One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction

• Bo Yang,
• Chuanye Tao,
• Taofeng Shao,
• Jianxian Gong and
• Chao Che

Beilstein J. Org. Chem. 2016, 12, 1487–1492, doi:10.3762/bjoc.12.145

• Bo Yang Chuanye Tao Taofeng Shao Jianxian Gong Chao Che Laboratory of Chemical Genomics, Engineering Laboratory for Chiral Drug Synthesis, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China 10.3762/bjoc.12.145 Abstract A novel three

Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA

• Svetlana V. Vasilyeva,
• Vyacheslav V. Filichev and
• Alexandre S. Boutorine

Beilstein J. Org. Chem. 2016, 12, 1348–1360, doi:10.3762/bjoc.12.128

• Svetlana V. Vasilyeva Vyacheslav V. Filichev Alexandre S. Boutorine Institute of Chemical Biology & Fundamental Medicine, SB of RAS, pr. Lavrent’eva 8, 630090 Novosibirsk, Russia Institute of Fundamental Sciences, Massey University, Private Bag 11-222, 4442 Palmerston North, New Zealand Structure

Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals

• Haipan Zhu,
• Peile Du,
• Jianjun Li,
• Ziyang Liao,
• Guohua Liu,
• Hao Li and
• Wei Wang

Beilstein J. Org. Chem. 2016, 12, 1340–1347, doi:10.3762/bjoc.12.127

• Chemistry, Shanghai Normal University, Shanghai 200234, China Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131-0001, USA 10.3762/bjoc.12.127 Abstract A cooperative catalytic strategy of chiral iminium catalysis by regioselective activation of the C=C bond in

Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX

• Gergely L. Tolnai,
• Jonathan P. Brand and
• Jerome Waser

Beilstein J. Org. Chem. 2016, 12, 745–749, doi:10.3762/bjoc.12.74

• blocks in synthetic organic chemistry. Recently, they have attracted also strong interest for applications in materials science and chemical biology [1]. One of the most important transformations of alkynes is the copper-catalyzed [3 + 2] cycloaddition with azides, which can be performed under mild

Elucidation of a masked repeating structure of the O-specific polysaccharide of the halotolerant soil bacteria Azospirillum halopraeferens Au4

• Elena N. Sigida,
• Yuliya P. Fedonenko,
• Alexander S. Shashkov,
• Nikolay P. Arbatsky,
• Evelina L. Zdorovenko,
• Svetlana A. Konnova,
• Vladimir V. Ignatov and
• Yuriy A. Knirel

Beilstein J. Org. Chem. 2016, 12, 636–642, doi:10.3762/bjoc.12.62

• oligosaccharides 1, 2 and 3. Acknowledgements This work was funded in part by the Russian Foundation for Basic Research (projects 14-04-01658 and 15-34-50191). The authors thank the Simbioz Center for the Collective Use of Research Equipment in the Field of Physical–Chemical Biology and Nanobiotechnology

Learning from the unexpected in life and DNA self-assembly

• Jennifer M. Heemstra

Beilstein J. Org. Chem. 2015, 11, 2713–2720, doi:10.3762/bjoc.11.292

• chemical biology lab with almost no formal training in molecular or cellular biology. Fortunately, David provided me the freedom to make mistakes and learn from those around me, which allowed me to grow in my knowledge of this field that was almost entirely new to me. Additionally, David and my other

Copper-catalyzed arylation of alkyl halides with arylaluminum reagents

• Bijay Shrestha and
• Ramesh Giri

Beilstein J. Org. Chem. 2015, 11, 2400–2407, doi:10.3762/bjoc.11.261

• Bijay Shrestha Ramesh Giri Department of Chemistry & Chemical Biology, The University of New Mexico, Albuquerque, NM 87131, USA 10.3762/bjoc.11.261 Abstract We report a Cu-catalyzed coupling between triarylaluminum reagents and alkyl halides to form arylalkanes. The reaction proceeds in the

A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations

• Xinlong Pang,
• Chao Chen,
• Ming Li and
• Chanjuan Xi

Beilstein J. Org. Chem. 2015, 11, 2365–2369, doi:10.3762/bjoc.11.258

• Xinlong Pang Chao Chen Ming Li Chanjuan Xi Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China, Tel: +86-10-62773684 College of Chemistry and Molecular Engineering, Qingdao University of

The marine sponge Agelas citrina as a source of the new pyrrole–imidazole alkaloids citrinamines A–D and N-methylagelongine

• Christine Cychon,
• Ellen Lichte and
• Matthias Köck

Beilstein J. Org. Chem. 2015, 11, 2029–2037, doi:10.3762/bjoc.11.220

• ) who gave members of the Köck research group the opportunity to participate in scientific expeditions to the Bahamas (1998 to 2008). We further thank Dr. F. Sasse and B. Hinkelmann (Department of Chemical Biology, Helmholtz Centre for Infection Research, Braunschweig, Germany) for performing the

Profluorescent substrates for the screening of olefin metathesis catalysts

• Raphael Reuter and
• Thomas R. Ward

Beilstein J. Org. Chem. 2015, 11, 1886–1892, doi:10.3762/bjoc.11.203

• recent applications, metathesis has also been used in chemical biology, either in the form of an artificial metalloenzyme [8][9][10] or for the post-translational modification of proteins [11]. To address these various challenges, a vast number of carbene complexes based on different transition metals

Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds

• Michaela Mühlberg,
• Michael G. Hoesl,
• Christian Kuehne,
• Jens Dernedde,
• Nediljko Budisa and
• Christian P. R. Hackenberger

Beilstein J. Org. Chem. 2015, 11, 784–791, doi:10.3762/bjoc.11.88

• modification; lectin; multivalency; Introduction The chemical modification of proteins has been developed to a core discipline in chemical biology with diverse applications in all areas of the life sciences, including pharmacology, biophysics, biotechnology and cell biology [1][2][3][4]. In addition to the

DNA display of glycoconjugates to emulate oligomeric interactions of glycans

• Alexandre Novoa and
• Nicolas Winssinger

Beilstein J. Org. Chem. 2015, 11, 707–719, doi:10.3762/bjoc.11.81

• Alexandre Novoa Nicolas Winssinger Department of Organic Chemistry, NCCR Chemical Biology, University of Geneva 30, quai Ernest Ansermet, 1211 Geneva, Switzerland 10.3762/bjoc.11.81 Abstract Glycans (carbohydrate portion of glycoproteins and glycolipids) frequently exert their function through

Sequence-specific RNA cleavage by PNA conjugates of the metal-free artificial ribonuclease tris(2-aminobenzimidazole)

• Friederike Danneberg,
• Alice Ghidini,
• Plamena Dogandzhiyski,
• Elisabeth Kalden,
• Roger Strömberg and
• Michael W. Göbel

Beilstein J. Org. Chem. 2015, 11, 493–498, doi:10.3762/bjoc.11.55

• Friederike Danneberg Alice Ghidini Plamena Dogandzhiyski Elisabeth Kalden Roger Stromberg Michael W. Gobel Institute for Organic Chemistry and Chemical Biology, Goethe Universität Frankfurt, Max-von-Laue-Straße 7, D-60438 Frankfurt am Main, Germany Karolinska Institutet, Department of Biosciences

Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo

• Alireza Shakoori,
• John B. Bremner,
• Mohammed K. Abdel-Hamid,
• Anthony C. Willis,
• Rachada Haritakun and
• Paul A. Keller

Beilstein J. Org. Chem. 2015, 11, 481–492, doi:10.3762/bjoc.11.54

• ; nitrogen heterocycles; rearrangement; Introduction One of the foci of current organic synthesis is the exploration of new chemical space, with an emphasis on significant heterocyclic molecular diversity [1][2]. Direct applications of such advances in medicinal chemistry, chemical biology and nanochemistry

A procedure for the preparation and isolation of nucleoside-5’-diphosphates

• Heidi J. Korhonen,
• Hannah L. Bolt and
• David R. W. Hodgson

Beilstein J. Org. Chem. 2015, 11, 469–472, doi:10.3762/bjoc.11.52

• synthesis; nucleic acids; nucleoside-5’-diphosphate; phosphorylation; Introduction Nucleoside-5'-phosphates are key to many mechanistic studies and chemical biology applications [1][2][3]. Synthetic approaches towards nucleoside-5'-phosphates are well-established [4], however, the methods tend to be

The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon–carbon bond formation via electrogenerated N-acyliminium ions

• Alan M. Jones and
• Craig E. Banks

Beilstein J. Org. Chem. 2014, 10, 3056–3072, doi:10.3762/bjoc.10.323

• chemical biology and epigenetics. Dhimane and co-workers utilised a strategy of anodic methoxylation to complete the first step in the synthesis of 106 (Scheme 24) [96][97]. The preparation of chiral (up to 99% ee) cyclic amino acids was achieved by Onomura and colleagues (Scheme 25) [20]. In their paper

Nucleic acid chemistry

• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2014, 10, 2928–2929, doi:10.3762/bjoc.10.311

• mature part of organic and bioorganic chemistry, the many questions that are still being raised by research in biology and chemical biology give sufficient motivation to continue to synthesize new nucleic acid probes and thereby further develop nucleic acid chemistry. Moreover, in addition to their

A small azide-modified thiazole-based reporter molecule for fluorescence and mass spectrometric detection

• Stefanie Wolfram,
• Hendryk Würfel,
• Stefanie H. Habenicht,
• Christine Lembke,
• Phillipp Richter,
• Eckhard Birckner,
• Rainer Beckert and
• Georg Pohnert

Beilstein J. Org. Chem. 2014, 10, 2470–2479, doi:10.3762/bjoc.10.258

• Macromolecular Chemistry, Friedrich Schiller University, Humboldtstr. 10, 07743 Jena, Germany Institute for Physical Chemistry, Friedrich Schiller University, Helmholtzweg 4, 07743 Jena, Germany 10.3762/bjoc.10.258 Abstract Molecular probes are widely used tools in chemical biology that allow tracing of

Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

• Anne-Katrin Späte,
• Verena F. Schart,
• Julia Häfner,
• Andrea Niederwieser,
• Thomas U. Mayer and
• Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

• Anne-Katrin Spate Verena F. Schart Julia Hafner Andrea Niederwieser Thomas U. Mayer Valentin Wittmann University of Konstanz, Department of Chemistry and Konstanz Research School Chemical Biology (KoRS-CB), Universitätsstraße 10, 78457 Konstanz, Germany University of Konstanz, Department of

• Biology and Konstanz Research School Chemical Biology (KoRS-CB), Universitätsstraße 10, 78457 Konstanz, Germany 10.3762/bjoc.10.232 Abstract Monitoring glycoconjugates has been tremendously facilitated by the development of metabolic oligosaccharide engineering. Recently, the inverse-electron-demand

• of Ac4GlcNCyoc (1) and Ac4GalNCyoc (2). Supporting Information File 564: Additional MOE experiments and NMR spectra. Acknowledgements This work was supported by the Deutsche Forschungsgemeinschaft (SFB 969), the University of Konstanz, and the Konstanz Research School Chemical Biology. We thank

Organophosphorus chemistry

• Paul R. Hanson

Beilstein J. Org. Chem. 2014, 10, 2087–2088, doi:10.3762/bjoc.10.217

• molecule therapeutic agents and pro-drugs substantiates their role in modern synthetic chemistry and chemical biology. Moreover, their central use as ligands and effectors in asymmetric catalysis, as well as key functional groups for the development of new synthetic methods, has taken the field to new

Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration

• Michele Mari,
• Simone Lucarini,
• Francesca Bartoccini,
• Giovanni Piersanti and
• Gilberto Spadoni

Beilstein J. Org. Chem. 2014, 10, 1991–1998, doi:10.3762/bjoc.10.207

• ]. Tryptophan and tryptophan analogs also have applications in chemical biology thanks to the highly environment-sensitive fluorescence properties of the indole ring [8][9][10][11][12][13][14][15][16][17] and when incorporated into peptides, they lead to compounds with increased resistance to enzymatic

The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases

• Ilja V. Fateev,
• Konstantin V. Antonov,
• Irina D. Konstantinova,
• Tatyana I. Muravyova,
• Frank Seela,
• Roman S. Esipov,
• Anatoly I. Miroshnikov and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2014, 10, 1657–1669, doi:10.3762/bjoc.10.173

• , Russia Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstraße 11, D-48149 Münster, Germany Institute of Bioorganic Chemistry, National Academy of Sciences, Acad. Kuprevicha 5/2, 220141 Minsk, Belarus 10.3762/bjoc.10.173 Abstract Two approaches to the

An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards ‘clickable’ biodegradable polylactide

• Quanxuan Zhang,
• Hong Ren and
• Gregory L. Baker

Beilstein J. Org. Chem. 2014, 10, 1365–1371, doi:10.3762/bjoc.10.139

• Quanxuan Zhang Hong Ren Gregory L. Baker Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA Athinoula A. Martinos Center for Biomedical Imaging, Department of

Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ₀)

• Sabin Llona-Minguez and
• Simon P. Mackay

Beilstein J. Org. Chem. 2014, 10, 1333–1338, doi:10.3762/bjoc.10.135

• Sabin Llona-Minguez Simon P. Mackay Strathclyde Institute of Pharmacy & Biomedical Sciences, University of Strathclyde, 165 Cathedral Street, Glasgow, G4 0RE, United Kingdom Science for Life Laboratory, Division of Translational Medicine & Chemical Biology, Department of Medical Biochemistry

Solid-phase-supported synthesis of morpholinoglycine oligonucleotide mimics

• Tatyana V. Abramova,
• Sergey S. Belov,
• Yulia V. Tarasenko and
• Vladimir N. Silnikov

Beilstein J. Org. Chem. 2014, 10, 1151–1158, doi:10.3762/bjoc.10.115

• Tatyana V. Abramova Sergey S. Belov Yulia V. Tarasenko Vladimir N. Silnikov Institute of Chemical Biology and Fundamental Medicine, SB RAS, Lavrent’ev Ave, 8, Novosibirsk 630090, Russia Novosibirsk State University, Pirogova St. 2, Novosibirsk 630090, Russia 10.3762/bjoc.10.115 Abstract An