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

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Abstract
The effect of chemical modification at the C1 position of GLA‐27, 4‐O‐phosphono‐D‐glucosamine carrying N‐3‐tetradecanoyloxytetradecanoyl [C14‐O‐(C14)] and 3‐O‐tetradecanoyl (C14) groups, was investigated. Replacement by SH or S‐acetyl groups of the OH group resulted in the enhancement of mitogenicity but gave rise to a reduction, in macrophage‐stimulating ability such as induction of tumor necrosis factor and enhancement of phagocytic and cellular acid phosphatase activities. Bisphosphorylation at C1 and C4 resulted in a slight decrease in mitogenicity or almost complete loss of the macrophage‐stimulating ability.

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