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Merck
CN

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

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About This Item

Empirical Formula (Hill Notation):
C18H32O15
CAS Number:
41263-94-9
Molecular Weight:
488.44
MDL number:
MFCD00079286
UNSPSC Code:
12352201
PubChem Substance ID:
24894719

Key Documents

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBN2624
109K3805
019K3792
127K3782
127H3784

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Myriam Coulet et al.
Regulatory toxicology and pharmacology : RTP, 68(1), 59-69 (2013-11-23)
In order to match the composition of human breast milk more closely, it is now possible to supplement commercial infant formula (IF) with synthesised oligosaccharides that are chemically identical to human milk oligosaccharides. The safety data generated on a new
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
K H Smalla et al.
Neuroreport, 9(5), 813-817 (1998-05-14)
Fucosylation of terminal galactose residues of brain glycoproteins in the alpha(1-2) position has been shown to be crucial for neuronal plasticity, including phenomena such as long-term potentiation and long-term memory formation. We raised antibodies against the plasticity-relevant fucalpha(1-2)gal epitope and
M H Mansour et al.
Molecular and biochemical parasitology, 69(2), 173-184 (1995-02-01)
Two novel lectins that bind selectively to a schistosome-associated fucosyllactose-related determinant have been characterized and purified from the hemolymph of Biomphalaria alexandrina, the snail vector of Schistosoma mansoni. Both lectins were purified by affinity chromatography on a column of equimolar
C Campbell et al.
Cell, 35(1), 303-309 (1983-11-01)
Two rare and dominant mutants of Chinese hamster ovary (CHO) cells, LEC11 and LEC12, express the mouse embryonic antigen SSEA-1. Parental CHO cells and the revertants, LEC11.R9 and LEC12.R10, do not express this antigen as detected by a sensitive radioimmunoassay
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