The labeling of unsaturated γ-hydroxybutyric acid by heavy isotopes of hydrogen: iridium complex-mediated H/D exchange by C─H bond activation vs reduction by boro-deuterides/tritides

Ales Marek, Martin Holst Friborg Pedersen, Stine B. Vogensen, Rasmus P. Clausen, Bente Frølund, Tomáš Elbert

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    3-Hydroxycyclopent-1-ene-1-carboxylic acid (HOCPCA (1)) is a potent ligand for high-affinity γ-hydroxybutyric acid binding sites in the central nervous system. Various approaches to the introduction of a hydrogen label onto the HOCPCA skeleton are reported. The outcomes of the feasible C─H activation of olefin carbon (C-2) by iridium catalyst are compared with the reduction of the carbonyl group (C-3) by freshly prepared borodeuterides. The most efficient iridium catalysts proved to be Kerr bulky phosphine N-heterocyclic species providing outstanding deuterium enrichment (up to 91%) in a short period of time. The highest deuterium enrichment (>99%) was achieved through the reduction of ketone precursor 2 by lithium trimethoxyborodeuteride. Hence, analogical conditions were used for the tritiation experiment. [3H]-HOCPCA selectively labeled on the position C-3 was synthetized with radiochemical purity >99%, an isolated yield of 637 mCi and specific activity = 28.9 Ci/mmol.
    Original languageEnglish
    JournalJournal of Labelled Compounds and Radiopharmaceuticals
    Volume59
    Issue number12
    Pages (from-to)476-483
    Number of pages8
    ISSN0362-4803
    DOIs
    Publication statusPublished - 2016

    Keywords

    • C─H activation
    • Borotritides
    • Hydrogen/deuterium exchange
    • Iridium catalyst
    • Tritium-labeled γ-hydroxybutyric acid

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