Quantifying the ability of the CF₂H group as a hydrogen bond donor

• Matthew E. Paolella,
• Daniel S. Honeycutt,
• Bradley M. Lipka,
• Jacob M. Goldberg and
• Fang Wang

Beilstein J. Org. Chem. 2025, 21, 189–199, doi:10.3762/bjoc.21.11

• systems significantly enhances its hydrogen bond donation ability, a result consistent with theoretical calculations. We anticipate that this chemistry will be valuable for designing functional molecules for chemical biology and medicinal chemistry applications. Keywords: bioisostere; difluoromethyl

Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling

• John M. Halford-McGuff,
• Thomas M. Richardson,
• Aidan P. McKay,
• Frederik Peschke,
• Glenn A. Burley and
• Allan J. B. Watson

Beilstein J. Org. Chem. 2024, 20, 3198–3204, doi:10.3762/bjoc.20.265

• ]. As such, the reaction has been used extensively throughout drug discovery [20][21], chemical biology [22][23], and materials science [24][25][26][27]. Orthogonal alkyne reactivity can also be observed under certain systems [28][29][30]. The reaction typically uses a Cu(II) pre-catalyst, which is

• to chemical biology (Scheme 3a). The utility of the germanyl triazole products was then assessed by subsequent derivatisation of exemplar compounds 15 and 21 (Scheme 3b). Chemoselective Suzuki–Miyaura cross-coupling of the BPin moiety in 21 was straightforward, giving 28 in excellent yield [73

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

• thiols, sulfoxides and sulfilimines have received significant attention in chemical biology and synthetic chemistry due to their versatile properties. Traditional approaches to sulfilimine synthesis typically include the oxidative imination of sulfides, often relying on transition-metal catalysts, which

Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents

• Naoki Takeda,
• Shuichi Akasaka,
• Susumu Kawauchi and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2024, 20, 2234–2241, doi:10.3762/bjoc.20.191

• azide–alkyne cycloaddition; Introduction The strain-promoted azide–alkyne cycloaddition (SpAAC) is one of the most representative metal-free click chemistry reactions [1][2][3][4][5]. SpAAC has been mainly employed in bioconjugation in the fields of chemical biology and medicinal chemistry due to its

• oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) was developed and employed in the same fields of chemical biology [6][7]. On the other hand, the use of the SpAAC in materials science was slow. We developed another class of metal-free click chemistry reactions, such as the [2 + 2

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

• Ka-Lung Hung Leong-Hung Cheung Yikun Ren Ming-Hin Chau Yan-Yi Lam Takashi Kajitani Franco King-Chi Leung The Hong Kong Polytechnic University Shenzhen Research Institute, Shenzhen 518057, China State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical

Methodology for awakening the potential secondary metabolic capacity in actinomycetes

• Shun Saito and
• Midori A. Arai

Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69

• therapeutic drugs [1], agrochemicals [2], veterinary medicines [3], medium supplements for selective microbial/cell culture [4][5][6], food preservatives/colorings [7][8], and biochemical reagents for pharmacological/chemical biology studies [9]. This review has focused particularly on compounds produced by

• discovery studies, has been losing momentum. In drug discovery studies in the field of chemical biology, it may be important to investigate the compounds obtained by silent gene activation. It is expected that compounds useful in a variety of fields will be discovered by making full use of such silent gene

• mentioned above, various substances and changes in the concentrations of metal ions can affect secondary metabolism, and secondary metabolite production may thus be activated by these factors [110]. Conclusion Natural products hold great potential as leads in drug development and as useful tools in chemical

Synthesis of the 3’-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding

• Mark Reihill,
• Hanyue Ma,
• Dennis Bengtsson and
• Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

• Mark Reihill Hanyue Ma Dennis Bengtsson Stefan Oscarson Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland 10.3762/bjoc.20.17 Abstract The synthesis of gram quantities of the TF antigen (β-ᴅ-Gal-(1→3)-α-ᴅ-GalNAc) and its 3’-sulfated analogue with a

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• Radical addition is a popular technique for post-polymerization modification of double-bond-containing polymers (Scheme 14). Thiol–ene and thiol–yne “click chemistry” are highly efficient radical processes well-adopted in synthetic chemistry, material fabrication, and chemical biology (cf. section 2.2

Asymmetric tandem conjugate addition and reaction with carbocations on acylimidazole Michael acceptors

• Brigita Mudráková,
• Renata Marcia de Figueiredo,
• Jean-Marc Campagne and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 881–888, doi:10.3762/bjoc.19.65

• solubility in water. Among exceptional properties belongs to easy post-transformation of acylimidazoles to common carbonyl analogs. These tunable properties allow the use of acylimidazoles in chemical biology research, which includes chemical synthesis of proteins/peptides, structure analysis, and functional

Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles

• Deepak Singh,
• Shyamal Pramanik and
• Soumitra Maity

Beilstein J. Org. Chem. 2023, 19, 666–673, doi:10.3762/bjoc.19.48

• Deepak Singh Shyamal Pramanik Soumitra Maity Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM) Dhanbad, JH 826004, India 10.3762/bjoc.19.48 Abstract The importance of functionalized imidazo heterocycles has often been featured in several impactful research both

Total synthesis: an enabling science

• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 474–476, doi:10.3762/bjoc.19.36

• the success of total synthesis and can be a source of new discoveries. Indeed, as a science allowing the preparation of useful functional compounds, it is strongly connected to biological and medicinal studies, while the development of natural-product-based tools for chemical biology often requires

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

• Louis Monsigny,
• Floriane Doche and
• Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

• ; palladium; synthetic method; Introduction Nowadays, fluorinated molecules represent an indispensable class of molecules in chemistry and in chemical biology. Thanks to the unique properties of the fluorine atom or fluorinated groups to modulate biological and physicochemical properties of the parent non

Asymmetric synthesis of a stereopentade fragment toward latrunculins

• Benjamin Joyeux,
• Antoine Gamet,
• Nicolas Casaretto and
• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 428–433, doi:10.3762/bjoc.19.32

• synthesize latrunculin analogues for chemical biology studies. In particular, our initial goal was to protect an inactive lactol-opened form of latrunculins, which could cyclize in vivo upon deprotection under a specific stimulus (light or enzyme, for instance) for biological applications. This challenge

Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• cholesterol biosynthesis (statins). However, the side effects of these drugs are controversial. Therefore, synthetic cholesterol derivatives came into focus for recent applications in chemical biology and materials science [6]. The advances have been summarized in comprehensive reviews [7][8]. In previous

Synthetic study toward the diterpenoid aberrarone

• Liang Shi,
• Zhiyu Gao,
• Yiqing Li,
• Yuanhao Dai,
• Yu Liu,
• Lili Shi and
• Hong-Dong Hao

Beilstein J. Org. Chem. 2022, 18, 1625–1628, doi:10.3762/bjoc.18.173

• Liang Shi Zhiyu Gao Yiqing Li Yuanhao Dai Yu Liu Lili Shi Hong-Dong Hao Department Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi 712100, China State Key Laboratory of Chemical Oncogenomics, Guangdong

Solid-phase total synthesis and structural confirmation of antimicrobial longicatenamide A

• Takumi Matsumoto,
• Takefumi Kuranaga,
• Yuto Taniguchi,
• Weicheng Wang and
• Hideaki Kakeya

Beilstein J. Org. Chem. 2022, 18, 1560–1566, doi:10.3762/bjoc.18.166

• serve as both drug leads and research tools for chemical biology [1]. Because the rediscovery rate of these compounds has increased in the last few decades, new approaches to explore natural products are in demand [2]. To this end, the combined-culture strategy has been applied to discover new natural

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• chemists consider? Grant-wise, the last 40 years have seen the rise of chemical biology and the discovery of many types of large constructs providing tools often useful for life science but far less effective in human medicine. An excellent review [226] has recently listed these approaches but even if they

• have to some degree improved the arsenal of compounds available for human medicine, the inherent pharmacological limitations of these large chemical constructs remains a major issue [227]. This means that for most health problems, “classic” medicinal chemistry is not going to be replaced by chemical

• biology. To contribute to medicinal chemistry, one axis remains to provide chemical libraries with new chemical entities, another would be to reconsider previous leads and attempt to improve them. A concern for the first axis is that securing a grant for the synthesis of series of drug-like molecules

Computational model predicts protein binding sites of a luminescent ligand equipped with guanidiniocarbonyl-pyrrole groups

• Neda Rafieiolhosseini,
• Matthias Killa,
• Thorben Neumann,
• Niklas Tötsch,
• Jean-Noël Grad,
• Alexander Höing,
• Thies Dirksmeyer,
• Jochen Niemeyer,
• Christian Ottmann,
• Shirley K. Knauer,
• Michael Giese,
• Jens Voskuhl and
• Daniel Hoffmann

Beilstein J. Org. Chem. 2022, 18, 1322–1331, doi:10.3762/bjoc.18.137

• Department of Molecular Biology II, Center for Medical Biotechnology (ZMB), University of Duisburg-Essen, Universitätsstraße 5, 45141 Essen, Germany Laboratory of Chemical Biology, Department of Biomedical Engineering and Institute for Complex Molecular Systems, Eindhoven University of Technology, PO Box 513

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

• Jamshid Amiri Moghaddam,
• Huijuan Guo,
• Karsten Willing,
• Thomas Wichard and
• Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

• Jamshid Amiri Moghaddam Huijuan Guo Karsten Willing Thomas Wichard Christine Beemelmanns Chemical Biology Leibniz Institute for Natural Product Research and Infection Biology e.V., Hans-Knöll-Institute, Beutenbergstraße 11a, 07745 Jena, Germany Bio Pilot Plant, Leibniz Institute for Natural

Amamistatins isolated from Nocardia altamirensis

• Till Steinmetz,
• Wolf Hiller and
• Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

• Till Steinmetz Wolf Hiller Markus Nett Department of Biochemical and Chemical Engineering, Laboratory of Technical Biology, TU Dortmund University, Emil-Figge-Strasse 66, 44227 Dortmund, Germany Department of Chemistry and Chemical Biology, TU Dortmund University, Germany 10.3762/bjoc.18.40

New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

• Long Zhao,
• Mao-Lin Yang,
• Min Liu and
• Ming-Wu Ding

Beilstein J. Org. Chem. 2022, 18, 286–292, doi:10.3762/bjoc.18.32

• Long Zhao Mao-Lin Yang Min Liu Ming-Wu Ding Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan, 430079, P. R. China 10.3762/bjoc.18.32

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

• Jiang-Song Zhai and
• Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

• availability of these compounds will provide promising candidates for chemical biology and drug discovery. Experimental General information Commercially available compounds were used without further purification. Solvents were dried according to standard procedures. Column chromatography was performed with

A photochemical C=C cleavage process: toward access to backbone N-formyl peptides

• Haopei Wang and
• Zachary T. Ball

Beilstein J. Org. Chem. 2021, 17, 2932–2938, doi:10.3762/bjoc.17.202

• concept described here might be useful for the synthetic unmasking of relatively sensitive imido structures. For chemical biology applications, the results point to a far more diverse photochemistry than previously assumed for vinylogous photocleavage systems. Although formyl hydrolysis to the “expected

Electrocatalytic C(sp³)–H/C(sp)–H cross-coupling in continuous flow through TEMPO/copper relay catalysis

• Bin Guo and
• Hai-Chao Xu

Beilstein J. Org. Chem. 2021, 17, 2650–2656, doi:10.3762/bjoc.17.178

• Bin Guo Hai-Chao Xu Key Laboratory of Chemical Biology of Fujian Province and College of Chemistry and Chemical Engineering, Xiamen University, People’s Republic of China 10.3762/bjoc.17.178 Abstract Electrocatalytic dehydrogenative C(sp3)–H/C(sp)–H cross-coupling of tetrahydroisoquinolines with

Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines

• Zara M. Seibel,
• Jeffrey S. Bandar and
• Tristan H. Lambert

Beilstein J. Org. Chem. 2021, 17, 2077–2084, doi:10.3762/bjoc.17.134

• Zara M. Seibel Jeffrey S. Bandar Tristan H. Lambert Department of Chemistry, Columbia University, New York, New York 10027, USA Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA 10.3762/bjoc.17.134 Abstract A procedure for the enantioselective synthesis