An optimized method for the synthesis of amino-functionalized phosphatidylcholine

作者：Kong Fanzhi^*; Morais Goreti Ribeiro; Falconer Robert A; Sutton Chris W

来源：Tetrahedron Letters, 2012, 53(5): 546-549.

DOI：10.1016/j.tetlet.2011.11.100

• Phosphatidylcholine (PC)
• Boc deprotection
• Phthalimide deprotection
• Phospholipid purification

Phosphatidylcholine analogues were synthesised as affinity ligands for the capture of membrane proteins. Several protecting group strategies were investigated to synthesize the amino-functionalized phosphatidylcholine: 11-aminoundecyl 2-(trimethylammonio)ethyl phosphate (4). The acid-mediated deprotection of the Boc group generated a mixture of the target products which could only be purified by HPLC. However, an alternative strategy, using the hydrazine-labile phthalimide group route, followed by a gel filtration step proved straightforward to afford the desired amino-functionalized phosphatidylcholine product in high yield and purity.

• 出版日期2012-2-1