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Beilstein J. Org. Chem. 2014, 10, 2580–2585, doi:10.3762/bjoc.10.270
Graphical Abstract
Figure 1: Structure of thiamine diphosphate (ThDP, 1).
Scheme 1: Mechanism of pyruvate decarboxylase and structures of some previously synthesised ThDP analogues.
Scheme 2: Dehydrative cyclization catalysed by gold(I) and its presumed mechanism [31].
Scheme 3: Synthesis of furan 12. Reagents and conditions: (i) TBDMS-Cl, N-methylimidazole. (ii) n-BuLi, −78 °...
Scheme 4: Synthesis of the furan analogue 17 of ThDP. Reagents and conditions: (i) MnO2, CHCl3, 72%; (ii) PhN...
Scheme 5: Coupled assay of PDC activity.
Figure 2: Time course inactivation of ZmPDC by various concentrations of furan 17.
Figure 3: Recovery of activity for ZmPDC inhibited by furan 17 (1.0 µM) and then incubated with ThDP (1.0 mM)...