Počet záznamů: 1  

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

  1. 1.
    0467405 - UOCHB-X 2017 RIV GB eng J - Článek v odborném periodiku
    Marek, Aleš - Pedersen, M. H. F. - Vogensen, S. B. - Clausen, R. P. - Frolund, B. - Elbert, Tomáš
    The labeling of unsaturated gamma-hydroxybutyric acid by heavy isotopes of hydrogen: iridium complex-mediated H/D exchange by C-H bond activation vs reduction by boro-deuterides/tritides.
    Journal of Labelled Compounds and Radiopharmaceuticals. Roč. 59, č. 12 (2016), s. 476-483. ISSN 0362-4803
    Institucionální podpora: RVO:61388963
    Klíčová slova: C-H activation * borotritides * hydrogen/deuterium exchange * iridium catalyst * tritium-labeled gamma-hydroxybutyric acid
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 1.745, rok: 2016

    3-Hydroxycyclopent-1-ene-1-carboxylic acid (HOCPCA (1)) is a potent ligand for high-affinity gamma-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. [H-3]-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.
    Trvalý link: http://hdl.handle.net/11104/0265508