Stereospecific synthesis of 5-phospho-α-d-arabinosyl-C-phosphonophosphate (pACpp): a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-d-arabinosyl pyrophosphate (pApp)

The stereospecific synthesis of 5-phospho-α-d-arabinosyl-C-phosphonophosphate (pACpp) from d-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-d-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro.