Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether

• Gianpaolo Gallo and
• Bartosz Lewandowski

Beilstein J. Org. Chem. 2025, 21, 541–546, doi:10.3762/bjoc.21.42

• receptors; molecular recognition; monosaccharides; tryptophan; Introduction Tryptophan plays a crucial role in a variety of biological processes [1][2]. For example, it is critical for electron transfer in proteins [3] and is a key component of several membrane proteins as well as short antimicrobial

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• conformational flexibility, allowing them to adopt four key conformations: 1,3-alternate, cone, partial cone, and 1,2-alternate [1][2]. Calix[4]pyrroles are one of the most studied hosts in supramolecular chemistry, finding use in applications of molecular recognition and extraction, drug delivery, ion transport

• metalloporphyrins that are easily accessible for the incoming substrates, pyrrole –N/NH moieties inside the core of metal-free porphyrins are mostly hidden and unavailable for any kind of intermolecular hydrogen-bonding interactions or molecular recognition as they are 'shielded' by the planar macrocyclic system

• with porphyrins, the direct linkage between their pyrrole units leads to a more contracted cavity compared to that of porphyrins. Similar to calix[4]pyrroles, synthetic metallo- and free-base (metal-free) porphyrins find various applications in the fields of medicine, energy, catalysis, molecular

C–H Trifluoromethylthiolation of aldehyde hydrazones

• Victor Levet,
• Balu Ramesh,
• Congyang Wang and
• Tatiana Besset

Beilstein J. Org. Chem. 2024, 20, 2883–2890, doi:10.3762/bjoc.20.242

• Victor Levet Balu Ramesh Congyang Wang Tatiana Besset INSA Rouen Normandie, Univ Rouen Normandie, CNRS, Normandie Univ, COBRA UMR 6014, INC3M FR 3038, F-76000 Rouen, France Beijing National Laboratory for Molecular Sciences CAS key Laboratory of Molecular Recognition and Function CAS Research

HFIP as a versatile solvent in resorcin[n]arene synthesis

• Hormoz Khosravi,
• Valeria Stevens and
• Raúl Hernández Sánchez

Beilstein J. Org. Chem. 2024, 20, 2469–2475, doi:10.3762/bjoc.20.211

• molecular recognition [12][46]. Despite extensive research, challenges remain in the acid-catalyzed resorcin[n]arene synthesis, for example: 1) reaction times for simple resorcin[n]arenes starting from aliphatic aldehydes and resorcinol generally require multiple days and up to a week (Scheme 1a) [9][26]; 2

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• potential applications in the arena of supramolecular chemistry in general, sensing, molecular recognition and self-assembly in particular in has yet to be explored. Moreover, applications of the truxene derivatives in catalysis are also scared, and needs to be advanced in future research. Experimental

Computational toolbox for the analysis of protein–glycan interactions

• Ferran Nieto-Fabregat,
• Maria Pia Lenza,
• Angela Marseglia,
• Cristina Di Carluccio,
• Antonio Molinaro,
• Alba Silipo and
• Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

• determinants that govern specific molecular interactions. Keywords: computational tools; glycan–protein interactions; MD; molecular recognition; Review Introduction Carbohydrates also referred to as saccharides, sugars, or glycans, constitute one of the main building blocks of biomolecules, alongside lipids

Electrophotochemical metal-catalyzed synthesis of alkylnitriles from simple aliphatic carboxylic acids

• Yukang Wang,
• Yan Yao and
• Niankai Fu

Beilstein J. Org. Chem. 2024, 20, 1497–1503, doi:10.3762/bjoc.20.133

• Yukang Wang Yan Yao Niankai Fu 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 10.3762/bjoc

Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets

• Guoqing Cheng and
• Naoki Komatsu

Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113

• complexation between host molecules and SWNTs are strongly related to the molecular structures, making it possible to tune the binding affinity [8]. The host molecules we employed so far for CNT separation through molecular recognition have been developed as “nanotweezers” [9], “nanocalipers” [10] and

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

• first part will be devoted to chemically responsive tweezers, including stimuli such as pH, metal coordination, and anion binding. Then, redox-active and photochemical tweezers will be presented. Keywords: coordination; molecular recognition; molecular switches; photoswitch; redox; supramolecular

• molecular tweezers has been in molecular recognition with reversible guest binding, we believe that the scope of applications can be significantly broader. Recent examples have demonstrated their potential to regulate biological activity, facilitate transmembrane transport, enable switchable catalysis

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• by exploiting them for molecular recognition (Figure 16A). The dual nature of hybrids offers promising prospects, with a coordination pocket enabling selective binding of organic molecules such as natural and non-natural amino acids, hormones, neurotransmitters and other biomolecules. In such

Complexes of resorcin[4]arene with secondary amines: synthesis, solvent influence on “in-out” structure, and theoretical calculations of non-covalent interactions

• Waldemar Iwanek

Beilstein J. Org. Chem. 2023, 19, 1525–1536, doi:10.3762/bjoc.19.109

• ], amino alcohols [10], and amino acids [11] have been studied due to their potential applications in supramolecular chemistry, drug delivery, and molecular recognition. The complexation of R[4]A with amines is based on the formation of hydrogen bonds between the hydroxy groups of the resorcinol units and

• affinity and selectivity towards specific amines. In addition to their potential applications in sensing and molecular recognition, R[4]A have also been studied for their potential pharmaceutical [13] and biochemical [14] applications. R[4]A typically exhibit complex structures containing over a hundred

Cyclodextrins as building blocks for new materials

• Miriana Kfoury and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

• . CDs are the most studied supramolecular hosts. They provide the most extensive database on molecular recognition in the literature, with more than 100,000 publications [2]. CDs owe their success not only to the unique molecular structure [3], which allows them to act as host compounds, but also to

A fluorescent probe for detection of Hg²⁺ ions constructed by tetramethyl cucurbit[6]uril and 1,2-bis(4-pyridyl)ethene

• Xiaoqian Chen,
• Naqin Yang,
• Yue Ma,
• Xinan Yang and
• Peihua Ma

Beilstein J. Org. Chem. 2023, 19, 864–872, doi:10.3762/bjoc.19.63

• form various host–guest inclusion complexes [16][17][18][19][20], which have broad application prospects in supramolecular catalysis [21][22][23], molecular recognition [24][25], and drug delivery [26][27]. In recent years, in the field of supramolecular chemistry, the detection of analytes based on

Supramolecular approaches to mediate chemical reactivity

• Pablo Ballester,
• Qi-Qiang Wang and
• Carmine Gaeta

Beilstein J. Org. Chem. 2022, 18, 1463–1465, doi:10.3762/bjoc.18.152

• 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 Dipartimento di Chimica e Biologia “A. Zambelli”, Università di Salerno, I-84084 Fisciano

• characteristic of supramolecular catalysis is that the general modes of activation based on intermolecular interactions can operate on substrates in a selective way, and in confined environment, like the active site of natural enzymes [5][6][7][8][9][10][11][12][13][14]. As a result, molecular recognition of the

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

• hydrazone groups. The use of N-TAAD derivatives as potential ligands and receptors was showcased through forming boron chelates and host–guest complexes with water and simple alcohols. Keywords: azaadamantanes; cyclotrimerization; hydrazones; inclusion complexes; molecular recognition; Introduction

• ), although lattice methanol molecules and chloride anions are present in the structure. The larger tris-Boc derivatives 4c·HCl and Bn-4c form the same guest–host complexes with methanol (Figure 3d). Thus, these TAAD-based systems may exhibit molecular recognition properties. Deprotected N-TAADs such as 19e

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

• Prodip Howlader and
• Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

• have led to a multitude of extremely useful functional applications (molecular recognition, ion sensing, catalysis, etc.) [9][22]. Since most of these structures are homoleptic in nature, i.e., they are constructed from a single type of ligand [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19

Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

• Hao Guo,
• Yu-Fei Ao,
• De-Xian Wang and
• Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

• Hao Guo Yu-Fei Ao De-Xian Wang Qi-Qiang Wang 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

Site-selective reactions mediated by molecular containers

• Rui Wang and
• Yang Yu

Beilstein J. Org. Chem. 2022, 18, 309–324, doi:10.3762/bjoc.18.35

• important fields in modern chemistry [13][14][15]. It is based on a wide range of noncovalent interactions between molecules [16][17][18] and has been applied to a variety of research areas including molecular recognition, molecular devices, nanochemistry, catalysis, etc. [13][14][15][16][17][18]. By

Halides as versatile anions in asymmetric anion-binding organocatalysis

• Lukas Schifferer,
• Martin Stinglhamer,
• Kirandeep Kaur and
• Olga García Macheño

Beilstein J. Org. Chem. 2021, 17, 2270–2286, doi:10.3762/bjoc.17.145

• , the regulation of membrane potentials is one of such applications, in which the transport of chloride anions is facilitated by noncovalent hydrogen bonding interactions (Figure 1a) [6]. Noncovalent interactions are in fact one of the essential factors for the molecular recognition in enzymatic

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

• –Crick base pairing at mixed sequences that do not have polypurine tracts is also possible, but requires chemical modifications to alter the binding properties of PNAs. These binding modes further illustrate the diversity of molecular recognition that can be achieved with PNAs. Taken together, the early

• suggesting that Io4 may be a promising alternative to T where stronger binding is desired [108]. PNA nucleobases for Hoogsteen recognition of pyrimidines: Triple helix formation, especially using tailored oligonucleotide analogues as PNA, could be a general and sequence specific approach for molecular

• recognition of dsDNA and dsRNA. However, the triple helical recognition has a severe sequence limitation – the requirement of polypurine tracts in target nucleic acids. Natural triple helices allow only T•A–T (or U•A–U) and C+•G–C triplets stabilized by two Hoogsteen hydrogen bonds (Figure 6) [94]. Analogous

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• -butyloxyproline, with the 4R analogue exhibiting a higher propensity for the polyproline helix structure than the 4S [17]. This differentiated conformational bias observed highlights the potential application of these amino acids as unique probes for molecular recognition studies. The synthesis of unnatural amino

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

• Alexander Zika and
• Franziska Gröhn

Beilstein J. Org. Chem. 2021, 17, 166–185, doi:10.3762/bjoc.17.17

• molecular recognition processes have been established based on different non-covalent interactions such as hydrogen bonding [9][10][11][12], π–π interaction [13][14][15][16][17], hydrophobic effects, and amphiphilicity [18][19][20][21]. It has been highly desirable to establish concepts that could be

Insight into functionalized-macrocycles-guided supramolecular photocatalysis

• Minzan Zuo,
• Krishnasamy Velmurugan,
• Kaiya Wang,
• Xueqi Tian and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15

• via photophysical analyses is relatively important. Hence, this review aims to summarize the photochemical transformation and catalytic reactivity of different guests within the various macrocyclic hosts of various sizes and shapes based on molecular recognition as well as the role of macrocyclic-host

Circularly polarized luminescent systems fabricated by Tröger's base derivatives through two different strategies

• Cheng Qian,
• Yuan Chen,
• Qian Zhao,
• Ming Cheng,
• Chen Lin,
• Juli Jiang and
• Leyong Wang

Beilstein J. Org. Chem. 2021, 17, 52–57, doi:10.3762/bjoc.17.6

• suggestions and discussion on our researchs on molecular recognition during his visit in Nanjing Univ. in 2011 and afterwards. Funding This work was supported by the National Natural Science Foundation of China (Nos. 21901113, 21871135, 21871136), and the Natural Science Foundation of Jiangsu Province (No

Selected peptide-based fluorescent probes for biological applications

• Debabrata Maity

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

• recognition; peptide-based; Introduction Molecular recognition involving amino acids or peptides are important factors in biochemical and medicinal processes [1][2][3]. Amino acids work as biosynthetic building blocks or as signaling molecules. For example, the well-known neurotransmitters glutamate and γ

• -aminobutyric acid associate with membrane-bound protein receptors and trigger changes in receptor shape and activity with subsequent signaling across the membrane. Noncovalent H-bonding and van der Waals interactions are the basis for the selective molecular recognition between a G-coupled protein receptor and

• antibiotic, is used for the treatment of resistant bacterial infections. Its interaction with a small peptidic segment of the bacteria cell wall is a classic example of molecular recognition [6][7]. Peptides are often substrates for protease enzymes [8][9]. Enzymologists have studied the chemical principles