Synthesis and antibacterial activity of mechanism-based inhibitors of KDO8P synthase and DAH7P synthase

KDO8PS (3-deoxy-D-manno-2-octulosonate-8-phosphate synthase) and DAH7PS (3-deoxy-D-arabino-2-heptulosonate-7-phosphate synthase) are attractive targets for the development of new anti-infectious agents. Both enzymes appear to proceed via a common mechanism involving the reaction of phosphoenolpyruvate (PEP) with arabinose 5-phosphate or erythrose-4-phosphate, to produce the corresponding ulosonic acids, KDO8P and DAH7P, respectively. The synthesis of new inhibitors closely related to the supposed tetrahedral intermediate substrates for the enzymes is described. The examination of the antibacterial activity of these derivatives is reported.     

Monoglycosyl, diglycosyl, and dinucleoside methylenediphosphonates: direct synthesis and antiviral activity

A direct and general access to D-glycosyl 3-, 5-, or 6-methylenediphosphonates, di-D-glycosyl 1,5-, 3,5-, 3,6-, 5,5-, or 6,6-methylenediphosphonates and dithymidine 3',5'-methylenediphosphonate is described. The method involves the one-pot alkylidenediphosphorylation of glycosyl or thymidine derivatives. No antiviral activity was detected against a panel of RNA and DNA viruses.     

Synthesis and structural analysis of vinylogous peptides

Summary A Z-orE-ethenyl group has been inserted between the α-carbon and the carboxyl group of the proline residue by stereoselective Horner synthesis. The resulting vinylogous amino acid has been coupled with amino compounds by classical methods, and model amino acid derivatives and dipeptides containing a Z-orE-CH=CMe group have been investigated in solution by¹H-NMR and IR spectroscopy, and in the solid state by X-ray diffraction. TheE-ethenyl group gives rise to an open conformation and the Z-conformer to a folded structure with an intramolecular hydrogen bond closing a ninemembered pseudocycle.