Construction of pillar[4]arene[1]quinone–1,10-dibromodecane pseudorotaxanes in solution and in the solid state

• Xinru Sheng,
• Errui Li and
• Feihe Huang

Beilstein J. Org. Chem. 2020, 16, 2954–2959, doi:10.3762/bjoc.16.245

• constructing functional materials from the bottom up as well as an important way to create new substances with functions [1][2][3][4][5]. Through ingenious designs and the applications of molecular recognition and self-assembly strategies, many exquisite supramolecular architectures have been fabricated

UV resonance Raman spectroscopy of the supramolecular ligand guanidiniocarbonyl indole (GCI) with 244 nm laser excitation

• Tim Holtum,
• Vikas Kumar,
• Daniel Sebena,
• Jens Voskuhl and
• Sebastian Schlücker

Beilstein J. Org. Chem. 2020, 16, 2911–2919, doi:10.3762/bjoc.16.240

• , Universitätsstrasse 7, 45141 Essen, Germany 10.3762/bjoc.16.240 Abstract Ultraviolet resonance Raman (UVRR) spectroscopy is a powerful vibrational spectroscopic technique for the label-free monitoring of molecular recognition of peptides or proteins with supramolecular ligands such as guanidiniocarbonyl pyrroles

• relevant peptide. In the case of RGD, the more pronounced differences between the UVRR spectra of the free and complexed GCI (1:1 mixture) clearly indicate a stronger binding of GCI to RGD compared with BA. A tentative assignment of the experimentally observed changes upon molecular recognition is based on

• (CBS) [6][7][8][9]. The GCP takes part selectively and efficiently in the complexation of carboxylates based on the electrostatic interaction between the positively charged CBS and the negatively charged carboxylate in the combination with hydrogen bonding, enabling molecular recognition even in the

NMR Spectroscopy of supramolecular chemistry on protein surfaces

• Peter Bayer,
• Anja Matena and
• Christine Beuck

Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203

• modulate protein–protein interactions. Here we present NMR methods that have been applied to characterize these molecular interactions and discuss the challenges of this endeavor. Keywords: molecular recognition; NMR; protein ligand interaction; protein surfaces; supramolecular chemistry; Introduction In

• as distance of targeted residues and their dynamics - must be taken into account. Supramolecular chemistry is ideally suited to address these challenges because it merges the knowledge of non-covalent molecular recognition with the possibility to combine multiple recognition units into one molecule

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

• Zhishu Zeng,
• Jun Xie,
• Guangyan Luo,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 2332–2337, doi:10.3762/bjoc.16.194

• involve three main intermolecular forces: a hydrophobic effect, hydrogen bonding and ion–dipole interactions at the carbonyl portals [7][8][9]. The high thermal stability [10], ease of synthesis [11], general absence of cytotoxicity or toxicity [12][13] and their good molecular recognition and binding

Design and synthesis of a bis-macrocyclic host and guests as building blocks for small molecular knots

• Elizabeth A. Margolis,
• Rebecca J. Keyes,
• Stephen D. Lockey IV and
• Edward E. Fenlon

Beilstein J. Org. Chem. 2020, 16, 2314–2321, doi:10.3762/bjoc.16.192

• . Keywords: alkynes; azides; host–guest; macrocycles; molecular knots; Introduction Macrocycles have played a central role in the development of molecular recognition, self-assembled molecular devices, and molecular topology [1][2][3][4][5][6]. For example, early work by Pedersen on crown ethers [1], Lehn

• (ammonium) 2 and bis(pyridinium) 3 (Figure 1). The electron-rich macrocycles of host 1 might also render it useful for other molecular recognition applications. A principle goal driving our second-generation TLC approach was to test the lower limit on the size of a molecular trefoil knot. In 2008 we

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• a tendency of crystal packing [17][18][19][20]. Since these chiral buckybowls contain stable convex or concave faces suitable for the generation of chiral molecular recognition sites which can be used for the construction of helical assemblies and have been used to coordinate the metal atom(s) [21

How and why plants and human N-glycans are different: Insight from molecular dynamics into the “glycoblocks” architecture of complex carbohydrates

• Carl A. Fogarty,
• Aoife M. Harbison,
• Amy R. Dugdale and
• Elisa Fadda

Beilstein J. Org. Chem. 2020, 16, 2046–2056, doi:10.3762/bjoc.16.171

• relationships in complex carbohydrates, with important implications in glycoengineering design. Keywords: complex carbohydrates; fucose; glycoblocks; molecular dynamics; molecular recognition; N-glycans; xylose; Introduction Complex carbohydrates (or glycans) are an essential class of biomolecules, directly

• implicated in the cell’s interactions with its environment, facilitating communication and infection [1][2]. These processes are often initiated by molecular recognition involving carbohydrate-binding proteins (lectins) or by glycan–glycan interactions [1][3][4][5], all events that hinge on specific

• also of how specific modifications affect molecular recognition. Computational Methods All starting structures were generated with the GLYCAM Carbohydrate Builder (http://www.glycam.org). For each sequence we selected the complete set of torsion angle values obtained by variation of the 1-6 dihedrals

Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions

• Clément Q. Fontenelle,
• Thibault Thierry,
• Romain Laporte,
• Emmanuel Pfund and
• Thierry Lequeux

Beilstein J. Org. Chem. 2020, 16, 1936–1946, doi:10.3762/bjoc.16.160

• the latter was not yet synthetized. It is expected that the introduction of fluorine into the carbon–carbon double bond, in a position equivalent to the ring oxygen of the naturally occurring nucleotide, will improve molecular recognition and activity. In addition, the polarity of the nucleotide and

Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines

• Vladimir Kubyshkin

Beilstein J. Org. Chem. 2020, 16, 1837–1852, doi:10.3762/bjoc.16.151

• analogues in complex biological systems such as peptides and proteins, especially in 19F NMR labelling, where fluorinated prolines can serve as spectroscopic probes. Potential areas for the application of fluorinated prolines are numerous, and include the design of molecular recognition systems [101

A dynamic combinatorial library for biomimetic recognition of dipeptides in water

• Florian Klepel and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2020, 16, 1588–1595, doi:10.3762/bjoc.16.131

• ), while AA binds significantly weaker (K ≈ 65–71 M−1). Keywords: artificial receptor; dynamic combinatorial chemistry; dynamic covalent chemistry; molecular recognition; thiolate–disulfide exchange; Introduction Peptides are one of the most abundant and structurally versatile motifs in nature. Thus

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

• Anniina Kiesilä,
• Jani O. Moilanen,
• Anneli Kruve,
• Christoph A. Schalley,
• Perdita Barran and
• Elina Kalenius

Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241

• in pyridine[4]arene is an anion-driven process. Keywords: cation binding; DFT calculations; ion mobility mass spectrometry; macrocycles; pyridinearenes; resorcinarenes; Introduction Resorcinarenes and their derivatives are known for the molecular recognition properties of their self-assembled

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• receptors for molecular recognition of anionic species, pH sensors, mechanically interlocked molecules, molecular machines, and molecular reactors. Keywords: anion recognition; catenane; chalcogen bonding; click reaction; molecular reactor; hydrogen bonding; pH sensor; rotaxane; supramolecular; 1,2,3

• have led to applications in molecular recognition, sensing, molecular machines and devices, supramolecular polymers, stimuli-responsive materials, supramolecular catalysis and drug-delivery systems [4][5][6][7]. Inspired by the attractive role of various N-heterocyclic building blocks such as

• -position of the triazoles (triazolium), and nucleophilic substitution of halogen can be used to introduce chalcogens (Se, Te). Thus, the corresponding triazolium macrocycles can take advantage respectively of halogen and chalcogen bonding as part of the molecular recognition (vide infra). In this review

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

• Meng-Di Gu,
• Yao Lu and
• Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

• molecular systems to study molecular recognition and the nature of noncovalent interactions. Functional macrocycles also provide essential components for the fabrication or assembly of sophisticated (supra)molecular structures [1][2][3][4], advanced materials [1][2][5][6][7][8][9][10] and machinery systems

• heteroatoms and meta-(het)arenes in an alternative manner. Because of the interplay between heteroatoms and aromatic rings, heteracalixaromatics possess versatile molecular recognition properties and have found wide supramolecular applications. Very recently, we have devised coronarenes [22] simply through

• cavities [22]. We have also shown that the combination of and the interplay between heteroatoms and para-(het)arylenes produce diverse macrocycles with coarse- and fine-tunable cavity shapes and sizes. The resulting coronarenes exhibit interesting molecular recognition properties towards anions, cations

Complexation of chiral amines by resorcin[4]arene sulfonic acids in polar media – circular dichroism and diffusion studies of chirality transfer and solvent dependence

• Bartosz Setner and
• Agnieszka Szumna

Beilstein J. Org. Chem. 2019, 15, 1913–1924, doi:10.3762/bjoc.15.187

• aromatic analytes afford strongly induced circular dichroism (ICD) signals in the near-UV and visible regions [18]. Endo-functionalized molecular tubes, first reported by the Glass group [19], were used by the Jiang group for molecular recognition and chiroptical sensing of epoxides in water. The absolute

Novel macrocycles – and old ones doing new tricks

• Wei Jiang and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2019, 15, 1838–1839, doi:10.3762/bjoc.15.178

• diversified. They are not only tools for studying molecular recognition and molecular machines, but are also key components for sensing, supramolecular catalysis, (chiral) separation, drug delivery, or smart materials. Many new macrocycles have recently been reported, with pillararenes being one of the most

Complexation of 2,6-helic[6]arene and its derivatives with 1,1′-dimethyl-4,4′-bipyridinium salts and protonated 4,4'-bipyridinium salts: an acid–base controllable complexation

• Jing Li,
• Qiang Shi,
• Ying Han and
• Chuan-Feng Chen

Beilstein J. Org. Chem. 2019, 15, 1795–1804, doi:10.3762/bjoc.15.173

• Jing Li Qiang Shi Ying Han Chuan-Feng Chen Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China University of Chinese Academy of Sciences, Beijing 100049, China

Host–guest interactions in nor-seco-cucurbit[10]uril: novel guest-dependent molecular recognition and stereoisomerism

• Xiaodong Zhang,
• Wei Wu,
• Zhu Tao and
• Xin-Long Ni

Beilstein J. Org. Chem. 2019, 15, 1705–1711, doi:10.3762/bjoc.15.166

• photophysical signals to identify the possible diastereomers of guests within nor-seco-cucurbit[10]uril (NS-CB[10]) cavities. Further experiments revealed that balancing the hydrophilic and hydrophobic effects of the guest in aqueous solution can improve the molecular recognition and binding ability of NS-CB[10

• ]. Keywords: fluorescent; host–guest interaction; macrocycles; molecular recognition; nor-seco-cucurbit[10]uril; pyrene; Introduction Host–guest interactions that trigger molecular recognition are a current topic of interest. For example, understanding the protein–ligand molecular recognition is of paramount

• , the top–center isomer of G2 within both host-1 and host-2 could be characterized because of the novel monomer and excimer photophysical property of pyrene as fluorophore. As a result, we demonstrated here a novel guest-controlled molecular recognition and stereoisomerism for the first time. Results

Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)

• Małgorzata Urbańczyk,
• Michał Jewgiński,
• Joanna Krzciuk-Gula,
• Jerzy Góra,
• Rafał Latajka and
• Norbert Sewald

Beilstein J. Org. Chem. 2019, 15, 1581–1591, doi:10.3762/bjoc.15.162

• better understanding of the correlation between structure and activity of AFGPs would not only improve the basic knowledge on molecular recognition, but could also help designing new tailored antifreeze agents for many applications, e.g., cooling systems, coating technology, ice-templating, food industry

An azobenzene container showing a definite folding – synthesis and structural investigation

• Abdulselam Adam,
• Saber Mehrparvar and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2019, 15, 1534–1544, doi:10.3762/bjoc.15.156

• ][22]. Beside the usage of the side chains of the amino acids and the azole rings for molecular recognition, the functional groups of the scaffolds of these cyclopeptides have also been applied as receptors for Y-shaped anions [23] and as ligands for copper(II) complexes [24][25]. Of special interest

2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes

• Li-Li Wang,
• Yi-Kuan Tu,
• Huan Yao and
• Wei Jiang

Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146

• –guest chemistry; macrocycles; molecular recognition; precious metal chloride complexes; Introduction Macrocyclic receptors are the major workhorses in supramolecular chemistry. Design and synthesis of new macrocyclic receptors with new properties is always attractive but is also challenging [1

• ]. Tetralactam macrocycles with four amide NH residues have been studied for ca. three decades and used in a wide range of fields including molecular recognition, optical sensing, molecular machine etc. [2][3][4][5][6][7][8][9][10][11][12][13]. The amide N−H groups directed into the cavity could form hydrogen

• bonds with guests, constituting the main driving forces for molecular recognition. This class of macrocycles, in particular the ones with single arene as sidewalls, have found wide applications in diverse fields: Leigh and co-workers reported many interlocked structures and molecular machines with

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

• Yu-Ying Wang,
• Yong Kong,
• Zhe Zheng,
• Wen-Chao Geng,
• Zi-Yi Zhao,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

• Yu-Ying Wang Yong Kong Zhe Zheng Wen-Chao Geng Zi-Yi Zhao Hongwei Sun Dong-Sheng Guo College of Chemistry, Key Laboratory of Functional Polymer Materials, State Key Laboratory of Elemento-Organic Chemistry, Tianjin Key Laboratory of Biosensing and Molecular Recognition, Nankai University, Tianjin

• supramolecular cavities [25]. Calixarenes are the third generation of macrocyclic compounds composed of phenolic units bridged with methylene groups at the o-positions of phenolic hydroxy groups [9]. We have focused on molecular recognition and self-assembly of water-soluble calixarene derivatives for a long

• luminescent materials, high-performance supramolecular dye lasers, and dye-sensitized solar cells. Although in our present study GC5A has served as a specific test case for molecular recognition of various dyes, such an investigation is inspirable for other artificial receptors, especially those of new

Efficient resolution of racemic crown-shaped cyclotriveratrylene derivatives and isolation and characterization of the intermediate saddle isomer

• Sven Götz,
• Andreas Schneider and
• Arne Lützen

Beilstein J. Org. Chem. 2019, 15, 1339–1346, doi:10.3762/bjoc.15.133

• they bear a chiral cavity that can be used for molecular recognition [19]. Probably the most famous example for this behavior is the chiral discrimination and determination of the absolute configuration of the two enantiomers of CHFClBr using an enantioenriched cryptophane-C [20][21]. Other examples

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

• .15.131 Abstract The molecular recognition in aqueous solution is extremely important because most biological processes occur in aqueous solution. Water-soluble members of the calix[n]arene family (e.g., p-sulfonato substituted) can serve as model systems for studying the nature and manner of interactions

Enantioselective Diels–Alder reaction of anthracene by chiral tritylium catalysis

• Qichao Zhang,
• Jian Lv and
• Sanzhong Luo

Beilstein J. Org. Chem. 2019, 15, 1304–1312, doi:10.3762/bjoc.15.129

• Qichao Zhang Jian Lv Sanzhong Luo Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, 100190, Beijing, China State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science

Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides

• Madhu Babu Tatina,
• Xia Mengxin,
• Rao Peilin and
• Zaher M. A. Judeh

Beilstein J. Org. Chem. 2019, 15, 1275–1280, doi:10.3762/bjoc.15.125

• molecular recognition, cell–cell interaction, immunological recognition and transmission of biological information [4][5][6]. They are easily transformed into important bioactive compounds such as oligosaccharides, glycopeptides, nucleosides, antibiotics, uronic acids and other natural products [1][2][3