Synthesis of nucleotide–amino acid conjugates designed for photo-CIDNP experiments by a phosphotriester approach

• Tatyana V. Abramova,
• Olga B. Morozova,
• Vladimir N. Silnikov and
• Alexandra V. Yurkovskaya

Beilstein J. Org. Chem. 2013, 9, 2898–2909, doi:10.3762/bjoc.9.326

• Tatyana V. Abramova Olga B. Morozova Vladimir N. Silnikov Alexandra V. Yurkovskaya 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 International Tomography Center

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

• Jun Hu,
• Jindan Wu,
• Qian Wang and
• Yong Ju

Beilstein J. Org. Chem. 2013, 9, 2877–2885, doi:10.3762/bjoc.9.324

• Jun Hu Jindan Wu Qian Wang Yong Ju Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, 100084, China, Department of Chemistry and Biochemistry, University of South Carolina, Columbia, 29208, USA

Towards stereochemical control: A short formal enantioselective total synthesis of pumiliotoxins 251D and 237A

• Jie Zhang,
• Hong-Kui Zhang and
• Pei-Qiang Huang

Beilstein J. Org. Chem. 2013, 9, 2358–2366, doi:10.3762/bjoc.9.271

• Jie Zhang Hong-Kui Zhang Pei-Qiang Huang Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China State Key Laboratory of Applied Organic Chemistry Lanzhou University

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

• Amit Kumar,
• Dipak D. Vachhani,
• Sachin G. Modha,
• Sunil K. Sharma,
• Virinder S. Parmar and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2013, 9, 2097–2102, doi:10.3762/bjoc.9.246

• sequence is atom economic and the application of a multicomponent reaction assures diversity. Keywords: alkynes; gold; indoles; multicomponent; spiroindolines; Ugi; Introduction The importance of nitrogen containing heterocyclic molecules in chemical biology is undisputed. The synthesis of such

Synthesis of enones, pyrazolines and pyrrolines with gem-difluoroalkyl side chains

• Assaad Nasr El Dine,
• Ali Khalaf,
• Danielle Grée,
• Olivier Tasseau,
• Fares Fares,
• Nada Jaber,
• Philippe Lesot,
• Ali Hachem and
• René Grée

Beilstein J. Org. Chem. 2013, 9, 1943–1948, doi:10.3762/bjoc.9.230

• ; palladium catalysis; pyrazolines; pyrrolines; Introduction A widely used strategy in bioorganic, medicinal chemistry and in chemical biology is the selected introduction of fluorine in organic molecules since it strongly modifies their properties [1][2][3][4][5][6][7][8][9]. On the other hand, heterocyclic

Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters

• Lin Yan,
• Zhiqiang Han,
• Bo Zhu,
• Caiyun Yang,
• Choon-Hong Tan and
• Zhiyong Jiang

Beilstein J. Org. Chem. 2013, 9, 1853–1857, doi:10.3762/bjoc.9.216

• Lin Yan Zhiqiang Han Bo Zhu Caiyun Yang Choon-Hong Tan Zhiyong Jiang Institute of Chemical Biology, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P. R. China Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, P. R. China Division of Chemistry

Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans

• Yifan Li and
• Jérôme Waser

Beilstein J. Org. Chem. 2013, 9, 1763–1767, doi:10.3762/bjoc.9.204

• allowing the direct and regioselective C–H functionalization of benzofurans [12]. In this context, the introduction of an alkyne would be particularly useful, as acetylenes are important building blocks in synthetic chemistry, chemical biology and materials science [13]. Nevertheless, to the best of our

ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in Candida albicans

• Willmen Youngsaye,
• Cathy L. Hartland,
• Barbara J. Morgan,
• Amal Ting,
• Partha P. Nag,
• Benjamin Vincent,
• Carrie A. Mosher,
• Joshua A. Bittker,
• Sivaraman Dandapani,
• Michelle Palmer,
• Luke Whitesell,
• Susan Lindquist,
• Stuart L. Schreiber and
• Benito Munoz

Beilstein J. Org. Chem. 2013, 9, 1501–1507, doi:10.3762/bjoc.9.171

• Willmen Youngsaye Cathy L. Hartland Barbara J. Morgan Amal Ting Partha P. Nag Benjamin Vincent Carrie A. Mosher Joshua A. Bittker Sivaraman Dandapani Michelle Palmer Luke Whitesell Susan Lindquist Stuart L. Schreiber Benito Munoz Chemical Biology Platform and Probe Development Center, Broad

Selective copper(II) acetate and potassium iodide catalyzed oxidation of aminals to dihydroquinazoline and quinazolinone alkaloids

• Matthew T. Richers,
• Chenfei Zhao and
• Daniel Seidel

Beilstein J. Org. Chem. 2013, 9, 1194–1201, doi:10.3762/bjoc.9.135

• Matthew T. Richers Chenfei Zhao Daniel Seidel Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA 10.3762/bjoc.9.135 Abstract Copper(II) acetate/acetic acid/O2 and potassium iodide/tert-butylhydroperoxide systems are shown

Synthesis and physicochemical characterization of novel phenotypic probes targeting the nuclear factor-kappa B signaling pathway

• Paul M. Hershberger,
• Satyamaheshwar Peddibhotla,
• E. Hampton Sessions,
• Daniela B. Divlianska,
• Ricardo G. Correa,
• Anthony B. Pinkerton,
• John C. Reed and
• Gregory P. Roth

Beilstein J. Org. Chem. 2013, 9, 900–907, doi:10.3762/bjoc.9.103

• the small-molecule compounds discovered within the HTS process. The program then advanced a broader probe-production initiative (MLPCN) in 2008. This consortium resulted in the harnessing of chemical biology resources from four comprehensive centers and five specialty centers, which focused on either

Quantification of N-acetylcysteamine activated methylmalonate incorporation into polyketide biosynthesis

• Stephan Klopries,
• Uschi Sundermann and
• Frank Schulz

Beilstein J. Org. Chem. 2013, 9, 664–674, doi:10.3762/bjoc.9.75

• . and a doctoral stipend to U. S. U. S. is a fellow of the International Max Planck Research School of Chemical Biology in Dortmund, Germany. Candida antarctica lipases A and B were a generous donation from c-LEcta GmbH (Leipzig, Germany), Glucidex was kindly donated by Roquette GmbH (Frankfurt, Germany).

End-labeled amino terminated monotelechelic glycopolymers generated by ROMP and Cu(I)-catalyzed azide–alkyne cycloaddition

• Ronald Okoth and
• Amit Basu

Beilstein J. Org. Chem. 2013, 9, 608–612, doi:10.3762/bjoc.9.66

• Ronald Okoth Amit Basu Department of Chemistry, Brown University, Providence, Rhode Island 02912, USA 10.3762/bjoc.9.66 Abstract Functionalizable monotelechelic polymers are useful materials for chemical biology and materials science. We report here the synthesis of a capping agent that can be

Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors

• Francesca Pertici,
• Norbert Varga,
• Arnoud van Duijn,
• Matias Rey-Carrizo,
• Anna Bernardi and
• Roland J. Pieters

Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25

• Francesca Pertici Norbert Varga Arnoud van Duijn Matias Rey-Carrizo Anna Bernardi Roland J. Pieters Department of Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The Netherlands Dipartimento di Chimica

An improved synthesis of a fluorophosphonate–polyethylene glycol–biotin probe and its use against competitive substrates

• Hao Xu,
• Hairat Sabit,
• Gordon L. Amidon and
• H. D. Hollis Showalter

Beilstein J. Org. Chem. 2013, 9, 89–96, doi:10.3762/bjoc.9.12

• these competition studies demonstrate a new application of FP-based probes seldom explored before. Keywords: biotin; fluorophosphonate; high turnover rate; reversible substrate; Introduction One of the goals of chemical biology is to develop small–molecule- and biomolecule-based probes to interrogate

Synthetic probes for the study of biological function

• Jeffrey Aubé

Beilstein J. Org. Chem. 2013, 9, 79–80, doi:10.3762/bjoc.9.10

• function. All three of these come together in the pursuit of new chemical probes for use in chemical biology. This Thematic Series highlights some of the numerous ways that molecular tools inform biological research. The choice of the phrase “chemical probe” was deliberately vague and indeed its meaning

• often lies in the ears of the listener. The most common context is the case of a molecule used in chemical biology to help unravel the role of a particular cellular pathway. Biologists have numerous tools at their disposal, of course, and one important reason to select a small organic molecule as an

Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

• Daniel Fürniss,
• Timo Mack,
• Frank Hahn,
• Sidonie B. L. Vollrath,
• Katarzyna Koroniak,
• Ute Schepers and
• Stefan Bräse

Beilstein J. Org. Chem. 2013, 9, 56–63, doi:10.3762/bjoc.9.7

• conjugation methods such as the Staudinger ligation [1] or the copper-catalyzed alkyne azide cycloaddition (CuAAC) [2][3], a large number of versatile and functional bioconjugates are accessible for various applications in chemical biology [4]. To date, many therapeutically active molecules are synthetic

Hydrophobic analogues of rhodamine B and rhodamine 101: potent fluorescent probes of mitochondria in living C. elegans

• Laurie F. Mottram,
• Safiyyah Forbes,
• Brian D. Ackley and
• Blake R. Peterson

Beilstein J. Org. Chem. 2012, 8, 2156–2165, doi:10.3762/bjoc.8.243

• expression of mitochondria-targeted fluorescent proteins. The high bioavailabilty of these novel fluorescent probes may facilitate the identification of agents and factors that affect diverse aspects of mitochondrial biology in vivo. Keywords: Caenorhabditis elegans; chemical biology; fission; fluorophores

• ; fluorescence; fusion; imaging; in vivo; microscopy; mitochondria; model organisms; organelle; rhodamine; spectroscopy; Introduction Fluorescent molecular probes represent critical tools for studies of chemical biology [1]. These compounds allow the creation of sensitive enzyme substrates, sensors of a wide

• facilitate the identification of inhibitors of mitochondrial fusion or fission effective in vivo, potentially enabling the discovery of new leads for the treatment of diseases associated with dysfunctional mitochondria. A challenge associated with chemical biology studies in C. elegans is the low

Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines

• Chittaranjan Bhanja,
• Satyaban Jena,
• Sabita Nayak and
• Seetaram Mohapatra

Beilstein J. Org. Chem. 2012, 8, 1668–1694, doi:10.3762/bjoc.8.191

• ]. Therefore, synthetic methodologies allowing rapid access to these heterocycles in optically enriched form are highly desirable in organic synthesis and chemical biology/medicinal chemistry. In the past few years very promising progress has been made in this intriguing area, and among the advances

Exploring chemical diversity via a modular reaction pairing strategy

• Joanna K. Loh,
• Sun Young Yoon,
• Thiwanka B. Samarakoon,
• Alan Rolfe,
• Patrick Porubsky,
• Benjamin Neuenswander,
• Gerald H. Lushington and
• Paul R. Hanson

Beilstein J. Org. Chem. 2012, 8, 1293–1302, doi:10.3762/bjoc.8.147

• measure, the 80 compounds reported herein may have elevated prospects for interesting chemical biology: the lowest QED values among these 80 compounds (QED = 0.819 for 1{3} and 1{4}) are actually significantly above the mean value (QED = 0.615) for the 771 known drugs analyzed by Hopkins et al., while

Multistep organic synthesis of modular photosystems

• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2012, 8, 897–904, doi:10.3762/bjoc.8.102

• University of Geneva, the European Research Council (ERC Advanced Investigator), the National Centre of Competence in Research (NCCR) Chemical Biology and the Swiss NSF for financial support.

Intramolecular bridges formed by photoswitchable click amino acids

• Christian Hoppmann,
• Ronald Kühne and
• Michael Beyermann

Beilstein J. Org. Chem. 2012, 8, 884–889, doi:10.3762/bjoc.8.100

• Christian Hoppmann Ronald Kuhne Michael Beyermann Department of Chemical Biology, Leibniz-Institut für Molekulare Pharmakologie, Robert-Rössle-Strasse 10, 13125 Berlin, Germany 10.3762/bjoc.8.100 Abstract Photoswitchable click amino acids (PSCaa) are amino acids bearing a side chain consisting of

Unprecedented deoxygenation at C-7 of the ansamitocin core during mutasynthetic biotransformations

• Tobias Knobloch,
• Gerald Dräger,
• Wera Collisi,
• Florenz Sasse and
• Andreas Kirschning

Beilstein J. Org. Chem. 2012, 8, 861–869, doi:10.3762/bjoc.8.96

• Tobias Knobloch Gerald Drager Wera Collisi Florenz Sasse Andreas Kirschning Institute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ), Leibniz University Hannover, Schneiderberg 1b, 30167 Hannover, Germany Department of Chemical Biology, Helmholtz Center for Infectious

Synthesis and characterization of Sant-75 derivatives as Hedgehog-pathway inhibitors

• Chao Che,
• Song Li,
• Bo Yang,
• Shengchang Xin,
• Zhixiong Yu,
• Taofeng Shao,
• Chuanye Tao,
• Shuo Lin and
• Zhen Yang

Beilstein J. Org. Chem. 2012, 8, 841–849, doi:10.3762/bjoc.8.94

• Chao Che Song Li Bo Yang Shengchang Xin Zhixiong Yu Taofeng Shao Chuanye Tao Shuo Lin Zhen Yang Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China Shenzhen Shengjie Biotech Co., Ltd., Shenzhen 518055

High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

• Henning S. G. Beckmann,
• Heiko M. Möller and
• Valentin Wittmann

Beilstein J. Org. Chem. 2012, 8, 819–826, doi:10.3762/bjoc.8.91

• Henning S. G. Beckmann Heiko M. Moller Valentin Wittmann Fachbereich Chemie and Konstanz Research School Chemical Biology (KoRS-CB), Universität Konstanz, 78457 Konstanz, Germany 10.3762/bjoc.8.91 Abstract A series of six mono-, di-, and trivalent N,N’-diacetylchitobiose derivatives was

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

• Elena A. Khatuntseva,
• Vladimir M. Men’shov,
• Alexander S. Shashkov,
• Yury E. Tsvetkov,
• Rodion N. Stepanenko,
• Raymonda Ya. Vlasenko,
• Elvira E. Shults,
• Genrikh A. Tolstikov,
• Tatjana G. Tolstikova,
• Dimitri S. Baev,
• Vasiliy A. Kaledin,
• Nelli A. Popova,
• Valeriy P. Nikolin,
• Pavel P. Laktionov,
• Anna V. Cherepanova,
• Tatiana V. Kulakovskaya,
• Ekaterina V. Kulakovskaya and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2012, 8, 763–775, doi:10.3762/bjoc.8.87

• Novosibirsk, Russian Federation Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, 8 prospect Acad. Lavrent’eva, 630090 Novosibirsk, Russian Federation G. K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of