Natural and modified nucleoside polyphosphates are indispensable tools in modern biological investigations. Their applications include but are not limited to polymerase chain reactions (PCR), single nucleotide polymorphism (SNP) detection, DNA/RNA labelling, non-specific mutagenesis, and DNA-sequencing including single molecule real time sequencing. It is known that the terminal phosphate labeled nucleoside 5 polyphosphates (n1⁄4 2-4, Figure 1) are better substrates for RNAand DNA-polymerases than c-labelled nucleoside 5 -triphosphates. One of the approaches to obtain derivatives like those shown in Figure 1, where X cannot be phosphorylated directly, includes the insertion of an intermediate aminoalkyl linker tethered to the terminal phosphate by a stable phosphoroester bond and coupling of two phosphorylated blocks to form a disubstituted polyphosphate chain. This may provide a wide variety of derivatives conjugated with fluorescent labels based on commercially available carboxyl containing dyes. Recently, we applied this strategy to the synthesis of a number of novel ADP conjugates, potential inhibitors of poly(ADPribosyl)polymerase 1. In that work, AMP and monophosphorylated amino alcohols protected at the amino group were coupled to give disubstituted pyrophosphates. Unlike pyrophosphate linkage formation, there are different strategies to obtain the linear polyphosphates by coupling two phosphorylated blocks. Among them, coupling that involves monoand triphosphate derivatives is more attractive due to the relative availability of parent monoand triphosphorylated species in contrast to diphosphates. Currently, there are several methods for the monoand triphosphorylation of alcohols including nucleoside derivatives. To provide the selective O-phosphorylation of amino alcohols containing aliphatic amino groups it is necessary to protect the

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氨基醇单磷酸酯和三磷酸酯合成中保护基的观察

天然和修饰的多磷酸核苷是现代生物学研究中不可或缺的工具。它们的应用包括但不限于聚合酶链反应 (PCR)、单核苷酸多态性 (SNP) 检测、DNA/RNA 标记、非特异性诱变和 DNA 测序，包括单分子实时测序。众所周知，末端磷酸标记的核苷 5 多磷酸（n1⁄4 2-4，图 1）比 c 标记的核苷 5-三磷酸是更好的 RNA 和 DNA 聚合酶底物。获得衍生物的方法之一，如图 1 所示，其中 X 不能直接磷酸化，包括通过稳定的磷酸酯键连接到末端磷酸酯的中间氨基烷基接头的插入和两个磷酸化嵌段的偶联以形成双取代的多磷酸酯链。这可以提供多种与基于市售含羧基染料的荧光标记缀合的衍生物。最近，我们将此策略应用于合成许多新型 ADP 偶联物，即聚（ADP核糖基）聚合酶 1 的潜在抑制剂。在这项工作中，AMP 和氨基保护的单磷酸化氨基醇偶联得到二取代的焦磷酸盐。与焦磷酸键的形成不同，通过偶联两个磷酸化嵌段来获得线性多磷酸酯有不同的策略。他们之中，与二磷酸相比，由于母体单磷酸化和三磷酸化物质的相对可用性，涉及单磷酸和三磷酸衍生物的偶联更具吸引力。目前，有几种方法用于醇的单磷酸化和三磷酸化，包括核苷衍生物。为了提供含有脂肪族氨基的氨基醇的选择性 O-磷酸化，有必要保护