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
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SYSNO ASEP 0467405 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název 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 Tvůrce(i) Marek, Aleš (UOCHB-X) RID, ORCID
Pedersen, M. H. F. (DK)
Vogensen, S. B. (DK)
Clausen, R. P. (DK)
Frolund, B. (DK)
Elbert, Tomáš (UOCHB-X) RID, ORCIDZdroj.dok. Journal of Labelled Compounds and Radiopharmaceuticals. - : Wiley - ISSN 0362-4803
Roč. 59, č. 12 (2016), s. 476-483Poč.str. 8 s. Jazyk dok. eng - angličtina Země vyd. GB - Velká Británie Klíč. slova C-H activation ; borotritides ; hydrogen/deuterium exchange ; iridium catalyst ; tritium-labeled gamma-hydroxybutyric acid Vědní obor RIV CC - Organická chemie Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000387759700001 EID SCOPUS 84991240422 DOI 10.1002/jlcr.3432 Anotace 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. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2017
Počet záznamů: 1