RESUMO
Methyl 2-C-allyl-2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero- D-talo-octonate (9a), the protected alpha-allyl C-glycoside of 3-deoxy-D-manno-2-octulosonic acid (KDO), has been synthesized using a photochemically initiated radical reaction. A phenyl thioglycoside (8) was used as the substrate and allyltributyltin as the acceptor. The stereoselectivity of the reaction was 90:10 in favour of the talo-isomer (alpha-).
Assuntos
Anti-Infecciosos/síntese química , Açúcares Ácidos/síntese química , Anti-Infecciosos/química , Radicais Livres , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Fotoquímica , Estereoisomerismo , Açúcares Ácidos/químicaRESUMO
The thioglycoside 5 of 3-deoxy-beta-D-manno-2-octulosonic acid (beta-KDO) has been synthesized in an attempt to make a simplified transition-state analogue inhibitor of the enzyme CMP-KDO synthetase (3-deoxy-D-manno-octulosonate cytidylyltransferase). Compound 5 was tested in vitro and was found to have no inhibitory activity.
Assuntos
Nucleotidiltransferases/antagonistas & inibidores , Açúcares Ácidos/síntese química , Estrutura Molecular , Relação Estrutura-Atividade , Açúcares Ácidos/farmacologiaRESUMO
Eight C-(beta-D-glycosyl) analogues (14-21) of Kdo (3-deoxy-D-manno-2-octulosonic acid) were obtained from isopropylidene-protected ester precursors and tested in vitro for their inhibitory activity on CMP-Kdo synthetase. None had more than minor inhibitory activity.
