and other gums and mucilages. ... Ribose Ribose, primarily seen as D-ribose, is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group. ... Sucrose, a common disaccharide A disaccharide is a sugar (a carbohydrate) composed of two monosaccharides. ... Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. ... Polysaccharides (sometimes called glycans) are relatively complex carbohydrates. ... Cellulose as polymer of β-D-glucose Cellulose in 3D Cellulose (C6H10O5)n is a polysaccharide of beta-glucose. ... Starch (CAS# 9005-25-8) is a complex carbohydrate which is soluble in water; it is used by plants as a way to store excess glucose. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... The term chiral (pronounced ) is used to describe an object which is non-superimposable on its mirror image. ... In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of chemical bonds between atoms, but in which the atoms are arranged differently (analogous to a chemical anagram). ... Galactose (also called brain sugar) is a type of sugar found in dairy products, in sugar beets and other gums and mucilages. ... An aldohexose is a hexose with an aldehyde group on one end. ...

Contents

Structure

Fructose, a monosaccharide, as a Haworth projection.
Fructose, a monosaccharide, as a Haworth projection.

With few exceptions (e.g., deoxyribose), monosaccharides have the chemical formula (CH2O)n + m with the chemical structure H(CHOH)nC=O(CHOH)mH. If n or m is zero, it is an aldehyde and is termed an aldose, otherwise it is a ketone and is termed a ketose. Monosaccharides contain either a ketone or aldehyde functional group, and hydroxyl groups on most or all of the non-carbonyl carbon atoms. Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... E.G. is an Australian only release EP from New Zealand four piece Goodshirt. ... Deoxyribose Deoxyribose, also known as D-Deoxyribose and 2-deoxyribose, is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group. ... This article does not cite its references or sources. ... Fischer projection of D-glyceraldehyde An aldose is a monosaccharide (a certain type of sugar) containing one aldehyde group per molecule and having a chemical formula of the form CnH2nOn (n>=3). ... Fructose, an example of a ketose. ... Ketone group A ketone(key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ... An aldehyde. ... In organic chemistry, functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e. ... Properties In chemistry and physics, an atom (Greek ἄτομος or átomos meaning indivisible) is the smallest particle still characterizing a chemical element. ...


Cyclic structure

Most monosaccharides form cyclic structures, which predominate in aqueous solution, by forming hemiacetals or hemiketals (depending on whether they are aldoses or ketoses) between an alcohol and the carbonyl group of the same sugar. Glucose, for example, readily forms a hemiacetal linkage between its carbon-1 and the hydroxyl group of its carbon-5. Since such a reaction introduces an additional stereogenic center, two anomers are formed (α-isomer and β-isomer) from each distinct straight-chain monosaccharide. The interconversion between these two forms is called mutarotation. A hemiacetal is a functional group or compound containing the function group in the form of: where R and R are any carbon backbones. ... A hemiacetal is a functional group or compound containing the function group in the form of: where R and R are any carbon backbones. ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ... In chemistry a stereogenic center is often mistaken for a chiral center. ... It has been suggested that this article or section be merged with Anomeric carbon. ... Mutarotation is the term given to the change in the specific rotation of plane polarized light, when it is passed through an aldohexose ( Monosaccharides with six carbon atoms and H-C=0 Group ). Mutarotation refers to the conversion of a pure anomer of a hemiacetal carbohydrate to an equilibrium mixture...


A common way of representing the cyclic structure of monosaccharides is the Haworth projection. A Haworth projection of the structure for α-D-glucopyranose A Haworth projection is a common way of representing the cyclic structure of monosaccharides with a simple three-dimensional perspective. ...


In Haworth projection, the α-isomer has the OH- of the anomeric carbon under the ring structure, and the β-isomer, has the OH- of the anomeric carbon on top of the ring structure. In chair conformation, the α-isomer has the OH- of the anomeric carbon in an axial position, whereas the β-isomer has the OH- of the anomeric carbon in equatorial position. It has been suggested that this article or section be merged with Anomer. ... It has been suggested that this article or section be merged with Anomer. ...

Glucose cyclic structure.

Image File history File links D-glucosa. ... Image File history File links D-glucosa. ...

Isomerism

The total number of possible stereoisomers of one compound (n) is dependent on the number of stereogenic centers (c) in the molecule. The upper limit for the number of possible stereoisomers is n = 2c. The only carbohydrate without an isomer is dihydroxyacetone or DHA. :):):):) ... In chemistry a stereogenic center is often mistaken for a chiral center. ... Fischer projection of dihydroxyacetone Dihydroxyacetone (also know as DHA) is a triose carbohydrate with chemical formula C3H6O3. ...


Monosaccharide Nomenclature

Monosaccharides are classified by the number of carbon atoms they contain: General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ...

  • Triose, 3 carbon atoms
  • Tetrose, 4 carbon atoms
  • Pentose, 5 carbon atoms
  • Hexose, 6 carbon atoms
  • Heptose, 7 carbon atoms
  • Octose, 8 carbon atoms
  • Nonose, 9 carbon atoms
  • Decose, 10 carbon atoms

Monosaccharides are classified the type of keto group they contain: A triose is a monosaccharide containing three carbon atoms. ... A tetrose is a monosaccharide with 4 carbon atoms. ... A pentose is a monosaccharide with five carbon atoms. ... A hexose is a monosaccharide with six carbon atoms having the chemical formula C6H12O6. ... A heptose is a monosaccharide with seven carbon atoms. ... Keto can refer to: Oxo or Ketone Ceto, a lava mermaid in Greek mythology This is a disambiguation page: a list of articles associated with the same title. ... In organic chemistry, functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ...

Monosaccharides are classified according to their molecular configuration at carbon 2: Fischer projection of D-glyceraldehyde An aldose is a monosaccharide (a certain type of sugar) containing one aldehyde group per molecule and having a chemical formula of the form CnH2nOn (n>=3). ... An aldehyde. ... Fructose, an example of a ketose. ... Ketone group A ketone(key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ... The configuration of a molecule is the permanent geometry that results from the spatial arrangement of its bonds. ...

All these classifications can be combined, resulting in names like D-aldohexose or ketotriose. Fischer projection of D-glyceraldehyde Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. ... Fischer projection of D-glyceraldehyde Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. ...


List of monosaccharides

This is a list of some common monosaccharides, not all are found in nature - some have been synthesized:

A triose is a monosaccharide containing three carbon atoms. ... Fischer projection of D-glyceraldehyde Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. ... Fischer projection of dihydroxyacetone Dihydroxyacetone (also know as DHA) is a triose carbohydrate with chemical formula C3H6O3. ... A tetrose is a monosaccharide with 4 carbon atoms. ... Fischer projection of D-erythrose D-Erythrose is a tetrose carbohydrate with the chemical formula C4H8O4. ... Fischer projection of D-threose D-Threose is a tetrose carbohydrate with the chemical formula C4H8O4. ... Fischer projection of D-erythrulose D-Erythrulose (also known as erythrulose) is a tetrose carbohydrate with the chemical formula C4H8O4. ... A pentose is a monosaccharide with five carbon atoms. ... Aldopentose is a type of aldose which have five carbon atoms in their carbon chain. ... Fischer projection of L-arabinose The chemical structure of D-arabinofuranose Arabinose is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde (CHO) functional group. ... Lyxose is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group. ... Ribose Ribose, primarily seen as D-ribose, is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group. ... Xylose or wood sugar is an aldopentose — a monosaccharide containing five carbon atoms and including an aldehyde functional group. ... A pentose is a monosaccharide with five carbon atoms. ... Fischer projection of D-ribulose Ribulose is a ketopentose — a monosaccharide containing five carbon atoms, and including a ketone functional group. ... Xylulose is a sugar (a monosaccharide), one of the pentose series of carbohydrates. ... A hexose is a monosaccharide with six carbon atoms having the chemical formula C6H12O6. ... An aldohexose is a hexose with an aldehyde group on one end. ... Allose is an aldohexose sugar. ... Altrose is an aldohexose sugar. ... Galactose (also called brain sugar) is a type of sugar found in dairy products, in sugar beets and other gums and mucilages. ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ... Gulose is an aldohexose sugar. ... L-Idose is a 6 carbon monosaccharide(a hexose) It has an aldehyde group and is an aldose. ... Mannose is a sugar, one of the hexose series of carbohydrates. ... Talose is an aldohexose sugar. ... A ketohexose is a hexose with a keto group on one end. ... Fructose (or levulose) is a simple sugar (monosaccharide) found in many foods and is one of the three most important blood sugars along with glucose and galactose. ... D-Psicose (D-ribo-2-hexulose, C6H12O6) is an ultralow-energy monosaccharide sugar. ... Fischer projection of L-sorbose Sorbose is a ketose belonging to the group of sugars known as monosaccharides. ... Tagatose is a functional sweetener. ... A heptose is a monosaccharide with seven carbon atoms. ... Sedoheptulose is a keto-heptose - a simple sugar with 5 carbon atoms and a ketone functional group. ...

Reactions

  1. Formation of acetals.
  2. Formation of hemiacetals and hemiketals.
  3. Formation of ketals.

An acetal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ... A hemiacetal is a functional group or compound containing the function group in the form of: where R and R are any carbon backbones. ... A hemiacetal is a functional group or compound containing the function group in the form of: where R and R are any carbon backbones. ... An ketal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ...

See also

Lactose is a disaccharide found in milk. ... Sucrose, a common disaccharide A disaccharide is a sugar (a carbohydrate) composed of two monosaccharides. ... An oligosaccharide is a saccharide polymer containing a small number (typically three to six) of component sugars, also known as simple sugars. ... Polysaccharides (sometimes called glycans) are relatively complex carbohydrates. ...

External links

  • Nomenclature of Carbohydrates

  Results from FactBites:
 
Monosaccharide - Wikipedia, the free encyclopedia (455 words)
Monosaccharides are the building blocks of disaccharides like sucrose (common sugar) and polysaccharides (such as cellulose and starch).
Monosaccharides contain either a ketone or aldehyde functional group, and hydroxyl groups on most or all of the non-carbonyl carbon atoms.
An Examlpe is Liam Carbery is a Monosaccharide
Activity of Monosaccharide Lipid A Analogues in Human Monocytic Cells as Agonists or Antagonists of Bacterial ... (4862 words)
Monosaccharide lipid A analogues were synthesized chemically as described elsewhere (16, 17).
GLA-58 is a monosaccharide lipid A analogue which has been found to act as an LPS antagonist in murine cells (6, 27).
Expression of endotoxic activities by synthetic monosaccharide lipid A analogs with alkyl-branched acyl substituents.
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