Deciphering the mechanism of γ-cyclodextrin’s hydrophobic cavity hydration: an integrated experimental and theoretical study

• Stiliyana Pereva,
• Stefan Dobrev,
• Tsveta Sarafska,
• Valya Nikolova,
• Silvia Angelova,
• Tony Spassov and
• Todor Dudev

Beilstein J. Org. Chem. 2024, 20, 2635–2643, doi:10.3762/bjoc.20.221

• residues, but α-CDs with 6 and γ-CDs with 8 glucopyranose units, respectively, have also been widely used as potent host structures encapsulating various substances of interest to science and industry. The shape of CDs is toroid-like with one opening (lower rim) wider than the other (upper rim). These

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

• gaining increasing interest in both academia and industry due to its numerous advantages and potential applications [1][2]. Electrochemical methods can reduce costs and waste generation by eliminating the need for chemical oxidants or reductants, and they can be safely and easily scaled up in flow

• reactors for industrial applications. The potential for upscaling and applicability towards LSF makes electrosynthesis particularly appealing for the fine-chemical and pharmaceutical industry. As the electrode potential can be fine-tuned over a continuous scale, higher functional group compatibility can be

Machine learning-guided strategies for reaction conditions design and optimization

• Lung-Yi Chen and
• Yi-Pei Li

Beilstein J. Org. Chem. 2024, 20, 2476–2492, doi:10.3762/bjoc.20.212

• these existing challenges, reaction optimization continues to play a vital role in both academia and industry in the age of big data [23]. Outlook and Perspectives As we explore the future of ML in designing and optimizing reaction conditions, several promising avenues and challenges are poised to shape

Improved deconvolution of natural products’ protein targets using diagnostic ions from chemical proteomics linkers

• Andreas Wiest and
• Pavel Kielkowski

Beilstein J. Org. Chem. 2024, 20, 2323–2341, doi:10.3762/bjoc.20.199

• ; Introduction Natural products (NPs) have been pivotal for the development of modern medicine accompanying humans from the prehistorical age [1]. In the last century, NPs became the main source of the active scaffolds for the pharmaceutical industry with focus on principle of one compound, one target, and one

Cell-free protein synthesis with technical additives – expanding the parameter space of in vitro gene expression

• Tabea Bartsch,
• Stephan Lütz and
• Katrin Rosenthal

Beilstein J. Org. Chem. 2024, 20, 2242–2253, doi:10.3762/bjoc.20.192

• and thscGAS-sfGFP. Parameter scope and robustness of CFPS The composition of reaction media for enzymatic applications, especially in the chemical industry, has been expanded to technical additives [60]. It was therefore tested whether CFPS is also compatible with the addition of technical additives

Finding the most potent compounds using active learning on molecular pairs

• Zachary Fralish and
• Daniel Reker

Beilstein J. Org. Chem. 2024, 20, 2152–2162, doi:10.3762/bjoc.20.185

• Science & Engineering Graduate (NDSEG) Fellowship Program. This research was supported by the Duke Science & Technology Initiative and by the NIH NIGMS grant R35GM151255. Conflict of Interest D.R. acts as a consultant to the pharmaceutical and biotechnology industry, as a mentor for Start2, and on the

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

• Zsuzsanna Fehér,
• Dóra Richter,
• Gyula Dargó and
• József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

• methods, such as the application of immobilised organocatalysts [14][15] and heterogeneous organocatalysis [16][17][18], could be a potential driver for the introduction of, for example, enantioselective organocatalysis in the pharmaceutical industry [19]. Knowledge of the factors that influence catalyst

• enantioselectivity (>90% ee) for over 250 cycles. Conclusion Solid-supported organocatalysts can provide an environmentally friendly and economical solution even for industrial processes. To maximise their adoption by industry, efficient catalysts that can be easily recycled need to be developed. Immobilisation on

• evolving development of solid-supported organocatalysts has significant potential for industrial applications, particularly in the pharmaceutical and fine chemical industry. The design of recyclable, robust and high-performance organocatalyst systems will continue to encourage innovation in this area

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

• various pocket descriptors on a large scale. Fpocket 1.0 outperforms industry standards by detecting a high percentage of pockets within the best-ranked ones and offers a fast, open-source solution for protein pocket detection (https://github.com/Discngine/fpocket). 3. GRID [115]: It is a computational

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• ], pyrazoles also find applications in OLED technology [20] and optical brighteners [21] in the textile and laundry industry. The ongoing quest for novel, potent, and efficient syntheses of pyrazoles prompts the search for the “ideal” synthesis [22][23], one that addresses all the synthetic challenges to meet

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

• Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

• applications in industry. Synthesis of triazolopyridinium salts [34][35][36]. Synthesis of pyrazoles [37]. Synthesis of indazoles from ketone-derived hydrazones [38]. Intramolecular C(sp2)–H functionalization of aldehyde-derived N-(2-pyridinyl)hydrazones for the synthesis of 1,2,4-triazolo[4,3-a]pyridines [39

Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity

• Moisés Alejandro Alejo Hernandez,
• Katia Pamela Villavicencio Sánchez,
• Rosendo Sánchez Morales,
• Karla Georgina Hernández-Magro Gil,
• David Silverio Moreno-Gutiérrez,
• Eddie Guillermo Sanchez-Rueda,
• Yanet Teresa-Cruz,
• Brian Choi,
• Armando Hernández Garcia,
• Alba Romero-Rodríguez,
• Oscar Juárez,
• Siseth Martínez-Caballero,
• Mario Figueroa and
• Corina-Diana Ceapă

Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159

• Acinetobacter baumannii [26], as supported by the current study. In addition, some lanthipeptides have been shown to have anticancer and immunomodulatory properties [11][27]. A low development of resistance to lanthipeptides has been observed, with nisin being the most well-known case in the food industry

pKalculator: A pK_a predictor for C–H bonds

• Rasmus M. Borup,
• Nicolai Ree and
• Jan H. Jensen

Beilstein J. Org. Chem. 2024, 20, 1614–1622, doi:10.3762/bjoc.20.144

• industry to implement such C–H transformations to diversify different types of molecules ranging from small drug-like molecules to intermediates and lead compounds. Especially late-stage functionalization is a promising emerging field that allows chemists to efficiently explore the chemical space in

Supramolecular assemblies of amphiphilic donor–acceptor Stenhouse adducts as macroscopic soft scaffolds

• Ka-Lung Hung,
• Leong-Hung Cheung,
• Yikun Ren,
• Ming-Hin Chau,
• Yan-Yi Lam,
• Takashi Kajitani and
• Franco King-Chi Leung

Beilstein J. Org. Chem. 2024, 20, 1590–1603, doi:10.3762/bjoc.20.142

• materials with visible-light-controlled microenvironments and future soft robotic systems. Experimental Materials All commercial reagents were purchased from Acros Organics, Aladdin, Alfa Aesar, Bidepharm, Dieckmann, Macklin, Sigma-Aldrich, and Tokyo Chemical Industry and used as received unless otherwise

Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor

• Koichi Mitsudo,
• Atsushi Osaki,
• Haruka Inoue,
• Eisuke Sato,
• Naoki Shida,
• Mahito Atobe and
• Seiji Suga

Beilstein J. Org. Chem. 2024, 20, 1560–1571, doi:10.3762/bjoc.20.139

• Supporting Information File 16: Experimental part. Acknowledgements The authors thank Prof. Yuta Nishina (Okayama University) and his group members for their help in preparing the MEA. The authors also thank Ishifuku Metal Industry Co., Ltd. and De Nora Permelec Ltd. for providing the catalysts and DSE

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

• Lu Li,
• Na Li,
• Xiao-Tian Mo,
• Ming-Wei Yuan,
• Lin Jiang and
• Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

• additives in the petrochemical industry [3]. Besides, 2-benzylanilines also serve as valuable building blocks in synthetic chemistry [4]. The classical route to this kind of aniline derivatives usually starts from parent anilines, which undergo Friedel–Crafts reaction with acyl halides followed by carbonyl

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

• Sigma-Aldrich Co., Nacalai Tesque Co., Tokyo Chemical Industry Co., Ltd., FUJIFILM Wako Pure Chemical Industries, Ltd. All organic solvents are purchased from Nacalai Tesque Co., FUJIFILM Wako Pure Chemical Industries, Ltd. and were used without purification unless indicated otherwise. The silica gel 60

Mechanistic investigations of polyaza[7]helicene in photoredox and energy transfer catalysis

• Johannes Rocker,
• Till J. B. Zähringer,
• Matthias Schmitz,
• Till Opatz and
• Christoph Kerzig

Beilstein J. Org. Chem. 2024, 20, 1236–1245, doi:10.3762/bjoc.20.106

• Foundation (DBU, Ph.D. fellowship to T.J.B.Z., grant number 20022/028). M.S. is grateful to the Chemical Industry Funds for a Kekulé fellowship.

The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids

• Carolina S. Marques,
• Aday González-Bakker and
• José M. Padrón

Beilstein J. Org. Chem. 2024, 20, 1213–1220, doi:10.3762/bjoc.20.104

• adducts, with stereochemistry control [4][5]. Unquestionable potential of application in the pharmaceutical industry is recognizable by the number of APIs obtained by this reaction approach [6][7]. The oxindole framework is a privileged unit, recognized massively by its extensive biological applications

Stability trends in carbocation intermediates stemming from germacrene A and hedycaryol

• Naziha Tarannam,
• Prashant Kumar Gupta,
• Shani Zev and
• Dan Thomas Major

Beilstein J. Org. Chem. 2024, 20, 1189–1197, doi:10.3762/bjoc.20.101

• derived from germecrene A. Keywords: carbocation; germacrene A; hedycaryol; stability trend; terpenes; Introduction Terpenoids form a large and highly diverse group of natural products with a wide range of usage in the pharmaceutical, cosmetic, agricultural, food, and energy industry. Among their

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

• Mohd Farhan Ansari,
• Atul Kumar Maurya,
• Abhishek Kumar and
• Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

• are of substantial importance for the fine chemical industry, pharmaceuticals, agrochemicals, dyes, and natural products [25]. The synthesis of amine derivatives can be accomplished using many powerful techniques, including Buchwald–Hartwig and Ullmann cross-coupling reactions, hydroamination

Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

• Ke Jiang,
• Cheng Pan,
• Limin Wang,
• Hao-Yang Wang and
• Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

• , CAS for helpful discussion and instrumental analysis. Funding The work was supported by the Industry-University-Research Collaborative Innovation Fund for Chinese Universities-DeZhou Project (2021DZ030) and the Natural Science Foundation of Shanghai (20ZR1413500); Shanghai Municipal Science and

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

• Luan A. Martinho and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

• existing ones. Keywords: GBB-3CR; imidazo[1,2-a]pyridine; microwave; phosphotungstic acid; Introduction Imidazo[1,2-a]pyridine is a privileged structure that plays an important role in organic synthesis and in the pharmaceutical industry. This scaffold is present in drugs with several biological

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• actinomycetes, which are believed to be rich sources of interestingly new compounds. Bioactive compounds are vastly beneficial in medicine, pharmaceutical industry, and agriculture [7][8]. The thoughtful exploration of novel sources for acquiring new compounds is crucial, and the strategies employed in this

• and biotechnological innovations. Continued research in this area has the potential to uncover valuable compounds that contribute to human health, pharmaceutical industry, and environmental sustainability. Experimental Taxonomic analysis Saccharopolyspora sp. KR21-0001 was isolated from soil in Ōha

Nucleophilic functionalization of thianthrenium salts under basic conditions

• Xinting Fan,
• Duo Zhang,
• Xiangchuan Xiu,
• Bin Xu,
• Yu Yuan,
• Feng Chen and
• Pan Gao

Beilstein J. Org. Chem. 2024, 20, 257–263, doi:10.3762/bjoc.20.26

• accessible and have significant importance in the pharmaceutical industry, positioning them as appealing candidates for C(sp3) coupling due to their availability as a common chemical feedstock. However, due to the high bond dissociation energy of the C–O bond and the poor leaving ability of the hydroxy group

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

• Ekaterina V. Kolupaeva,
• Narek A. Dzhangiryan,
• Alexander F. Pozharskii,
• Oleg P. Demidov and
• Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

• and used in medicine, food industry, catalysts, dyes, functional materials, oil refining, and electronics [1][2]. Quinoline and its derivatives have antibiotic, antimalarial, antitumor, anti-inflammatory, antihypertensive, and antiretroviral properties [3][4]. Therefore, at present, there is a need