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Selective transformations of complex molecules are enabled by aptameric protective groups
Selective modifications of structurally complex molecules bearing multiple reactive functional groups often require cumbersome multistep synthetic efforts. Here, aptameric protective groups based on short RNA sequences are described — they bind to neamine antibiotics, simultaneously protecting several functionalities and enabling regio- and chemoselective functionalizations.
- Andreas A. Bastian
- , Alessio Marcozzi
- & Andreas Herrmann
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Total synthesis of marinomycin A using salicylate as a molecular switch to mediate dimerization
Marinomycin A is a member of a new class of bis-salicylate-containing polyene macrodiolide, with potent antibiotic activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF). Here, a triply convergent synthesis of this agent is described that uses the salicylate moiety as a novel molecular switch for the chemoselective construction of the macrodiolide.
- P. Andrew Evans
- , Mu-Hua Huang
- & Sergio Maroto
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News & Views |
Tackling tunicamycin
The tunicamycins, secondary metabolites of various Streptomyces species, are invaluable tools in glycobiology. It has now been shown that their biosynthesis involves an unusual exo-glycal intermediate produced by previously unknown short-chain dehydrogenase/reductase activity.
- Ethan D. Goddard-Borger
- & Stephen G. Withers
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Article |
Biosynthesis of the tunicamycin antibiotics proceeds via unique exo-glycal intermediates
Construction of the remarkable 11-carbon frame of the antibiotic tunicamycin is shown to use cyclic enol ethers (exo-glycals) — the first time such intermediates have been seen in biology. Exo-glycal synthase TunA uses an elegantly subtle mechanism to control regioselectivity and with exo-glycal epimerase TunF sets a logical chemical stage for downstream radical C–C coupling.
- Filip J. Wyszynski
- , Seung Seo Lee
- & Benjamin G. Davis