Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• operationally simple fluorination strategy suitable for bioactive structural motifs. Manganese-catalyzed late-stage C–H azidation In organic synthesis, organic azides are of considerable significance in the fields of medicinal chemistry, chemical biology, and nanotechnology as they can participate in elegant

• -containing peptide 37g. Conclusion Metal-catalyzed late-stage functionalization has shown significant potential in the fields of medicinal chemistry, agrochemistry, and chemical biology. While transition metal catalysis has been a reliable and efficient strategy for late-stage functionalization, it suffers

Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols

• Jie Zheng,
• Shuyu Meng and
• Quanrui Wang

Beilstein J. Org. Chem. 2021, 17, 1481–1489, doi:10.3762/bjoc.17.104

• + antagonist, and exhibits promising anti-oxidant properties. 4-Phenyl-2-propionamidotetralin (4-P-PDOT, 3, Figure 1) [5] is a melatonin MT2 selective antagonist that can be used to map melatonin receptor subtypes in tissue and serves as a chemical biology tool to identify sub-type selective analogues with

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

• Christopher Liczner Kieran Duke Gabrielle Juneau Martin Egli Christopher J. Wilds Department of Chemistry and Biochemistry, Concordia University, Montréal, Québec H4B 1R6, Canada Department of Biochemistry, Vanderbilt Institute of Chemical Biology, and Center for Structural Biology, School of

CF₃-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry

• Anthony J. Fernandes,
• Armen Panossian,
• Bastien Michelet,
• Agnès Martin-Mingot,
• Frédéric R. Leroux and
• Sébastien Thibaudeau

Beilstein J. Org. Chem. 2021, 17, 343–378, doi:10.3762/bjoc.17.32

• beneficial effects generally resulting from the introduction of these fluorinated motifs [13], also participated in this development. These fluorine effects are nowadays remarkably established in many domains, including medicinal, organic, and organometallic chemistry, catalysis, chemical biology, and

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

• use of 19F NMR in the broad field of chemical biology [Cobb, S. L.; Murphy, C. D. J. Fluorine Chem. 2009, 130, 132–140] and present here a summary of the literature from the last decade that has the technique as the central method of analysis. The topics covered include the synthesis of new

• biosynthesis and biodegradation of fluorinated organic compounds is also described. Keywords: biotransformation; chemical biology; fluorine; 19F NMR; probes; protein structure; Introduction Although fluorine is abundant in the environment, it is not a nutrient nor is it a feature of biochemistry for most

• important element in the broader space of chemical biology [2]. Many commercial and industrial compounds are fluorinated, including refrigerants, degreasers, drugs, pesticides and anti-stick materials, and consequently there is a high degree of interaction between fluorinated compounds and nature [3

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

• biological interaction, searching for structural data, and then searching for the molecular rationale. This is the connection between biology, chemical biology, and chemistry. The Galaxy project is a popular open web-based platform for accessible, reproducible, and transparent computational research [1

Automated high-content imaging for cellular uptake, from the Schmuck cation to the latest cyclic oligochalcogenides

• Rémi Martinent,
• Javier López-Andarias,
• Dimitri Moreau,
• Yangyang Cheng,
• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2020, 16, 2007–2016, doi:10.3762/bjoc.16.167

• Remi Martinent Javier Lopez-Andarias Dimitri Moreau Yangyang Cheng Naomi Sakai Stefan Matile School of Chemistry and Biochemistry, National Centre of Competence in Research (NCCR) Chemical Biology, University of Geneva, Geneva, Switzerland 10.3762/bjoc.16.167 Abstract Recent progress with

• for help with the high-content microscopy and analysis, J. A. Kritzer (Tufts University) and M. Hensel (Osnabrück University) for providing materials, and the Bioimaging and ACCESS platforms for services. Funding We thank the University of Geneva, the NCCR Chemical Biology, the NCCR Molecular Systems

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

• Shun Saito,
• Kota Atsumi,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Naoya Oku,
• Md. Rokon Ul Karim,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

• ], medium supplements for selective microbial/cell culture [6][7][8], or biochemical reagents for pharmacological/chemical biology studies [9] and continue to be indispensable to support and improve human welfare and social life. In recent years, in accordance with the advancement of genome and in silico

Design and synthesis of diazine-based panobinostat analogues for HDAC8 inhibition

• Sivaraman Balasubramaniam,
• Sajith Vijayan,
• Liam V. Goldman,
• Xavier A. May,
• Kyra Dodson,
• Sweta Adhikari,
• Fatima Rivas,
• Davita L. Watkins and
• Shana V. Stoddard

Beilstein J. Org. Chem. 2020, 16, 628–637, doi:10.3762/bjoc.16.59

• , TN 38112, USA Department of Chemical Biology and Therapeutics, St. Jude Children’s Research Hospital, Memphis, TN 38105-3678, USA 10.3762/bjoc.16.59 Abstract Guided by computational analysis, herein we report the design, synthesis and evaluation of four novel diazine-based histone deacetylase

Opening up connectivity between documents, structures and bioactivity

• Christopher Southan

Beilstein J. Org. Chem. 2020, 16, 596–606, doi:10.3762/bjoc.16.54

• discovery and chemical biology. Over the last decade commercial sources have manually extracted DARCP from ≈300,000 documents encompassing ≈7 million compounds interacting with ≈10,000 targets. Over a similar time, the Guide to Pharmacology, BindingDB and ChEMBL have carried out analogues DARCP extractions

• . However, in the broader context of bioactive chemistry, it becomes indivisible from the related domains of chemical biology (directed towards mechanistic insight rather that direct drug discovery), enzymology, pharmacology, and toxicology in addition to the development of insecticides or herbicides

• have initiated D-C feeds in PubChem but two of these, Prous Science Drugs of the Future and Nature Communications, ceased in 2012 and 2014 respectively. This has left only Nature Chemical Biology and Nature Chemistry as still active with 12481 and 15276 author-specified CID structures respectively

Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis

• David C. B. Siebert,
• Roman Sommer,
• Domen Pogorevc,
• Michael Hoffmann,
• Silke C. Wenzel,
• Rolf Müller and
• Alexander Titz

Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286

• David C. B. Siebert Roman Sommer Domen Pogorevc Michael Hoffmann Silke C. Wenzel Rolf Muller Alexander Titz Chemical Biology of Carbohydrates, Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), D-66123 Saarbrücken, Germany Deutsches

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

• Valentina A. Ol’shevskaya,
• Elena G. Kononova and
• Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

• heterocycles have also been used as linkers and for labeling biomolecules in chemical biology [43]. Moreover, this synthetic approach provides high yields, selectivity, mild reaction conditions and simple purification methods. It was demonstrated that the CuAAC reaction of porphyrins 3a and 3b with N

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

• Lei Zhang,
• Greta Linden and
• Olalla Vázquez

Beilstein J. Org. Chem. 2019, 15, 2500–2508, doi:10.3762/bjoc.15.243

• first compounds here reported, may find applications in different fields such as chemical biology, nanotechnology and materials science. Keywords: azobenzene; hemithioindigo; peptide nucleic acid (PNA); photoswitch; visible-light irradiation; Introduction Light-driven control of oligonucleotide

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

• Meng-Di Gu Yao Lu Mei-Xiang Wang MOE Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing 100084, China 10.3762/bjoc.15.193 Abstract Functionalized O6-corona[3]arene[3]tetrazines were synthesized efficiently and

Installation of -SO₂F groups onto primary amides

• Jing Liu,
• Shi-Meng Wang,
• Njud S. Alharbi and
• Hua-Li Qin

Beilstein J. Org. Chem. 2019, 15, 1907–1912, doi:10.3762/bjoc.15.186

• Sharpless and co-workers in 2014, for creating molecular connections based on the unique stability–reactivity pattern of the S(VI)–F bond with reliability and efficiency, which has been widely applied in organic synthesis, chemical biology and drug discovery [1][2][3][4][5][6][7][8][9][10][11][12][13][14

• novel sulfonyl fluorides for SuFEx click chemistry with great potential to be applied in the development of covalent inhibitors. Further studies of this class of molecules in chemical biology and drug discovery are underway in our laboratory. Representative sulfonyl fluoride compounds applied in

• medicinal chemistry and chemical biology. Synthesis background of N-fluorosulfonyl amides and fluorosulfates. Screening of the substrate scope of amides. Reaction conditions: a mixture of amides 1 (1.0 mmol), DBU (5.0 mmol, 5.0 equiv), and DMSO (1.0 mL) was added to a reaction flask before SO2F2 was

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• materials for relevant MCRs such as those based on imine and isocyanide. The focus is mainly posed on proving the amenability of MCRs for the diversity-oriented derivatization of naturally occurring steroids and the construction of complex steroid-based platforms for drug discovery, chemical biology and

A chemically contiguous hapten approach for a heroin–fentanyl vaccine

• Yoshihiro Natori,
• Candy S. Hwang,
• Lucy Lin,
• Lauren C. Smith,
• Bin Zhou and
• Kim D. Janda

Beilstein J. Org. Chem. 2019, 15, 1020–1031, doi:10.3762/bjoc.15.100

• Yoshihiro Natori Candy S. Hwang Lucy Lin Lauren C. Smith Bin Zhou Kim D. Janda Departments of Chemistry, Immunology and Microbial Science, Skaggs Institute for Chemical Biology; The Scripps Research Institute, 10550 N Torrey Pines Rd, La Jolla, CA, 92037, USA Faculty of Pharmaceutical Sciences

Catalytic asymmetric oxo-Diels–Alder reactions with chiral atropisomeric biphenyl diols

• Chi-Tung Yeung,
• Wesley Ting Kwok Chan,
• Wai-Sum Lo,
• Ga-Lai Law and
• Wing-Tak Wong

Beilstein J. Org. Chem. 2019, 15, 955–962, doi:10.3762/bjoc.15.92

• Chi-Tung Yeung Wesley Ting Kwok Chan Wai-Sum Lo Ga-Lai Law Wing-Tak Wong The Hong Kong Polytechnic University Shenzhen Research Institute, Shenzhen, PR China State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong

• 1–6.a Supporting Information Supporting Information File 396: Experimental data. Acknowledgements The authors gratefully acknowledge the fundings from the Basic Research Program of Shenzhen (No. JCYJ20160531184120814), State Key Laboratory of Chemical Biology and Drug Discovery, and The Hong Kong

Halogen bonding and host–guest chemistry between N-alkylammonium resorcinarene halides, diiodoperfluorobutane and neutral guests

• Fangfang Pan,
• Mohadeseh Dashti,
• Michael R. Reynolds,
• Kari Rissanen,
• John F. Trant and
• Ngong Kodiah Beyeh

Beilstein J. Org. Chem. 2019, 15, 947–954, doi:10.3762/bjoc.15.91

• Fangfang Pan Mohadeseh Dashti Michael R. Reynolds Kari Rissanen John F. Trant Ngong Kodiah Beyeh College of Chemistry, Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis

A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade

• Hong Yan,
• Zhong-Yi Mao,
• Zhong-Wei Hou,
• Jinshuai Song and
• Hai-Chao Xu

Beilstein J. Org. Chem. 2019, 15, 795–800, doi:10.3762/bjoc.15.76

• Hong Yan Zhong-Yi Mao Zhong-Wei Hou Jinshuai Song Hai-Chao Xu State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, iChEM and College of Chemistry and Chemical Engineering, Xiamen University, People’s Republic of China College of

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• in Quantitative and Chemical Biology under the award number T32 GM109825 and Indiana University provided to Chelsea Rintelmann and the post-doctoral research fellowship from the National Institute of Allergy and Infectious Diseases (Award Number 5T32AI007511) provided to Tara Grinnage-Pulley. This

Cyclopropene derivatives of aminosugars for metabolic glycoengineering

• Jessica Hassenrück and
• Valentin Wittmann

Beilstein J. Org. Chem. 2019, 15, 584–601, doi:10.3762/bjoc.15.54

• Jessica Hassenruck Valentin Wittmann University of Konstanz, Department of Chemistry and Konstanz Research School Chemical Biology (KoRS-CB), Universitätsstr. 10, 78457 Konstanz, Germany 10.3762/bjoc.15.54 Abstract Cyclopropenes have been proven valuable chemical reporter groups for metabolic

Aqueous olefin metathesis: recent developments and applications

• Valerio Sabatino and
• Thomas R. Ward

Beilstein J. Org. Chem. 2019, 15, 445–468, doi:10.3762/bjoc.15.39

• tremendous impact in organic synthesis, enabling a variety of applications in polymer chemistry, drug discovery and chemical biology. Although challenging, the possibility to perform aqueous metatheses has become an attractive alternative, not only because water is a more sustainable medium, but also to

• exploit biocompatible conditions. This review focuses on the progress made in aqueous olefin metatheses and their applications in chemical biology. Keywords: aqueous catalysis; artificial metalloenzymes; chemical biology; green chemistry; olefin metathesis; ruthenium catalysts; stapled peptides

•  1c). This review focuses on the recent improvements of olefin metathesis in aqueous media and the resulting applications in bioinorganic chemistry and chemical biology. Review Challenges in aqueous metathesis The first examples of aqueous metathesis were reported in the late 1980s [25][26]. ROMP

Computational characterization of enzyme-bound thiamin diphosphate reveals a surprisingly stable tricyclic state: implications for catalysis

• Ferran Planas,
• Michael J. McLeish and
• Fahmi Himo

Beilstein J. Org. Chem. 2019, 15, 145–159, doi:10.3762/bjoc.15.15

• Ferran Planas Michael J. McLeish Fahmi Himo Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden Department of Chemistry and Chemical Biology, Indiana University-Purdue University Indianapolis, Indianapolis IN 46202, USA 10.3762/bjoc.15.15

Synthesis and biological evaluation of 1,2-disubstituted 4-quinolone analogues of Pseudonocardia sp. natural products

• Stephen M. Geddis,
• Teodora Coroama,
• Suzanne Forrest,
• James T. Hodgkinson,
• Martin Welch and
• David R. Spring

Beilstein J. Org. Chem. 2018, 14, 2680–2688, doi:10.3762/bjoc.14.245

• Institute of Structural and Chemical Biology, and Department of Chemistry, University of Leicester, George Porter Building, University Road, Leicester, LE1 7RH, UK 10.3762/bjoc.14.245 Abstract A series of analogues of Pseudonocardia sp. natural products were synthesized, which have been reported to possess