N-Acetyllactosamine

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.

N-Acetyllactosamine
Names
IUPAC name
N-[β-D-Galactopyranosyl-(1→4)-(2-deoxy-D-glucos-2-yl)]acetamide
Systematic IUPAC name
N-[(2R,3R,4S,5R)-3,5,6-Trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.164.310
KEGG
UNII
  • 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/s1
    Key: KFEUJDWYNGMDBV-LODBTCKLSA-N
  • 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
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).
Infobox references

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
  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.
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