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44559

Sigma-Aldrich

2-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-D-mannose

≥98.0% (TLC)

Synonym(s):

N-Acetylglucosaminyl-β-1,2-mannose, β-D-GlcNAc-(1→2)-D-Man

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About This Item

Empirical Formula (Hill Notation):
C14H25NO11
CAS Number:
34621-73-3
Molecular Weight:
383.35
UNSPSC Code:
12352201
NACRES:
NA.25

assay

≥98.0% (TLC)

suitability

conforms to structure for Infrared spectrum

storage temp.

−20°C

SMILES string

CC(N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO)=O

InChI

1S/C14H25NO11/c1-5(19)15-9-13(24)12(23)8(4-18)26-14(9)25-7(3-17)11(22)10(21)6(20)2-16/h3,6-14,16,18,20-24H,2,4H2,1H3,(H,15,19)/t6-,7-,8-,9-,10-,11-,12-,13-,14-/m1/s1

InChI key

WCIQTQUMKQRLKV-ZTGOBPNGSA-N

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Biochem/physiol Actions

Disaccharide fragment found in N-acetyl-lactosaminic type glycans of N-glycoproteins.

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC1836
BCBP6436V
BCBP6436

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Tammy T Fang et al.
Journal of the American Chemical Society, 129(31), 9721-9736 (2007-07-17)
Mass spectrometry of hexose-containing disaccharides often yields product ions of m/z 221 in the negative ion mode. Using a Paul trap, isolation and collision-induced dissociation of the m/z 221 anions yielded mass spectra that easily differentiated their stereochemistry and anomeric
Velavan Ramasamy et al.
Journal of molecular biology, 353(1), 53-67 (2005-09-15)
beta-1,4-Galactosyltransferase-I (beta4Gal-T1) transfers galactose from UDP-galactose to N-acetylglucosamine (GlcNAc) residues of the branched N-linked oligosaccharide chains of glycoproteins. In an N-linked biantennary oligosaccharide chain, one antenna is attached to the 3-hydroxyl-(1,3-arm), and the other to the 6-hydroxyl-(1,6-arm) group of mannose
Benjamin Pluvinage et al.
Structure (London, England : 1993), 19(11), 1603-1614 (2011-11-15)
The complete degradation of N-linked glycans by the pathogenic bacterium Streptococcus pneumoniae is facilitated by the large multimodular cell wall-attached exo-β-D-N-acetylglucosaminidase StrH. Structural dissection of this virulence factor using X-ray crystallography showed it to have two structurally related glycoside hydrolase
Yong-Liang Jiang et al.
The Journal of biological chemistry, 286(50), 43004-43012 (2011-10-21)
The β-N-acetylhexosaminidase (EC 3.2.1.52) from glycoside hydrolase family 20 (GH20) catalyzes the hydrolysis of the β-N-acetylglucosamine (NAG) group from the nonreducing end of various glycoconjugates. The putative surface-exposed N-acetylhexosaminidase StrH/Spr0057 from Streptococcus pneumoniae R6 was proved to contribute to the
Zoi Pipirou et al.
Glycobiology, 21(6), 806-812 (2011-01-25)
The biochemical properties of mouse LSECtin, a glycan-binding receptor that is a member of the C-type lectin family found on sinusoidal endothelial cells, have been investigated. The C-type carbohydrate-recognition domain of mouse LSECtin, expressed in bacteria, has been used in

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