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44367

Sigma-Aldrich

Lewis-a trisaccharide

≥98.0% (TLC)

Synonym(s):

α-L-Fuc-(1→4)-[β-D-Gal-(1→3)]-D-GlcNAc, Galactosyl-β-1,3-(fucosyl-α-1,4)-N-acetylglucosamine, Lea-Trisaccharide

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About This Item

Empirical Formula (Hill Notation):
C20H35NO15
CAS Number:
56570-03-7
Molecular Weight:
529.49
MDL number:
MFCD00214078
UNSPSC Code:
12352201
PubChem Substance ID:
329756500
NACRES:
NA.25

assay

≥98.0% (TLC)

form

solid

technique(s)

thin layer chromatography (TLC): suitable

storage temp.

−20°C

SMILES string

OC1[C@H](NC(C)=O)[C@@H](O[C@@H]([C@H](O)[C@H]2O)O[C@H](CO)[C@@H]2O)[C@H](O[C@H](O[C@H]3C)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](CO)O1

InChI

1S/C20H35NO15/c1-5-10(25)12(27)14(29)19(32-5)35-16-8(4-23)33-18(31)9(21-6(2)24)17(16)36-20-15(30)13(28)11(26)7(3-22)34-20/h5,7-20,22-23,25-31H,3-4H2,1-2H3,(H,21,24)/t5-,7+,8+,9+,10+,11-,12+,13-,14-,15+,16+,17+,18?,19-,20-/m0/s1

InChI key

CFDVGUXRLQWLJX-QGTNPELVSA-N

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Biochem/physiol Actions

Lewis a trisaccharide is a fucosyloligosaccharide present in human milk and colostrum, which is important for the protection of infants against infection by pathogenic microorganisms. Lewis a trisaccharide is found on the surface of erythrocytes and is a tumor-related antigen. Used as analytical standard, enzyme substrate, in blood group typing, and antibody binding assays.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD0016
BCCB3707
BCCB2856
BCBP8243V
BCBP8243

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Chemical synthesis of 2-acetamido-2-deoxy-4-O-(a-L-fucopyranosyl)-3-O-(?-D-galactopyranosyl)-D-glucose. Lewis a blood-group antigenic determinant.
Lemieux, R.U. and Driguez, H.
Journal of the American Chemical Society, 97, 4063-4069 (1975)
H Kogelberg et al.
Glycobiology, 4(1), 49-57 (1994-02-01)
Sulphated blood group Lewis(a)/Lewis(x) (Le(a)/Le(x)) type sequences, with sulphate at the 3-position of galactose, have emerged as potent ligands for the endothelial adhesion molecule E-selectin and the leukocyte adhesion molecule L-selectin. As a first step in elucidating the molecular basis
A C Fitchette-Lainé et al.
The Plant journal : for cell and molecular biology, 12(6), 1411-1417 (1998-02-05)
In plants, N-linked glycans are processed in the Golgi apparatus to complex-type N-glycans of limited size containing a beta(1,2)-xylose and/or an alpha(1,3)-fucose residue. Larger mono- and bi-antennary N-linked complex glycans have not often been described. This study has re-examined the
Atit Silsirivanit et al.
Cancer science, 104(10), 1278-1284 (2013-07-03)
Early and specific diagnosis is critical for treatment of cholangiocarcinoma (CCA). In this study, a carbohydrate antigen-S27 (CA-S27) monoclonal antibody (mAb) was established using pooled CCA tissue-extract as immunogen. The epitope recognized by CA-S27-mAb was a new Lewis-a (Le(a)) associated
Ben J Appelmelk et al.
Journal of immunology (Baltimore, Md. : 1950), 170(4), 1635-1639 (2003-02-08)
Dendritic cells (DC) are instrumental in handling pathogens for processing and presentation to T cells, thus eliciting an appropriate immune response. C-type lectins expressed by DC function as pathogen-recognition receptors; yet their specificity for carbohydrate structures on pathogens is not

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