Synthesis of c-di-GMP analogs with thiourea, urea, carbodiimide, and guanidinium linkages.

ABSTRACT: 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.

SUBMITTER: Gaffney BL 

PROVIDER: S-EPMC3933394 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature