Synthesis and characterization of lyso-GM3 (II3Neu5Ac Lactosyl sphingosine), de-N-acetyl-GM3 (II3NeuNH2 lactosyl Cer), and related compounds.

摘要: Abstract Various GM 3 derivatives which are present in A431 cells have different effects on the activity of EGF receptor kinase. In order to systematically study these effects, following been synthesized: de- N -acetyl-GM (D 1 ), -acetyl-lyso-GM 2 lyso-GM with -acetylsphingosine 4 and 5 ). A crucial step for preparation D is use mild alkaline conditions hydrolysis under -acetyl group sialic acid preferentially hydrolyzed. For , allowed preferential -acetylation amino neuraminic moiety were devised, i.e. was incorporated a dipalmitoylphosphatidylcholine (dpPC) liposome sphingosine protected -acetylated acetate water-soluble catalyst, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (DEC). When an aqueous micellar solution treated DEC, occurred mainly at yielding . contrast, when acetic anhydride sodium hydrogencarbonate, groups both neuraminosyl sphingosyl residues, The structures verified by H-n.m.r. spectroscopy mass spectrometry.