Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry.

Five alditol analogs 1b-1f of a novel glycolipid acremomannolipin A (1a), the potential Ca(2+) signal modulator isolated from Acremonium strictum, were synthesized by employing a stereoselective ß-mannosylation of appropriately protected mannose with five hexitols with different stereochemistry, and their potential on modulating Ca(2+) signaling were evaluated. All these analogs were more potent compared to the original compound 1a, and proved that mannitol stereochemistry of 1a was not critical for the potent calcium signal modulating.