Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Facile access to pyridinium-based bent aromatic amphiphiles: nonionic surface modification of nanocarbons in water

• Lorenzo Catti,
• Shinji Aoyama and
• Michito Yoshizawa

Beilstein J. Org. Chem. 2024, 20, 32–40, doi:10.3762/bjoc.20.5

• ][9][10][11]. The development of new amphiphiles with large polyaromatic panels for strong aromatic–aromatic interactions and nonionic side-chains on the other hand would grant access to water-soluble nanocarbons with tunable surface properties, which could expand noncovalent nanocarbon chemistry and

Selected peptide-based fluorescent probes for biological applications

• Debabrata Maity

Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247

• peptidic arms equipped with lysine and an artificial strong anion binding site, the guanidinocarbonylpyrrole (GCP) moiety (Figure 2A). These arms also contain tryptophan for dissimilar aromatic interactions with different nucleobases. The fluorescence intensity of probe 1 increases by more than 4-fold at

Enzyme-instructed morphological transition of the supramolecular assemblies of branched peptides

• Dongsik Yang,
• Hongjian He and
• Bing Xu

Beilstein J. Org. Chem. 2020, 16, 2709–2718, doi:10.3762/bjoc.16.221

• branched peptides after the enzymatic reaction, we used Nap–ᴅ-Phe–ᴅ-Phe (Nap-ff) to provide aromatic–aromatic interactions from diphenylalanine for self-assembly because Nap-ff is a versatile motif to enable the self-assembly of many small molecules [46]. More specifically, we choose Nap-ffky since lysine

• allows the conjugation of the cleavable side chain, and tyrosine provides additional aromatic–aromatic interactions, as shown in a recent cryo-EM structure (PDB: 6X5I) [41]. Based on the above rationale, the DEDDDLLIG sequences attach to the ε-amine of the lysine residue of the tetrapeptide Nap-ffky to

Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator

• Poulami Jana,
• Filip Šupljika,
• Carsten Schmuck and
• Ivo Piantanida

Beilstein J. Org. Chem. 2020, 16, 2201–2211, doi:10.3762/bjoc.16.185

• chromophore in the DNA/RNA grooves aside expulsion of water solvating the NDI, also allows for aromatic interactions, either edge-to-face with base pairs or even with another NDI molecule (aggregation within groove). Both events strongly affect the UV–vis spectrum of the NDI chromophore. In any case, strong

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

• Giacomo Mari,
• Lucia De Crescentini,
• Serena Benedetti,
• Francesco Palma,
• Stefania Santeusanio and
• Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

• to position 13 of the BER skeleton, usually causes a geometric propensity for additional stacking-type, noncovalent aromatic interactions with cellular targets forming stronger complexes with nucleic acids than BER [9][10][11][12]. In fact, the so obtained functionalized BER shows better anticancer

• activity [13][14][15][16][17][18][19], and an increased DNA and RNA binding efficacy [4][6][9], due to its aromatic interactions with the biological macromolecules [20]. Another interesting and promising derivative is dihydroberberine (DHBER), the reduced form of BER. The enaminic function of this alkaloid

From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

• Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

• -helices; aromatic interactions; β-hairpin peptides; cation–π interactions; dynamic combinatorial chemistry; histone; molecular recognition in water; nucleosome; π–π-stacking; post-translational modification; supramolecular chemistry; Review Childhood influences When thinking about how to start writing

• chemist! This was a risky move as an assistant professor to venture into a new field in which I had no established record. But I have always been one to follow my interests, and it worked out for me in the end. I continued to be interested in aromatic interactions and their potential role in biology as a

• postdoc. Seminal work probing the electrostatic component of π–π stacking and edge-face aromatic interactions as well as cation–π interactions was being published at the time, as well as tantalizing suggestions about their relevance in biological structure and function. In particular, I was inspired by

A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy

• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14

• . There also remain debates about whether the π-cation or face-edge aromatic interactions are unusual or even important. Therefore, model studies that shed light on the strength and nature of supramolecular contacts continue to be critically important. One important emerging area I would like to highlight

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• mechanism affects the VEGFR-2 signaling pathway by forming hydrogen bonds and aromatic interactions within the ATP-binding region of the VEGFR-2 kinase unit [31]. Shankar and Srivastava et al. [32] treated PANC-1 xenograft mice with ellagic acid (7) and measured the expression of protein kinase B (Akt

Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum and
• Bing Xu

Beilstein J. Org. Chem. 2014, 10, 2406–2413, doi:10.3762/bjoc.10.250

• exploration [26]. As an amino acid, Phe or naphthAla increases molecular aromatic–aromatic interactions [19][21][27]. Arg-Gly-Asp, which is a well-established tripeptidic epitope, that modulates mammalian cell adhesion through binding with integrins on the cell membrane [28][29]. Thymine or adenine, as a

Chiral phosphines in nucleophilic organocatalysis

• Yumei Xiao,
• Zhanhu Sun,
• Hongchao Guo and
• Ohyun Kwon

Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218

• to furnish a wide range of spirocyclopenteneoxindoles in moderate to excellent yields and ee's (Scheme 38). The yields and stereoselectivities were significantly influenced not by electronic effects but by aromatic interactions. Aryl-substituted MBH carbonates reacted smoothly to afford

Molecular assembly of amino acid interlinked, topologically symmetric, π-complementary donor–acceptor–donor triads

• M. B. Avinash,
• K. V. Sandeepa and
• T. Govindaraju

Beilstein J. Org. Chem. 2013, 9, 1565–1571, doi:10.3762/bjoc.9.178

• and 3 in aqueous DMSO and aqueous NMP could be ascribed to solvatophobic interactions. 2D NOESY studies of 1, 2 and 3 in DMSO revealed the presence of weak aromatic interactions between pyrene and NDI (see Supporting Information File 1). Moreover the amide NH proton of 1, 2 and 3 showed spatial

• functionality in 2 is believed to facilitate some favourable aromatic interactions with NDI and pyrene modules, and thereby results in hierarchical helical bundles. Further, energy minimized molecular structures of the triads, 1 and 2 were obtained by using the Gaussian-09 software (Hartree–Fock method with 3

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

• Jiayang Li,
• Yi Kuang,
• Junfeng Shi,
• Yuan Gao,
• Jie Zhou and
• Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

• from the salicylic acid groups. In order to confirm that the aromatic–aromatic interactions originating from Phe–Phe are essential for the self-assembly of the hydrogelators of NSAIDs to form the nanofibers as the matrices of the hydrogels, we studied the gelation properties of the conjugates of NSAIDs

Anion–π interactions influence pK_a values

• Christopher J. Cadman and
• Anna K. Croft

Beilstein J. Org. Chem. 2011, 7, 320–328, doi:10.3762/bjoc.7.42

• potential, therefore, for aromatic interactions to mediate reactions involving anions [23], and it is likely that these types of interactions will be extremely relevant in catalysis, particularly in biological systems [24]. To probe this possibility in more detail, we have prepared a selection of simple

Exceptionally small supramolecular hydrogelators based on aromatic–aromatic interactions

• Junfeng Shi,
• Yuan Gao,
• Zhimou Yang and
• Bing Xu

Beilstein J. Org. Chem. 2011, 7, 167–172, doi:10.3762/bjoc.7.23

• less explored. We have shown that aromatic–aromatic interactions induce the self-assembly of glycopeptides [30] or pentapeptidic derivatives [31] in water to form nanofibers and supramolecular hydrogels. These results, together with the supramolecular hydrogelators made from dipeptide conjugates with

• fluorenyl or naphthyl groups, clearly support the simple notion that aromatic–aromatic interactions in water may direct the formation of hydrogen bonding and would be useful for the supramolecular self-assembly of small molecules in water. However, despite the progress noted above, an important question

• still remains to be answered: What is the minimal set of aromatic–aromatic interactions and hydrogen bonding for molecular self-assembly in water to produce supramolecular nanofibers and hydrogels? About a decade ago, Menger [32] and coworkers showed that an aroyl L-cystine derivative, which has a

Recognition properties of receptors consisting of imidazole and indole recognition units towards carbohydrates

• Monika Mazik and
• André Hartmann

Beilstein J. Org. Chem. 2010, 6, No. 9, doi:10.3762/bjoc.6.9

• formation of the CH···π interactions with the aromatic rings of the receptor (for discussions on the importance of carbohydrate–aromatic interactions, see refs. [57][58][59][60][61][62][63]; for examples of CH-π interactions in the crystal structures of the complexes formed between artificial receptors and

Inversion symmetry and local vs. dispersive interactions in the nucleation of hydrogen bonded cyclic n-mer and tape of imidazolecarboxamidines

• Sihui Long,
• Venkatraj Muthusamy,
• Peter G. Willis,
• Sean Parkin and
• Arthur Cammers

Beilstein J. Org. Chem. 2008, 4, No. 23, doi:10.3762/bjoc.4.23

• process of C1 dimer, 8b perturbed hydrogen bonding away from optimum. Aromatic stacking is quoted anywhere between 2 and 0.5 kcal/mol so a scenario in which the eight aromatic-interactions in dimer 8b perturbed the energies of the hydrogen bonds is very reasonable. The red circles in Figure 10 represent