Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , 610 Taylor Road, Piscataway, New Jersey 08854, United States.
Org Lett. 2014 Jan 3;16(1):158-61. doi: 10.1021/ol403154w. Epub 2013 Dec 6.
The first syntheses of neutral thiourea, urea, and carbodiimide analogs, along with two guanidinium analogs, of the bacterial signaling molecule cyclic diguanosine monophosphate (c-di-GMP) are reported. The key intermediate, obtained in nine steps, is a 3'-amino-5'-azido-3',5'-dideoxy derivative. The 5'-azide serves as a masked amine from which the amine is obtained by Staudinger reduction, while the 3'-amine is converted to an isothiocyanate that, while stable to chromatography, and Staudinger conditions, nevertheless reacts well with the 5'-amine.
报道了细菌信号分子环二鸟苷酸单磷酸（c-di-GMP）的中性硫脲、脲和碳二亚胺类似物以及两个胍类似物的首次合成。关键中间体经九步反应得到，为 3'-氨基-5'-叠氮-3'，5'-二脱氧衍生物。5'-叠氮基作为掩蔽胺，通过斯塔德勒还原得到胺，而 3'-氨基则转化为异硫氰酸酯，尽管其在层析和斯塔德勒条件下稳定，但仍能与 5'-胺很好地反应。
