N-Acetyllactosamine

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

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.

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