Fucose
Structural formula | ||||||||||
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Fischer projection , open-chain representation | ||||||||||
General | ||||||||||
Surname | Fucose | |||||||||
other names |
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Molecular formula | C 6 H 12 O 5 | |||||||||
Brief description |
white solid |
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properties | ||||||||||
Molar mass | 164.16 g · mol -1 | |||||||||
Physical state |
firmly |
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Melting point |
150-153 ° C |
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solubility |
soluble in water and ethanol |
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safety instructions | ||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Fucose (not to be confused with fructose ) is a monosaccharide and one of the essential sugars that are required for cell-cell communication. It is also called methylpentose because it is a methylated deoxy sugar . Fucose occurs in two enantiomeric forms: L- Fucose (also isodulcite) and D- Fucose . The L -form is the one common in nature (which is rarely the case with sugars), while the D -form is an artificially produced galactose analogue. If “Fucose” is mentioned in this text or in the scientific literature without any additional name ( prefix ), L- Fucose is meant.
Occurrence
Fucose and the like occur in humans. a. in extracellular muco and glycoproteins , in breast milk (bifidus factor) and in blood group substances (A, B and H, Lea). In bacteria, it occurs as an antigenic polysaccharide in the bacterial cell wall. In brown algae and seaweed, one can find fucoidan , a sulfated polysaccharide that contains fucose as well as other sugars.
Extraction and presentation
Fucose is industrially biosynthesized from fructose-6-phosphate.
properties
Fucose is a monosaccharide with six carbon atoms (i.e. a hexose ) and an aldehyde group on the C1 atom ( aldose ). In contrast to most hexoses, however, the C6 atom lacks the hydroxyl group .
use
Fucose is used to produce fucosides (cardiac digitalis glycosides ).
Biological importance
Fucose can be used, among other things, for post-translational modification of proteins ( fucosylation ) by fucosyltransferase . Disorders of fucosylation disorders occur in humans ( leukocyte adhesion defect type II ). The compound can be used to treat the disease. A genetic defect that results in the non-formation of fucose leads, in addition to some damage, to an insensitivity to ricin .
The splitting off of fucose from proteins is ensured by the α-L- fucosidase in the lysosome . If fucose cannot be split off due to a genetic defect, fucosidosis occurs .
Web links
Individual evidence
- ↑ a b Data sheet L - (-) - Fucose at Acros, accessed on February 26, 2010.
- ↑ Entry on Fucose. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
- ↑ a b Data sheet D - (+) - Fucose, ≥98% from Sigma-Aldrich , accessed on February 13, 2013 ( PDF ).
- ↑ Data sheet L - (-) - Fucose, ≥99% from Sigma-Aldrich , accessed on February 13, 2013 ( PDF ).
- ↑ Mysterious Diseases (Quarks & Co January 19, 2010) from minute 26:00
- ↑ Kristin Kruthaup: Ricin compatibility: This man is immune to the poison . In: THE WORLD . January 12, 2018 ( welt.de [accessed January 15, 2018]).