F0393

Sigma-Aldrich

2′-Fucosyl-D-lactose

from human milk, ≥98% (HPAE/PAD)

Synonym(s):
α-L-Fuc-(1→2)-β-D-Gal-(1→4)-D-Glc
Empirical Formula (Hill Notation):
C18H32O15
CAS Number:
Molecular Weight:
488.44
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

biological source

human milk

assay

≥98% (HPAE/PAD)

form

powder

solubility

H2O: 2 mg + 0.2 mL, clear, colorless

storage temp.

2-8°C

SMILES string

C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]2O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)[C@@H](O)[C@H](O)[C@@H]1O

InChI

1S/C18H32O15/c1-4-7(21)9(23)13(27)17(29-4)33-15-10(24)8(22)5(2-19)31-18(15)32-14-6(3-20)30-16(28)12(26)11(14)25/h4-28H,2-3H2,1H3/t4-,5+,6+,7+,8-,9+,10-,11+,12+,13-,14+,15+,16?,17+,18-/m0/s1

InChI key

SNFSYLYCDAVZGP-ZTFPOLCTSA-N

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Application

2′-Fucosyl-D-lactose is used as substrate to identify, differentiate and characterize fucosidases. It is also used in the development of biosensors to identify anti-infective oligosaccharides. 2′-Fucosyl-D-lactose is used to differentiate IL-8 receptor specificity and function. It may be used to study is effects on intestinal microbiota and as a reference compound in assays developed to detect and measure milk sugars.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F0393.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

RIDADR

NONH for all modes of transport

WGK Germany

3

Certificate of Analysis
Certificate of Origin
Determination of the structures of fucosyl-lactose and difucosyl-lactose from the milk of monotremes, using 13C-n.m.r. spectroscopy.
G A Jenkins et al.
Carbohydrate research, 126(1), 157-161 (1984-03-01)
Nikola Kostlánová et al.
The Journal of biological chemistry, 280(30), 27839-27849 (2005-06-01)
Plant pathogens, like animal ones, use protein-carbohydrate interactions in their strategy for host recognition, attachment, and invasion. The bacterium Ralstonia solanacearum, which is distributed worldwide and causes lethal wilt in many agricultural crops, was shown to produce a potent L-fucose-binding...
T Urashima et al.
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology, 116(3), 311-314 (1997-03-01)
1. An oligosaccharide was isolated from extracts of crabeater seal milk by preparative paper chromatography. 2. The saccharide was identified as Fuc alpha 1-2Ga1 beta 1-4G1c by 1H-NMR spectroscopy. 3. This work represents the first identification of an oligosaccharide, other...
Improved method for the isolation of 2' fucosyllactose from human milk.
A Anderson et al.
Journal of chromatography, 211(1), 170-174 (1981-06-26)
Zhuo-Teng Yu et al.
Glycobiology, 23(2), 169-177 (2012-10-03)
Breast-fed infant microbiota is typically rich in bifidobacteria. Herein, major human milk oligosaccharides (HMOS) are assessed for their ability to promote the growth of bifidobacteria and to acidify their environment, key features of prebiotics. During in vitro anaerobic fermentation of...

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