Effect of chemical modification at C1 of the glucosamine backbone of lipid A‐subunit analog GLA‐27 on manifestation of immunopharmacological activity

Abstract

The effect of chemical modification at the Cl position of GLA-27,4-O-phosphono-D-glucosamine carrying N-3-tetradecanoyloxytetradecanoyl [C,,-0-(C,,)] and 30tetradecanoyl (C,,) groups, was investigated. Replacement by SH or Sacetyl groups of the OH group resulted in the enhancement of mitogenicity but gave rise to a reduction, in macrophagestimulating ability such as induction of tumor necrosis factor and enhancement of phagocytic and cellular acid phosphatase activities. Bisphosphorylation at Cl and C4 resulted in a slight decrease in mitogenicity or almost complete loss of the macrophage-stimulating ability.