Warnecke Svenja, Meier Chris
Organic Chemistry, Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.
J Org Chem. 2009 Apr 17;74(8):3024-30. doi: 10.1021/jo802348h.
A new and efficient method for the synthesis of nucleoside di- and triphosphates as well as dinucleoside polyphosphates (Np(n)N') is described. 5-Acceptor-substituted (5-nitro and 5-chloro) cycloSal-nucleotides are used as starting material that were reacted with a variety of phosphate nucleophiles as pyrophosphate or nucleotides to the corresponding products in short times and very good yields. After consumption of the starting cycloSal-phosphate triester, first the protecting groups were cleaved and finally the products were isolated after RP-column chromatography. Examples are shown for all five pyrimidine and purine bases found in natural nucleosides as well as one non-natural pyrimidine base to prove that the method can be applied generally.
描述了一种合成核苷二磷酸和三磷酸以及二核苷多磷酸(Np(n)N')的新型高效方法。5-受体取代的(5-硝基和5-氯)环Sal-核苷酸用作起始原料,其与各种磷酸盐亲核试剂(如焦磷酸或核苷酸)在短时间内反应,以非常高的产率得到相应产物。起始的环Sal-磷酸三酯消耗完后,首先去除保护基团,最后通过反相柱色谱法分离产物。给出了天然核苷中发现的所有五种嘧啶和嘌呤碱基以及一种非天然嘧啶碱基的示例,以证明该方法可普遍应用。