ORGN 732 |
| Lysophospholipids have recently attracted a great deal of attention as it was discovered that in addition to their role in phospholipid metabolism they function as second messengers, exhibiting a broad range of biological activities in their own right. Along these lines lysophosphatidylcholines have been shown to be highly potent extracellular regulators of cell growth, differentiation, and a series of related processes through G-protein coupled receptors. Synthetic lysophospholipids are needed to elucidate their mechanism of action in vivo, and to study the enzymes involved in their metabolism. We will present a new stereospecific synthesis of lysophosphatidylcholines using 3-p-toluenesulfonyl-sn-glycerol as chiral synthon for construction of the target compounds. The sequence relies on orthogonal protection of the glycerol skeleton, including chemoselective manipulation of the methoxyacetyl function in the presence of other ester groups in the molecule. Preparation of synthetic lysophosphatidylcholines with chain-terminal reporter groups provides precursors of double-labeled phosphatidylcholines with spectroscopic markers. |
|
Lipids, Nucleotides, Biosynthesis, and Mimetics
8:00 AM-12:00 PM, Thursday, 1 September 2005 Washington DC Convention Center -- 202B, Oral
Division of Organic Chemistry |