Synthesis and glycosidase inhibition evaluation of (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol

Zhang, En; Bai, Peng-Yan; Sun, Wei; Wang, Shang; Wang, Mingming; Xu, Shuai-Min; Liu, Hong‐Min

doi:10.1016/j.carres.2016.08.003

Cited by 4 publications

(1 citation statement)

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“…Indeed, C-4 of glucose entails the expected configuration found at C-3 in the target compounds. Furthermore, diastereoselective additions to the well-known glucose-derived furanone 22 (Scheme ) are usually guided by the 1,2- O -isopropylidene moiety, which enforces the nucleophile to bind from the β-face . This was demonstrated with a range of nucleophiles such as methylmagnesium bromide or even CF 3 SiMe 3, affording in this latter case the requisite configuration to the targeted α-trifluoromethyl alcohol …”

Section: Resultsmentioning

confidence: 99%

Carbohydrate-Templated Syntheses of Trifluoromethyl-Substituted MEP Analogues for the Study of the Methylerythritol Phosphate Pathway

Simonet,

Herrscher,

Witjaksono

et al. 2023

J. Org. Chem.

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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, whereas trifluoro-MEcPP induced 40% inhibition of IspG at 1 mM.

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Section: Resultsmentioning

confidence: 99%