Design, synthesis and In Vitro evaluation on glucosamine-6P synthase of aromatic analogs of 2-Aminohexitols-6P

• Autor(a) principal: Dias,Danielle F.
• Data de Publicação: 2010
• Outros Autores: Roux,Céline, Durand,Philippe, Iorga,Bogdan, Badet-Denisot,Marie A., Badet,Bernard, Alves,Ricardo J.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000400014
• topic: glucosamine synthase; inhibitors; aminohexitols derivatives

The aminosugars are very important structural components of bacterial and fungi cell walls. Glucosamine-6-phosphate synthase (GlmS), which catalyses the first step of the aminosugar biosynthetic pathway i.e. the formation of D-glucosamine-6-phosphate from D-fructose-6-phosphate, is therefore an interesting target in the fight against microorganisms. In this work is described the synthesis of aromatic analogs of 2-amino-2-deoxy-D-glucitol-6-phosphate (ADGP) and its epimer 2-amino-2-deoxy-D-manitol-6-phosphate (ADMP), two important inhibitors of GlmS. The aromatic analogs displayed modest inhibitory activity against GlmS, with IC50 in the mmol L-1 range.