Biomimetic synthesis and structural refinement of the macrocyclic dimer aminoglycoside 66-40C--the remarkably selective self-condensation of a putative aldehyde intermediate in the submerged culture medium producing sisomicin.
Aminoglycoside 66-40C, an unprecedented 16-membered bis-azadiene macrocyclic natural product isolated from the Micromonospora producer of the antibiotic sisomicin, was synthesized following a biomimetic strategy which definitively established its origin as arising from a remarkably selective non-enzymatic macro-dimerization.
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, QC, Canada H3C 3J7. stephen.hanessian@umontreal.ca
Maianti
Juan Pablo
JP
D000617:Aminoglycosides / Q000737:chemistry*; D003470:Culture Media; D019281:Dimerization; D008958:Models, Molecular; D018716:Molecular Mimicry; D012853:Sisomicin / Q000096:biosynthesis*
D000617:Aminoglycosides; D003470:Culture Media; C015614:aminoglycoside 66-40C; D012853:Sisomicin