Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete Kocuria sp.: application of ¹J_C,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites

• Md. Rokon Ul Karim,
• Enjuro Harunari,
• Amit Raj Sharma,
• Naoya Oku,
• Kazuaki Akasaka,
• Daisuke Urabe,
• Mada Triandala Sibero and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 2719–2727, doi:10.3762/bjoc.16.222

• Md. Rokon Ul Karim Enjuro Harunari Amit Raj Sharma Naoya Oku Kazuaki Akasaka Daisuke Urabe Mada Triandala Sibero Yasuhiro Igarashi Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan Shokei Gakuin University, 4

Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator

• Poulami Jana,
• Filip Šupljika,
• Carsten Schmuck and
• Ivo Piantanida

Beilstein J. Org. Chem. 2020, 16, 2201–2211, doi:10.3762/bjoc.16.185

• Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia, Laboratory for Physical Chemistry and Corrosion, Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, University of Zagreb, Croatia 10.3762/bjoc.16.185 Abstract A novel

Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups

• Xiaoyun Hu,
• Jianxin Guo,
• Cui Wang,
• Rui Zhang and
• Victor Borovkov

Beilstein J. Org. Chem. 2020, 16, 1875–1880, doi:10.3762/bjoc.16.155

• Xiaoyun Hu Jianxin Guo Cui Wang Rui Zhang Victor Borovkov College of Chemistry and Materials South-Central University for Nationalities, Wuhan, China Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia 10.3762/bjoc.16.155 Abstract

Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio

• Dandan Li,
• Enjuro Harunari,
• Tao Zhou,
• Naoya Oku and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154

• Dandan Li Enjuro Harunari Tao Zhou Naoya Oku Yasuhiro Igarashi Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan 10.3762/bjoc.16.154 Abstract Liquid cultures of Vibrio sp. SI9, isolated from the outer tissue

• obtained from the Biotechnology Resource Center, National Institute of Technology and Evaluation and the JCRB Cell Bank, National Institute of Biomedical Innovation, Health and Nutrition, respectively. Funding This work was supported in part by JSPS KAKENHI Grant Number JP19K05848 to Y. I and JP18K05827 to

Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)

• Cora Hertzer,
• Stefan Kehraus,
• Nils Böhringer,
• Fontje Kaligis,
• Robert Bara,
• Dirk Erpenbeck,
• Gert Wörheide,
• Till F. Schäberle,
• Heike Wägele and
• Gabriele M. König

Beilstein J. Org. Chem. 2020, 16, 1596–1605, doi:10.3762/bjoc.16.132

• Cora Hertzer Stefan Kehraus Nils Bohringer Fontje Kaligis Robert Bara Dirk Erpenbeck Gert Worheide Till F. Schaberle Heike Wagele Gabriele M. Konig Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany Institute for Insect Biotechnology, Justus-Liebig

4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

• Dandan Li,
• Naoya Oku,
• Yukiko Shinozaki,
• Yoichi Kurokawa and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124

• Dandan Li Naoya Oku Yukiko Shinozaki Yoichi Kurokawa Yasuhiro Igarashi Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan National Institute of Technology, Toyama College, 13 Hongo-machi, Toyama City, Toyama

• 939-8630, Japan Department of Bioscience and Biotechnology, Fukui Prefectural University, Eiheiji-cho, Fukui, Japan 10.3762/bjoc.16.124 Abstract 4-Hydroxy-3-methyl-2(1H)-quinolone (1), a molecule known for a long time and recently discovered from a Brassicaceae plant Isatis tinctoria without

In silico rationalisation of selectivity and reactivity in Pd-catalysed C–H activation reactions

• Liwei Cao,
• Mikhail Kabeshov,
• Steven V. Ley and
• Alexei A. Lapkin

Beilstein J. Org. Chem. 2020, 16, 1465–1475, doi:10.3762/bjoc.16.122

• Liwei Cao Mikhail Kabeshov Steven V. Ley Alexei A. Lapkin Department of Chemical Engineering and Biotechnology, University of Cambridge, Cambridge CB3 0AS, UK Cambridge Centre for Advanced Research and Education in Singapore, CARES Ltd., CREATE Way, CREATE Tower #05-05, 138602 Singapore Department

Activated carbon as catalyst support: precursors, preparation, modification and characterization

• Melanie Iwanow,
• Tobias Gärtner,
• Volker Sieber and
• Burkhard König

Beilstein J. Org. Chem. 2020, 16, 1188–1202, doi:10.3762/bjoc.16.104

• Melanie Iwanow Tobias Gartner Volker Sieber Burkhard Konig Fraunhofer Institute for Interfacial Engineering and Biotechnology IGB, Bio-, Electro- and Chemocatalysis BioCat, Straubing Branch, Schulgasse 11a, 94315 Straubing, Germany Department of Chemistry and Pharmacy, University of Regensburg

• , Universitätsstraße 31, 93040 Regensburg, Germany Technical University of Munich, Campus Straubing for Biotechnology and Sustainability, Schulgasse 16, 94315 Straubing, Germany 10.3762/bjoc.16.104 Abstract The preparation of activated carbon materials is discussed along selected examples of precursor materials, of

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

• Shun Saito,
• Kota Atsumi,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Naoya Oku,
• Md. Rokon Ul Karim,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

• Shun Saito Kota Atsumi Tao Zhou Keisuke Fukaya Daisuke Urabe Naoya Oku Md. Rokon Ul Karim Hisayuki Komaki Yasuhiro Igarashi Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan Biological Resource Center

Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes

• Aya Yoshimura,
• Hitoshi Kimura,
• Kohei Kagawa,
• Mayuka Yoshioka,
• Toshiki Itou,
• Dhananjayan Vasu,
• Takashi Shirahata,
• Hideki Yorimitsu and
• Yohji Misaki

Beilstein J. Org. Chem. 2020, 16, 974–981, doi:10.3762/bjoc.16.86

• Aya Yoshimura Hitoshi Kimura Kohei Kagawa Mayuka Yoshioka Toshiki Itou Dhananjayan Vasu Takashi Shirahata Hideki Yorimitsu Yohji Misaki Department of Materials Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

• Ming-Xi Bi,
• Shuai Liu,
• Yangen Huang,
• Xiu-Hua Xu and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62

• Ming-Xi Bi Shuai Liu Yangen Huang Xiu-Hua Xu Feng-Ling Qing Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, China Key Laboratory of

KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones

• Qiao Lin,
• Shiling Zhang and
• Bin Li

Beilstein J. Org. Chem. 2020, 16, 492–501, doi:10.3762/bjoc.16.44

• Qiao Lin Shiling Zhang Bin Li School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, Guangdong Province, P.R. China 10.3762/bjoc.16.44 Abstract An efficient and simple KOt-Bu-promoted selective ring-opening N-alkylation of 2-methyl-2-oxazoline or 2-(methylthio)-4,5

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku,
• Nobuyasu Matsuura,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

• Amit Raj Sharma Enjuro Harunari Naoya Oku Nobuyasu Matsuura Agus Trianto Yasuhiro Igarashi Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan Okayama University of Science, 1-1 Ridaicho, Okayama 700-0005, Japan

Understanding the role of active site residues in CotB2 catalysis using a cluster model

• Keren Raz,
• Ronja Driller,
• Thomas Brück,
• Bernhard Loll and
• Dan T. Major

Beilstein J. Org. Chem. 2020, 16, 50–59, doi:10.3762/bjoc.16.7

• : Department of Molecular Biology and Genetics, Aarhus University, Gustav Wieds Vej 10, 8000 Aarhus C, Denmark present address: Danish Research Institute of Translational Neuroscience - DANDRITE, Nordic-EMBL Partnership for Molecular Medicine, Aarhus C, Denmark Werner Siemens Chair of Synthetic Biotechnology

• with numerous pharmacological [7][8] and biological activities have been reported, rendering them important targets for medical and biotechnology research [9]. Chemical synthetic and sustainable biosynthetic strategies in synergy with the biological activity of different terpene natural products have

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

• Soleiman E. Helaly,
• Wilawan Kuephadungphan,
• Patima Phainuphong,
• Mahmoud A. A. Ibrahim,
• Kanoksri Tasanathai,
• Suchada Mongkolsamrit,
• Janet Jennifer Luangsa-ard,
• Souwalak Phongpaichit,
• Vatcharin Rukachaisirikul and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

• , Narathiwat 96000, Thailand Computational Chemistry Laboratory, Chemistry Department, Faculty of Science, Minia University, 61519, Egypt National Centre for Genetic Engineering and Biotechnology (BIOTEC), NSTDA, 113 Thailand Science Park, Phahonyothin Road, Klong Nueng, Klong Luang, Pathum Thani 12120

• ); the German Federal Ministry of Education and Research (BMBF); the National Center for Genetic Engineering and Biotechnology (BIOTEC) Platform Technology Management (grant no. P19-50231), the National Science and Technology Development Agency (NSTDA); and the Prince of Songkla University Graduate

Two new aromatic polyketides from a sponge-derived Fusarium

• Mada Triandala Sibero,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Ocky K. Karna Radjasa,
• Agus Sabdono,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289

• , Indonesia Marine Science Techno Park, Diponegoro University, Teluk Awur Campus, St. Undip, Jepara District, Central Java, Indonesia Biotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan 10.3762/bjoc.15.289 Abstract In our natural product screening

Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

• László Orha,
• József M. Tukacs,
• László Kollár and
• László T. Mika

Beilstein J. Org. Chem. 2019, 15, 2907–2913, doi:10.3762/bjoc.15.284

• K113177) and the Higher Education Excellence Program of the Ministry of Human Capacities in the frame of Biotechnology research area of Budapest University of Technology and Economics (BME FIKP-BIO). L.T. Mika is grateful for the support of a Scholarship of József Varga Foundation, Budapest University of

Synthetic terpenoids in the world of fragrances: Iso E Super^® is the showcase

• Alexey Stepanyuk and
• Andreas Kirschning

Beilstein J. Org. Chem. 2019, 15, 2590–2602, doi:10.3762/bjoc.15.252

• natural products. Biotechnology is another way to harness fragrance components be it enzymatic or microbial. Nowadays engineered microbes are at hand that, e.g., produce scents, such as patchouli, by fermenting sugar. Patchouli is a complex mixture of sesquiterpenes ((−)-patchoulol, (+)-norpatchoulenol

• linked with a bouquet of methods to broaden the platform of molecules with favourable olfactory properties. These include chemical synthesis, microbiology and molecular biology associated with biotechnology and combinations based on these methods. Hence also the most recent developments in synthetic

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

• Anniina Kiesilä,
• Jani O. Moilanen,
• Anneli Kruve,
• Christoph A. Schalley,
• Perdita Barran and
• Elina Kalenius

Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241

• Berlin, Germany Michael Barber Centre for Collaborative Mass Spectrometry, Manchester Institute of Biotechnology, School of Chemistry, The University of Manchester, Princess Street, Manchester, UK 10.3762/bjoc.15.241 Abstract Pyridine[4]arenes have previously been considered as anion binding hosts due

Current understanding and biotechnological application of the bacterial diterpene synthase CotB2

• Ronja Driller,
• Daniel Garbe,
• Norbert Mehlmer,
• Monika Fuchs,
• Keren Raz,
• Dan Thomas Major,
• Thomas Brück and
• Bernhard Loll

Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228

• and Genetics, Aarhus University, Gustav Wieds Vej 10, 8000 Aarhus C, Denmark present address: Danish Research Institute of Translational Neuroscience - DANDRITE, Nordic-EMBL Partnership for Molecular Medicine, Aarhus C, Denmark Werner Siemens Chair of Synthetic Biotechnology, Dept. of Chemistry

• mutagenesis have exciting applications for the sustainable production of high value bioactive substances. Keywords: biotechnology; CotB2; crystal structure; cyclooctatin; diterpene; reaction mechanism; terpene synthase; Introduction Terpenes represent one of the most diverse groups of natural biomolecules

• . Driller was supported by Elsa-Neumann and Nüsslein-Volhard stipends. D. T. Major acknowledges support from the Israel Science Foundation (Grant #2146/15 and 1683/18). T. Brück gratefully acknowledges funding by the Werner Siemens foundation for establishing the field of Synthetic Biotechnology at the

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

• Amit Raj Sharma,
• Enjuro Harunari,
• Tao Zhou,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

• Amit Raj Sharma Enjuro Harunari Tao Zhou Agus Trianto Yasuhiro Igarashi Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan Faculty of Fisheries and Marine Sciences, Diponegoro University, Tembalang Campus, St

Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids

• Melodi Demiray,
• David J. Miller and
• Rudolf K. Allemann

Beilstein J. Org. Chem. 2019, 15, 2184–2190, doi:10.3762/bjoc.15.215

• Biotechnology and Biological Sciences Research Council (BBSRC) through grants (BB/H01683X/1, BB/M022463/1, BB/N012526/1) and the Engineering and Physical Sciences Research Council (EPSRC) through grant (EP/K502819/1).

Installation of -SO₂F groups onto primary amides

• Jing Liu,
• Shi-Meng Wang,
• Njud S. Alharbi and
• Hua-Li Qin

Beilstein J. Org. Chem. 2019, 15, 1907–1912, doi:10.3762/bjoc.15.186

• Jing Liu Shi-Meng Wang Njud S. Alharbi Hua-Li Qin State Key Laboratory of Silicate Materials for Architectures; School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430070, China Biotechnology Research group, Deportment of Biological

Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)

• Małgorzata Urbańczyk,
• Michał Jewgiński,
• Joanna Krzciuk-Gula,
• Jerzy Góra,
• Rafał Latajka and
• Norbert Sewald

Beilstein J. Org. Chem. 2019, 15, 1581–1591, doi:10.3762/bjoc.15.162

• of used backbone dihedral onto cluster size of peptide 4. Supporting Information Supporting Information File 504: Supplemental materials. Acknowledgements The authors acknowledge the support from DAAD (Project 57063993), Wroclaw Centre of Biotechnology, programme The Leading National Research

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

• Maryna V. Murlykina,
• Oleksandr V. Kolomiets,
• Maryna M. Kornet,
• Yana I. Sakhno,
• Sergey M. Desenko,
• Victoriya V. Dyakonenko,
• Svetlana V. Shishkina,
• Oleksandr A. Brazhko,
• Vladimir I. Musatov,
• Alexander V. Tsygankov,
• Erik V. Van der Eycken and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

• (LOMAC), KU Leuven, Celestijnenlaan 200F, B-3001, Leuven, Belgium Laboratory of Biotechnology of Physiologically Active Substances, Zaporizhzhia National University, Zhukovsky str., 66, Zaporizhzhya, Ukraine, 69600 National Technical University “Kharkiv Polytechnic Institute”, Kyrpychova str., 2, 61002