Facile synthesis and stabilization of 2-arachidonylglycerol via its 1,3-phenylboronate ester
Seltzman, H., Fleming, D., Hawkins, G., & Carroll, F. (2000). Facile synthesis and stabilization of 2-arachidonylglycerol via its 1,3-phenylboronate ester. Tetrahedron Letters, 41(19), 3589-3592.
2-Arachidonylglycerol (2-Ara-Gl) was synthesized via the intermediacy of its 1,3-phenylboronic acid ester. The boronate ester is easily stable enough to enable chromatographic resolution from the corresponding 1-Ara-Gl boronate ester on normal phase elution yet immediately and completely hydrolyzes to 2-Ara-Gl and phenylboronic acid, without isomerization, by simple solution in aqueous-organic solvents. The phenylboronate ester of this 2-acylglycerol has the added advantage of being markedly more stable to both isomerization and oxidation upon storage than the labile 2-Ara-Gl. (C) 2000 Elsevier Science Ltd. All rights reserved