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Synthesis

Making mannopeptimycins

First total synthesis of antibiotic natural products could lead to more potent analogs

by Bethany Halford
March 14, 2016 | APPEARED IN VOLUME 94, ISSUE 11

The bacteria-battling natural products known as mannopeptimycins have been known to go mano a mano against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus and win handily. The mannopeptimycins have an unusual structure and a novel mode of action, making them an interesting target for chemical synthesis because analogs might improve their antibacterial activity or reveal more details about how they work. But preparing the cyclic hexapeptides decorated with sugar groups has proven challenging. Chemists have made pieces of these compounds, but until now, a total synthesis of the entire structure with its attached sugars has been elusive. The biggest hurdle has been generating an N-glycosylated guanidine moiety in the molecule. No such chemical motif has ever been found in any other natural product. Chemists led by Gong Chen of Nankai University were able to add the sugar unit to the hindered guanidine nitrogen by using gold catalysis and incorporated this transformation into the first total syntheses of mannopeptimycins α and β (J. Am. Chem. Soc. 2016, DOI: 10.1021/jacs.6b01384). They hope the advance will enable exploration of previously inaccessible mannopeptimycin derivatives.

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