2'-fucosyl lactose
2'-O-fucosyllactose
Identification
| Name | 2'-fucosyl lactose |
| IUPAC | (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]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal |
| CAS Number | 41263-94-9 |
| FDA UNII | XO2533XO8R |
| Molecular Formula | C18 H32 O15 |
| Molecular Weight | 488.44104000 |
| MDL Number | MFCD00079286 |
| Nikkaji Number | J1.099.711I |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | GRN 546 |
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 1e+006 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | food additive |
| Recommendation for 2'-fucosyl lactose usage levels up to | not for fragrance use. |
| Recommendation for 2'-fucosyl lactose flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(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]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal
2'-
fucosyllactose
2'-O-
fucosyllactose
D-
glucose, O-6-deoxy-alpha-L-galactopyranosyl-(1-2)-O-beta-D-galactopyranosyl-(1-4)-
PubMed:
Structural characterisation of human galectin-4 C-terminal domain -elucidating the molecular basis for recognition of glycosphingolipids, sulfated saccharides and blood group antigens.
PubMed:
Attenuation of food allergy symptoms following treatment with human milk oligosaccharides in a mouse model.
PubMed:
Recognition of human milk oligosaccharides by bacterial exotoxins.
PubMed:
Maternal fucosyltransferase 2 status affects the gut bifidobacterial communities of breastfed infants.
PubMed:
In vitro impact of human milk oligosaccharides on enterobacteriaceae growth.
PubMed:
Effects of a human milk oligosaccharide, 2'-fucosyllactose, on hippocampal long-term potentiation and learning capabilities in rodents.
PubMed:
Fecal microbiota composition of breast-fed infants is correlated with human milk oligosaccharides consumed.
PubMed:
Oligosaccharide composition of breast milk influences survival of uninfected children born to HIV-infected mothers in Lusaka, Zambia.
PubMed:
A 3-week pre-clinical study of 2â²-fucosyllactose in farm piglets.
PubMed:
The human milk oligosaccharide 2'-fucosyllactose modulates CD14 expression in human enterocytes, thereby attenuating LPS-induced inflammation.
PubMed:
Structure and substrate specificity of a eukaryotic fucosidase from Fusarium graminearum.
PubMed:
Direct evidence for the presence of human milk oligosaccharides in the circulation of breastfed infants.
PubMed:
Can an ancestral condition for milk oligosaccharides be determined? Evidence from the Tasmanian echidna (Tachyglossus aculeatus setosus).
PubMed:
Fecal metabolomics of healthy breast-fed versus formula-fed infants before and during in vitro batch culture fermentation.
PubMed:
Human milk oligosaccharides influence maturation of human intestinal Caco-2Bbe and HT-29 cell lines.
PubMed:
Selective proliferation of intestinal Barnesiella under fucosyllactose supplementation in mice.
PubMed:
Ultra high performance liquid chromatography-tandem mass spectrometry method for the determination of soluble milk glycans in rat serum.
PubMed:
Pre-clinical safety evaluation of the synthetic human milk, nature-identical, oligosaccharide 2'-O-Fucosyllactose (2'FL).
PubMed:
WbgL: a novel bacterial α1,2-fucosyltransferase for the synthesis of 2'-fucosyllactose.
PubMed:
2'-fucosyllactose: an abundant, genetically determined soluble glycan present in human milk.
PubMed:
Select human milk oligosaccharides directly modulate peripheral blood mononuclear cells isolated from 10-d-old pigs.
PubMed:
Bioengineered 2'-fucosyllactose and 3-fucosyllactose inhibit the adhesion of Pseudomonas aeruginosa and enteric pathogens to human intestinal and respiratory cell lines.
PubMed:
The human milk metabolome reveals diverse oligosaccharide profiles.
PubMed:
Utilization of major fucosylated and sialylated human milk oligosaccharides by isolated human gut microbes.
PubMed:
"Amide resonance" in the catalysis of 1,2-α-L-fucosidase from Bifidobacterium bifidum.
PubMed:
Construction of Escherichia coli strains with chromosomally integrated expression cassettes for the synthesis of 2'-fucosyllactose.
PubMed:
Neutral and acidic milk oligosaccharides of the striped skunk (Mephitidae: Mephitis mephitis).
PubMed:
Human milk oligosaccharides inhibit rotavirus infectivity in vitro and in acutely infected piglets.
PubMed:
In vitro fermentation characteristics of select nondigestible oligosaccharides by infant fecal inocula.
PubMed:
Comprehensive profiles of human milk oligosaccharides yield highly sensitive and specific markers for determining secretor status in lactating mothers.
PubMed:
The principal fucosylated oligosaccharides of human milk exhibit prebiotic properties on cultured infant microbiota.
PubMed:
Lacto-N-tetraose, fucosylation, and secretor status are highly variable in human milk oligosaccharides from women delivering preterm.
PubMed:
Bi- to tetravalent glycoclusters: synthesis, structure-activity profiles as lectin inhibitors and impact of combining both valency and headgroup tailoring on selectivity.
PubMed:
Whole cell biosynthesis of a functional oligosaccharide, 2'-fucosyllactose, using engineered Escherichia coli.
PubMed:
Development of biosensor-based assays to identify anti-infective oligosaccharides.
PubMed:
Chemical characterization of milk oligosaccharides of an African lion (Panthera leo) and a clouded leopard (Neofelis nebulosa).
PubMed:
Utilization of natural fucosylated oligosaccharides by three novel alpha-L-fucosidases from a probiotic Lactobacillus casei strain.
PubMed:
Determination of sialyl and neutral oligosaccharide levels in transition and mature milks of Samoan women, using anthranilic derivatization followed by reverse phase high performance liquid chromatography.
PubMed:
Fucosylated glycan inhibition of human hepatocellular carcinoma cell migration through binding to chemokine receptors.
PubMed:
Two distinct alpha-L-fucosidases from Bifidobacterium bifidum are essential for the utilization of fucosylated milk oligosaccharides and glycoconjugates.
PubMed:
Multivalent human blood group ABH and Lewis glycotopes are key recognition factors for a LFuc>Man binding lectin from phytopathogenic Ralstonia solanacearum.
PubMed:
Improved determination of milk oligosaccharides using a single derivatization with anthranilic acid and separation by reversed-phase high-performance liquid chromatography.
PubMed:
1,2-alpha-l-Fucosynthase: a glycosynthase derived from an inverting alpha-glycosidase with an unusual reaction mechanism.
PubMed:
Structural basis of the catalytic reaction mechanism of novel 1,2-alpha-L-fucosidase from Bifidobacterium bifidum.
PubMed:
Variation of major neutral oligosaccharides levels in human colostrum.
PubMed:
Oligosaccharides in colostrum of Italian and Burkinabe women.
PubMed:
Interactions of the fucose-specific Pseudomonas aeruginosa lectin, PA-IIL, with mammalian glycoconjugates bearing polyvalent Lewis(a) and ABH blood group glycotopes.
PubMed:
Purification and characterization of extracellular 1,2-alpha-L-fucosidase from Bacillus cereus.
PubMed:
The fucose-binding lectin from Ralstonia solanacearum. A new type of beta-propeller architecture formed by oligomerization and interacting with fucoside, fucosyllactose, and plant xyloglucan.
PubMed:
An unusual anti-H lectin inhibited by milk from individuals with the Bombay phenotype.
PubMed:
Molecular cloning and characterization of Bifidobacterium bifidum 1,2-alpha-L-fucosidase (AfcA), a novel inverting glycosidase (glycoside hydrolase family 95).
PubMed:
Crystal structures of Erythrina cristagalli lectin with bound N-linked oligosaccharide and lactose.
PubMed:
Characterization of oligosaccharides in milk of bearded seal (Erignathus barbatus).
PubMed:
Differences in oligosaccharide pattern of a sample of polar bear colostrum and mid-lactation milk.
PubMed:
Chemical characterization of the oligosaccharides in milk of high Arctic harbour seal (Phoca vitulina vitulina).
PubMed:
[Studies of oligosaccharide specificity of perch roe fucolectin, using gold labeled neoglycoproteins].
PubMed:
Determination of each neutral oligosaccharide in the milk of Japanese women during the course of lactation.
PubMed:
Cloning of a rat gene encoding the histo-blood group A enzyme. Tissue expression of the gene and of the A and B antigens.
PubMed:
High-resolution crystal structures of Erythrina cristagalli lectin in complex with lactose and 2'-alpha-L-fucosyllactose and correlation with thermodynamic binding data.
PubMed:
Chemical characterization of the oligosaccharides in beluga (Delphinapterus leucas) and Minke whale (Balaenoptera acutorostrata) milk.
PubMed:
Comparison of oligosaccharides in milk specimens from humans and twelve other species.
PubMed:
Synthesis of the milk oligosaccharide 2'-fucosyllactose using recombinant bacterial enzymes.
PubMed:
Structural characterization of fucose-containing oligosaccharides by high-performance liquid chromatography and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
PubMed:
Chemical characterisation of the oligosaccharides in hooded seal (Cystophora cristata) and Australian fur seal (Arctocephalus pusillus doriferus) milk.
PubMed:
Chemical characterization of milk oligosaccharides of the polar bear, Ursus maritimus.
PubMed:
Structural basis of carbohydrate recognition by lectin II from Ulex europaeus, a protein with a promiscuous carbohydrate-binding site.
PubMed:
A lectin from an edible mushroom Pleurotus ostreatus as a food intake-suppressing substance.
PubMed:
Variability of human milk neutral oligosaccharides in a diverse population.
PubMed:
Isolation and characterization from porcine serum of a soluble sulfotransferase responsible for 6-O-sulfation of the galactose residue in 2'-fucosyllactose: implications in the synthesis of the ligand for L-selectin.
PubMed:
Chemical characterization of milk oligosaccharides of the Japanese black bear, Ursus thibetanus japonicus.
PubMed:
Occurrence of an unusual lactose sulfate in dog milk.
PubMed:
Purification and characterization of a lymph node sulfotransferase responsible for 6-O-sulfation of the galactose residues in 2'-fucosyllactose and other sialyl LewisX-related sugars.
PubMed:
Fucosyltransferase activities in human pancreatic tissue: comparative study between cancer tissues and established tumoral cell lines.
PubMed:
Identification of fucose alpha(1-2) galactose epitope-containing glycoproteins from rat hippocampus.
PubMed:
Milk oligosaccharide profiles by reversed-phase HPLC of their perbenzoylated derivatives.
PubMed:
Multiple fucosyltransferases and their carbohydrate ligands are involved in spermatogenic cell-Sertoli cell adhesion in vitro in rats.
PubMed:
Identification of 2'-fucosyllactose in milk of the crabeater seal (Lobodon carcinophagus).
PubMed:
Immobilized Lotus tetragonolobus agglutinin binds oligosaccharides containing the Le(x) determinant.
PubMed:
Localized agglutinin staining in muscle capillaries from normal and very old atrophic human muscle using winged bean (Psophocarpus tetragonolobus) lectin.
PubMed:
Thermodynamics of monosaccharide and disaccharide binding to Erythrina corallodendron lectin.
PubMed:
Remodeling of mouse milk glycoconjugates by transgenic expression of a human glycosyltransferase.
PubMed:
Glycosidic specificity of fucosyltransferases present in rat epididymal spermatozoa.
PubMed:
Characterization of Biomphalaria alexandrina-derived lectins recognizing a fucosyllactose-related determinant on schistosomes.
PubMed:
Presence of multiple fucosyltransferases in rat Sertoli cells and spermatogenic cells.
PubMed:
Purification and characterization of alpha-L-fucosidase from Chinese hamster ovary cell culture supernatant.
PubMed:
Fucose and fucose-containing sugar epitopes enhance hippocampal long-term potentiation in the freely moving rat.
PubMed:
Lactose as affinity eluent and a synthetic sulfated copolymer as inhibitor, in conjunction with synthetic and natural acceptors, differentiate human milk Lewis-type and plasma-type alpha-L-fucosyltransferases.
PubMed:
Purification and properties of the alpha-3/4-L-fucosyltransferase released into the culture medium during the growth of the human A431 epidermoid carcinoma cell line.
PubMed:
Purification of the Lewis blood-group gene associated alpha-3/4-fucosyltransferase from human milk: an enzyme transferring fucose primarily to type 1 and lactose-based oligosaccharide chains.
PubMed:
Assay of alpha 1,3 N-acetyl-D-galactosaminyl transferase by affinity chromatography.
PubMed:
Variations in human liver fucosyltransferase activities in hepatobiliary diseases.
PubMed:
Thermodynamic analysis of ligand binding to winged bean (Psophocarpus tetragonolobus) acidic agglutinin reveals its specificity for terminally monofucosylated H-reactive sugars.
PubMed:
Complete purification and characterization of alpha-3-N-acetylgalactosaminyltransferase encoded by the human blood group A gene.
PubMed:
Liquid ion-exchange chromatography under pressure of milk oligosaccharides using a pulsed amperometric detector.
PubMed:
Separation of human milk oligosaccharides by recycling chromatography. First isolation of lacto-N-neo-difucohexaose II and 3'-Galactosyllactose from this source.
PubMed:
Blood group ABO and Lewis antigens in bladder tumors: correlation between glycosyltransferase activity and antigen expression.
PubMed:
Substrate specificity of fucosyltransferase purified from human parotid saliva.
PubMed:
Studies on anti-H reagents.
PubMed:
Characterisation of a blood-group A-active tetrasaccharide synthesised by a blood-group B gene-specified glycosyltransferase.
PubMed:
Determination of the structures of fucosyl-lactose and difucosyl-lactose from the milk of monotremes, using 13C-n.m.r. spectroscopy.
PubMed:
Regulatory mutations in CHO cells induce expression of the mouse embryonic antigen SSEA-1.
PubMed:
A monoclonal antibody that precipitates the glycoprotein receptor for epidermal growth factor is directed against the human blood group H type 1 antigen.
PubMed:
An enzyme basis for blood type A intermediate status.
PubMed:
Purification of an almond emulsin fucosidase on Cibacron blue-sepharose and demonstration of its activity toward fucose-containing glycoproteins.
PubMed:
A case of weak blood group B expression (Bm) associated with abnormal blood group galactosyltransferase.
PubMed:
Abnormal blood group galactosyltransferase in blood type A1B-subjects whose sera contain anti-B agglutinin.
PubMed:
Improved method for the isolation of 2' fucosyllactose from human milk.
PubMed:
Human salivary fucosyltransferases : evidence for two distinct alpha-3-L-fucosyltransferase activities one or which is associated with the Lewis blood group Le gene.
PubMed:
Membrane abnormality in red blood cells with weak type B expression.
PubMed:
Probable biosynthetic pathway for the synthesis of the B antigen for Bh variants.
PubMed:
A comparison of the alpha-L-fucosidase activities of human liver and serum.
PubMed:
Porcine A blood group-specific N-acetylgalactosaminyltransferase.
PubMed:
[Serum glycosyltransferase activity associated with antigen biosynthesis in blood groups A and B. Study of normal B group and cis AB group subjects].
PubMed:
Qualitative differences in the N-acetyl-D-galactosaminyltransferases produced by human A1 and A2 genes.
PubMed:
N-acetyl-D-galactosaminyltransferase in human serum and erythrocyte membranes.
PubMed:
Correlation between secretor status and the occurrence of 2'-fucosyllactose in human milk.