Síntese e modificações de derivados heterocíclicos de D-arabinose: potenciais inibidores de glicose-6-fosfato isomerase e de glicosamina-6-fosfato sintase Synthesis and modifications of heterocyclic derivatives of D-arabinose: potential inhibitors of glucose-6-phosphate isomerase and glucosamine-6-phosphate synthase

• Main Authors: Renato Márcio Ribeiro Viana, Maria Auxiliadora Fontes Prado, Ricardo José Alves
• Format: Article
• Language: English
• Published: Sociedade Brasileira de Química 2008-01-01
• Series: Química Nova
• Subjects: D-arabinose; heterocycles; enzyme inhibitors
• Online Access: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422008000700021
• ISSN: 0100-4042; 1678-7064

<abstract language="eng">The synthesis of -5-(D-arabino-1,2,3,4-tetrahydroxybutyl)tetrazole and -2-(D-arabino-1,2,3,4-tetra-acetoxybutyl)-5-methyl-1,3,4-oxadiazole from D-arabinose is described. Attempts at removing the protecting groups of the oxadiazole derivative were unsuccessful, leading to products resulting from the opening of the oxadiazole ring. The unprotected tetrazole derivative was selectively phosphorylated at the primary hydroxyl group with diethylphosphoryl chloride. The resulting 5-[D-arabino-4-(diethylphosphoryloxy)-1,2,3-trihydroxybutyl]tetrazole is a protected form of a potential inhibitor of the enzymes glucose-6-phosphate isomerase and glucosamine synthase.