An improved method for synthesizing cyclic bis(3′-5′)diguanylic acid (c-di-GMP)
An improved method for synthesizing cyclic bis(3′-5′)diguanylic acid (c-di-GMP)
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DOI：
10.1246/bcsj.77.2089
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发表时间：
2004-11-01
影响因子：
4
通讯作者：
Hayakawa, Y
中科院分区：
文献类型：
--
作者：
Hyodo, M;Hayakawa, Y
本文介绍了一种合成具有生物学意义的环状双（3 '-5'）二鸟苷酸（c-diGMP）的新方法，其产率高于以往报道的合成方法。在新的合成中，以下两个手段，在以前报道的合成中使用的地方，作为主要策略，以获得在产品收率的增加。一种是使用二叔丁基硅烷二基保护鸟苷的3 '-和5'-羟基;这种方法允许区域选择性地生产2 '-O-（叔丁基二甲基甲硅烷基）鸟苷衍生物，其是合成的关键中间体。另一种是使用二甲基甲脒基团作为鸟嘌呤碱基的2-NH 2官能团的保护剂，其可以容易地引入并导致优异的产率。
This paper describes a new method for synthesizing biologically important cyclic bis(3'-5')diguanylic acid (c-diGMP) in a higher yield than that previously reported to be available by our synthetic method. In the new synthesis, the following two means, in place of those used in the previously reported synthesis, are employed as main strategies to obtain an increase in product yield. One is the use of di-tert-butylsilanediyl protection for 3'- and 5'-hydroxy groups of guanosine; this method allows regioselective production of a 2'-O-(tert-butyldimethylsilyl)guanosine derivative that is a key intermediate for the synthesis. The other is the use of a dimethylformamidine group as a protector for the 2-NH2 function of the guanine base, which can be easily introduced and results in an excellent yield.