通过1-羟基苯并三唑磷酸三酯法合成核酸甲基膦酸酯。
Synthesis of nucleic acid methylphosphonates via the 1-hydroxybenzotriazole phosphotriester approach.
作者信息
Marugg J E, de Vroom E, Dreef C E, Tromp M, van der Marel G A, van Boom J H
出版信息
Nucleic Acids Res. 1986 Mar 11;14(5):2171-85. doi: 10.1093/nar/14.5.2171.
Abstract
Dinucleoside methylphosphonates can easily be prepared starting from properly protected d-nucleosides and the bifunctional phosphorylating reagent methyl-O,O-bis(1-benzotriazolyl)phosphate. Separation of the diastereoisomers of 5'-DMTR-d-Ap(Me)T-3'-lev affords optically pure dinucleoside methylphosphonates which, after removal of the 3'-levulinoyl group, have been used for the synthesis of the two optically pure diastereoisomers of the hexamer d-CpGpAp(Me)TpCpG. Further, a one-pot procedure for the preparation of uridine-3',5'-cyclic methylphosphonate will be described. We also found that 3',5'-methylphosphonate linkages in RNA are not stable towards mild acid treatment.
摘要
从适当保护的d-核苷和双功能磷酸化试剂甲基-O,O-双(1-苯并三唑基)磷酸酯开始，可以很容易地制备二核苷甲基膦酸酯。5'-DMTR-d-Ap(Me)T-3'-乙酰丙酸酯的非对映异构体的分离得到了光学纯的二核苷甲基膦酸酯，在除去3'-乙酰丙酰基后，它们被用于合成六聚体d-CpGpAp(Me)TpCpG的两种光学纯非对映异构体。此外，还将描述一种制备尿苷-3',5'-环甲基膦酸酯的一锅法。我们还发现，RNA中的3',5'-甲基膦酸酯键对温和的酸处理不稳定。
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