New azodyrecins identified by a genome mining-directed reactivity-based screening

• Atina Rizkiya Choirunnisa,
• Kuga Arima,
• Yo Abe,
• Noritaka Kagaya,
• Kei Kudo,
• Hikaru Suenaga,
• Junko Hashimoto,
• Manabu Fujie,
• Noriyuki Satoh,
• Kazuo Shin-ya,
• Kenichi Matsuda and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

• N2H4-detecting reactivity-based screening led to the identification of four new analogs and two types of biosynthetic gene clusters of azodyrecins, demonstrating its utility in natural product discovery and deorphanization of biosynthetic gene clusters. Evaluation of cytotoxicities of azodyrecins A

• N2H4 as the indicator of an azoxy bond, we conducted a reactivity-based screening for aliphatic azoxy natural products. This led to the identification of two new producers of azodyrecins, as well as the new analogs 7–10, demonstrating the utility of this reactivity-based strategy for natural products

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

• Yin Chen,
• Jinqiu Ren,
• Ruimin Yang,
• Jie Li,
• Sheng-Xiong Huang and
• Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

• biochemical characterization indicated that the DatA is a polyporic acid synthetase, which helped to propose a possible biosynthetic pathway for daturamycins in S. sp. KIB-H1544 (Figure 3B). Finally, the discovery of daturamycins, identification, and characterization of dat biosynthetic gene cluster allowed

• , the extract was purified by silica gel chromatography and semipreparative HPLC to yield daturamycin A (1) (4.5 mg), daturamycin B (2) (1.8 mg), daturamycin C (3) (8.7 mg), terferol (4) (2.4 mg), BTH-II0204-207: D (5) (2.1 mg), betulinan A (6) (6.2 mg). Identification of new compounds Daturamycin A (1

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

• Shou-Mao Shen,
• Qing Yang,
• Yi Zang,
• Jia Li,
• Xueting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

• . Acknowledgements We thank Dr. Lin Gong from Institute of Oceanology, Chinese Academy of Sciences for the taxonomic identification of the sponge material. Funding This work was financially supported by the National Natural Science Foundation of China (No. 81991521) and the SKLDR/SIMM Project (No. SIMM2013ZZ-06).

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

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

•  3C). The experimental ECD spectrum of 2 showed a negative Cotton effect at 233 nm and positive Cotton effects at 217 and 257 nm, which showed a similarity with those of calculated ECD spectrum of 1R,4R,5S,6S,8S,10S-(ent-2a). Enzyme hydrolysis and following sugar identification were performed using

• identification were performed and monosaccharide of 3 was identified as ᴅ-glucopyranose (Supporting Information File 1, Figure S26). Thus, the structure of 3 was determined as (1R,4R,5S, 6S,10S)-1,10;4,5-diepoxy-6-O-β-ᴅ-glucopyranosyl-glechomafuran. Compound 4 was purified as a colorless gum. The HRESIMS

Chemistry of polyhalogenated nitrobutadienes, 17: Efficient synthesis of persubstituted chloroquinolinyl-1H-pyrazoles and evaluation of their antimalarial, anti-SARS-CoV-2, antibacterial, and cytotoxic activities

• Viktor A. Zapol’skii,
• Isabell Berneburg,
• Ursula Bilitewski,
• Melissa Dillenberger,
• Katja Becker,
• Stefan Jungwirth,
• Aditya Shekhar,
• Bastian Krueger and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2022, 18, 524–532, doi:10.3762/bjoc.18.54

• B3) within the Hessian Excellence Program (I.B., M.D.). Author Contributions Conceptualization, V.A.Z. and D.E.K.; Synthesis and spectroscopic identification of the synthesized compounds, V.A.Z. and B.K; Evaluation of the biological activity of the synthesized compounds, K.B., U.B., I.B., M.D., S.J

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• considerable attention due to their importance in microbial systems, once several studies have shown that structural variations in microbial quinones have chemotaxonomic significance and can be used in the classification and identification of various microbial species [8]. With their particular and quite

Four bioactive new steroids from the soft coral Lobophytum pauciflorum collected in South China Sea

• Di Zhang,
• Zhe Wang,
• Xiao Han,
• Xiao-Lei Li,
• Zhong-Yu Lu,
• Bei-Bei Dou,
• Wen-Ze Zhang,
• Xu-Li Tang,
• Ping-Lin Li and
• Guo-Qiang Li

Beilstein J. Org. Chem. 2022, 18, 374–380, doi:10.3762/bjoc.18.42

• metabolites with great variety and bioactivities. Previous chemical studies on soft corals Lobophytum, widely distributed in the world, resulted in the identification of lobane diterpene [1], cembranoids [2], and biscembranoids [3] with different bioactivities. Moreover, structurally specific steroids

• mg), 6 (15.5 mg) and 7 (10.2 mg). Fr.412 (210 mg) was chromatographed on semi-preparative HPLC (ODS, 5 µm, 250 × 10 mm; methanol/water, 85:15, v/v; 2.0 mL/min) to give compound 1 (2.5 mg), 2 (5.8 mg) and 3 (13.3 mg). Identification of new compounds Compound 1: colorless crystals; [α]D25 −19.28 (c

• species identification. Funding This work was supported by the National Natural Science Foundation of China (Nos. U2006204, 41776136, 2181101213, 81991522, and 41876161).

Borylated norbornadiene derivatives: Synthesis and application in Pd-catalyzed Suzuki–Miyaura coupling reactions

• Robin Schulte and
• Heiko Ihmels

Beilstein J. Org. Chem. 2022, 18, 368–373, doi:10.3762/bjoc.18.41

• identification of novel stable derivatives as well, such as 5b, 5c, and 5i. But unfortunately, there is no clear trend for a substituent effect on the reaction outcome, as both donor- and acceptor-substituted haloarenes resulted in essentially the same range of yields, i.e. from good yields (e.g., 4b, 4h, and 4j

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

• bacterium Nocardia altamirensis DSM 44997, which had originally been isolated from a microbial cave wall community and represents a non-pathogenic strain [5]. Our analysis led to the identification of six iron-chelating molecules belonging to the amamistatin family. Four of these compounds (1–4) have not

• was determined by HRESIMS with a molecular ion at m/z 716.3820 [M + H]+ (calcd for C36H54N5O10, 716.3820). A comparison with published data led to the identification of compound 5 as the known siderophore amamistatin B [7]. Compound 6 (2.4 mg) was isolated as a slight reddish oil. The molecular

Trichloroacetic acid fueled practical amine purifications

• Aleena Thomas,
• Baptiste Gasch,
• Enzo Olivieri and
• Adrien Quintard

Beilstein J. Org. Chem. 2022, 18, 225–231, doi:10.3762/bjoc.18.26

• dicyclohexylamine (Table 3, entry 1), a broad range of primary amines could also be separated from the aromatic impurities (Table 3, entries 2–10). As for other purification techniques, the challenge lies in the identification of the appropriate solvent to dissolve well the initial mixture and induce the amine–TCA

• importance, this technique is also efficient for the isolation of highly complex natural amines such as brucin, isolated in 57% yield using TCA (Table 3, entry 14). As mentioned, identification of a suitable solvent solubilizing the initial mixture and enabling precipitation/crystallization of the amine salt

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• neuroprotective effects [6]. As part of a continuing study of our group targeting at the identification of bioactive natural products from the medicinal plants and endophytes [7][8], the chemical constituents of the stems and roots of W. nutans were investigated. This work resulted into the isolation and

• identification of a new bis-coumarin glucoside 1, together with three known bis- and tricoumarin glucosides 2–4, two flavonoid glycosides 5 and 6, and eleven lignan glucosides 7–17 (Figure 1). Herein, we present the isolation and structural elucidation of these natural products and their in vitro biological

• chromatographed over a HW-40 CC eluting with MeOH to obtain six fractions (B5.4.1–5.4.6), further purified by semipreparative RP-HPLC using a mobile phase of MeCN/H2O (20: 80–50: 50 gradient system, v/v, 3 mL/min) to afford compounds 1 (7.0 mg), 2 (15.0 mg), 5 (20.0 mg), and 6 (10.0 mg). Identification of new

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• macrocycle and of the Lys–His bond, which is part of the cross-link, is prevented by the stapling (Figure 3 and Supporting Information File 1, Figures S8 to S10). Conformational analysis The identification of two isomers of P5 by LC–MS led us investigate the possibility of diastereomers and conformers in the

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

• , byproducts or transiently stable intermediates were sometimes indicated by HPLC and/or NMR of these photocleavage reactions [16][17]. These observations prompted a more detailed study of the components present during photocleavage reactions of small-molecule models, leading to the identification of the N

First total synthesis of hoshinoamide A

• Haipin Zhou,
• Zihan Rui,
• Yiming Yang,
• Shengtao Xu,
• Yutian Shao and
• Long Liu

Beilstein J. Org. Chem. 2021, 17, 2924–2931, doi:10.3762/bjoc.17.201

• Entrepreneurship Program (Grant No. 2019CXXL077); Hubei Province Key Laboratory of Occupational Hazard Identification and Control, Wuhan University of Science and Technology (Grant No. OHIC2020Y06).

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

• Ilya A. P. Jourjine,
• Lukas Zeisel,
• Jürgen Krauß and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

• identification of the first representatives, dengibsin (1a) and dengibsinin (1b) in 1985 from the orchid Dendrobium gibsonii [1], numerous further natural fluorenones, typically bearing hydroxy and methoxy substituents, but also aminoalkyl side chains, as in caulophine (1e) [2] and caulophylline A (1f) [3], were

AlBr₃-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles

• Yelizaveta Gorbunova,
• Dmitry S. Ryabukhin and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2021, 17, 2663–2667, doi:10.3762/bjoc.17.180

• 2m correspondingly were obtained; other regioisomers were not isolated in amounts that were high enough for their identification. This transformation was also tested with another strong Lewis acid, aluminum chloride (AlCl3), for the reaction of nitrile 1a with benzene. However, in this case, mainly

Ligand-dependent stereoselective Suzuki–Miyaura cross-coupling reactions of β-enamido triflates

• Tomáš Chvojka,
• Athanasios Markos,
• Svatava Voltrová,
• Radek Pohl and
• Petr Beier

Beilstein J. Org. Chem. 2021, 17, 2657–2662, doi:10.3762/bjoc.17.179

• base led to the identification of Pd(PPh3)4 (10 mol %), arylboronic acid (1 equiv), K3PO4 (2 equiv) in THF/H2O 1:1 as ideal conditions providing enamides 2aa and 3aa in a 93:7 ratio in 90% 19F NMR yield (Table S1 in Supporting Information File 1). The optimized conditions were applied to the scope

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• correlation with biological activity. This analysis attributed two detected [M − H]− signals to dihydrobrevipolides C and F. Nevertheless, further structural identification was not performed. Conclusion The characteristic structural features of 5,6-dihydro-α-pyrone derivatives isolated from Hyptis brevipes

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• × 250 mm) columns, and a mobile phase solvent gradient consisting of H2O (Milli-Q filter water 18 MΩ·cm, Millipore, Germany), 100% MeOH (Sigma-Aldrich, UK), and TFA (Sigma-Aldrich, UK). Bacterial isolation and identification The bacterial strain was isolated from soil sediments collected from the Oyun

Phenolic constituents from twigs of Aleurites fordii and their biological activities

• Kyoung Jin Park,
• Won Se Suh,
• Da Hye Yoon,
• Chung Sub Kim,
• Sun Yeou Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2021, 17, 2329–2339, doi:10.3762/bjoc.17.151

•  2). Alkaline hydrolysis of 16 yielded codiacyanoglucoside (16a) and gallic acid (16b). The identification of 16a and 16b was conducted by comparison of their 1H NMR and MS data [24][25]. Consequently, the structure of 16 was determined to be codiacyano glucosyl-2′,6′-O-digallate, named

• analyzed by GC–MS. The identification of ᴅ-glucose and ʟ-rhamnose was carried out by coinjection of the hydrolysate with standard silylated samples, giving a single peak at 9.730 and 9.712 min, respectively. Authentic samples (Sigma-Aldrich, St. Louis, MO, USA) that were treated in the same way showed a

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

• Luiz Claudio Ferreira Pimentel,
• Lucas Villas Boas Hoelz,
• Henayle Fernandes Canzian,
• Frederico Silva Castelo Branco,
• Andressa Paula de Oliveira,
• Vinicius Rangel Campos,
• Floriano Paes Silva Júnior,
• Rafael Ferreira Dantas,
• Jackson Antônio Lamounier Camargos Resende,
• Anna Claudia Cunha,
• Nubia Boechat and
• Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

• 1980s, has led to the identification of the (phenylamino)pyrimidine (PAP) structure [5][6]. The addition of an additional pyridine ring to PAP raised its cellular activity, producing PAPP, which, after some more chemical modifications, culminated in imatinib (IMT) [7]. PAPP has been used to develop new

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

An initiator- and catalyst-free hydrogel coating process for 3D printed medical-grade poly(ε-caprolactone)

• Jochen Löblein,
• Thomas Lorson,
• Miriam Komma,
• Tobias Kielholz,
• Maike Windbergs,
• Paul D. Dalton and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2021, 17, 2095–2101, doi:10.3762/bjoc.17.136

• spatially resolved polymer identification based on chemical functionalities. A unique peak at 1111 cm−1 was identified and is attributed to backbone stretching of aliphatic chains [ν(C–C)] in PCL. Also, a characteristic band at 829 cm−1 was detected which can be assigned to PHEMA and refers to the

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

• active (Table 1, entry 6). With the identification of cyclopropenimine 5 as our optimal catalyst [44], we examined the effect of the reaction medium. Solvents such as benzene (Table 1, entry 7), TBME (Table 1, entry 8), and toluene (Table 1, entry 10) produced reactivities on par with ethyl acetate and