2'-Fucosyllactose
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| Category | Raw Materials of Healthcare Products |
| Catalog number | BBF-05816 |
| CAS | 41263-94-9 |
| Molecular Weight | 488.44 |
| Molecular Formula | C18H32O15 |
| Purity | 98% |
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Description
2'-Fucosyllactose is produced by microbial fermentation of transgenic Escherichia coli strains. It is a human milk sugar oligosaccharide used in infant nutrition.
Specification
| Synonyms | 2'FL; Fuc-a-1,2-Gal-b-1,4-Glc; 2FL; 2'-Fucosyl-D-lactose; D-Glucose, O-6-deoxy-alpha-L-galactopyranosyl-(1-2)-O-beta-D-galactopyranosyl-(1-4)-; α-l-fuc-(1→2)-β-d-gal-(1→4)-d-glc |
| Storage | Store at 2-8°C under inert atmosphere |
| 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]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal |
| Canonical SMILES | CC1C(C(C(C(O1)OC2C(C(C(OC2OC(C(CO)O)C(C(C=O)O)O)CO)O)O)O)O)O |
| 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 |
| InChI Key | HWHQUWQCBPAQQH-BWRPKUOHSA-N |
Properties
| Appearance | Off-white to Pale Yellow Solid |
| Boiling Point | 902.2±65.0°C (Predicted) |
| Melting Point | >203°C (dec.) |
| Density | 1.548 g/cm3 |
| Solubility | Soluble in DMSO (Slightly), Methanol (Slightly), Water (Slightly) |
Reference Reading
1.Screening of enzymatic synthesis and expression of Lewis determinants in human colorectal carcinoma.
Fernández-Briera A1, Cuevas E2, Gil-Martín E3. Rev Esp Enferm Dig. 2015 Oct;107(10):598-607. doi: 10.17235/reed.2015.3789/2015.
BACKGROUND: Although colorectal carcinogenesis has been intensively studied, the published investigations do not provide a consistent description of how different carbohydrate determinants of colorectal epithelium are modified in colorectal cancer (CRC).
2.Structural Basis for Norovirus Inhibition by Human Milk Oligosaccharides.
Weichert S1, Koromyslova A2, Singh BK2, Hansman S3, Jennewein S4, Schroten H1, Hansman GS5. J Virol. 2016 Apr 14;90(9):4843-8. doi: 10.1128/JVI.03223-15. Print 2016 May 1.
Histo-blood group antigens (HBGAs) are important binding factors for norovirus infections. We show that two human milk oligosaccharides, 2'-fucosyllactose (2'FL) and 3-fucosyllactose (3FL), could block norovirus from binding to surrogate HBGA samples. We found that 2'FL and 3FL bound at the equivalent HBGA pockets on the norovirus capsid using X-ray crystallography. Our data revealed that 2'FL and 3FL structurally mimic HBGAs. These results suggest that 2'FL and 3FL might act as naturally occurring decoys in humans.
3.The human milk oligosaccharide 2'-fucosyllactose augments the adaptive response to extensive intestinal.
Mezoff EA1, Hawkins JA2, Ollberding NJ3, Karns R4, Morrow AL5, Helmrath MA2. Am J Physiol Gastrointest Liver Physiol. 2016 Mar 15;310(6):G427-38. doi: 10.1152/ajpgi.00305.2015. Epub 2015 Dec 23.
Intestinal resection resulting in short bowel syndrome (SBS) carries a heavy burden of long-term morbidity, mortality, and cost of care, which can be attenuated with strategies that improve intestinal adaptation. SBS infants fed human milk, compared with formula, have more rapid intestinal adaptation. We tested the hypothesis that the major noncaloric human milk oligosaccharide 2'-fucosyllactose (2'-FL) contributes to the adaptive response after intestinal resection. Using a previously described murine model of intestinal adaptation, we demonstrated increased weight gain from 21 to 56 days (P < 0.001) and crypt depth at 56 days (P < 0.0095) with 2'-FL supplementation after ileocecal resection. Furthermore, 2'-FL increased small bowel luminal content microbial alpha diversity following resection (P < 0.005) and stimulated a bloom in organisms of the genus Parabacteroides (log2-fold = 4.1, P = 0.035). Finally, transcriptional analysis of the intestine revealed enriched ontologies and pathways related to antimicrobial peptides, metabolism, and energy processing.
4.FUT2-dependent breast milk oligosaccharides and allergy at 2 and 5 years of age in infants with high hereditary allergy risk.
Sprenger N1, Odenwald H2,3,4, Kukkonen AK5, Kuitunen M6, Savilahti E6, Kunz C7. Eur J Nutr. 2016 Feb 24. [Epub ahead of print]
PURPOSE: Manifestation of allergic disease depends on genetic predisposition, diet and commensal microbiota. Genetic polymorphism of mothers determines their breast milk glycan composition. One major determinant is the fucosyltransferase 2 (FUT2, secretor gene) that was shown to be linked to commensal microbiota establishment. We studied whether FUT2-dependent breast milk oligosaccharides are associated with allergic disease in breast-fed infants later in life.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
