Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process

• Kazuhiro Okamoto,
• Naoki Shida and
• Mahito Atobe

Beilstein J. Org. Chem. 2024, 20, 264–271, doi:10.3762/bjoc.20.27

• current (Figure 2B, blue line). We considered that the inter- and intramolecular chemoselectivities were derived from the pKa of the proton sources. The pre-organization of the amide substrate and phosphate bases is an important process in PCET [13]. Recently, Gschwind et al. published a detailed NMR

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

• Josipa Matić,
• Tana Tandarić,
• Marijana Radić Stojković,
• Filip Šupljika,
• Zrinka Karačić,
• Ana Tomašić Paić,
• Lucija Horvat,
• Robert Vianello and
• Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

• formed an exciplex [15], and conjugates formed of pyrene and an amino acid-fluorescent nucleobase derivative qAN1, differing in length and flexibility between fluorophores [16]. Due to pre-organization, both conjugates strongly interacted with ds-DNA/RNA grooves with similar affinity but opposite

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

• Artem N. Semakin,
• Ivan S. Golovanov,
• Yulia V. Nelyubina and
• Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

• ). Such symmetrization can be explained by a pre-organization of N-amido groups through the coordination of water/alcohol leading to the host–guest complex observed in the X-ray. The formation of the inclusion complexes H2O@TAADs 4a and MeOH@4c·H+ was additionally explored by DFT calculations at the

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

• Christopher Liczner,
• Kieran Duke,
• Gabrielle Juneau,
• Martin Egli and
• Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

• well accommodated in the minor groove and making a stabilizing interaction with a trapped water molecule and the adjacent phosphate (Figure 6). It’s this pre-organization of the MOE groups, making the duplex more rigid, which is hypothesized to cause the increase in RNA binding affinity. Furthermore

Comparative ligand structural analytics illustrated on variably glycosylated MUC1 antigen–antibody binding

• Christopher B. Barnett,
• Tharindu Senapathi and
• Kevin J. Naidoo

Beilstein J. Org. Chem. 2020, 16, 2540–2550, doi:10.3762/bjoc.16.206

• conformational preference at Asp3 and Thr4 which correlates with the preferred states seen for the glycosylated antigen in solution. There is some evidence of a pre-structuring or pre-organization effect, where O-glycosylation shifts the conformational equilibrium of the peptide towards conformations that are

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

• Valya K. Nikolova,
• Cristina V. Kirkova,
• Silvia E. Angelova and
• Todor M. Dudev

Beilstein J. Org. Chem. 2019, 15, 1321–1330, doi:10.3762/bjoc.15.131

• is shown that the metal cations induce different pre-organization of the calixarene structure upon binding. The preferred binding site for the guest metal cations is the plane of the upper rim (with p-sulfonato groups), i.e., the sulfonate groups of hosts serve as anchoring points for the positively

Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules

• Hendrik V. Schröder and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190

• . A strategy to stabilize the mixed-valence and radical-cation dimer even at room temperature and to overcome the entropic penalty of their formation is to facilitate a spatial proximity of two or more TTF units by a suitable covalent link [37][38]. This pre-organization can also be generated in

What contributes to an effective mannose recognition domain?

• Christoph P. Sager,
• Deniz Eriş,
• Martin Smieško,
• Rachel Hevey and
• Beat Ernst

Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255

• ; multivalency; pre-organization; Review Recognition of carbohydrate ligands For the recognition of carbohydrate ligands, nature has explored binding sites of different shapes and properties. The large family of C-type lectins (CLECs) exhibits carbohydrate-recognition domains (CRDs) which incorporate a calcium

• binding site pre-organization, are more difficult to assess and accordingly have been highlighted in this review. Mannose-binding CLECs are involved in various pathways of the human innate immune response, including the blood dendritic cell antigen 2 (BDCA-2, also known as CD303) [18], langerin (CD207

• desolvation penalty [69][70]. Pre-organization vs flexibility. Carbohydrate–lectin interactions benefit from the low conformational flexibility of pyranoses. This could be impressively demonstrated in a case study comparing a septanose with a manno-configured pyranose derivative [71]. Although in both cases

Conformational equilibrium in supramolecular chemistry: Dibutyltriuret case

• Karina Mroczyńska,
• Małgorzata Kaczorowska,
• Erkki Kolehmainen,
• Ireneusz Grubecki,
• Marek Pietrzak and
• Borys Ośmiałowski

Beilstein J. Org. Chem. 2015, 11, 2105–2116, doi:10.3762/bjoc.11.227

• observations are in line with computations that are very useful in drawing conclusions. The use of benzoates with regularly changed properties may be the method of choice in analysis of complexes. The pre-organization of molecules used in supramolecular chemistry is, in general, important to this field. On the

Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1858–1866, doi:10.3762/bjoc.9.217

• transformations in homogeneous media, and various mixtures of products are obtained. Pre-organization of the reactants in the solid state [3] or by various templates in solution has been the best solution to this problem [4][5]. Cyclic host molecules large enough to accommodate two reacting molecules are the

• the dominant factor, but rather the pre-organization of the guest molecules in the CD cavity prior to excitation has the greatest effect. The distribution of the stereoisomers appears to be mainly topochemically [5] controlled because of the short lifetime of the excited state of COU. Quantum

• photoproduct from aqueous solution by liquid/liquid extraction simplifies the scale up. Yields of photodimer based on the complex were nearly quantitative. The observed supramolecular catalysis was explained by the high pre-organization resulting from the tight packing of the two guests in the cavity, which

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

• selective recognition of ammonium ions depends on steric and molecular complementarity and the pre-organization [17] of interacting functional groups. As far back as 1890, Fischer suggested that enzyme–substrate interactions function like a “lock and key” between an initially empty host and a guest that

• “key” in the complementary binding site or an inclusion compound. This host pre-organization leads to a major enhancement of the overall energy of guest complexation. The binding is energetically favored: Both enthalpic – a less solvent accessible area leads to a less strongly solvated guest with fewer

• hetero crown ethers) and N+–H bonds [101]. The cyclic arrangement leads to a pre-organization of the host [102], whereby selectivity is determined by the ring size. Primary ammonium ions are complexed with highest affinity by 18-crown-6 derivatives [9] (Figure 2). Table 1 summarizes exemplarily the