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N-Acetyllactosamine

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N-Acetyllactosamine
Names
IUPAC name N-acetamide
Systematic IUPAC name N-oxy}hexan-2-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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.164.310 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13-,14+/m1/s1Key: KFEUJDWYNGMDBV-LODBTCKLSA-N
SMILES
  • CC(=O)N1(((O1O)CO)O2((((O2)CO)O)O)O)O
Properties
Chemical formula C14H25NO11
Molar mass 383.350 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

N-Acetyllactosamine (LacNAc) (also known as CD75) is a nitrogen-containing disaccharide, a lactosamine derivative that is substituted with an acetyl group on its glucosamine component.

The N-acetyllactosamine is a component of many glycoproteins and functions as a carbohydrate antigen that is thought to play roles in normal cellular recognition as well as in malignant transformation and metastasis. It is also found in the structure of human milk oligosaccharides and has prebiotic effects.

References

  1. Katzman RL (June 1972). "Isolation of N-Acetyllactosamine and Galactosyl-β-D-(1 → 4)-N-acetyllactosamine from Beef Brain Glycopeptides" (PDF). The Journal of Biological Chemistry. 247 (12): 3744–9. doi:10.1016/S0021-9258(19)45097-7. PMID 5033387.
  2. Zhou D (February 2003). "Why are glycoproteins modified by poly-N-acetyllactosamine glyco-conjugates?". Current Protein & Peptide Science. 4 (1): 1–9. doi:10.2174/1389203033380304. PMID 12570780.
  3. Ito N, Yokota M, Nagaike C, Morimura Y, Hatake K, Matsunaga T (January 1996). "Histochemical demonstration and analysis of poly-N-acetyllactosamine structures in normal and malignant human tissues". Histology and Histopathology. 11 (1): 203–14. PMID 8720464.
  4. Alavijeh MK, Meyer AS, Gras SL, Kentish SE (February 2020). "Simulation and economic assessment of large-scale enzymatic N-acetyllactosamine manufacture" (PDF). Biochemical Engineering Journal. 154: 107459. doi:10.1016/j.bej.2019.107459. S2CID 214143153.

External links

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