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

• , antifungal, nematicidal, and cytotoxic activities (Figure 1) [1][2][3]. Since the discovery of the natural azoxy compound macrozamin in 1951 as the first example of a nitrogen–nitrogen bond-containing natural product [4], azoxy compounds have been isolated from various natural sources including bacteria

Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

• Fang-Ru Li,
• Xiaoxu Lin,
• Qian Yang,
• Ning-Hua Tan and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

• diterpenoids are two categories of diterpenoids that are widely distributed in terrestrial plants, fungi, and a few bacteria and possess broad pharmacological bioactivities [1][2][3]. Representative natural products containing these skeletons are terpentecin (cytotoxic and antibiotic), salvinorin A (kappa

The stereochemical course of 2-methylisoborneol biosynthesis

• Binbin Gu,
• Anwei Hou and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 818–824, doi:10.3762/bjoc.18.82

• recognized that many soil bacteria including various genera from the actinobacteria [3][4][5][6][7] and myxobacteria [8] produce the volatile musty odour compound 2-methylisoborneol (1). The compound is also found in marine Streptomyces strains [9] and aquatic cyanobacteria that can cause drinking water

• from Micromonospora humi can convert DMAPP into (R)-2-Me-IPP with a methyltransferase [27], naturally providing the C6 building block for this hypothetical alternative pathway towards 1 (Scheme 1B). Today the genomes of many bacteria from the genus Streptomyces have been made available, showing that

• the genes for the biosynthesis of 1 are present in about half of the species [28], which is reflected by the frequent detection of 1 among the volatiles emitted by a large number of streptomycetes and closely related bacteria [3][4][5][6][7]. A series of side products of the 2MIBS has been identified

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

• prenyltransferase; Introduction Marine bacteria harbor an enormous potential to produce structurally diverse natural products, including prenylated aromatic metabolites [1][2]. Prenylation of metabolites most often confers increased biological activities due to enhanced lipophilicity, solubility, and improved

• biosynthetic repertoire of marine bacteria [14][15], the diversity of the encoded and yet often unexplored bacterial Ptases of Flavobacteria and Saccharomonospora strains sparked our interest. In this study we investigated three yet poorly described homologous Ptases within the UbiA superfamily and evaluated

• their substrate scope by heterologous production and enzymatic bioassays. Results of our study showcase that marine bacteria harbor still a broad unexplored enzymatic repertoire. Results and Discussion In silico analysis of Ptases in marine Flavobacteria and the genus Saccharomonospora In a first step

Structural basis for endoperoxide-forming oxygenases

• Takahiro Mori and
• Ikuro Abe

Beilstein J. Org. Chem. 2022, 18, 707–721, doi:10.3762/bjoc.18.71

• endoperoxide containing alkaloids, terpenoids, and polyketides have been isolated from plants, animals, bacteria, fungi, and other organisms (Figure 1) [6][7]. Because of the high reactivity of the cyclic peroxide O–O bond, these compounds exhibit various biological activities [1][2][3][4][5]. For example

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

• Anas J. Rasras,
• Mohamed El-Naggar,
• Nesreen A. Safwat and
• Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

• acid with the heterocyclic moiety 1,3,4-oxadizole was synthesized, and tested for antimicrobial activity against Gram-positive, Gram-negative bacteria, and fungi. Among the synthesized compounds, the most potent derivatives against S. aureus were 4t, 4i, 4p, and 4c with MIC values between 31 and 70 µg

• /mL, while compound 4p was the most active one against Bacillus subtilis with a MIC value of 70 µg/mL. Interestingly, compounds 4a and 4u exerted selective activity against Gram-positive bacteria. The synthesized compounds showed good activity against A. fumigatus and C. albicans and compound 4v

• exhibited selective activity against fungi only. Keywords: antibacterial; cholic acid; heterocyclic; Mannich reaction; oxadiazole; Introduction Microbial infections caused by Gram-negative and Gram-positive bacteria embarrass the health care system worldwide [1]. Pathogens such as Escherichia coli

The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

• Martin Vrbický,
• Karel Macek,
• Jaroslav Pochobradský,
• Jan Svoboda,
• Miloš Sedlák and
• Pavel Drabina

Beilstein J. Org. Chem. 2022, 18, 438–445, doi:10.3762/bjoc.18.46

• -2-one antibiotics only the S-enantiomers are able to block bacterial ribosomes, which leads to the prevention of translation processes in bacteria [9][10]. With regards to these facts, a high enantiomeric purity is one of the fundamental requirements in the production of such pharmaceutical

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

• must be able to control the uptake of this important nutrient from the environment. In bacteria and fungi this is usually accomplished with the help of siderophores [2]. Siderophores are small molecules which, upon secretion, solubilize and coordinate ferric iron with high affinity. The ability to bind

• filamentous Actinobacteria, which live as saprophytes and were reported from a variety of environments. Although the soil is likely the primary reservoir of these bacteria, a considerable number of Nocardia strains was isolated from human tissue and can be associated with infectious diseases [5]. The genus

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• (GH) families and play fundamental roles in the biology of humans, viruses, bacteria and parasitic protozoa by cleaving glycosidic linkages and releasing (or transferring) sialic acid from sialylated substrates [2]. In fact, sialidases have been associated with the pathogenesis of various diseases and

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

• antimicrobial activities [27], the antimicrobial activity of compounds 1–4 was also evaluated against the bacteria Escherichia coli, Staphylococcus aureus subsp. aureus, Salmonella enterica subsp. enterica, and Pseudomonas aeruginosa. However, all of them were found to be devoid of inhibitory activity (MIC >250

• assay was conducted by the previously described method [29]. Add the sample to be tested into the 96-well culture plate, the maximum concentration of the used compounds was 100 μM. Add bacteria liquid to each well, the final concentration is 5 × 105 CFU/mL. Incubate at 37 °C for 24 h, the OD value at

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

• Yasuhiro Igarashi,
• Yiwei Ge,
• Tao Zhou,
• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku and
• Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

• repeated cadaverine–succinic acid motifs terminated by a hydroxamic acid functionality, were elucidated by NMR and negative MS/MS experiments. Compounds 1–3 were inactive against bacteria and a yeast but displayed cytotoxicity against 3Y1 rat embryonic fibroblasts and P388 murine leukemia cells at GI50 in

• attractive resource of new therapeutics, which are not found from terrestrial bioresources [4][5][6]. While a large majority of marine microbe-derived natural products are from fungi and actinomycetes, less attention has been paid to non-actinomycetal bacteria [6][7][8][9]. Particularly, secondary

• metabolites from Gram-negative bacteria are still quite limited, despite the predominance of this group in the marine environment [10][11]. The genus Tenacibaculum belongs to the family Flavobacteriaceae within the phylum Bacteroidetes. Members of this genus are Gram-negative, aerobic, motile by gliding, and

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• hydrocarbons (PAHs) [5][6]. Among all of the compounds in this class, 1,2- and 1,4-naphthoquinones stand out, as they are present in plants, fungi, lichens, bacteria, algae, viruses, insects, and higher organisms and perform several biochemical functions, such as defense, transference of electrons in various

• the synthesis of dyes. Then, he prepared several naphthalene sulfonic derivatives and tested them for their effects on bacteria and viruses, but none of the compounds presented important activity. Hashimoto and co-workers [54] were the first to apply β-NQSNa for the qualitative analysis of

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

• Shun Saito,
• Kanji Indo,
• Naoya Oku,
• Hisayuki Komaki,
• Masashi Kawasaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

• were weakly inhibitory against Kocuria rhizophila at MIC 100 μg/mL and none were cytotoxic against P388 at the same concentration. Keywords: Couchioplanes; prenylated tryptophan; rare actinomycete; unsaturated fatty acid; Introduction Actinomycetes, a subgroup of filamentous Gram-positive bacteria

• H-13 (Figure 6). Thus, an S-configuration, corresponding to an ʟ-chirality for tryptophan, was assigned. Compounds 1–6 were not cytotoxic against P388 murine leukemia cells (IC50 > 100 μM), nor antimicrobial against five bacteria, Bacillus subtilis, Staphylococcus aureus, Ralstonia solanacearum

• necessary for their biosynthesis. Prenylated indoles are widely distributed among bacteria, fungi and plants, and all seven positions are subject of prenylation except for the bridgehead carbons [34]. Compound 6 is the acetylated derivative of 6-(3,3-dimethylallyl)-ʟ-tryptophan from Streptomyces sp. SN-593

Total synthesis of the O-antigen repeating unit of Providencia stuartii O49 serotype through linear and one-pot assemblies

• Tanmoy Halder and
• Somnath Yadav

Beilstein J. Org. Chem. 2021, 17, 2915–2921, doi:10.3762/bjoc.17.199

• Tanmoy Halder Somnath Yadav Department of Chemistry, Indian Institute of Technology (ISM), Dhanbad, 826004, Jharkhand, India 10.3762/bjoc.17.199 Abstract Capsular polysaccharides of pathogenic bacteria have been reported to be effective vaccines against diseases caused by them. Providencia

• polysaccharides are one of the important constituents of the surface lipopolysaccharides (LPS) of the cell wall of Gram-negative bacteria. These antigens are responsible for several functions that include adhesion to the host cells and are also found to contribute to the evasion of the host immune responses

• ]. Providencia is a genus of Gram-negative bacteria that belongs to the enterobacteria family and is responsible for causing several enteric infections including urinary tract infections. Providencia includes mainly five virulent species – P. alcalifaciens, P. rettgeri, P. rustigianii, P. stuartii, and P

Host–guest interaction and properties of cucurbit[8]uril with chloramphenicol

• Lin Zhang,
• Jun Zheng,
• Guangyan Luo,
• Xiaoyue Li,
• Yunqian Zhang,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2021, 17, 2832–2839, doi:10.3762/bjoc.17.194

• Streptomyces venezuelae [1], which has a certain inhibitory effect on many Gram-positive and -negative cocci bacteria, as well as anaerobic bacteria [2], and is used for the treatment of typhoid, meningitis, chlamydia, eye infections, purulent wounds and other diseases [3]. Chloramphenicol is slightly soluble

• properties than CPE alone. Ana I. Ramos et al. [7] studied the inclusion compound of CPE and cyclodextrin and reported its effect on Enterococcus, Bacillus, Staphylococcus and other bacteria. As a new type of supramolecular host compound, cucurbit[n]urils [8][9][10][11][12][13][14][15][16][17][18][19] (Q[n]s

Biological properties and conformational studies of amphiphilic Pd(II) and Ni(II) complexes bearing functionalized aroylaminocarbo-N-thioylpyrrolinate units

• Samet Poyraz,
• Samet Belveren,
• Sabriye Aydınoğlu,
• Mahmut Ulger,
• Abel de Cózar,
• Maria de Gracia Retamosa,
• Jose M. Sansano and
• H. Ali Döndaş

Beilstein J. Org. Chem. 2021, 17, 2812–2821, doi:10.3762/bjoc.17.192

• spectroscopic techniques. The biological properties of the freshly prepared compounds were screened against S. aureus, B. subtilis, A. hydrophila, E. coli, and A. baumannii bacteria and antituberculosis activity against M. tuberculosis H37Rv strains. Also, the antifungal activity was studied against C. albicans

• organometallic compounds were screened for their antibacterial activity against a range of Gram-positive (Staphylococcus aureus, Bacillus subtilis) and Gram-negative (Aeromonas hydrophila, Escherichia coli, Acinetobacter baumannii) bacteria and antimycobacterial activity against M. tuberculosis H37Rv strains

• anti(myco)bacterial and antifungal activity of newly prepared organometallic compounds were investigated against some Gram-positive, Gram-negative bacteria, M. tuberculosis H37Rv strains and C. albicans, C. tropicalis, C. glabrata fungi. The screened novel complexes showed different degrees of

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• explored [43], as within the colon are many polysaccharides and a large number of bacteria which secrete enzymes [41]. Within this work, varying the concentration of various pH-sensitive polymers was considered in terms of swelling, and it was shown that abrupt changes in swelling could be obtained at a

Visible-light-mediated copper photocatalysis for organic syntheses

• Yajing Zhang,
• Qian Wang,
• Zongsheng Yan,
• Donglai Ma and
• Yuguang Zheng

Beilstein J. Org. Chem. 2021, 17, 2520–2542, doi:10.3762/bjoc.17.169

• ; mechanisms of copper photocatalysis; photoinduced copper-based catalysis; photoredox catalysis; special features of copper photocatalysis; Introduction Solar light is an inexhaustible and free energy source for green plants and bacteria. Photosynthetic organisms absorb solar energy and convert it into

Targeting active site residues and structural anchoring positions in terpene synthases

• Anwei Hou and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 2441–2449, doi:10.3762/bjoc.17.161

• from Streptomyces mobaraensis (SmTS1) represents the first identified type I sesterterpene synthase (StTPS) from bacteria [16]. This enzyme converts GFPP into multiple products seven of which could be isolated and structurally characterised as sestermobaraenes A–F (1–6) and sestermobaraol (7) (Figure 2

Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions

• Andrey I. Puzanov,
• Dmitry S. Ryabukhin,
• Anna S. Zalivatskaya,
• Dmitriy N. Zakusilo,
• Darya S. Mikson,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2021, 17, 2417–2424, doi:10.3762/bjoc.17.158

• against cancer [6][7], tuberculosis [8], Gram-positive bacteria [9], and they are used in treatment of epilepsy [10] and Alzheimer disease [11][12][13]. The synthesis of compounds of the 1,2,4-oxadiazole series is an actual task in organic and medicinal chemistry (see selected reviews on this topic [14

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

• Satya Kumar Avula,
• Syed Raza Shah,
• Khdija Al-Hosni,
• Muhammad U. Anwar,
• Rene Csuk,
• Biswanath Das and
• Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

• significantly higher by demonstrating minimum OD among all tested compounds, while compound 7e and metronidazole treated bacteria exhibited maximum OD. Similarly, a slight OD enhancement was recorded in bacterial growth under all tested compounds from 24–48 h. However, the trend of suppressed bacterial OD by

A visible-light-induced, metal-free bis-arylation of 2,5-dichlorobenzoquinone

• Pieterjan Winant and
• Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 2315–2320, doi:10.3762/bjoc.17.149

• nature makes them crucial players in both the regulation of reactive oxygen species and biological stress levels in human tissue [9], as well as in the photosynthesis of plants and bacteria [10]. Aside from their use in therapeutics, quinones possess unique photophysical and electronic properties

Synthesis of O⁶-alkylated preQ₁ derivatives

• Laurin Flemmich,
• Sarah Moreno and
• Ronald Micura

Beilstein J. Org. Chem. 2021, 17, 2295–2301, doi:10.3762/bjoc.17.147

• in the biosynthetic pathway of the hypermodified tRNA nucleoside queuosine (Q) (Scheme 1) [5]. The core structure of the nucleobase is 7-aminomethyl-7-deazaguanine, a pyrrolo[2,3-d]pyrimidine also termed prequeuosine base (preQ1) [6][7]. In many bacteria, preQ1 binds to specific mRNA domains and

Nomimicins B–D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

• Zhiwei Zhang,
• Tao Zhou,
• Taehui Yang,
• Keisuke Fukaya,
• Enjuro Harunari,
• Shun Saito,
• Katsuhisa Yamada,
• Chiaki Imada,
• Daisuke Urabe and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2194–2202, doi:10.3762/bjoc.17.141

• absolute configuration was determined by combination of NOESY/ROESY and ECD analyses. Nomimicins B, C, and D showed antimicrobial activity against Gram-positive bacteria, Kocuria rhizophila and Bacillus subtilis, with MIC values in the range of 6.5 to 12.5 μg/mL. Nomimicins B and C also displayed

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

• ., bacteria, biomolecules [15], enzymes [16]) or physical stimuli (e.g., light [17][18][19], temperature [12][18], mechanical forces, as well as electric [20][21] and magnetic fields [22][23][24]) [1][25][26]. As a result of these environmental triggers, smart materials exhibit a defined reversible change in