2-O-beta-D-glucosylglycerol based analogues of sulfoquinovosylacylglycerols

Sulfoquinovosylacylglycerols(SQAG) are sulfoglycoglycerolipids discovered in photosynthetic microorganisms, a large number of marine algae and higher plants by Benson in 1959,1 in which sulfoquinovose (6-deoxy-6-sulfo-glucose) is -linked to the sn-3 position of a diacylglycerol. Recently reported2-3 biological activities of SQAG, including inhibitory effects on HIV-reverse transcriptase, mammalian DNA polymerase, proliferation of some cancer cell lines, angiogenesis and apoptosis induction, make these compounds very attractive for their potential in cancer therapy. Here we report the synthesis of SQAG analogues based on the skeleton of 2-O-beta-D-glucosylglycerol to which previously prepared biologically active glucoglycerolipid analogues are related.4 A chemoenzymatic strategy has been used to selectively insert the proper chemical functionalities (i.e. acyl chains) at the desired positions of glucosylglycerol to obtain the target compounds. Their potential as anti-tumor-promoters and angiogenesis inhibitors will be also discussed.