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- W2022808760 abstract "Nodularins and microcystins are complex natural isopeptidichepatotoxins that serve as subnanomolar inhibitors of the eukaryoticserine–threonine protein phosphatases, PP1 and PP2A. In Part 1 (A.P. Mehrotra, K. L. Webster and D. Gani, J. Chem. Soc.,Perkin Trans. 1, 1997, preceding paper) each of the keystructural or potentially reactive motifs within each macrocycle typewas assessed as a contributor towards phosphatase inhibitory efficacyand a stripped-down nodularin-type macrocycle was identified as asuitable precursor to potentially active synthetic inhibitors.Subsequently, synthetic routes to the 19-membered nodularin macrocyclicsystem were developed, using solution-phase chemistry, whichdemonstrated that only certain cyclisation protocols were viable. Herewe describe an extension of this chemistry to provide a 19-memberednodularin macrocycle,cyclo-[(3R)-3-hydroxymethyl-β-Ala-(R)-Glu-α-OMe-γ-Sar-(R)-Asp-α-OMe-β-(S)-Phe-],appropriately functionalised with a hydroxymethyl group for theincorporation of lipophilic side-chains. We also demonstrate that the25-membered microcystin macrocycle,cyclo-[β-Ala-(R)-Glu-α-OMe-γ-Sar-(R)-Ala-(S)-Leu-(R)-Asp-α-OMe-β-(S)-Phe-], can be prepared in good yield using similar protocols in whichmacrocyclisation is effected through the reaction of the amino group ofthe (2S)-phenylalanine residue with theβ-pentafluorophenyl ester of the (2R)-asparticacid residue." @default.
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- W2022808760 date "1997-01-01" @default.
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- W2022808760 title "Design and preparation of serine–threonine protein phosphatase inhibitors based upon the nodularin and microcystin toxin structures: Part 2.1 Synthesis of a functionalised nodularin macrocycle and a stripped-down microcystin macrocycle" @default.
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- W2022808760 doi "https://doi.org/10.1039/a702410j" @default.
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