This week’s HOT papers featuring a copper-catalyzed aromatic C–H bond halogenation and more

These two articles are HOT as recommended by the referees. And we’ve made them free to access for 4 weeks.

Copper-catalyzed aromatic C–H bond halogenation with lithium halides under aerobic conditions
Song Mo, Yamin Zhu and Zengming Shen
DOI: 10.1039/c3ob40185e

Copper-catalyzed aromatic C–H bond halogenation with lithium halides under aerobic conditions

Free to access for 4 weeks


Direct acylation of N-benzyltriflamides from the alcohol oxidation level via palladium-catalyzed C–H bond activation
Jihye Park, Aejin Kim, Satyasheel Sharma, Minyoung Kim, Eonjeong Park, Yukyoung Jeon, Youngil Lee, Jong Hwan Kwak, Young Hoon Jung and In Su Kim
DOI: 10.1039/c3ob40140e

Direct acylation of N-benzyltriflamides from the alcohol oxidation level via palladium-catalyzed C–H bond activation

Free to access for 4 weeks 

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A photo-triggerable drug carrier on the front cover of OBC Issue 16

A photo-triggerable drug carrier based on cleavage of PEG lipids by photosensitiser-generated reactive singlet oxygen

Welcome to OBC Issue 16, 2013!

This week’s front cover highlights the work of Atsushi Ikeda and co-workers at the Nara Institute of Science and Technology, Japan. They developed a photo-triggerable drug carrier based on cleavage of PEG lipids by photosensitiser fullerene derivatives. This interesting methodology has the potential to facilitate the development of novel liposomal drug carriers for use in biomedical research.

A photo-triggerable drug carrier based on cleavage of PEG lipids by photosensitiser-generated reactive singlet oxygen
Chikako Komeda, Atsushi Ikeda, Jun-ichi Kikuchi, Norihiro Ishida-Kitagawa, Hisashi Tatebe, Kazuhiro Shiozaki and Motofusa Akiyama
DOI: 10.1039/c2ob27199k

On the inside front cover is the work of Francisco Santoyo-Gonzalez and collegues at the University of Granada, Spain. They report an easy Vinyl sulfone-based ferrocenylation reagents: applications in conjugation and bioconjugationvinyl sulfone functionalisation of ferrocene derivatives which facilitates the preparation of a variety of versatile ferrocenylation reagents. Their methodology allows the facile preparation of a variety of conjugates and bioconjugates derivatives under mild conditions.

Vinyl sulfone-based ferrocenylation reagents: applications in conjugation and bioconjugation
Alicia Megia-Fernandez, Fernando Hernandez-Mateo and Francisco Santoyo-Gonzalez
DOI: 10.1039/c3ob27209e

 

Both articles can be read for free for the next 6 weeks!

 

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This week’s HOT papers featuring recent advances in the synthesis of aromatic nitro compounds and more…

These articles are HOT as recommended by the referees. And we’ve made them free to access for 4 weeks.

Recent advances in the synthesis of aromatic nitro compounds
Guobing Yan and Minghua Yang
DOI: 10.1039/c3ob27354g  

recent advances in the synthesis of aromatic nitro compounds  

Free to access for 4 weeks


Facile dimethylarsenic exchange and pyramidal inversion in its cysteine and glutathione adducts
D. Scott Bohle and Yuxuan Gu
DOI: 10.1039/c3ob40268a 

Facile dimethylarsenic exchange and pyramidal inversion in its cysteine and glutathione adducts  

Free to access for 4 weeks  


PEGylation enables the specific tumor accumulation of a peptide identified by phage display
Walter Mier, Susanne Krämer, Sabine Zitzmann, Annette Altmann, Karin Leotta, Ursula Schierbaum, Martina Schnölzer, Michael Eisenhut and Uwe Haberkorn
DOI: 10.1039/c3ob27475f  

 

PEGylation enables the specific tumor accumulation of a peptide identified by phage display   

Free to access for 4 weeks  


Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer 2: generation of captodatively stabilised radicals
Mark E. Wood, Sabine Bissiriou, Christopher Lowe and Kim M. Windeatt
DOI: 10.1039/c3ob40275d  

Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer 2: generation of captodatively stabilised radicals   

Free to access for 4 weeks  

 

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Nucleic Acids: new life, new materials – web themed issue now published!

Read this joint OBC, ChemComm and RSC Advances web themed issue, showcasing some of the best research in Nucleic Acids chemistry

Organic & Biomolecular Chemistry, ChemComm and RSC Advances are delighted to announce the publication of a timely web collection on:

Nucleic Acids: new life, new materials

Guest-edited by:

Michael Gait (MRC, Laboratory of Molecular Biology, Cambridge, UK) Nadrian Seeman (New York University, USA)
Makoto Komiyama (University of Tsukuba, Japan) Oliver Seitz (Humboldt-Universität zu Berlin, Germany)
David Liu (Harvard University, USA) Jason Mickelfield (University of Manchester, UK)


Through over 70 communications, full papers, feature articles and perspectives, this collection guides the reader through the most recent and exciting findings in nucleic acids research and applications in emerging areas.

Some of the work presented in this virtual collection is also dedicated to the memory of Professor Har Gobind Khorana (1922 – 2011) and Dr Daniel McGillivray Brown (1923 – 2012) acknowledging their legacy to the nucleic acids community.

“The ingenuity of nucleic acids chemists is formidable, particularly in the newly emerging areas involving DNA architecture combined with novel chemical modifications and material composites. This web collection nicely showcases this potential.”
Read this and more in the guest-editors’ Editorial for the issue


As a taster, this collection of articles includes:

Pyridostatin analogues promote telomere dysfunction and long-term growth inhibition in human cancer cells
Sebastian Müller, Deborah A. Sanders, Marco Di Antonio, Stephanos Matsis, Jean-François Riou, Raphaël Rodriguez and Shankar Balasubramanian
Org. Biomol. Chem., DOI: 10.1039/C2OB25830G, Paper

A clocked finite state machine built from DNA
Cristina Costa Santini, Jonathan Bath, Andy M. Tyrrell and Andrew J. Turberfield
Chem. Commun., DOI: 10.1039/C2CC37227D

Theoretical model of substrate-assisted self-assembly of DNA nanostructures
Shogo Hamada and Satoshi Murata
RSC Adv., DOI: 10.1039/C2RA20764H

Reduction of metal ions by boranephosphonate DNA
Subhadeep Roy, Magdalena Olesiak, Petra Padar, Heather McCuen and Marvin H. Caruthers
Org. Biomol. Chem., DOI: 10.1039/C2OB26661J

Dehydration from conserved stem regions is fundamental for ligand-dependent conformational transition of the adenine-specific riboswitch
Vinit Kumar, Tamaki Endoh, Kentaro Murakami and Naoki Sugimoto
Chem. Commun., DOI: 10.1039/C2CC34506D

DNA glycoclusters and DNA-based carbohydrate microarrays: From design to applications
François Morvan, Sébastien Vidal, Eliane Souteyrand, Yann Chevolot and Jean-Jacques Vasseur
RSC Adv., DOI: 10.1039/C2RA21550K

The bacterial second messenger c-di-GMP: probing interactions with protein and RNA binding partners using cyclic dinucleotide analogs
Carly A. Shanahan and Scott A. Strobel
Org. Biomol. Chem., DOI: 10.1039/C2OB26724A

A DNA based five-state switch with programmed reversibility
Jonathan R. Burns, Søren Preus, Daniel G. Singleton and Eugen Stulz
Chem. Commun., DOI: 10.1039/C2CC35799B

Two-photon excitation of the fluorescent nucleobase analogues 2-AP and tC
R. S. K. Lane and S. W. Magennis
RSC Adv., DOI: 10.1039/C2RA21881J

…and many more.

We hope that you will find this collection enjoyable and stimulating to read!

Please feel free to send the link to the issue to other researchers who you think may be interested.

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“On-water” catalysis to facilitate chemical transformations: read Chris McErlean’s comments on this new methodology

Read the authors’ comments on their HOT research…

We are delighted to have received the authors’ comments from Christopher S. P. McErlean on the recently published HOT article “Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis”.

“Chemistry creates. It is the only discipline in which you can design or imagine a new entity and then go away and build it. Of course, it is always easier said than done, so synthetic organic chemists spend a good deal of their time exploring ways to build molecules more efficiently. That’s what the McErlean Research Group does at the University of Sydney. We are primarily focused on making synthesis easier.

Every undergraduate chemist knows that the aromatic Claisen rearrangement is a great way to build functionalized phenols. The reaction is so prevalent in heterocycle synthesis that we tend not to reference the original work – it is assumed knowledge. Our group envisaged that the aromatic aza-Claisen rearrangement would be an equally powerful way to make functionalised anilines, but the known reaction conditions are just too forcing to be useful.

“On-water” reactions rely on interfacial water to catalyze chemical transformations. Exactly how the interfacial water does this has been the source of much recent debate. Most of the protagonists have relied on computationally derived evidence to support one theory or another. We thought that we could kill two birds with one stone by using on-water catalysis to facilitate the aromatic aza-Claisen rearrangement and probe the kinetics of this transformation.

The outcomes of our work are twofold: an easy way to build functionalised naphthylamines and anilines, and experimental evidence that supports the acid-catalyzed nature of on water chemistry.

We hope that chemists employ this operationally simple synthetic tool to build life-changing molecules, and we hope that our results will spur more experimental chemists to provide hard data regarding the on-water phenomenon.”

This Communication is free to access for the next 4 weeks!

Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis
Kaitlin D. Beare and Christopher S. P. McErlean
DOI: 10.1039/C3OB40118A   

Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis

Interested in Christopher S. P. McErlean‘s research? Why not also read these recently published articles:

An in-water, on-water domino process for synthesis
Norcott, Philip; Spielman, Calan; McErlean, Christopher S. P.
Green Chem., 2012, 14, 605.
DOI: 10.1039/c2gc16259h

Total synthesis of C-19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran
Nesbitt, Caroline L.; McErlean, Christopher S. P.
Org. Biomol. Chem., 2011, 9, 2198.
DOI: 10.1039/c0ob00754d

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Multi-component synthesis of peptide–sugar conjugates on the cover of OBC Issue 15

The latest issue of Organic & Biomolecular Chemistry is now available online. With a pizza on the front cover, it couldn’t get any more Italian than that! Take a look at our wonderful covers from two Italian groups and discover all about the new research behind them.

Welcome to OBC Issue 15, 2013!

Multi-component synthesis of peptide-sugar conjugatesThe outside front cover highlights a research article by Volonterio et al. in Milan describing an efficient multi-component domino process for the synthesis of peptide-urea and glyco-urea–peptide conjugates. This novel one-pot reaction allows the synthesis of a wide array of structurally diverse peptide-sugar conjugates in high yield and in a regioselective manner, from easily accessible starting materials, under mild conditions. Glycopeptides play an important role in biology and medicine and are indispensable tools for probing biological process.  The possibility to obtain libraries of peptide-sugar conjugates, containing enzymatically more stable linkages, makes a highly-significant impact in the field of drug discovery research.

Multi-component synthesis of peptide–sugar conjugates
Maria Cristina Bellucci, Giancarlo Terraneo and Alessandro Volonterio
DOI: 10.1039/C3OB27176E

On the inside front cover is the result of a collaboration from scientists at the University of Cagliari, Florence and Southampton. Caltagirone and co-Bis-ureidic receptors for pyrophosphate optical sensingworkers report the synthesis and characterisation of a new family of bis-ureidic receptors (L1–L6). The 1H NMR, absorption, luminescence properties, as well as the X-ray structure of system L6, and ion-binding behaviour have been studied in detail and theoretical calculations have helped to explain the binding properties observed. These findings provide insight in the development of new colorimetric and luminescent flexible anion probes. 

A new family of bis-ureidic receptors for pyrophosphate optical sensing
Claudia Caltagirone, Carla Bazzicalupi, Francesco Isaia, Mark E. Light, Vito Lippolis, Riccardo Montis, Sergio Murgia, Martina Olivaria and Giacomo Piccia
DOI: 10.1039/ C3OB27244C

Both articles can be read for free for the next 6 weeks!

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This week’s HOT papers featuring the total synthesis of (±)-sacidumlignans D and A and much more

These articles are HOT as recommended by the referees. And we’ve made them free to access for 4 weeks.

Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction
Jian-Jian Zhang, Chang-Song Yan, Yu Peng, Zhen-Biao Luo, Xiao-Bo Xua and Ya-Wen Wang
DOI: 10.1039/ C3OB00053B 

 Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction   

Free to access for 4 weeks 


A traceless aryl-triazene linker for DNA-directed chemistry
Christian Hejesen, Lars K. Petersen, Nils Jakob V. Hansen and Kurt V. Gothelf
DOI: 10.1039/C3OB27504C   

 A traceless aryl-triazene linker for DNA-directed chemistry  

   Free to access for 4 weeks  


Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis
Kaitlin D. Beare and Christopher S. P. McErlean
DOI: 10.1039/C3OB40118A   

Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis   

Free to access for 4 weeks  


Reversible protein affinity-labelling using bromomaleimide-based reagents
Ramiz I. Nathani, Vijay Chudasama, Chris P. Ryan, Paul R. Moody, Rachel E. Morgan, Richard J. Fitzmaurice, Mark E. B. Smith, James R. Baker and Stephen Caddick
DOI: 10.1039/C3OB40239H 

 

Reversible protein affinity-labelling using bromomaleimide-based reagents     

Free to access for 4 weeks

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Work on metallo-β-lactamase inhibitors commended as Ricky Cain wins the latest OBC poster prize

Congratulations to Ricky Cain who was presented with the OBC poster prize award on the occasion of the Royal Society of Chemistry Organic Division North East Regional Meeting, held at the University of Huddersfield on Monday 4 March 2013.

Ricky is a postgraduate research student working under the supervision of Profs. Colin Fishwick and Peter Johnson at the University of Leeds,  and won for his work on the Design and synthesis of metallo-β-lactamase inhibitors. Ricky receives a one-year personal subscription to OBC.

Professor Joe Sweeney (University of Huddersfield) Dr Anne Horan (Royal Society of Chemistry) Ricky Cain (University of Leeds) Dr David Rees (Astex Pharmaceuticals and President of RSC Organic Division)

 Photo provided by the University of Huddersfield.

Also read the news item featured on the University of Leeds, School of Chemistry homepage.

Congratulations again to Ricky on his award! The OBC team wishes him all the very best with his future research work.

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Cube-octameric silsesquioxanes on the front cover of OBC Issue 14!

Welcome to Organic & Biomolecular Chemistry Issue 14, 2013.

Cube-octameric silsesquioxanes (COSS)

This week front cover highlights a perspective article by Sebastian Fabritz et al. from the Kolmar group at Darmstadt University of Technology on cube-octameric silsesquioxanes. These small compact and highly symmetric nanoparticles have recently attracted increased attention as scaffold for tailor-made bioconjugates. The low toxicity, combined with solubility in aqueous systems and a half-life sufficient for in vivo studies make these structures attractive targets for a number of applications, among them drug delivery, tumor diagnostics and therapy.

Bioconjugation on cube-octameric silsesquioxanes
Sebastian Fabritz, Sebastian Hörner, Olga Avrutina and Harald Kolmar
DOI: 10.1039/c2ob26807h

On the inside front cover is the work of Jian-Mei Lu and co-workers describing an effective alternative method for the synthesis of diarylmethane N-Heterocyclic carbene–palladium(II)–1-methylimidazole complexderivatives, which utilises a readily available N-heterocyclic carbene–palladium(II)–1-methylimidazole complex. This efficient catalyst allowed the Suzuki–Miyaura coupling of benzylic chlorides with arylboronic acids or potassium phenyltrifluoroborate in neat water under mild conditions.

N-Heterocyclic carbene–palladium(II)–1-methylimidazole complex catalyzed Suzuki–Miyaura coupling of benzylic chlorides with arylboronic acids or potassium phenyltrifluoroborate in neat water
Yun Zhang, Meng-Ting Feng and Jian-Mei Lu
DOI: 10.1039/c3ob27353a 

 

 

Both articles can be read for free for the next 6 weeks!

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HOT- Novel regio- and chemoselective C–H oxygenation

In this HOT article, Rao and co-workers report a novel Rh(II) and Ru(II) catalysed regio- and chemoselective C-H oxygenation for the facile synthesis of a variety of functionalised phenols from easily accessible arenes. The reaction demonstrates excellent reactivity, ortho-selectivity, good functional group tolerance and high yields. This practical method allowed the synthesis of a few 2-acylphenols in gram-scale and its utility has been well exemplified in further applications in heterocycle synthesis and direct modification of drug Fenofibrate.

Rh(II) or Ru(II) catalyzed C–H oxygenation of aryl ketones for the facile synthesis of diverse functionalized phenols

Broadening the catalyst and reaction scope of region- and chemoselective C–H oxygenation: a convenient and scalable approach to 2-acylphenols by intriguing Rh(II) and Ru(II) catalysis
Gang Shan, Xuesong Han, Yun Lin, Shanyou Yu and Yu Rao
DOI: 10.1039/C3OB27457H

Free to access for 4 weeks

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