Fucose

Structural formula
Fischer projection , open-chain representation
General
Surname	Fucose
other names	6-deoxy-galactose Methylpentose L - (-) - fucose (2 R , 3 S , 4 S , 5 R ) -2,3,4,5-tetrahydroxyhexanal ( D -Fucose) (2 S , 3 R , 4 R , 5 S ) -2,3,4,5-tetrahydroxyhexanal ( L -Fucose)
Molecular formula	C 6 H 12 O 5
Brief description	white solid
External identifiers / databases
CAS number 2438-80-4 (β- L -fucose) 3615-37-0 ( D -Fucose) PubChem 444863 Wikidata Q66589589
properties
Molar mass	164.16 g · mol -1
Physical state	firmly
Melting point	150-153 ° C
solubility	soluble in water and ethanol
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
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 .

β- L -fucose as fucopyranose in the armchair representation.

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

Wiktionary: Fucose  - explanations of meanings, word origins, synonyms, translations

Commons : Fucose  - collection of images, videos and audio files

Individual evidence

1. ↑ ^{a b} Data sheet L - (-) - Fucose at Acros, accessed on February 26, 2010.
2. ↑ Entry on Fucose. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
3. ↑ ^{a b} Data sheet D - (+) - Fucose, ≥98% from Sigma-Aldrich , accessed on February 13, 2013 ( PDF ).
4. ↑ Data sheet L - (-) - Fucose, ≥99% from Sigma-Aldrich , accessed on February 13, 2013 ( PDF ).
5. ↑ Mysterious Diseases (Quarks & Co January 19, 2010) from minute 26:00
6. ↑ Kristin Kruthaup: Ricin compatibility: This man is immune to the poison . In: THE WORLD . January 12, 2018 ( welt.de [accessed January 15, 2018]).

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !