IOCB covers 2021

Josef Michl Festschrift Virtual Special Issue. The cover art was created to celebrate Josef Michl's achievements over the course of his distinguished scientific carrier. Depicted chemical structures (carboranes, polysilanes, diphenylisobensofuranes, staffanes, etc.) represent only a tiny fraction of the compounds he was interested in and that were subjects of important discoveries in photochemistry, organic, inorganic, computational, physical, and supramolecular chemistry. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Havlas, Z.; Kaleta, J. Tribute to Josef Michl. J. Phys. Chem. A 2021, 125, 1801–1801. https://doi.org/10.1021/acs.jpca.1c01072
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The delivery of bioorthogonal reagents to mitochondria of live cells enables organelle-specific activation of biologically active compounds from the respective caged precursors. The optimized reagents can be used at low effective concentrations, and targeting of the organelle leads to significantly improved potency. The strategy could be used to perform chemical reactions and activate functional molecules in a subcellular-specific manner. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Dzijak, R.; Galeta, J.; Vázquez, A.; Kozák, J.; Matoušová, M.; Fulka, H.; Dračínský, M.; Vrabel, M. Structurally Redesigned Bioorthogonal Reagents for Mitochondria-Specific Prodrug Activation. JACS Au 2021, 1, 23–30. https://doi.org/10.1021/jacsau.0c00053 
  
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Showcasing joint research conducted in Dr Kaleta’s laboratory (Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Czech Republic) in co-operation with Prof. Masson’s laboratory (Department of Chemistry and Biochemistry, Ohio University, Ohio, United States) Stuffed pumpkins: mechanochemical synthesis of host–guest complexes with cucurbit[7]uril Solvent-free mechanochemical synthesis represents a new path towards unique types of cucurbit[ n ]uril/guest inclusion complexes that are not accessible due to limited solubility of the individual components or their low stability in solution. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Dračínský, M.; Hurtado, C. S.; Masson, E.; Kaleta, J. Stuffed pumpkins: mechanochemical synthesis of host–guest complexes with cucurbit[7]uril. Chem. Commun. 2021, 57, 2132–2135. https://doi.org/10.1039/D1CC00240F
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Modified deazapurine nucleosides with potent selective anti-trypanosomal activities and low toxicity to human cells. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Perlíková, P.; Krajczyk, A.; Doleželová, E.; Slapničková, M.; Milisavljevic, N.; Slavětínská, L. P.; Tloušt’ová, E.; Gurská, S.; Džubák, P.; Hajdúch, M.; Zíková, A.; Hocek, M. Synthesis and Antitrypanosomal Activity of 6-Substituted 7-Methyl-7-deazapurine Nucleosides. ACS Infect. Dis. 2021, 7, 917–926. https://doi.org/10.1021/acsinfecdis.1c00062
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The front cover picture illustrates the reaction of N-fluoroalkylated-1,2,3-triazoles with aluminum trihalide, proceeding via a vinyl cation (illustrated as the structure in brackets in the middle) to afford structurally diverse N-haloalkenyl imidoyl halides. These products are formed in a stereoselective fashion on both double bonds and have been utilized in the synthesis of various N-alkenyl compounds, such as enamides, enamidines, enimines, N-alkenyl tetrazoles, and other. In this work, Beier and co-workers show a new, mild and efficient 1,2,3-triazole denitrogenative ring-opening process mediated by easily available Lewis acids. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Markos, A.; Janecký, L.; Chvojka, T.; Martinek, T.; Martinez-Seara, H.; Klepetářová, B.; Beier, P. Haloalkenyl Imidoyl Halides as Multifacial Substrates in the Stereoselective Synthesis of N-Alkenyl Compounds. Adv. Synth. Catal. 2021, 363, 3258–3266. https://doi.org/10.1002/adsc.202100009
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In our cover image, we compare the “diamond” to an “eye”, through which we can “see” the biological world quantitatively; i.e., the things and/or processes (e.g., magnetic field, temperature, electronic and nuclear spins) in the biological world could be quantitatively “seen” by the “diamond eye”. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Zhang, T.; Pramanik, G.; Zhang, K.; Gulka, M.; Wang, L.; Jing, J.; Xu, F.; Li, Z.; Wei, Q.; Cigler, P.; Chu, Z. Toward Quantitative Bio-sensing with Nitrogen–Vacancy Center in Diamond. ACS Sens. 2021, 6, 2077–2107. https://doi.org/10.1021/acssensors.1c00415 
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The guy's dilemma of how to quench the annulation reaction of benzonitriles with N-methyl 2-toluamide, mediated by n-BuLi: adding water or pouring the mixture into water, symbolized by taking a shower or jumping into a bathtub. Each mode gives a different product. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Matouš, P.; Májek, M.; Kysilka, O.; Kuneš, J.; Maříková, J.; Růžička, A.; Pour, M.; Kočovský, P. Reaction Outcome Critically Dependent on the Method of Workup: An Example from the Synthesis of 1-Isoquinolones. J. Org. Chem. 2021, 86, 8078–8088. https://doi.org/10.1021/acs.joc.1c00561 
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The Front Cover shows reductive electrochemical cleavage of the carbon-chlorine bond in 2,2-dichlorobicyclo[1.1.1]pentane-1,3-dicarboxylic acid leading to corresponding monochlorinated cage. (Cover art: Tomáš Belloň / IOCB Prague)

• Article: Kaleta, J.; Hromadová, M.; Pospíšil, L. Electrochemical Cleavage of Carbon-Chlorine Bonds in Multiply Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids. ChemElectroChem 2021, 8, 3243–3249. https://doi.org/10.1002/celc.202100372
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Phosphorus-based self-immolative linkers activated by light sequentially release two phenolic cargos. Structurally modifying the lactate spacer responsible for self-immolation allows adjustable cargo release, ranging from minutes to days. The cargo release rate can be additionally tuned by varying the cargos. NMR spectroscopy coupled to UV light illumination enabled us to track and characterize products released during the self-immolation process.

• Article: Šimon, P.; Tichotová, M.; Gallardo, M. G.; Procházková, E.; Baszczyňski, O. Phosphate-Based Self-Immolative Linkers for Tuneable Double Cargo Release. Chem. Eur. J. 2021, 27, 12763–12775. https://doi.org/10.1002/chem.202101805
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Cover art: Tomáš Belloň / IOCB Prague

• Article: Kalčic, F.; Dračínský, M.; Janeba, Z. Diverse synthetic approaches towards C1′-branched acyclic nucleoside phosphonates. Org. Biomol. Chem. 2021, 19, 6958–6963. https://doi.org/10.1039/D1OB00751C 
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Cover art: Tomáš Belloň / IOCB Prague

• Article: Bakardjiev, M.; Holub, J.; Růžičková, Z.; Růžička, A.; Fanfrlík, J.; Štíbr, B.; McKee, M. L.; Hnyk, D. Transformation of various multicenter bondings within bicapped-square antiprismatic motifs: Z-rearrangement. Dalton Trans. 2021, 50, 12098–12106. https://doi.org/10.1039/D0DT04225K
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