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

A new building block for DNA network formation by self-assembly and polymerase chain reaction

• Holger Bußkamp,
• Sascha Keller,
• Marta Robotta,
• Malte Drescher and
• Andreas Marx

Beilstein J. Org. Chem. 2014, 10, 1037–1046, doi:10.3762/bjoc.10.104

• Holger Busskamp Sascha Keller Marta Robotta Malte Drescher Andreas Marx Department of Chemistry and Konstanz Research School Chemical Biology, University of Konstanz, Universitätsstraße 10, 78457 Konstanz, Germany 10.3762/bjoc.10.104 Abstract The predictability of DNA self-assembly is exploited

• . Supporting Information File 232: Experimental part. Acknowledgements We acknowledge funding by the Konstanz Research School Chemical Biology and within the programme Molekulare Bionik of the Ministerium für Wissenschaft, Forschung und Kunst, Baden-Württemberg. This project was supported by the DFG (DR 743/2

Cuevaenes C–E: Three new triene carboxylic derivatives from Streptomyces sp. LZ35ΔgdmAI

• Jing-Jing Deng,
• Chun-Hua Lu,
• Yao-Yao Li,
• Shan-Ren Li and
• Yue-Mao Shen

Beilstein J. Org. Chem. 2014, 10, 858–862, doi:10.3762/bjoc.10.82

• Jing-Jing Deng Chun-Hua Lu Yao-Yao Li Shan-Ren Li Yue-Mao Shen Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan, Shandong 250012, P. R. China 10.3762/bjoc.10.82 Abstract Two pairs of geometrical

Staudinger ligation towards cyclodextrin dimers in aqueous/organic media. Synthesis, conformations and guest-encapsulation ability

• Malamatenia D. Manouilidou,
• Yannis G. Lazarou,
• Irene M. Mavridis and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 774–783, doi:10.3762/bjoc.10.73

• chemical biology in the last decade [5][6]. Introduced by Bertozzi and co-workers, the concept of ligation was based on the design of an intramolecular electrophilic trap, such as the ester carbonyl in methyl terephthalate 2 (Scheme 1b), that upon encounter of an azide (e.g. PhN3) can capture the

Copper–phenanthroline catalysts for regioselective synthesis of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions

• Rupankar Paira,
• Tarique Anwar,
• Maitreyee Banerjee,
• Yogesh P. Bharitkar,
• Shyamal Mondal,
• Sandip Kundu,
• Abhijit Hazra,
• Prakas R. Maulik and
• Nirup B. Mondal

Beilstein J. Org. Chem. 2014, 10, 692–700, doi:10.3762/bjoc.10.62

• Rupankar Paira Tarique Anwar Maitreyee Banerjee Yogesh P. Bharitkar Shyamal Mondal Sandip Kundu Abhijit Hazra Prakas R. Maulik Nirup B. Mondal Department of Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4 Raja S.C. Mullick Road, Jadavpur, Kolkata

Preparation of new alkyne-modified ansamitocins by mutasynthesis

• Kirsten Harmrolfs,
• Lena Mancuso,
• Binia Drung,
• Florenz Sasse and
• Andreas Kirschning

Beilstein J. Org. Chem. 2014, 10, 535–543, doi:10.3762/bjoc.10.49

• Kirsten Harmrolfs Lena Mancuso Binia Drung 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

Zirconoarylation of alkynes through p-chloranil-promoted reductive elimination of arylzirconates

• Xiaoyu Yan,
• Chao Chen and
• Chanjuan Xi

Beilstein J. Org. Chem. 2014, 10, 528–534, doi:10.3762/bjoc.10.48

• Xiaoyu Yan Chao Chen Chanjuan Xi Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China 10.3762

Direct and indirect single electron transfer (SET)-photochemical approaches for the preparation of novel phthalimide and naphthalimide-based lariat-type crown ethers

• Dae Won Cho,
• Patrick S. Mariano and
• Ung Chan Yoon

Beilstein J. Org. Chem. 2014, 10, 514–527, doi:10.3762/bjoc.10.47

• Dae Won Cho Patrick S. Mariano Ung Chan Yoon Department of Chemistry, Yeungnam University, Gyeongsan, Gyeongbuk 712-749, Korea Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131, USA Department of Chemistry and Chemistry Institute of Functional Materials

Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)amino]acetyl}amino)benzophenone; a case of configurationally stable stereogenic nitrogen

• Hiroki Moriwaki,
• Daniel Resch,
• Hengguang Li,
• Iwao Ojima,
• Ryosuke Takeda,
• José Luis Aceña and
• Vadim A. Soloshonok

Beilstein J. Org. Chem. 2014, 10, 442–448, doi:10.3762/bjoc.10.41

• Hiroki Moriwaki Daniel Resch Hengguang Li Iwao Ojima Ryosuke Takeda Jose Luis Acena Vadim A. Soloshonok Department of Chemistry, Institute of Chemical Biology & Drug Discovery, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, United States Hamari Chemicals Ltd. 1-4-29

Synthesis of the B-seco limonoid core scaffold

• Hanna Bruss,
• Hannah Schuster,
• Rémi Martinez,
• Markus Kaiser,
• Andrey P. Antonchick and
• Herbert Waldmann

Beilstein J. Org. Chem. 2014, 10, 194–208, doi:10.3762/bjoc.10.15

• -Hahn-Straße 6, 44227 Dortmund, Germany Chemical Biology, Zentrum für Medizinische Biotechnologie, Fakultät für Biologie, Universität Duisburg-Essen, Universitätsstraße 2, 45117 Essen, Germany 10.3762/bjoc.10.15 Abstract Synthetic investigations towards the structurally complex and highly decorated

• natural product classes to inspire the synthesis of probes and reagents for chemical biology and medicinal chemistry research, we aimed at the development of a synthetic strategy to get access to the B-seco limonoid scaffold by means of a [3,3]-sigmatropic rearrangement as key step enabling the formation

Physalin H from Solanum nigrum as an Hh signaling inhibitor blocks GLI1–DNA-complex formation

• Midori A. Arai,
• Kyoko Uchida,
• Samir K. Sadhu,
• Firoj Ahmed and
• Masami Ishibashi

Beilstein J. Org. Chem. 2014, 10, 134–140, doi:10.3762/bjoc.10.10

• -in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS), a Grant-in-Aid for Scientific Research on Innovative Areas ‘Chemical Biology of Natural Products’ from The Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT), Special Funds for

Synthesis of novel derivatives of 5-hydroxymethylcytosine and 5-formylcytosine as tools for epigenetics

• Anna Chentsova,
• Era Kapourani and
• Athanassios Giannis

Beilstein J. Org. Chem. 2014, 10, 7–11, doi:10.3762/bjoc.10.2

• (5hmC) and 5-formylcytosine (5fC) derivatives that can be used as tools in the emerging field of epigenetics for deciphering chemical biology of TET-mediated processes. Keywords: 3,6-dihydrodeoxycytidine derivatives; DNA demethylation; epigenetics; 5-hydroxymethylcytosine (5hmC) derivatives; TET

• to play a decisive role in their self-renewal process [27]. Interestingly, the levels of 5hmC in several cancer types are strongly reduced relative to the corresponding normal tissue around the tumor [28]. To gain deeper insights into the chemical biology of DNA demethylation pathways further

Studies toward bivalent κ opioids derived from salvinorin A: heteromethylation of the furan ring reduces affinity

• Thomas A. Munro,
• Wei Xu,
• Douglas M. Ho,
• Lee-Yuan Liu-Chen and
• Bruce M. Cohen

Beilstein J. Org. Chem. 2013, 9, 2916–2924, doi:10.3762/bjoc.9.328

• Abuse Research and Department of Pharmacology, Temple University School of Medicine, Philadelphia, PA 19140, USA Department of Chemistry and Chemical Biology, Harvard University, Cambridge MA 02138, USA 10.3762/bjoc.9.328 Abstract The recent crystal structure of the κ-opioid receptor (κ-OR) revealed

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