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. Author manuscript; available in PMC: 2017 Jan 26.
Published in final edited form as: Nat Prod Rep. 2014 Aug;31(8):1026–1042. doi: 10.1039/c3np70128j

Scheme 1.

Scheme 1

Orthosomycin biosynthesis. A) Proposed scheme for formation of ring G, L-lyxose. AviE2 has been shown to catalyze the decarboxylation of UDP-D-glucuronic acid to UDP-D-xylose. B) Scheme for formation of 2,6-di-O-methyl-D-mannose from 6-O-methyl-D-glucose. AviX12 catalyzes a unique radical epimerization reaction while AviG6 methylates the 2-hydroxyl presumably after epimerization. C) Formation of L-evernitrose from L-epi-vancosamine. ORF36 catalyzes the oxidation of the nitrogen from the amino to the nitroso oxidation state. It is likely spontaneous oxidation of the nitroso congener which leads to the nitro form.