Chemistry:2'-Fucosyllactose

2′-Fucosyllactose

Names
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
CAS Number	41263-94-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:147155
ChemSpider	149055
KEGG	G00268
PubChem CID	170484
UNII	XO2533XO8R Y
InChI InChI=1S/C18H32O15/c1-5-9(24)12(27)14(29)17(30-5)33-16-13(28)11(26)8(4-21)31-18(16)32-15(7(23)3-20)10(25)6(22)2-19/h2,5-18,20-29H,3-4H2,1H3/t5-,6-,7+,8+,9+,10+,11-,12+,13-,14-,15+,16+,17-,18-/m0/s1 Key: HWHQUWQCBPAQQH-BWRPKUOHSA-N
SMILES C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O
Properties
Chemical formula	C18H32O15
Molar mass	488.439 g·mol−1
Density	1.681 g/cm3
Solubility in water	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).
Infobox references

Tracking categories (test):

• SizeSet

2′-Fucosyllactose (2′-FL) is an oligosaccharide, more precisely, 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. It was first discovered in the 1950s in human milk. The oligosaccharide's primary isolation technique has been in use since 1972.

Production

This compound may be biosynthesized in quantity using E. coli.

Metabolism

File:2′-fucosyllactose Reaction Diagram.tiff

Uses

As with other oligosaccharides, a widely regarded characteristic of 2'-fucosyllactose is its ability to protect against infectious diseases namely in preventing epithelial level adhesions of toxins and pathogens. The 2FL stimulates the growth of certain bifidobacteria and receptor analogons which lends to toxic and pathogenic protection, all this being most prevalent in infants. Among the pathogens that 2FL is known to protect against are Campylobacter jejuni, Salmonella enterica serotype Typhimurium, Helicobacter pylori, among others.