Synthesis and Spectroscopic Characterization of [1′-14C]Ubiquinone-2, [1′-14C]-5-Demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-Demethoxyubiquinone-2

Klei, Anita van der; Jong, R. L. P. De; Lugtenburg, J.; Tielens, Aloysius G.M.

doi:10.1002/1099-0690(200209)2002:17<3015::aid-ejoc3015>3.0.co;2-g

Cited by 25 publications

(9 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Apparently, there are differences in the proton assignments regarding those reported by Curini et al, even so, the deviation is significant in the chemical shift of proton H5 (0.17 ppm). On the other hand, the 1 H NMR chemical shifts of compound 6 are also consistent with those obtained by Van Der Klei et al, with 0.04 ppm as the largest difference.…”

Section: Methodssupporting

confidence: 90%

Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements

et al. 2019

View full text Add to dashboard Cite

Collinin is a derivative of coumarin that has shown remarkable potential against cancer, tuberculosis, periodontitis, and other prevalent diseases, and is usually extracted from plants of the Rutaceae family at a very low yield. In this work, collinin and a position-isomer herein called isocollinin were synthesized at different scales (from 1 to 50 g of precursor) by a route consisting of two parallel and two sequential chemical reactions. The isomers were characterized by 1H NMR, 13C NMR, nuclear Overhauser enhancement spectroscopy NMR, melting temperature, and melting enthalpy. For each isomer, the Hansen solubility parameters and the radius of its solubility sphere were experimentally determined by solubility tests in 15 common solvents and two solvent blends. The solubility of each isomer in pressurized CO2 was determined at 30 and 50 °C from 72.2 to 112.9 bar, by an in situ high-pressure spectrometry technique, which was validated with the anthracene–CO2 system. The solubility of both isomers in CO2 increased with pressure in the range of temperatures and pressures considered, but that of collinin exhibited an asymptotic behavior around 80.8 and 104.8 bar, at 30 and 50 °C, respectively.

show abstract

Section: Methodssupporting

confidence: 90%

Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements

et al. 2019

View full text Add to dashboard Cite

show abstract

“…These data might suggest that COQ8 is poised to sense CoQ precursors within the membrane and to then couple the hydrolysis of ATP to the partial extraction of these lipids into the aqueous matrix environment where they could be modified by other CoQ biosynthesis enzymes. Testing this model directly will require the chemical synthesis of CoQ precursor molecules (Barkovich et al, 1997;; van der Klei et al, 2002) or their purification from endogenous sources like ∆ubi E. coli (Aussel et al, 2014) or ∆coq S. cerevisiae overexpressing Coq8p (Xie et al, 2012). Alternatively, it remains possible that the observed ATPase activity is a proxy for small molecule kinase activity in vivo;; however, as COQ8-dependent small molecule phosphorylation was not observed in our assays, these data indicate that endogenous small molecule substrate(s) would likely be distinct from the free hydroxyl group(s) of CoQ intermediates, the most intuitive candidate substrates.…”

Section: Discussionmentioning

confidence: 99%

Conserved lipid and small molecule modulation of COQ8 reveals regulation of the ancient UbiB family

Reidenbach

Kemmerer

Aydin

et al. 2017

Preprint

View full text Add to dashboard Cite

SummaryHuman COQ8A (ADCK3) and Saccharomyces cerevisiae Coq8p (collectively COQ8) are UbiB family proteins essential for mitochondrial coenzyme Q (CoQ) biosynthesis. However, the biochemical activity of COQ8 and its direct role in CoQ production remain unclear, in part due to lack of known endogenous regulators of COQ8 function and of effective small molecules for probing its activity in vivo. Here we demonstrate that COQ8 possesses evolutionarily conserved ATPase activity that is activated by binding to membranes containing cardiolipin and by phenolic compounds that resemble CoQ pathway intermediates. We further create an analog-sensitive version of Coq8p and reveal that acute chemical inhibition of its endogenous activity in yeast is sufficient to cause respiratory deficiency concomitant with CoQ depletion. Collectively, this work defines lipid and small molecule modulators of an ancient family of atypical kinase-like proteins and establishes a chemical genetic system for further exploring the mechanistic role of COQ8 in CoQ biosynthesis.

show abstract

“…Aiming to exploit the reactivity of the naphthoquinone system, we protected the free hydroxyl of 2-hydroxy-3-iodonaphthalene-1,4-dione (2) using groups with two different electronic demands. Therefore, 2-methoxy-3-iodonaphthalene-1,4-dione (5) and 3-iodo-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate (6), were prepared from 2 by the reaction with dimethyl sulfate 26 and acetic anhydride, 27 respectively. These compounds were then submitted to the optimized conditions described above and on both reactions we observed that a loss of the protecting group had occurred.…”

Section: Chemistrymentioning

confidence: 99%

Suzuki-Miyaura Coupling between 3-Iodolawsone and Arylboronic Acids. Synthesis of Lapachol Analogues with Antineoplastic and Antileishmanial Activities

Gomes¹,

Militão²,

Costa³

et al. 2016

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

A series of 2-hydroxy-3-arylnaphthalene-1,4-diones (3-aryllawsones) were synthesized by Suzuki-Miyaura cross coupling reaction of 3-iodolawsone with arylboronic acids/esters. The hydroxylated resulting products were transformed into their corresponding N,N-diethyl carbamates. The antineoplastic and antileishmanial activities of the compounds were evaluated and compared with lapachol and its carbamate, providing promising results.

show abstract

Synthesis and Spectroscopic Characterization of [1′-14C]Ubiquinone-2, [1′-14C]-5-Demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-Demethoxyubiquinone-2

Cited by 25 publications

References 20 publications

Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements

Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements

Conserved lipid and small molecule modulation of COQ8 reveals regulation of the ancient UbiB family

Suzuki-Miyaura Coupling between 3-Iodolawsone and Arylboronic Acids. Synthesis of Lapachol Analogues with Antineoplastic and Antileishmanial Activities

Contact Info

Product

Resources

About