Carbohydrate-Templated Syntheses of Trifluoromethyl-Substituted MEP Analogues for the Study of the Methylerythritol Phosphate Pathway
Basile Simonet,
Vivien Herrscher,
Clea Witjaksono
et al.
Abstract:Trifluoromethyl analogues of methylerythritol
phosphate (MEP) and
2-C-methyl-erythritol 2,4-cyclodiphosphate (MEcPP),
natural substrates of key enzymes from the MEP pathway, were prepared
starting from d-glucose as the chiral template to secure
absolute configurations. The obligate trifluoromethyl group was inserted
with complete diastereoselectivity using the Ruppert–Prakash
nucleophile. Target compounds were assayed against the corresponding
enzymes showing that trifluoro-MEP did not disrupt IspD activity,
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