N-Acetyllactosamine

N-Acetyllactosamine
Names

IUPAC name N-[(2R,3R,4R,5S,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
Other names β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose; 2-(Acetylamino)-2-deoxy-4-O-hexopyranosylhexopyranose
Identifiers
CAS Number	32181-59-2^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16153^Y
ChEMBL	ChEMBL457432^Y
ChemSpider	7975931^Y
ECHA InfoCard	100.164.310
KEGG	C00611^Y
PubChem	439271
SMILES CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O)CO)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O
Properties
Chemical formula	C₁₄H₂₅NO₁₁
Molar mass	383.35 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

N-Acetyllactosamine also known as 2-(acetylamino)-2-deoxy-4-O-hexopyranosylhexopyranose is a nitrogen containing disaccharide.^[1]

The N-acetyllactosamine is a component of many glycoproteins^[2] and functions as a carbohydrate antigen that is thought to play roles in normal cellular recognition as well as in malignant transformation and metastasis.^[3]

References

↑ Katzman RL (1972). "Isolation of N-Acetyllactosamine and Galactosyl-β-D-(1 → 4)-N-acetyllactosamine from Beef Brain Glycopeptides" (PDF). J. Biol. Chem. 247 (12): 3744–9. PMID 5033387.
↑ Zhou D (2003). "Why are glycoproteins modified by poly-N-acetyllactosamine glyco-conjugates?". Curr. Protein Pept. Sci. 4 (1): 1–9. PMID 12570780.
↑ Ito N, Yokota M, Nagaike C, Morimura Y, Hatake K, Matsunaga T (1996). "Histochemical demonstration and analysis of poly-N-acetyllactosamine structures in normal and malignant human tissues". Histol. Histopathol. 11 (1): 203–14. PMID 8720464.

N-acetyllactosamine at the US National Library of Medicine Medical Subject Headings (MeSH)

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