Synthesis of 1,4-azaphosphinine nucleosides and evaluation as inhibitors of human cytidine deaminase and APOBEC3A

• Maksim V. Kvach,
• Stefan Harjes,
• Harikrishnan M. Kurup,
• Geoffrey B. Jameson,
• Elena Harjes and
• Vyacheslav V. Filichev

Beilstein J. Org. Chem. 2024, 20, 1088–1098, doi:10.3762/bjoc.20.96

• Maksim V. Kvach Stefan Harjes Harikrishnan M. Kurup Geoffrey B. Jameson Elena Harjes Vyacheslav V. Filichev School of Food Technology and Natural Sciences, Massey University, Private Bag 11 222, Palmerston North 4442, New Zealand Maurice Wilkins Centre for Molecular Biodiscovery, Thomas Building

• bacteria and fungi but not in mammalian cells, acts only on cytosine. Cytidine deaminase (CDA) as a key enzyme in the pyrimidine salvage pathway in mammals deaminates both cytidine and 2'-deoxycytidine. Members of the apolipoprotein B mRNA editing enzyme, catalytic polypeptide-like (APOBEC) family, such as

• considered for the development of new nucleobases mimicking transitions states and an intermediate of cytosine deamination to improve potency of DNA-based A3 inhibitors. A) Deamination of cytosine, dC and C as individual nucleosides or as part of a polynucleotide chain. B) Previously described CDA inhibitors

Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

• Vladislav V. Nikol’skiy,
• Mikhail E. Minyaev,
• Maxim A. Bastrakov and
• Alexey M. Starosotnikov

Beilstein J. Org. Chem. 2024, 20, 1069–1075, doi:10.3762/bjoc.20.94

• Vladislav V. Nikol'skiy Mikhail E. Minyaev Maxim A. Bastrakov Alexey M. Starosotnikov N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, 119991 Moscow, Russia 10.3762/bjoc.20.94 Abstract An efficient method for the synthesis of isoxazolo[4,5-b]pyridines has been developed on

• the basis of readily available 2-chloro-3-nitropyridines via the intramolecular nucleophilic substitution of the nitro group as a key step. The previously unknown base-promoted Boulton–Katritzky rearrangement of isoxazolo[4,5-b]pyridine-3-carbaldehyde arylhydrazones into 3-hydroxy-2-(2-aryl[1,2,3

• ]triazol-4-yl)pyridines was observed. Keywords: aromatic nitro compounds; Boulton–Katritzky rearrangement; isoxazolo[4,5-b]pyridines; nucleophilic substitution; 1,2,3-triazoles; Introduction Nitrogen heterocycles represent a very important class of organic compounds that has found application in various

Novel route to enhance the thermo-optical performance of bicyclic diene photoswitches for solar thermal batteries

• Akanksha Ashok Sangolkar,
• Rama Krishna Kadiyam and
• Ravinder Pawar

Beilstein J. Org. Chem. 2024, 20, 1053–1068, doi:10.3762/bjoc.20.93

• ) type-I is generated by increasing the unsaturated bridge length of the NBD/QC pair thus having a short saturated bridge, and (b) type-II designed by elongating the unsaturated bridge of the BOD/TCO pair thus have elongated saturated bridge, too. Further, the effect of the presence of different polarity

• , there exists a competition for the dissociation of the β or γ-bond that yields undesired thermal degradation products through pathway A or the parent diene via pathway B, respectively. This dissociation follows a highly asynchronous but concerted reaction mechanism and may involve bispericyclic post

• Perdew–Burke–Ernzerhof (PBE) functional along with the inclusion of the Grimme’s D3 dispersion correction. (a) Previously studied BBD-based photoswitches, (b) recently reported protocol to synthesize a BBD structure with elongated unsaturated bridge [37], (c) BBD-based photoswitches studied in the

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• 73019, United States 10.3762/bjoc.20.92 Abstract Presented here is the design, synthesis, and study of a variety of novel hydrogen-bonding-capable π-conjugated N-heteroacenes, 1,4-dihydropyrazino[2,3-b]quinoxaline-2,3-diones (DPQDs). The DPQDs were accessed from the corresponding weakly hydrogen

• device fabrication with the electron acceptor C60. Subsequently, the design was extended to “ditopic” systems with diverse HB-capable units such as PH, 2,4-diamino-1,3,5-triazine (DAT), and barbiturate (B) that can form trimeric and hexameric “rosettes”, respectively [16]. The Sokolowski and Głowacki

• constructed via intermolecular N–H∙∙∙N interactions. However, vacuum-deposited films afforded poor hole transport. In separate work, Bunz et al. reported the serendipitous and understated synthesis of an H-bonding capable 1,4-dihydropyrazino[2,3-b]quinoxaline-2,3-dione (Figure 1a) [23]. In 2018, Takeda et al

Novel analogues of a nonnucleoside SARS-CoV-2 RdRp inhibitor as potential antivirotics

• Luca Julianna Tóth,
• Kateřina Krejčová,
• Milan Dejmek,
• Eva Žilecká,
• Blanka Klepetářová,
• Lenka Poštová Slavětínská,
• Evžen Bouřa and
• Radim Nencka

Beilstein J. Org. Chem. 2024, 20, 1029–1036, doi:10.3762/bjoc.20.91

• compounds 3a (first reported by Cannalire et al. [22]) and 3b,c. Simplification of the hit molecule: synthesis of thiazolopyridone derivatives Further, a novel type of inhibitor containing a thiazolopyridone core and the corresponding azo derivative, namely 4a,b, were synthesized. The synthetic route was

• led to the corresponding carboxylic acids 24 and 29, and from there, the desired final compounds 4a,b were obtained in a straightforward two-step synthesis. Biochemical study: inhibition of SARS-CoV-2 RdRp We aimed to determine the inhibitory activity of the final compounds 2, 16, 3a–c and 4a,b

• most successful modification. The potential of the truncated derivatives was further illustrated by the thiazolopyridone and thiadiazolopyridone compounds 4a,b, which showed inhibition with IC50 = 88.1 μM and 128.7 μM, respectively. Even though the measured inhibitory concentration was higher than that

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

• Naoki Miyamoto,
• Daichi Koseki,
• Kohei Sumida,
• Elghareeb E. Elboray,
• Naoko Takenaga,
• Ravi Kumar and
• Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

• various new applications. Synthetic approaches of diaryliodonium(III) trifluoroacetates. Synthesis of diaryliodonium(III) carboxylates. Scope of dummy ligands. Substrate scope of aryl(TMP)iodonium(III) acetates. a) 0.50 mmol scale of 1i. b) 1,3,5-Trimethoxybenzene (2.1 equiv) was used. c) Bis

• (trifluoroacetoxyiodo)benzene was used instead of 1a. Substrate scope of the carboxylic acids and iodosylarenes. a) The reaction was conducted for 4 h. b) 2.0 mL TFE was used. Representative applications of aryl(TMP)iodonium(III) carboxylates. Supporting Information Supporting Information File 2: Further experimental

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

• nanographene host. In addition to the main peaks, satellite peaks clearly appear at the higher energy side (ca. +3 eV), which indicates that the FeCp2 molecules partially become cationized (positively charged) in FeCp2-ACFs-150. Figure 3a and b show the C1s spectra for FeCp2-ACFs-150 and ACFs in a narrow

• magnified for clarity, where the base lines are shifted vertically from each other for clarity. b) The excitation microwave power dependence of ESR linewidth (ΔHpp) for ACFs and FeCp2-ACFs-55. The square root of the excitation microwave power dependence of the relative ESR intensities for ACFs and FeCp2

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

• Alyssa S. Eggly Namuunzul Otgontseren Carson B. Roberts Amir Y. Alwali Haylie E. Hennigan Elizabeth I. Parkinson Department of Chemistry, Purdue University, West Lafayette, Indiana 47906, United States Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette

• 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

• hormones isolated to date. A) A diagram of an example of a molecular probe. B) The maleimide-based probe (6) for furans. A) General Diels–Alder reaction scheme. B) MMF derivatives explored in this reaction. A. Reaction scheme. B. Representative mass spectra of MMF5 cycloadduct 24 with 3:1 isotopic ratio

Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• carbonylative double cyclization process was developed obtaining 3,4-dihydro-1H-furo[3,4-b]indol-1-ones from suitably functionalized 2-alkynylanilines [20]. The reaction occurs in the presence of PdI2 (1 mol %) as catalyst and KI (10 mol %) as co-catalyst in MeCN at 120 °C for 24 h. At the end of the process

• determined by 1H NMR spectroscopy (Scheme 15). More recently, in 2016, still in Söderberg’s group, the synthesis of 2,2′-bi-1H-indoles, 2,3′-bi-1H-indoles, 3,3′-bi-1H-indoles, indolo[3,2-b]indoles, and indolo[2,3-b]indoles via reductive cyclization Pd-catalyzed was developed [36]. The reaction was possible

• leading to product formation with good to excellent isolated yields (Scheme 16). On the other hand, the synthesis of indolo[3,2-b]indoles and indolo[2,3-b]indoles were not selective leading to byproducts such as 5,7-dihydro-6H-indolo[2,3-c]quinolin-6-one, 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-one, and

Enhancing structural diversity of terpenoids by multisubstrate terpene synthases

• Min Li and
• Hui Tao

Beilstein J. Org. Chem. 2024, 20, 959–972, doi:10.3762/bjoc.20.86

• terpenes are shown. MEP: methylerythritol 4-phosphate; MVA: mevalonate; PT: prenyltransferase; TS: terpene synthase; MT: methyltransferase. Representative terpenoids produced by plant MSTSs. a) 6 and 7 are products of PamTps1 from Plectranthus amboinicus, 8–10 are products of CoTPS5 from Cananga odorata; b

• a new product of an EvVS variant with a swapped PT domain. b) From bacteria: compound 35 is a representative product of bacteria MSTSs VenA; compouns 36, 37, and 40 are products of two long β-prene TSs BclTS and BalTS. Terpenoid products of TSs using chemically synthesized noncanonical prenyl

• substrates. a) Products of BcBOT2 using iso-FPPs 45–47. b) Biotransformation of 51 by BcBOT2. c) Products of two TSs PenA and Omp6/7 using FPP ether derivative 52. PenA generated compounds 53–57 and 59, whereas Omp6/7 produced 54–59. Biotransformation of noncanonical prenyl analogs 60–65 using two terpene

Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck–Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles

• Arnaldo G. de Oliveira Jr.,
• Martí F. Wang,
• Rafaela C. Carmona,
• Danilo M. Lustosa,
• Sergei A. Gorbatov and
• Carlos R. D. Correia

Beilstein J. Org. Chem. 2024, 20, 940–949, doi:10.3762/bjoc.20.84

• conditions: b) 4de (0.105 mmol, 1.0 equiv), PhSH (0.16 mmol, 1.5 equiv), K2CO3 (0.21 mmol, 2 equiv), MeCN (1 mL), DMSO (0.4 mL), 25 °C, 2 h. Enantiomeric ratio (er) determined by high-performance liquid chromatography (HPLC) analysis of the purified compounds. A rationale for the catalytic cycle for the Heck

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

• model of the sugar. Also in the first section of the visual validation report is a plot of the B-factor (temperature factor) versus the real space correlation coefficient (RSCC) (Figure 2). A well-refined, well-built model would be expected to have a B-factor that increases somewhat linearly as the RSCC

• coefficient plotted against the B-factor, which enables the refinement of the sugars to be assessed. A slight negative correlation would be expected for a well-refined model. Results taken from the Privateer database report for 3QVP [28]. Table of two-dimensional Symbol Nomenclature for Glycan (SNFG

Direct synthesis of acyl fluorides from carboxylic acids using benzothiazolium reagents

• Lilian M. Maas,
• Alex Haswell,
• Rory Hughes and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2024, 20, 921–930, doi:10.3762/bjoc.20.82

• , reacting BT-SCF3 with carboxylic acids 1 under similar conditions provides (trifluoromethyl)thioesters 3 via a concerted deoxytrifluoromethylthiolation process from tetrahedral intermediate A affording thiocarbamate by-product B [31]. To test whether thioester species could act as intermediates in the

• . Mechanistic experiments. (a) Conversion of thioester 3a into acyl fluoride 2a in the presence of DIPEA. (b) Conversion of thioester 3a into acyl fluoride 2a in the presence of carboxylate and fluoride nucleophiles. (c) Two-stage deoxyfluorination reaction using 0.5 equiv of BT-SCF3. 19F NMR yields using α,α,α

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

• -tetrazoles (1,5-DS-1H-Ts) B. The performance of post-condensation reactions of UA-4CR adducts has resulted in various 1,5-DS-1H-Ts containing heterocyclic compounds [28][29][30][31][32], such as bis-heterocyclic lactam-tetrazoles [33][34], 2-tetrazolylmethyl-2,3,4,9-tetrahydro-1H-β-carbolines [35

• -pyrazino[2,1-a]isoquinolin-6(5H)-ones 6c–k in 73–79% yields. The presence of electron-donating or electron-withdrawing groups on the aromatic ring did not show significant effects on the Heck reaction. Products 6c–k were obtained in higher yields than products 6a,b. We believe that the secondary amine in

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

• by column chromatography (heptane/ethyl acetate). Representative procedure B for the synthesis of 4a–j. A mixture of 2 (402 µmol; 102 mg), Pd(CH3CN)2Cl2 (5 mol %; 23 µmol; 6 mg), CuI (5 mol %; 21 µmol; 4 mg) was dissolved in 1,4-dioxane (5 mL) and stirred for 5 min under an argon atmosphere. NEt3 (11

• layers were dried over Na2SO4, concentrated under reduced pressure, and purified by column chromatography (heptane/ethyl acetate). Uracil derivatives in drugs. Present work as compared to previous studies [25][57][58][59]. ORTEP diagram of 5a front view (a) and side view (b). a) Interactions of the

• 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

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

• , DMF/H2O, 60 °C, 18 h. (b) Pd(OAc)2, PPh3, CuI, phenylacetylene, Et3N, 50 °C, 5 h. (c) CuI, neocuproine, 4-MeOC6H4SH, NaOt-Bu, toluene, 110 °C, 13 h. (d) CuI, ʟ-proline, DMF, 80 °C, 14 h. (e) CuI, imidazole, Cs2CO3, DMF, 120 °C, 15 h. (f) 3-Methoxy-2-(trimethylsilyl)phenyl triflate, CsF, MeCN, rt, 18 h

(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

Confirmation of the stereochemistry of spiroviolene

• Yao Kong,
• Yuanning Liu,
• Kaibiao Wang,
• Tao Wang,
• Chen Wang,
• Ben Ai,
• Hongli Jia,
• Guohui Pan,
• Min Yin and
• Zhengren Xu

Beilstein J. Org. Chem. 2024, 20, 852–858, doi:10.3762/bjoc.20.77

• , respectively. The formation of all three products 9–11 can be explained as follows (Scheme 2A) [28][29][30][31]: Due to the favorable formation of cis-5,5-fused B/C ring system, the borane reagent is preferred to approach the double bond of 1 from the α-face, to give either a secondary 1-organoborane

• spiroviolene and related natural products. Heterologous production of spiroviolene using the isopentenol utilization pathway. A) Gas chromatogram of the EtOAc extract of the fermentation broth. B) EI mass spectrum of spiroviolene. Possible cyclization mechanisms for spiroviolene (1) and related natural

• products. A) Revised cyclization mechanism for 1 that is related to deoxycondiogenol (4). B) Originally proposed cyclization mechanism for the misassigned structure 1'. C) Possible cyclization mechanism for GJ1012A (3). D) Structures of biogenetically related diterpenes during the proposed cyclization

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

• diaryliodonium salt 2a. Naphthol 1a forms intermediate B with A after participation with the Cu(II) catalyst. Intermediate B generates C by radical substitution. A final intramolecular transesterification yields the benzocoumarin product 3aa. Conclusion In summary, we have employed ortho-ester-substituted

• -oxyl; BHT = butylated hydroxytoluene. Optimization of reaction conditions.a Scope of naphthols and phenols for the synthesis of 3,4-benzocoumarins.a,b. Scope of ortho-ester-substituted diaryliodonium salts.a Supporting Information Supporting Information File 16: Experimental procedures, LC–MS spectra

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

• (Pj), Pseudonocardia spinosispora DSM 44797 (Ps), Mycobacterium sp. 1465703.0 (Ms), Microbispora rosea subsp. nonnitritogenes strain NRRL B-2631 (Mr)], which were synthesized and cloned into E. coli recombinant expression vectors. These homologs ranged in amino acid sequence identity from 46 to 76

• of NNG. Cells were incubated overnight in 1/5 LB, 20 µM IPTG, 3 mM NNG with appropriate antibiotics, incubated overnight at 37 °C. Molecular mass determination of purified NnlA homologs by A) SDS-PAGE or B) analytical size exclusion chromatography. Homolog labeled in figure. Mobile phase and sample

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• endocyclic olefin led to a series of separable allylic chlorides 16 and 17a,b, from direct displacement or transposition of the allylic system (Scheme 3). This substrate has previously been examined in the reaction with SOCl2 by Matsumoto et al. in THF and CH2Cl2 and similar results were obtained [28]. When

Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids from Streptomyces clavuligerus

• Dongxu Zhang,
• Wenyu Du,
• Xingming Pan,
• Xiaoxu Lin,
• Fang-Ru Li,
• Qingling Wang,
• Qian Yang,
• Hui-Min Xu and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2024, 20, 815–822, doi:10.3762/bjoc.20.73

• University, Nanjing 211198, China 10.3762/bjoc.20.73 Abstract Drimane-type sesquiterpenoids (DMTs) are characterized by a distinctive 6/6 bicyclic skeleton comprising the A and B rings. While DMTs are commonly found in fungi and plants, their presence in bacteria has not been reported. Moreover, the

• biosynthetic pathways for DMTs have been primarily elucidated in fungi, with identified P450s only acting on the B ring. In this study, we isolated and characterized three bacterial DMTs, namely 3β-hydroxydrimenol (2), 2α-hydroxydrimenol (3), and 3-ketodrimenol (4), from Streptomyces clavuligerus. Through

• these, drimane-type sesquiterpenoids (DMTs) are distinct due to their chemical structures, which feature a decahydronaphthalene core adorned with methyl groups, mirroring the A/B rings found in labdane-derived diterpenoids [5][6] (Figure 1a). DMTs exhibit significant biological activities, such as those

Advancements in hydrochlorination of alkenes

• Daniel S. Müller

Beilstein J. Org. Chem. 2024, 20, 787–814, doi:10.3762/bjoc.20.72

• addition. Therefore, anti-Markovnikov products are generally not observed. b) In contrast to the reactions with HBr (peroxide effect) [31][32], the formation of anti-Markovnikov products is low even in the presence of peroxides or photochemical activation. For instance, Whitmore and co-workers observed

• ex-situ as demonstrated very recently by De Borggraeve and co-workers (Figure 5A) [67]. In a first chamber (A) HCl (gas) was prepared from NaCl and H2SO4 which then was directed towards a second chamber (B) which contains the alkene under solvent-free conditions. The scope of this reaction (Figure 5B

•  15A). Activated and non-activated alkenes readily undergo hydrochlorination to form the corresponding tertiary and secondary chlorides (Scheme 15C). However, terminal alkenes required more forcing conditions (3 equiv of 92 and 20% of B(C6F5)3). The oligomerization of 3-chlorostyrene (product 102

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

• part (α, β, γ, δ, and ε). The observed splitting of the protons a and b was presumably due to a diastereotopic effect of the methine proton c, similar to the spectrum of the monoadduct. Figure 6a shows the 13C NMR spectra of 5a in D2O and of the monoadduct in CDCl3. Together with the 1H NMR, COSY, HSQC

• by HRESIMS. HRESIMS (m/z): [M + 4H]4+ calcd for C135H149N43O16, 657.0536; found, 657.0540. a) Synthesis of C60–oligopeptide conjugates 5a–c and b) synthesis of compound 3. Fulleropyrrolidine-based biscarboxylic acid derivative 3 was prepared by Prato reaction and subsequent deprotection. Compound 3

• –peptide conjugate 5a in D2O (above) and of the precursor monoadduct in CDCl3 (bottom) at 600 MHz. 13C NMR spectrum of C60–peptide conjugate 5a in D2O and of the precursor monoadduct in CDCl3 at 150 MHz (a) and expansion of the sp2 carbon region (b). The asterisks in (a) correspond to a TFA impurity

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