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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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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.
The compound may be biosynthesized in quantity using E. coli.[3][4][5][6]
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As with many other oligosaccharides, a characteristic of 2′-FL is its ability to protect against infectious diseases[7] by preventing epithelial-level adhesion of toxins and pathogens.[8] 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.[8]
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