N-Acetyllactosamine
(Redirected from N-acetyllactosamine)
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Preferred 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]oxy}oxan-3-yl]acetamide | |
Other names
β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose; 2-(Acetylamino)-2-deoxy-4-O-hexopyranosylhexopyranose
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
KEGG | |
PubChem CID
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UNII | |
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Properties | |
C14H25NO11 | |
Molar mass | 383.350 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Acetyllactosamine (LacNAc) (also known as CD75) is a nitrogen-containing disaccharide,[1] a lactosamine derivative that is substituted with an acetyl group on its glucosamine component.
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] It is also found in the structure of human milk oligosaccharides and has prebiotic effects.[4]
References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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
- N-acetyllactosamine at the US National Library of Medicine Medical Subject Headings (MeSH)