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Encyclopedia > Mannose
Mannose
Identifiers
CAS number 31103-86-3
PubChem 18950
MeSH Mannose
Properties
Molecular formula C6H12O6
Molar mass 180.156
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references
D and L forms
D and L forms
Haworth projection of mannose in its α-D-mannopyranose form.

Mannose is a sugar monomer of the hexose series of carbohydrates. Image File history File links D-Mannose_Keilstrich. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... Medical Subject Headings (MeSH) is a huge controlled vocabulary (or metadata system) for the purpose of indexing journal articles and books in the life sciences. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Image File history File links DL-Mannose. ... Image File history File links DL-Mannose. ... Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... 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. ... This article is about sugar as food and as an important and widely-traded commodity. ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... A hexose is a monosaccharide with six carbon atoms having the chemical formula C6H12O6. ... Lactose is a disaccharide found in milk. ...

Contents

Metabolism

Mannose enters the carbohydrate metabolism stream in two steps: A few of the metabolic pathways in a cell. ...

A phosphorylated serine residue Phosphorylation is the addition of a phosphate (PO4) group to a protein or a small molecule or the introduction of a phosphate group into an organic molecule. ... Mannose-6-phosphate (M6P) is a molecule bound by lectin in the immune system. ... A hexokinase is an enzyme that phosphorylates a six-carbon sugar, a hexose, to a hexose phosphate. ... Fructosephosphates are sugar phosphates based upon fructose. ... Mannose phosphate isomerase is an enzyme which converts fructose-6-phosphate and mannose-6-phosphate. ...

Formation

Mannose can be formed by the oxidation of mannitol. Mannitol or hexan-1,2,3,4,5,6-hexol (C6H8(OH)6) is an osmotic diuretic agent and a weak renal vasodilator. ...


It can also be formed from D-glucose in the Lobry-de Bruyn-van Ekenstein transformation The Lobry-de Bruyn-van Ekenstein transformation also known as the Lobry-de Bruyn-van-Alberda-van-Ekenstein transformation is a base catalyzed Aldose-Ketose-Isomerization in carbohydrate chemistry [1] . A typical rearrangement reaction is that between glyceraldehyde and dihydroxyacetone in a chemical equilibrium. ...


Etymology

The root of both "mannose" and "manitol" is manna, which the Bible records as the food supplied to the Israelites during their journey through the Sinai Peninsula. Manna is a sweet secretion of several trees and shrubs, such as Fraxinus ornus. Not to be confused with the rune Mannaz. ... This Gutenberg Bible is displayed by the United States Library. ... Binomial name Fraxinus ornus L. Fraxinus ornus (Flowering Ash or Manna Ash) is a species of ash which occurs in Europe. ...


Cranberry juice

D-Mannose, which appears in some fruits including cranberry, has been postulated to prevent the adhesion of bacteria to the epithelium of the urinary tract and Urinary bladder through a mechanism presumed to be competitive in nature with the polysaccharide coating of the cystic epithelium. While no studies have objectively verified this mechanism, anecdotal reports from patients show some improvement in symptoms.[citation needed]


Configuration

The fact that D-mannose has the same configuration at its penultimate carbon as D-glyceraldehyde is unsurprising as that is what defines the dextro classification. However, mannose differs from D-glucose by inversion of the C2 chiral centre. This apparently simple change leads to the drastically different chemistry of the two hexoses, as it does the remaining six hexoses. Fischer projection of D-glyceraldehyde Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. ...


Mnemonic

The hexoses can be remembered conveniently by the following phrase:

"All (allose) altruists (altrose) gladly (glucose) make (mannose) gum (gulose) in (idose) gallon (galactose) tanks (talose)."

Allose is an aldohexose sugar. ... Altrose is an aldohexose sugar. ... Glucose (Glc), a monosaccharide (or simple sugar), is an 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. ... Galactose (also called brain sugar) is a type of sugar found in dairy products, in sugar beets and other gums and mucilages. ... Talose is an aldohexose sugar. ...

See also

Glycosylation is the process or result of addition of saccharides to proteins and lipids. ... alpha-Mannosidase is an enzyme involved in the cleavage of the alpha form of mannose. ... A hexose is a monosaccharide with six carbon atoms having the chemical formula C6H12O6. ... The mannose receptor is a calcium-dependent lectin. ...

References

External links


  Results from FactBites:
 
D-mannose - bladder infections and cystitis (590 words)
One day 7 months ago I was suffering from a really bad urine infection - increasing spasms, cold sweats, and feeling really unwell and I just knew I had to find something to stop these infections.
So I researched online and found a product called Waterfall D-Mannose which is a pure blend of the high alpha and beta manomers of a rare mannose sugar extracted from sweet forest timbers.
I read the information on the website and found it really interesting so I bought a sample to try, really thinking in the back of my mind that it would probably be a waste of money.
Olympus MIC-D: Polarized Light Gallery - Mannose (461 words)
As a six-carbon simple sugar, mannose (or dextro-mannose) is a stereoisomer of glucose that is found as an uncommon, naturally occurring saccharide in some plants, particularly legumes, and other food plants.
With oral mannose, the sugar coats the bacteria so that they don't hold onto the lining and then urine is able to flush them away.
Mannose is also used in veterinary medicine for treating uterine bacterial infections because there are no unwanted side effects (including killing "good" bacteria or normal gut flora), and because the sugar avoids the developed resistance quandary posed by antibiotics and many strains of microbes.
  More results at FactBites »

 
 

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