Author Archive

Vaccines for heroin

The number of deaths due to heroin overdoses has severely increased in last decade, and regular consumption of heroin leads to serious health concerns.

Vaccination is one of the emerging choices among heroin rehabilitation therapies. In general, these vaccines contain heroin-like hapten as a pharmacophore that acts as an antagonist. This antagonist has high affinity for heroin receptors but does not activate them, hence reverses the effects of heroin. Because of inherent chemical instability, when entered in to bloodstream these anti-heroin drugs rapidly metabolise into several by-products, which makes development of effective vaccines against heroin particularly challenging.

Recently an American research group at National Institute on Drug Abuse (NIDA) lead by Professor Kenner Rice has reported the synthesis and immunological evaluation for a series of haptens.

The team has emphasised the hydrolytic stability of hapten scaffolds and envisioned that hapten with amido groups at both the C3 and C6 positions should be more stable than a hapten with an ester in one of those positions. Insertion of a 3-amino group and the construction of a C-6α-(2-oxo-propyl) group stereoselectively was the challenging task towards the synthesis of designed hapten derivatives. The group has tackled the synthetic hurdle by adopting convergent synthesis approach and validating the stereochemistry by single X ray crystallography.

Furthermore, in vivo Immunological studies of all three new synthetic haptens reveals that one derivative DiAmHap (3) is chemically more stable and better candidate for a heroin vaccine than 6-PrOxyHap (1) and DiPrOxyHap (2). This work is a very positive step towards the development of vaccines for heroin abuse.

Synthesis and immunological effects of heroin vaccines
Fuying Li, Kejun Cheng,  Joshua F. G. Antoline, Malliga R. Iyer, Gary R. Matyas, Oscar B. Torres, Rashmi Jalah, Zoltan Beck, Carl R. Alving, Damon A. Parrish, Jeffrey R. Deschamps, Arthur E. Jacobson and Kenner C. Rice
DOI: 10.1039/C4OB01053A

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Amino acids: fluorescensors for mercury ions

Many human activities have been responsible for heavy metal poisoning in recent years, Mercury (Hg) poisoning being one of them. Mercury occurs in several forms and even trace concentrations of mercury ions in crops, fish or the human body are enough to produce potentially toxic effects to vital organs. Mercury poisoning can lead to several diseases including Acrodynia (also known as the pink disease), the Hunter-Russell syndrome and the Minamata disease.

Selective detection of mercury, particularly in aqueous media, has been a key area for analytical chemists, since traditional analytical techniques for mercury detection are time consuming, laborious and involve expensive instrumentation. In this work, Korean researcher Keun-Hyeung Lee and co-workers have developed a pair of very sensitive amino acid based fluorescence-ON probes for the exclusive detection of mercury ions in aqueous solution.

The team has combined the fluorescence properties of pyrene and Hg(II) binding ability of tyrosine residues for the design and synthesis of two novel fluorescensors. Both newly-synthesised probes show emission maxima at 386 and 400 nm in the absence of Hg(II) ion. Upon titration with Hg(II) ions, both probes show exponential fluorescence enhancement and display a remarkable red shift (90-100 nm) emission. These probes are also highly selective for mercury ions in the presence of a range of other metal ions and are effective in aqueous solutions.

The team further clarifies the binding mode of these sensors and the coordination of the metal ion. This method can be implemented for rapid and quantitative detection of Hg(II) from various polluted water sources. This work also underscores the unconventional use of an amino acid as a chemosensor.

Ratiometric fluorescence chemosensor based on tyrosine derivatives for monitoring mercury ions in aqueous solutions
Ponnaboina Thirupathi, Ponnaboina Saritha (née Gudellin) and Keun-Hyeung Lee
DOI: 10.1039/C4OB01044B

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Introducing two new article types for Organic & Biomolecular Chemistry

OBC is introducing two new review article types: Reviews and Perspectives. These replace previous review article types and offer our authors and readers an even broader range of reviews, opinions and commentaries on the latest developments in organic chemistry and chemical biology.

Reviews
OBC Reviews are short, easy-to-read review articles covering current areas of interest to the OBC audience. Flexible in style, they give a concise and critical appraisal of recent advances in an established field or a new area of research.

Authors are encouraged to include their own views on developments, trends and future directions, with speculation about the future potential of the field particularly encouraged. Reviews are typically 6-12 pages in length. 

Reviews replace the previous Perspective and Emerging Area article types. While there is a change in name, the flexibility and breadth of style and content remain very much the same. Authors can write on established topics of current interest or emerging topics that are in the early stages of development. All of these styles will be consolidated under the Review name.*

Perspectives
OBC Perspectives are changing. These are now a new article style which will highlight pieces of exciting, recently-published research. Written by the authors of the original research, Perspectives will give a personal viewpoint on the topic, discussing their research in the wider context of the field and the future potential for the area.

Perspectives are designed to be short (2-4 printed pages) articles, briefly covering:

  • The background to the research area; its importance and previous developments
  • A summary of the key aspects of the research paper(s) recently published by the author
  • An outlook on future progression of the field, including how the author’s research could impact that

 Each Perspective will focus on just one or two recently-published research papers by the author. They will not cover large aspects of an author’s previous research.

 For guidelines on the new article types please click on the following links: Reviews | Perspectives.

*As a result of these changes the Emerging Area article type has been discontinued. Any emerging area style article should now be submitted under the Review article type.

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RSC Organic Division Poster Symposium 2013, sponsored by F. Hoffmann-La Roche, Ltd.

The poster symposium, for final year organic chemistry PhD students, will take place at The Chemistry Centre, Burlington House, London on Monday 2nd December 2013. The symposium offers final year PhD students a chance to showcase their research to their peers, leading academics and industrial chemists, and is open to all branches of organic chemistry.

The symposium has a tradition of being the most competitive and highly regarded organic chemistry symposium for PhD students in the UK, with generous support provided by F. Hoffmann-La Roche, Ltd. There will be a first prize of £500, two runner-up prizes of £250, and a “selected by Industry Prize”. Industrial delegates will be asked to make this selection with a particular emphasis on the potential for application in an industrial context and the winner will also receive a prize of £500.

Closing date for submissions is Wednesday 2nd October. Further information and abstract submission, via the online submission form, can be found on the symposium webpage.

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OBC poster prizes at the 5th Chemical Protein Synthesis

Congratulations to Stijn Agten and Claudia Bello who both received OBC poster prizes at the 5th Chemical Protein Synthesis meeting in Vienna last month.

Stijn Agten, from the group of Professor Tilman Hackeng at Maastricht University, The Netherlands won for a poster entitled “Chemoselective reactions in proteins and peptides using an optimized oxime strategy: the demise of levulinic acid”, while Claudia Bello from the Institute of Biological Chemistry at University of Vienna presented a poster entitled “A Chemoenzymatic Approach for the Preparation of Site-Specifically O-Glycosylated MUC1 variants for Proteomic Studies”.

Both winners receive a year’s subscription to OBC.

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RSC India roadshow 2013

Members of RSC Editorial Boards and staff have just returned from the RSC India Roadshow. More than 1500 delegates attended the three events in Kolkata, Bangalore and Pune, where both international and local speakers presented their latest research.
A packed audience for Professor George Whiteside's lecture at IISc Bangalore
A packed audience at Professor George Whitesides’ lecture at IISc Bangalore

At each event Professor George Whitesides, Chair of the Lab on a Chip Editorial Board, gave a plenary lecture which was followed by parallel symposia on Chemical Biology and Physical & Materials chemistry. Visit the RSC India Roadshow website to see more information and photos from the events.

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OBC symposium concludes in Beijing

The final day of the OBC symposium saw us arrive at Peking University.

Professor Lei Liu presenting at Peking University

The day opened with PKU head of organic chemistry Professor Zhenfeng Xi welcoming us to the institute, and this was followed by Andrei Yudin’s final presentation and then Professor Guanxin Liang from Nankai University showing a variety of natural product syntheses from his lab. The morning was rounded off by Dirk Trauner.

The first afternoon session showcased the work of Professors from two institutes in Beijing. Professor Lei Liu from Tsinghua University presented on protein synthesis while Professor Sanzhong Luo from the Institute of Chemistry, Chinese Academy of Sciences showed his latest research on asymmetric binary-acid catalysis.

The second afternoon session saw OBC Chair Jeffrey Bode giving another demonstration of his research into amide-forming reactions, and then Professor Zhi-Xiang Yu from Peking University gave an interesting overview of the potential power of computational chemistry in natural products synthesis.

Our visit to Beijing was a great way to finish this first OBC symposium and we’re very grateful to local organiser Professor Jianbo Wang and all of the speakers.

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OBC Symposium moves to Lanzhou University

Following a successful first day in Shanghai, the OBC Symposium travelled to Lanzhou. On arrival we were greeted by a huge banner opposite the entrance. No one visiting the University would be in any doubt that OBC were in town!

The OBC symposium banner at the entrance to Lanzhou University

The day started with a welcome by Director of the State Key Laboratory of Applied Organic Chemistry at Lanzhou Professor Yongqiang Tu, which was followed by Dirk Trauner’s presentation on natural product synthesis. The morning was rounded-off by Professor Xiaoming Feng from Sichuan University, who guided us through his research on asymmetric catalysis using chiral N,N’-Dioxide ligands.

Professor Andrei Yudin at Lanzhou University

Following lunch Professor Hongbin Zhang from Yunnan University presented the syntheses of some bioactive alkaloids. Professor Tu then returned to the stage to continue the natural products synthesis theme by giving an overview of his work on syntheses which employ 1,2-migration reactions. Andre Yudin gave another overview of his work using amphoteric molecules and the final talk of the day was given by Professor Hanmin Huang from Lanzhou Institute of Chemical Physics, on C-C and C-N bond formation via C-H activation.

All in all it was a very enjoyable visit to Lanzhou. Our thanks go to Professor Tu for hosting us, Professor Wei Wang and his colleagues for local organisation and to all the speakers.

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OBC Symposium starts at Shanghai Institute of Organic Chemistry

The 1st Organic & Biomolecular Chemistry International symposium is underway. This event, visiting three prominent organic chemistry departments in China, brings together speakers from China, Europe and North America.

OBC participants

Participants at the OBC Symposium at SIOC

First stop for the symposium was Shanghai Institute of Organic Chemistry, and day was started with an introduction from SIOC Director Professor Kuling Ding. The opening lecture was given by Professor Guo-Qiang Lin, who gave an overview of his work on the synthesis of chiral dienes, useful ligands for transition metal catalysis. Following that OBC Chair Professor Jeffrey Bode (ETH Zurich, Switzerland) presented developments from his group on amide-forming reactions. After the break Professor Dawei Ma (SIOC) showed some of his recent work in the synthesis of the bioactive alkaloids Berbamine and the Communesins.

Professor Dawei Ma presents his research

After lunch Professor Dirk Trauner (LMU Munich, Germany) gave an energetic overview of a number of natural product syntheses, probing reactions beyond the limits of biomimetic synthesis. Next up was Professor Xuhong Qian (East China University of Science and Technology, Shanghai), who gave an overview of his development of dyes for fluorescent sensing and anticancer applications. After coffee Professor Andrei Yudin (University of Toronto) described a number of areas where his group has been using amphoteric molecules, and the day was rounded off by Professor Yong Tang (SIOC) and his work with pendant-bisoxazoline ligands.

Professor Yong Tang speaking at the symposium

Many thanks to all the speakers, chairs and attendees for making this a successful start to the OBC Symposium. Particular thanks go to Professor Shuli You and his colleagues at SIOC for the local organisation of the meeting.

Next stop, Lanzhou….

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Organic & Biomolecular Chemistry International Symposium

The first Organic & Biomolecular Chemistry International Symposium will take place in China in April 2012. The symposium will be comprised of three one-day meetings, each one featuring a selection of lectures covering organic and bioorganic chemistry by some of the world’s leading international scientists.

The meetings will be held at Shanghai Institute of Organic Chemistry, Lanzhou University and Peking University. The symposium is organised by Organic & Biomolecular Chemistry, the Royal Society of Chemistry and the local host organisations. The OBC International Symposium will take place as follows:
• Monday 16th April 2012 – Shanghai Institute of Organic Chemistry, Shanghai, China
• Wednesday 18th April 2012 – Lanzhou University, Lanzhou, China
• Friday 20th April 2012 – Peking University, Beijing, China

For more information please visit the symposium website.

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