Fig. 2.

Synthesis of JGD 3-Sulfo-Lac with 3′-O-sulfo-d-lactose (suLac) headgroup, and the chemical structure of 3-Lac with d-lactose (Lac) headgroup. Reagents and conditions: (i) 2-(2-(2-chloroethoxy)ethoxy)ethanol, BF₃·Et₂O, CH₂Cl₂, 0 °C to 23 °C, 15 h, 80%; (ii) NaN₃, DMF, 80 °C, 15 h, 74%; (iii) MeONa, MeOH, pH = 10, 23 °C, 7 h, 95%; (iv) Bu₂SnO, dry MeOH, 60 °C, 3 h; SO₃·NMe₃, 1,4-dioxane, 23 °C, 48 h; and Ac₂O, pyridine, 23 °C, 15 h, 65%; (v) MeONa, MeOH, pH = 12, 23 °C, 10 h, 91%; (vi) CuSO₄·5H₂O, sodium ascorbate, THF, water, 23 °C, 24 h, 55%. The diameter (D_DLS) and polydispersity index (PDI) were determined by DLS at 0.1 mM of sugar in PBS (PBS 1×, pH 7.4).