Spin and charge interactions between nanographene host and ferrocene

• Akira Suzuki,
• Yuya Miyake,
• Ryoga Shibata and
• Kazuyuki Takai

Beilstein J. Org. Chem. 2024, 20, 1011–1019, doi:10.3762/bjoc.20.89

• Fe2p peaks and the increase in shake-up peak intensity of the C1s in the XPS spectrum proved the emergence of charge-transfer host–guest interaction in FeCp2-ACFs-150, supported by the red-shift of the G-band in the Raman spectrum. The six-times enhancement in the spin concentration in FeCp2-ACFs-150

• for FeCp2-ACFs-150 due to their tiny abundance, the G-band for FeCp2-ACFs-150 shifts by 3 cm−1 to the lower wavenumber side compared to ACFs. The red shift indicates the weakening of C=C bonding in nanographene caused by filling anti-bonding states (π* states) due to electron injection into

• clarification. XPS spectrum for FeCp2-ACFs-150 in the Fe2p region shown with fitting curves. XPS spectra of (left) FeCp2-ACFs-150 and (right) ACFs in the C1s region with fitting curves. Raman spectra for ACFs and FeCp2-ACFs-150. Each raw data (black) was fitted to the G-band (blue) and D-band (red) components

A Diels–Alder probe for discovery of natural products containing furan moieties

• Alyssa S. Eggly,
• Namuunzul Otgontseren,
• Carson B. Roberts,
• Amir Y. Alwali,
• Haylie E. Hennigan and
• Elizabeth I. Parkinson

Beilstein J. Org. Chem. 2024, 20, 1001–1010, doi:10.3762/bjoc.20.88

• utilizing the probe in additional strains to probe for novel natural products similar to the MMFs. A) Bioactive natural products containing a furan ring (blue) or 3-furoic acid moiety (red): plakorsin D, wortmannin, tournefolin C, rosefuran, and flufuran and their respective biological activities. B) MMF

Monitoring carbohydrate 3D structure quality with the Privateer database

• Jordan S. Dialpuri,
• Haroldas Bagdonas,
• Lucy C. Schofield,
• Phuong Thao Pham,
• Lou Holland and
• Jon Agirre

Beilstein J. Org. Chem. 2024, 20, 931–939, doi:10.3762/bjoc.20.83

• conformational landscape of pyranose sugars. A well-modelled ᴅ-sugar would be expected to be in the lowest-energy conformation and have a theta angle close to 0° and would be indicated by a blue point; deviations from the ideal conformation are highlighted with a red cross. Right: Real space correlation

Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• molecules within and between a layer with two molecules at the top and the bottom of the unit cell. b) Determined from X-ray structural analysis at 123 K. Element color: carbon (grey), hydrogen (white), oxygen (red) and nitrogen (blue). The thermal ellipsoids are drawn at the 50% probability level. UV–vis

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

• residues outside of the heme pocket are colored in magenta. Nitrogen, oxygen, and iron atoms are colored blue, red, and orange, respectively. Figure generated using PyMOL. Phylogenetic tree of NnlA homologs with accession numbers. Branch lengths correspond to amino acid substitutions per position. Numbers

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

• production of antibiotics such as actinorhodin (ACT, 8), undecylprodigiosin (RED, 21), and calcium-dependent antibiotic (CDA, 22) in Streptomyces coelicolor M145 (Figure 3b). Chen et al. and Shu et al. reported that under stress associated with high concentrations of glutamate, AfsQ1/Q2 is important not only

• for maintaining the metabolic homeostasis of nutrient utilization but also for biosynthesis of antibiotics such as ACT, RED, CDA and the yellow pigment coelimycin P2 in Streptomyces coelicolor strains M145 [60][61]. Depletion of a metal component essential for growth activates the production of

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

• isolated from the fruit of Gardenia jasminoides Ellis and the stigma tissue of Crocus sativus L. Crocins are the main active ingredients of C. sativus, a precious medicinal plant known as the "gold of spices". They are also responsible for the characteristic red color of saffron. Compounds of the crocin

Substrate specificity of a ketosynthase domain involved in bacillaene biosynthesis

• Zhiyong Yin and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2024, 20, 734–740, doi:10.3762/bjoc.20.67

• -ketoisocaproate starter unit with introduction of an S configured stereocentre (highlighted in red in Scheme 1) [15]. The domain organisation of module 3 containing no enoylreductase (ER) domain furthermore suggests the formation of an α,β-unsaturated intermediate, and not a full reduction at this stage, in

Isolation and structure determination of a new analog of polycavernosides from marine Okeania sp. cyanobacterium

• Kairi Umeda,
• Naoaki Kurisawa,
• Ghulam Jeelani,
• Tomoyoshi Nozaki,
• Kiyotake Suenaga and
• Arihiro Iwasaki

Beilstein J. Org. Chem. 2024, 20, 645–652, doi:10.3762/bjoc.20.57

• . Polycavernoside E (1) exhibited moderate antitrypanosomal activity against Trypanosoma brucei rhodesiense. Furthermore, the isolation of polycavernoside E (1) from marine cyanobacteria provides additional evidence that marine cyanobacteria, and not red algae, are responsible for the biosynthesis of

• polycavernosides. Keywords: macrolide glycoside; marine cyanobacterium; marine natural products; polycavernosides; terminal alkyne; Introduction In 1991, an outbreak of food poisoning caused by a species of red algae known as ‘Polycavernosa tsudai’ occurred in Guam, which resulted in killing of three people. Two

• novel macrolide glycosides, polycavernosides A (2) and B (3), were reported as the causative compounds for the illness [1]. After that, the second fatal food poisoning incidents occurred in the Philippines caused by the ingestion of polycavernoside A (2)-contaminated red algae [2]. Subsequently

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

• Andrew D. Gillie,
• Matthew G. Wakeling,
• Bethan L. Greene,
• Louise Male and
• Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

• fused imidazolium core (Scheme 2). No reaction was observed between 6a and [Ir(cod)Cl]2 in the presence of NEt3. A solution of the free carbene was prepared from 6 and reacted with [Ir(cod)Cl]2 and then CO to afford the AImOxIr(CO)Cl complex 15. A minor side-product with a strong red colour was formed

A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A

• Michael O. Akintubosun and
• Melanie A. Higgins

Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51

• inositols with NAD+, (b) myo-inositol with NAD+ or NADP, and (c) myo-inositol at different pH values (orange is HEPEs, green is Tris, blue is CHES, and red is CAPS). NAD(P)H concentrations were measured after 20 minutes. Michaelis–Menten plots for Hyg17 using varying concentrations of (d) myo-inositol, (e

• for inositol dehydrogenases. (b) Comparison of the hygromycin A (red) and hygromycin A-like (orange) biosynthetic gene clusters. A more detailed comparison can be found in Supporting Information File 1, Table S2. Kinetic parameters for Hyg17. Supporting Information Supporting Information File 36

Possible bi-stable structures of pyrenebutanoic acid-linked protein molecules adsorbed on graphene: theoretical study

• Yasuhiro Oishi,
• Motoharu Kitatani and
• Koichi Kusakabe

Beilstein J. Org. Chem. 2024, 20, 570–577, doi:10.3762/bjoc.20.49

• graphene Conformations of PASE are interconverted by mutual transition when the molecule is twisted around one of the carbon–carbon single bonds in the alkyl chain. The rotational motion connecting conformation 1 and conformation 2 happens around the single bond indicated by the solid red line in Figure 1a

• activation barrier-type pathway. The pathway connecting conformations 1 and 2 appears as a torsion of the alkyl chain around the carbon–carbon single bond, as indicated by the solid red line in Figure 1a. This is a kind of rotational motion. We determined the dihedral angles formed by the four carbon atoms

• connected by the red line in Figure 3, and the values of dihedral angles for conformations 1, 2, and the conformation at the activation barrier top are collected in Table 1. From these values, we can interpret the torsion as an approximate rotation. We call the rotations 0, π/3, and 2π/3 as an approximation

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

• °, fold angle 4.38°). The molecular packing of compound 3b was characterized by the presence of numerous π–π interactions (Figure 4). Intermolecular interactions in the benzo[b]thiophene fragment (red planes in Figure 4) were characterized by the following parameters: plane centroid–plane centroid

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

• monocotyledon weeds in wheat, including resistant species, we tested the three selected 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines 7b, 7c, and 13b against commercially relevant weeds in corn, e.g., crabgrass or red fingergrass (DIGSA) and goosegrass or crowsfoot grass (ELEIN), together with Johnson grass (SORHA

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

• to red). Next, the mixtures were incubated at 37 °C for 1 h. After incubation, 25 µL of 1 M HCl was added to each sample for neutralization. The mixtures were concentrated to dryness in vacuo, dissolved in acetonitrile, and analyzed by LC–MS. Biological activity Antioxidant activity The antioxidant

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• . Key 1H-1H COSY (bond lines), and HMBC (red arrows) correlations of 1–3. NOE correlations of compounds 1 and 2 (solid line indicates β-orientation and dashed lines represent α-orientation). X-ray crystal structure of compounds 1–3 (with a thermal ellipsoid probability of 50%). Proposed biosynthetic

Enhanced host–guest interaction between [10]cycloparaphenylene ([10]CPP) and [5]CPP by cationic charges

• Eiichi Kayahara,
• Yoshiyuki Mizuhata and
• Shigeru Yamago

Beilstein J. Org. Chem. 2024, 20, 436–444, doi:10.3762/bjoc.20.38

• between the Hirshfeld surface and the contacting atoms, most sp2-hybridzed carbon atoms of the [10]CPP host have short contact with the Hirshfeld surface, as shown in green, despite the tilting of [10]CPP and [5]CPP. In the crystal packing, there were two orientations, as highlighted in blue and red in

• Figure 7e. In the packing shown in red, the host–guest complex is alternately stacked with two counterions to forms a one-dimensional (1D) columnar structure in which the complex is tilted at approximately 45° relative to the short axis (Figure 7f and Supporting Information File 1, Figure S3

• −/1,2-dichloroethane upon scanning in (a) positive and (b) negative directions. UV–vis–NIR spectra of [10]CPP⊃[5]CPP2+[B(C6F5)4−]2 (black), [10]CPP (blue), and [5]CPP2+[B(C6F5)4−]2 (red) in CH2Cl2. Top and side view of [10]CPP⊃[5]CPP2+ complexes a) 1, b) 2, and c) 3 obtained by DFT calculation at the

Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters

• Carlos R. Azpilcueta-Nicolas and
• Jean-Philip Lumb

Beilstein J. Org. Chem. 2024, 20, 346–378, doi:10.3762/bjoc.20.35

• decarboxylative transformations of NHPI esters using a phenothiazine-based organophotoredox catalyst PTH1. This type of catalyst is believed to facilitate SET to NHPI esters through the formation of EDA complexes. Interestingly, upon addition of RAE 58 to a solution of PTH1, a noticeable red shift in the UV–vis

Spatial arrangements of cyclodextrin host–guest complexes in solution studied by ¹³C NMR and molecular modelling

• Konstantin Lebedinskiy,
• Ivan Barvík,
• Zdeněk Tošner,
• Ivana Císařová,
• Jindřich Jindřich and
• Radim Hrdina

Beilstein J. Org. Chem. 2024, 20, 331–335, doi:10.3762/bjoc.20.33

• was detected for carbons 1 and 3 (in red color). The same 1D 13C NMR spectra were measured for guest molecule 1 in host cavities of β-CD and γ-CD, showing almost no split of prochiral carbon peaks and suggesting a higher degree of conformational flexibility of the host–guest complexes than for the

• well-separated light and dark clouds (belonging to different prochiral carbons from a pair) have larger radii and run deeper into the α-CD cavity than the red density with mixed light and dark clouds. Accordingly, our NMR experiment only showed splitting for the green and blue atoms (see Figure 1

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

• ]. Validating binding in solution and assessing binding affinity As CMA1 both exhibited multiple binding sites and robust binding to blood group epitopes (H-antigen), we hypothesized that it would be capable of agglutinating red blood cells, justifying its new name. When testing the protein recombinantly

• array and dividing the results by the standard deviation. Agglutination assay The hemagglutinating activity of CMA1 was determined in V-bottom 96-well plates by a twofold serial dilution procedure in PBS using rabbit red blood cells (Atlantis France). 25 µL of 4% erythrocyte suspension was added to an

• heatmap via the get_heatmap function of glycowork. Representative glycans are shown. Assessing and quantifying in-solution binding of CMA1. (a) Erythrocyte agglutination assay. Using rabbit red blood cells, CMA1 protein recombinantly produced in mammalian cells was used in a two-fold dilution series to

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

• α- and β-bonds were systematically observed at different temperatures. The protons of the two methyl groups around δ 2.30 ppm were used as diagnostic signals. For the major isomer (red dots, Figure 2), the spectrum exhibits two singlets at δ = 2.27 and 2.28 ppm, corresponding to the two different

• methyl groups in the six-membered ring formed in the cycloaddition and coming from the starting diyne 1a (highlighted in red in Scheme 2). In contrast, for the minor isomer (green dots), which has Cs symmetry, the two methyl groups (highlighted in green in Scheme 2) appear as a single peak at δ = 2.40

• protons marked in red and the ones marked in green might be those of the β-isomer (29%). Unfortunately, NMR experiments did not allow to differentiate between α- and β-3a derivatives. The reaction was carried out also with bis(fulleroid) derivative 2b, exhibiting the same behavior. Conclusion In this

Catalytic multi-step domino and one-pot reactions

• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

• in the Full Research Paper by Nath and co-workers. The newly synthesized porphyrin derivatives displayed significant red-shifted absorption and emission compared to simple meso-tetraarylporphyrins [14]. The Carlone group reports an Enders-type triple cascade reaction toward cyclohexenals, using

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

• to the presence of the electron-withdrawing ester groups. Importantly, only the Z-form of 18c was found to be stable enough with a half-life of 2.8 min at room temperature in acetonitrile (77% of Z-isomer in PSS) and 4.1 minutes in toluene (91% of Z-isomer in PSS) after irradiation with red light

• , recently attracted increased attention as red-light photoswitches. The investigation of the photophysical properties of these compounds began in 2017 with the work by Hecht, Jacquemin and co-workers [42]. In their study, a series of symmetrical as well as unsymmetrical N,N'-diaryl-substituted indigos 19a–h

• the existence of the isomeric mixtures in the dark state. Interestingly, the initial E/Z ratio was restored when the compounds were left in darkness after irradiation with red light (660 nm). The time required for the restoration of the initial state varied from 58 s (in the presence of electron

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

• in red and antimicrobial-binding motifs highlighted with blue arcs. R1 = H or Ac; R2 = H or Ac; R3 = OH, OMe or NH2; R4 = H or COOH; R5 = Gly5, Ala2, Ala-Ser/Ala or ᴅ-Asp; R6 = OH, OMe or NH2. These structural modifications are described in detail by Münch and co-workers [9]. For more details on

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• shoulder emission at 612 nm. When the solvent was changed from toluene to benzonitrile and the polarity of the solvent increased, the emission at 612 nm remained almost unchanged, while the emission at 675 nm significantly quenched with a red shift of 35 nm. In the transient absorption spectra of 60 in