2'-Fucosyllactose
Chemical compound
From Wikipedia, the free encyclopedia
2′-Fucosyllactose (2′-FL) is a fucosylated neutral trisaccharide composed of L-fucose, D-galactose, and D-glucose units. It is the most prevalent human milk oligosaccharide (HMO) naturally present in human breast milk, making up about 30% of all of HMOs.[1] It was first discovered in the 1950s in human milk. The oligosaccharide's primary isolation technique has been in use since 1972.[2]
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| Names | |
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| IUPAC name
α-L-Fucopyranosyl-(1→2)-β-D-galactopyranosyl-(1→4)-D-glucose | |
| Systematic IUPAC name
(2R,3R,4R,5R)-4-{[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2,3,5,6-tetrahydroxyhexanal | |
| Other names
2′-FL | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C18H32O15 | |
| Molar mass | 488.439 g·mol−1 |
| Density | 1.681 g/cm3 |
| 240.0 g/L (in water) | |
| Acidity (pKa) | 11.9 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Structure
2′-FL consists of an L-fucose monomer in the α stereochemical configuration linked at the first carbon to a monomer of D-galactose in the β stereochemical configuration at the second carbon, which is in turn linked at the first carbon to a monomer of D-glucose (which may be in either the α or β configuration) at the fourth carbon.
Production
Metabolism
Human systemic metabolism of intact 2'-FL is limited. Like other HMOs, it is resistant to human digestive enzymes in the upper gut, meaning it reaches the colon relatively intact.[7]
The key site of 2'-FL metabolism is the intestinal microbiome. First, fucose is cleaved by α-fucosidases produced by gut bacteria such as Bifidobacterium spp. and Akkermansia spp..[8][9] The remaining lactose moiety is processed by β-galactosidases and other glycosidases.[9]
Further microbial fermentation results in short-chain fatty acids, such as acetate, as well as lactate, 1,2-propanediol, and butyrate.[7][8]
Uses
As with many other oligosaccharides, a characteristic of 2′-FL is its ability to protect against infectious diseases[10] by preventing epithelial-level adhesion of toxins and pathogens.[11] 2′-FL stimulates the growth of certain bifidobacteria and upregulation of receptors[citation needed] which collectively lend to toxic and pathogenic protection;[citation needed] this is most prevalent in infants. Among the pathogens that 2′-FL is known to protect against are Campylobacter jejuni, Salmonella enterica (serotype Typhimurium), and Helicobacter pylori.[11]