Neu5Acα2-8Neu5Acα2-3Galβ1-4GlcNAc (disialyl lacto-N-triose II or DSLNT II) is a sialylated tetrasaccharide human milk oligosaccharide (HMO) characterized by a unique α2-8 linked disialyl motif where N-acetylneuraminic acid (Neu5Ac) caps another Neu5Acα2-3Gal, extended to the type-2 chain GlcNAc core. This structure, biosynthesized by ST8Sia-II (GD3 synthase) followed by ST3Gal-III/IV on lacto-N-triose II, represents a minor but bioactive HMO fraction (<1% total HMOs) pivotal for neonatal immunity and gut maturation. The terminal α2-8/α2-3 sialyl configuration mimics ganglioside epitopes, serving as high-affinity decoy receptors for sialic acid-binding respiratory/enteric viruses (e.g., influenza, norovirus) and selectins mediating leukocyte trafficking. In prebiotic contexts, it selectively nourishes Bifidobacterium longum subsp. infantis sialidases, modulating microbiota sialometabolism and reducing pathogen adhesion. Therapeutically, synthetic DSLNT II probes Siglec-7/9 inhibitory receptors for cancer immunotherapy, anti-inflammatory glycotherapeutics, and infant formula supplementation to mimic colostrum sialylation patterns protective against necrotizing enterocolitis (NEC).
Appearance
White to pale yellow lyophilized amorphous powder.
Highly hygroscopic; supplied freeze-dried under nitrogen.
Source
Trace levels in transitional human milk/colostrum (0.01-0.1 g/L).
Enzymatic/chemical synthesis using porcine/bacterial ST8Sia2 on Neu5Acα2-3Galβ1-4GlcNAc acceptor.