Preparation of deazapurine nucleosides by microbial transglycosylation.

LETICIA BENTANCOR; MATÍAS NÓBILE; ELIZABETH LEWKOWICZ; ADOLFO IRIBARREN

Olomouc, Czech Republic

Simposio; VI Simposio Internacional de Biocatalisis y Biotransformaciones (BIOTRANS 2003); 2003

Benzimidazole nucleosides have shown inhibitory effect on human cytomegalovirus infections, herpes viruses  and other RNA viruses and in some cases possess mutagenic properties. The chemical synthesis of these nucleosides is complex and stereounspecific and affords low yields . To our best knowledge, only ribo- and deoxyribofuranosyl nucleosides of benzimidazole have been previously synthesised using microbial transglycosylation and guanosine as starting material. Based on our experience, benzimidazole nucleosides carrying natural and modified sugar moieties were prepared starting from  available pyrimidine ones.  The selected microorganisms were screened from our bacterial collection, affording yields between 60-90% after optimisation of the reaction conditions