The Synthesis of Enantiopure a-Fluoro and a,a-Difluoro-b3-Arginine Derivatives

Taryn March, Jamie Freemont, Geoff Dumsday, Martin Johnston, Peter Duggan

    Research output: Contribution to journalArticle

    1 Citation (Scopus)

    Abstract

    The synthesis of a set of monofluorinated, difluorinated, and non-fluorinated N-acetylated-β3-arginine esters, potential inhibitors of trypsin-like proteases, is described. Elaboration to the target compounds from previously reported enantiopure precursors derived from 3-hydroxypropanal involved 6-7 steps and was achieved in 48-65% overall yield. The α,α-difluoro-β3-arginine derivative was found to be particularly prone to hydrolysis. Three β3-arginine derivatives were tested for their ability to inhibit trypsin, the α,α-difluoro compound being assayed in the form of a carboxylate zwitterion.

    Original languageEnglish
    Pages (from-to)997-1004
    Number of pages8
    JournalAustralian Journal of Chemistry
    Volume67
    Issue number7
    DOIs
    Publication statusPublished - 2014

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