In: Organic & Biomolecular Chemistry, 2020, vol. 18, no. 40, p. 8034–8057
Metathesis reactions are one of the most reliable and prevalent ways of creating a C– C bond in synthesis. Photochemical variants exist, and they have proven extremely useful for the construction of complex molecules, from natural products to Möbius rings. A variety of starting materials can undergo photometathesis reactions, including alkenes, alkynes, carbonyls, thiocarbonyls, and...
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In: ACS Sensors, 2020, vol. 5, no. 8, p. 2338–2343
Reactions templated by nucleic acids are currently at the heart of applications in biosensing and drug release. The number of chemical reactions selectively occurring only in the presence of the template, in aqueous solutions, and at room temperature and able to release a chemical moiety is still very limited. Here, we report the use of the p-nitrophenyl carbonate (NPC) as a new reactive...
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In: CHIMIA International Journal for Chemistry, 2019, vol. 73, no. 9, p. 720–723
Photochemical reactions are often presented as intrinsically environmentally friendly ('green'). This may be indeed the case, but only in particular circumstances. This short essay comments on various aspects of the greenness of photochemical reactions, both in a historical (when only mercury-based hard UV light sources were available) and a current (with the recent introduction of LED...
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In: The Journal of Organic Chemistry, 2019, vol. 84, no. 12, p. 7776–7785
A self-immolative dendritic structure was synthesized. It is based on phenol derivatives with three hydroxymethyl arms at both ortho and para positions of the core unit, potentially releasing up to 27 leaving groups in a third-generation dendrimer. The triggering event is the photolysis of a photosentive ortho-nitrobenzyl group. In doing so, we expected to transform a weak chemical or...
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In: Natural Product Research, 2019, vol. 33, no. 5, p. 642–650
Triclisinone (2), a new ochnaflavone derivative, was isolated from the aerial parts of Triclisia gilletii, along with known drypemolundein B (1) and eight other known compounds. The chemical shifts of drypemolundein B (1) have been partially revised based on reinterpretation of NMR spectroscopic data. The eight other secondary metabolites are composed of: (+)-nonacosan-10-ol (3); stigmasterol...
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In: RSC Advances, 2018, vol. 8, no. 42, p. 23881–23890
Sulfur Mustard (SM) is a blistering agent used as a chemical weapon. Glutathione (GSH) is involved in the β-lyase degradation pathway of SM and recently, bioadducts between SM and GSH were observed in vitro. While these bioadducts have never been isolated from in vivo tests or real poisoning with SM, they could be of interest as potential future biomarkers for the retrospective validation of...
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In: European Journal of Organic Chemistry, 2018, vol. 2018, no. 3, p. 316–328
The photochemical extrusion of gaseous nitrogen from 2,5-disubstituted tetrazoles to generate reactive nitrilimines in situ represents an efficient and attractive way to form dipoles that can be used to provide useful chemicals via 1,3-dipolar cycloadditions. The concept of “photoclick chemistry” already inspired numerous researchers, who exploited photochemical processes involving...
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In: Revista Brasileira de Farmacognosia, 2017, vol. 27, no. 6, p. 739-743
A new C-glycosylflavone, apigenin 7-methyl ether 6-C-[β-xylopyranosyl-(1→3)-β- glucopyranoside] named distemonanthoside was isolated from the stem bark of Distemonanthus benthamianus Baill., Fabaceae, along with six known compounds, sitosterol 3-O-β-d-glucopyranoside, 4-methoxygallic acid, syringic acid, quercetin, 6″- O-acetylvitexin, quercetin 3-O-β-d-glucopyranoside. The structures...
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In: Natural Product Research, 2017, vol. 31, no. 24, p. 2875-2884
Phytochemical investigation of the stem bark of Campylospermum zenkeri led to the isolation of five known compounds: (Z,Z)-9,12-octadecadienoic acid (1), serotobenine (2), agathisflavone (3), lophirone A (4) and lophirone F (5), together with a new derivative of procyanidin B, a catechin dimer named zenkerinol (6). Serotobenine (2) is structurally related to decursivine which shows moderate...
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In: CHIMIA International Journal for Chemistry, 2016, vol. 70, no. 3, p. 182-185
The mechanism of photochemical reactions can be difficult to study because of the very short-lived intermediates involved. State-of-the art ultrafast spectroscopic tools can be used to probe these processes, but we will show in this account that old- fashioned techniques, such as the determination of quantum yields, the measurement of isotope effects or the use of triplet quenchers and...
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