One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline

• Jiawei Niu,
• Yuhui Wang,
• Shenghu Yan,
• Yue Zhang,
• Xiaoming Ma,
• Qiang Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2024, 20, 912–920, doi:10.3762/bjoc.20.81

• ]isoquinolin-6(5H)-ones 6. One-pot synthesis for tetrazolyl-1,2,3,4-tetrahydroisoquinolines 8. Gram-scale two-step one-pot synthesis of 6c. Conditions for one-pot Ugi-azide and Heck reactions.a Supporting Information Supporting Information File 30: General reaction procedures, compound characterization data

Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles

• Jun Kikuchi,
• Roi Nakajima and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2024, 20, 891–897, doi:10.3762/bjoc.20.79

• -membered aromatic azacycles, imidazole completely failed to undergo the present N-alkenylation, whereas the reaction of 1,2,4-triazole was too sluggish to allow for the isolation and unambiguous characterization of the expected product. Next, the reaction of pyrazole (2a) was explored using different

• . Optimization of reaction conditions.a Supporting Information Supporting Information File 22: Experimental procedures and characterization data of new compounds. Acknowledgements We thank the Central Glass Co., Ltd. for the generous donation of 1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-ol (HFAB). Funding This

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

• and characterization data of all products, copies of 1H, 13C, 19F NMR spectra of all compounds. Acknowledgements The authors thank the Research Center of Analysis and Test of the East China University of Science and Technology for the help on the characterization and Professor Zhen-Jiang Xu from SIOC

Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria

• Kara A. Strickland,
• Brenda Martinez Rodriguez,
• Ashley A. Holland,
• Shelby Wagner,
• Michelle Luna-Alva,
• David E. Graham and
• Jonathan D. Caranto

Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75

• they are found in bacteria found in widespread classes and environments. Herein, we report the characterization of five NnlA homologs. It is shown that all five homologs exhibited NNG degradation activity. Isolation and characterization of four of these homologs showed that all contain heme, the

• further characterization. The H73A Vs NnlA variant, previously shown to lack NNG degradation activity, was used as a negative control [21]. E. coli transformants containing the expression vectors were incubated at 37 °C overnight in diluted lysogeny broth (LB) containing NNG and IPTG, the latter component

• . Other conserved positions could be required for subunit association in the active homodimer. Discussion The combined activity and characterization data indicate that each of the five homologs were similar to Vs NnlA in terms of oligomerization (Figure 2B), heme occupancy (Table 1 and Figure 3), NNG

Synthesis and characterization of water-soluble C₆₀–peptide conjugates

• Yue Ma,
• Lorenzo Persi and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2024, 20, 777–786, doi:10.3762/bjoc.20.71

• . Purple arrows in (b) indicate the split peaks. The 1H NMR spectrum of purified 5b was measured in D2O with 2% NaOD (Figure S12, Supporting Information File 1). 13C NMR analysis of the same sample was not possible due to the high ionic strength of the solution. NMR characterization was performed using a

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

• Victoria M. Alpatova,
• Evgeny G. Rys,
• Elena G. Kononova and
• Valentina A. Ol'shevskaya

Beilstein J. Org. Chem. 2024, 20, 767–776, doi:10.3762/bjoc.20.70

• synthesis and characterization of tris(carboranyl)porphyrins of A3B-type (where “B” corresponds to the substituent responsible for bioconjugate coupling) based on the transformations of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin which was used as a basic compound for the synthesis of new boronated

• NMR spectra for all synthesized compounds. Supporting Information Supporting Information File 2: Experimental details and characterization data. Acknowledgments This work was performed employing the equipment of Center for molecular composition studies of INEOS RAS. Funding This work was supported

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• ) [95]. Xu et al. identified GjCCD4a from G. jasminoides. Through prokaryotic expression and in vitro characterization, GjCCD4a was found to cleave the 7,8-/7',8'-double bonds of lycopene (5), β-carotene (6), and zeaxanthin (7). Further investigation revealed that GjCCD4a originated from tandem

• , and UGTs are the key players in crocin biosynthesis. Empowered by the genomic, transcriptomic, and metabolomic analysis and biochemical characterization, many such enzymes have been identified. Some proteins, exemplified by GjCCD4a and GjUGT94E13, exhibit broad substrate promiscuity and high catalytic

Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

• Senze Qiao,
• Zhongyu Cheng and
• Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

• strategy has been widely employed in the TE domains characterization and chemoenzymatic synthesis of other bioactive macrocyclic peptides, such as surfactin [40], streptogramin B [41], cereulide [42], seongsanamide E [43], etc. In 2005, Marahiel and co-workers accomplished the chemoenzymatic synthesis of

• -acetylcysteamine. Via bioinformatics analysis, Parkinson and co-workers most recently reported the characterization of Ulm16, the PBP-TE predicted to cyclize ulleungymycin. Compared with previously studied PBP-TEs, Ulm16 showed much higher efficiency and broader substrate scope, producing a variety of ullemgymycin

Genome mining of labdane-related diterpenoids: Discovery of the two-enzyme pathway leading to (−)-sandaracopimaradiene in the fungus Arthrinium sacchari

• Fumito Sato,
• Terutaka Sonohara,
• Shunta Fujiki,
• Akihiro Sugawara,
• Yohei Morishita,
• Taro Ozaki and
• Teigo Asai

Beilstein J. Org. Chem. 2024, 20, 714–720, doi:10.3762/bjoc.20.65

• TCs, AsPS and AsCPS, in the fungus Arthrinium sacchari. AsPS consists of catalytically active α and inactive β domains, whereas AsCPS contains βγ domains and a truncated α domain. Heterologous expression in Aspergillus oryzae and biochemical characterization of recombinant proteins demonstrated that

• Aspergillus oryzae and biochemical characterization of recombinant enzymes unveiled a fungal two-enzyme pathway to isopimaradiene, which is unprecedented for fungal LRDs. Results and Discussion To explore the fungal LRDs, we searched our in-house database by BLAST using known fungal bifunctional TCs such as

• synthesize a diterpene skeleton: After the initial cyclization of GGPP possibly catalyzed by a putative class II enzyme AsCPS, the resulting labdane or related skeleton would undergo cyclization by a putative class I enzyme AsPS. To assess this hypothesis, we conducted the functional characterization of AsPS

SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes

• Julien Borrel and
• Jerome Waser

Beilstein J. Org. Chem. 2024, 20, 701–713, doi:10.3762/bjoc.20.64

• Temperature screening.a Additive screening. Fine-tuning of the reaction conditions. Supporting Information Supporting Information File 68: General methods, photochemistry set-up, reaction optimization, experimental procedures and compounds characterization. Funding The authors thank the Ecole Polytechnique

Production of non-natural 5-methylorsellinate-derived meroterpenoids in Aspergillus oryzae

• Jia Tang,
• Yixiang Zhang and
• Yudai Matsuda

Beilstein J. Org. Chem. 2024, 20, 638–644, doi:10.3762/bjoc.20.56

• structural diversity of fungal meroterpenoids and potentially aiding the functional characterization of these tailoring enzymes. Biosynthesis of selected fungal meroterpenoids. (A, B) Dearomatizing prenylation reactions in the biosynthesis of (A) 3,5-dimethylorsellinic acid (DMOA)- and (B) 5-methylorsellinic

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• Co., Ltd, Yantai, China. Fungus isolation and characterization The fungus Penicillium shentong XL-F41 was isolated from soil collected in Shentong Mountain, Shandong Province, China, in June 2022. It was cultured on potato dextrose agar (PDA) at 28 °C. Sequencing and comparison with the GenBank

Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Irina V. Dubonosova,
• Olga Yu. Karlutova,
• Oleg P. Demidov,
• Alexander D. Dubonosov and
• Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

• , and quantum yields of the 2a–c→3a–c rearrangementa. Supporting Information Supporting Information File 26: Experimental procedures and characterization data for all new compounds 1, 2a–c and 3a–c. Supporting Information File 27: 1H and 13C NMR, IR and HRMS spectra of all novel compounds. Supporting

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• LEMPA. Supporting Information Supporting Information File 18: General synthetic procedures, characterization of all target compounds, methods for biological and biochemical testing, and scans of 1H and 13C NMR spectra of the new 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines. Acknowledgements We would like

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

• Alexander S. Hampton,
• David R. W. Hodgson,
• Graham McDougald,
• Linhua Wang and
• Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

• submission numbers: 2288841–2288848. Supporting Information File 2: Experimental procedures, characterization data, and copies of 1H, 19F and 13C{1H} NMR spectra. Acknowledgements We thank Dr Dmitry S. Yufit for conducting X-ray crystallographic studies. Parts of this work have already been published in

(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

• Nataliia V. Kirij,
• Andrey A. Filatov,
• Yurii L. Yagupolskii,
• Sheng Peng and
• Lee Sprague

Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40

• (Z)-isomer and ≈11 Hz for (E)-isomer). The 2-chloro-1,1,1,4,4,4-hexafluorobut-2-enes were first described by Haszeldine in 1952 [1] and only then the (Z)-isomer. We report here the isolation and complete characterization of both (E)- and (Z)-isomers. The spectral characteristics of product 6b

Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

• Nahed Ketata,
• Linhao Liu,
• Ridha Ben Salem and
• Henri Doucet

Beilstein J. Org. Chem. 2024, 20, 427–435, doi:10.3762/bjoc.20.37

• -dihalobenzenes. Pd-catalyzed Heck reaction followed by direct arylation of 1,1-diphenylethylene with 1,2-dihalobenzenes. Influence of the conditions on the Pd-catalyzed reaction of 1,8-dibromonaphthalene with 1,2,3,4-tetrafluorobenzene.a Supporting Information Supporting Information File 43: Characterization

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

• Eugeny Ivakhnenko,
• Vasily Malay,
• Pavel Knyazev,
• Nikita Merezhko,
• Nadezhda Makarova,
• Oleg Demidov,
• Gennady Borodkin,
• Andrey Starikov and
• Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

• , 6a,b, and 10c in toluene. CV parameters and calculated energy levels of 4a–h, 5a–c, 6a,b, and 10c. Supporting Information Supporting Information File 40: Synthetic details, compound characterization and additional analytic data, including copies of spectra and Cartesian coordinates. Funding This

Elucidating the glycan-binding specificity and structure of Cucumis melo agglutinin, a new R-type lectin

• Jon Lundstrøm,
• Emilie Gillon,
• Valérie Chazalet,
• Nicole Kerekes,
• Antonio Di Maio,
• Ten Feizi,
• Yan Liu,
• Annabelle Varrot and
• Daniel Bojar

Beilstein J. Org. Chem. 2024, 20, 306–320, doi:10.3762/bjoc.20.31

• garnered attention for their roles as laboratory probes and potential therapeutics. Here, we report the discovery and characterization of Cucumis melo agglutinin (CMA1), a new R-type lectin from melon. Our findings reveal CMA1’s unique glycan-binding profile, mechanistically explained by its 3D structure

• development, immunity, and stress signaling [2][3]. In light of the burgeoning interest in the intersection of glycobiology and biomedicine, the characterization of new lectins has carved out a significant niche in scientific research. Specifically, lectins have emerged as invaluable tools for staining cells

• melon [18], yet not much else is known about binding specificities exhibited by lectins derived from melons. In particular, existing research in this area often lacks a comprehensive characterization that includes both functional and structural analysis of these lectins. Here, we introduce a novel

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• endoperoxide formation. To overcome these issues, the “precursor approach” was developed and relies on the synthesis, purification and characterization of soluble and stable precursors of the target active π-CPCs, followed by their (solution) processing and their final deprotection once assembled in thin-films

• in-solution organic chemistry techniques, ii) for their improved processing, as well as iii) for their in situ structural characterization and electronic investigation both at the material and single-molecule scales. Reactions involving the elimination of carbon-based small molecules, i.e., retro

• ” is particularly interesting, since the as-prepared π-extended structures can undergo in-depth structural characterization and electronic investigations in situ at the single molecule scale, thanks to scanning probe microscopy and spectroscopy. The synthetic route relying on O-extrusion was thus

Unveiling the regioselectivity of rhodium(I)-catalyzed [2 + 2 + 2] cycloaddition reactions for open-cage C₇₀ production

• Cristina Castanyer,
• Anna Pla-Quintana,
• Anna Roglans,
• Albert Artigas and
• Miquel Solà

Beilstein J. Org. Chem. 2024, 20, 272–279, doi:10.3762/bjoc.20.28

• derivatives are relatively scarce, likely owing to the challenges associated with their synthesis and the characterization of asymmetric structures. The findings of this study contribute to the ongoing efforts in the field of fullerene chemistry and provide a foundation for further exploration of

• (fulleroid) derivatives 2a and 2b. Supporting Information Supporting Information File 22: General materials and methods, experimental procedures and characterization of all new compounds. Acknowledgements Dr. Carles Fuertes-Espinosa is acknowledged for assistance in HPLC and UV–vis experiments. Funding We

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

• )thianthrenium salt.a Supporting Information Supporting Information File 16: Experimental procedures, characterization data for all new compounds, and NMR spectra of products. Funding We are grateful for the financial support from the National Natural Science Foundation of China (22001227), the China

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• forward and backward isomerization of N,N'-diacetylindigo (9a) in toluene without isolation of the Z-form [49]. The Fischer method remains relevant up to date and is frequently used for the characterization of the photoinduced forms of various indigoid photoswitches [50][51][52][53][54]. To assess an

Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

• Milandip Karak,
• Cian R. Cloonan,
• Brad R. Baker,
• Rachel V. K. Cochrane and
• Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

• Supporting Information Supporting Information File 12: Experimental procedures, characterization data, and selected copies of 1H, 13C, and 31P NMR spectra. Acknowledgements We extend our gratitude to Professor Alethea Tabor and Professor Stefan Howorka from University College London for their valuable

Chiral phosphoric acid-catalyzed transfer hydrogenation of 3,3-difluoro-3H-indoles

• Yumei Wang,
• Guangzhu Wang,
• Yanping Zhu and
• Kaiwu Dong

Beilstein J. Org. Chem. 2024, 20, 205–211, doi:10.3762/bjoc.20.20

• . Reaction optimization studies.a The effect of Hantzsch esters and other reaction parameters.a Supporting Information Supporting Information File 4: Full experimental details and characterization data of all compounds. Funding We are grateful for the financial support provided by the National Nature