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Tagetitoxin – real structure finally revealed?

For centuries, natural products have been linked to medicine through traditional remedies and since played an important role in drug discovery.

New structure of tagetitoxin

New tagetitoxin structure based on 2D NMR correlations

Despite competition from other drug discovery methods, natural products have provided their fair share of clinical candidates and commercial drugs. Furthermore, the isolation, synthesis and biological evaluation of natural products often lead to lasting impressions in science.

In a recent study lead by Dr Abil Aleiv of the University College London, the structure of the known natural product tagetitoxin has been revised based on a detailed analysis of newly acquired NMR and MS data. The group employed 2D 1H–13C HMBC correlations and long-range JCH couplings in conjunction with computational analysis to correlate JCH couplings with predicted values.

For several years, the structure of tagetitoxin remained a mystery. First identified in 1981 by Mitchell, the structure was only partially characterized by MS and was proposed to be an 8-membered heteroatomic ring.  Revised structures have since been published by Mitchel (1989), Vassylyev (2005) and Gronwald (2005). Despite all these efforts, conflicting results and incomplete analyses resulted in the absolute configuration remaining undetermined.

Structures of tagetitoxin previously published by Mitchel (1989), Vassylyev (2005) and Gronwald (2005)

Early analysis of complex structures was generally difficult as spectrometers were relatively insensitive and experiments were performed at low-fields strengths. Through the increasing prevalence and utility of modern 2D NMR experiments in the past decade, NMR has become a powerful and enabling tool for structure elucidation and confirmation.

In addition, the key to Dr Aliev’s findings lies in confirming the purity of the tagetitoxin sample the group had acquired. They noted that the compound gradually decomposed in aqueous solutions if left for prolonged periods of time, which they suspect led to additional peaks being observed in previously reported NMR spectra.

This exciting work showcases the importance of technical advances in determining the structure of biologically active natural products with greater ease and confidence. As a result, advances in lead development and the identification of important families of pharmacophores for drug discovery can be attained with greater efficiency, which may contribute to a revival of interest in natural products for drug discovery purposes.

To find out more see:

The structure of tagetitoxin
Abil E. Aliev, Kersti Karu, Robin E. Mitchell and Michael J. Porter
DOI: 10.1039/c5ob02076j


Victoria Corless is currently completing her Ph.D. in organic chemistry with Prof. Andrei Yudin at The University of Toronto. Her research is centred on the synthesis of kinetically amphoteric molecules, which offer a versatile platform for the development of chemoselective transformations with particular emphasis on creating novel biologically active molecules.

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OBC Call for Papers – Selective Chemistry with Peptides and Proteins Themed Issue

Organic & Biomolecular Chemistry is delighted to announce a call for paper for its latest themed issue on: Selective Chemistry with Peptides and Proteins

Guest Editor: Philip Dawson (The Scripps Research Institute, San Diego, USA)

Deadline for Submission: 11 April 2016

OBC offers fast decisions and publication (average time from receipt to first decision for peer reviewed articles is 12 days for communications and 19 days for papers). Colour publication is free and all articles are indexed in MEDLINE. You can choose for your article to be handled by the Cambridge office or one of our Associate Editors: Christian Hackenberger, Lei Liu, Margaret Brimble or Jin-Quan Yu.

Scope

This issue will cover topics including native chemical ligation and other chemical reactions to prepare proteins and peptides, and selective protein modification. We would welcome either a primary research article or a review.

Research in OBC is published as communications (for urgent work – up to 5 pages in length) or full papers. There is also the opportunity to write a Perspective or Review article for the issue, and if you would be interested in this please let us know. All submissions will be subject to rigorous peer review to meet the usual high standards of OBC. Guidelines are available at rsc.li/1K0EgYx and rsc.li/1OoQWQh.

If you are interested in taking part in this issue, please email OBC: obc-rsc@rsc.org

Manuscripts can be submitted using the Royal Society of Chemistry’s online article submission service. Please clearly state that the manuscript is submitted for the themed issue on Selective Chemistry with Peptides and Proteins.

To view recent articles or find out more about OBC, please visit the journal’s homepage:

Organic & Biomolecular ChemistryRapid publication of high quality organic chemistry research


Please note that articles will be published online as soon as ready to ensure no delay in dissemination of your work. Articles for the web theme will be published in regular issues of the journal. The themed issue will then be published online once all articles have been published. Click here for an example of a previous web theme issue in OBC.

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2016 RSC Prizes and Awards in Organic Chemistry & Chemical Biology now open for nomination

The 2016 RSC Prizes and Awards are now open for nomination!

Nominations will close on 15 January 2016.


For more than 140 years, our Prizes and Awards programme has been acknowledging and celebrating exceptional talent in the chemical sciences, and with your support we are hoping that 2016 will even more successful!

Last year’s winners include Chemists such as Prof. Wilfred van der Donk (University of Illinois), Prof. Tim Donohoe (University of Oxford), Prof. Shuli You (Shanghai Institute of Organic Chemistry), Prof. Philip Gale (University of Southampton), Prof. Herman Overkleeft (Leiden University), Prof. Alison Ashcroft and Prof. Sheena Radford (University of Leeds).

This year we have 63 prizes and awards open for nominations of individuals, teams and organisations covering the breadth of the chemical sciences across academia, education and industry.

This year’s prizes in the field of Organic Chemistry & Chemical Biology include:

CBID (Chemistry Biology Interface Division) awards –

Organic Awards –

For 2016 our Longstaff Prize is also open – since 1881 we have awarded this prize once every three years to one of our members who has achieved the most to advance the science of chemistry.

Submit your suggestions now!

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Shanti Swarup Bhatnagar Prize for Chemical Sciences awarded

Every year since 1958, the Council of Scientific and Industrial Research (CSIR) awards the Shanti Swarup Bahtnagar Prize for Chemical Sciences to up to two Indian scientists up to the age of 45 for exceptional and outstanding research.

Shanti Swarup Bhatnagar Prize Winner 2015One of this year’s winners, Srinivasa Reddy, received the prize for his notable work in the fields of organic synthesis and medicinal chemistry. The research group of Dr Reddy is situated at the CSIR-National Chemical Laboratory in Pune, India, and not only works on the design and synthesis of new agrochemicals for advanced crop protection,1 but also develops new concepts and drugs for the treatment of diseases such as diabetes and Alzheimer’s.2–4

The prize includes a citation, a plaque and a cash prize and will be distributed by the Prime Minister of India. As part of the award the awardee will also be giving a lecture later on the topic of the award.

In line with this, at the end of this month one of the biggest and most important Indian meetings will be held in Jaipur – the 17th NOST-Organic Chemistry Conference, at which our India representative Deeksha Gupta will be present and one of OBC’s Editorial Board members, Christian Hackenberger will be giving a talk on the ‘Synthesis and Cellular Delivery of Functional Proteins’.

References

1 Srinivasa et al., “Silicon Incorporated Morpholine Antifungals: Design, Synthesis, and Biological Evaluation”, ACS Med. Chem. Lett., 2015, DOI: 10.1021/acsmedchemlett.5b00245.

2 Srinivasa et al., “Identification of noreremophilane-based inhibitors of angiogenesis using zebrafish assays”, Org. Biomol. Chem., 2015, DOI: 10.1039/C5OB01594D.

3 Srinivasa et al., “Synthesis of palmyrolide A and its cis-isomer and mechanistic insight into trans–cis isomerisation of the enamide macrocycle”, Chem. Commun., 2013, DOI: 10.1039/C3CC40541A

4 Srinivasa et al., “Zinc mediated allylations of chlorosilanes promoted by ultrasound: Synthesis of novel constrained sila amino acids”, Org. Biomol. Chem., 2014, DOI: 10.1039/C4OB00294F

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RSC Organic Division Poster Symposium 2015

RSC Organic Division Poster Symposium 2015, headline sponsored by F. Hoffmann-La Roche, Ltd.

Abstract submission is now open.

This poster symposium for final year organic chemistry PhD students will take place at The Royal Society of Chemistry at Burlington House, in London, Monday 30 November 2015.

The closing date for submissions is Wednesday 30 September 2015.
Get more information or submit an abstract now.


This symposium offers final year PhD students a chance to showcase their research to their peers, leading academics and industrial chemists. It is open to all branches of organic chemistry – in its broadest interpretation – and has a tradition of being the most competitive and highly-regarded organic chemistry symposium for PhD students in the UK and Ireland.

There will be a first prize of £500, two runner-up prizes of £250, and a ‘selected by Industry’ prize – also of £500. Industrial delegates will select this winner based on the potential for application in an industrial context.

We would like to thank F. Hoffmann-La Roche, Ltd. and our industry sponsors for their generous support of this event.

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Poster prize winners at ESOC

Congratulations to the Poster Prize winners at ESOC 2015.

The winners are:

  • Michael E. Muratore (OBC Best Oral Comm Prize) – “The versatility of gold(I) catalysis applied to the total synthesis of (-)-nardoaristolone B and lundurine C”
  • Joanna Wencel-Delord (OBC Poster Prize) – “Asymmetric C-H activation and dynamic kinetic resolution: new tool for the synthesis of axially chiral biaryls”
  • Szilár Varga (ChemComm Poster Prize) – “Organocatalytic approach to indole terpenoids”
  • Ana M. Matos (MedChemComm Poster Prize) – “Genista tenera as a source of new innovative molecular leads against diabetes and related amyloid disorders: phytochemistry, synthesis and mechanism of action”

The European Symposium of Organic Chemistry is a biannual event which is held all over Europe.  The 19th European Symposium of Organic Chemistry was held from 12th – 16th of July in Lisbon, at the Universidade de Lisboa.   The conference is aimed at stimulating new emerging areas in Organic Chemistry.

Photos of the winners below (from left to right): Michael E. Muratore, Joanna Wencel-Delord, Ana M. Matos and Szilár Varga.

Michael E. Muratore (OBC Best Oral Comm Prize) Joanna Wencel-Delord (OBC Poster Prize)
Ana M. Matos (MedChemComm Poster Prize) Szilár Varga (ChemComm Poster Prize)
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Fast decisions and publication in Organic & Biomolecular Chemistry

At Organic & Biomolecular Chemistry we understand the importance of getting your work seen by your peers in the organic chemistry community as soon as possible.

This is why we get you a decision as fast as possible without compromising on the quality of the review process.

The average time for you to get the first decision on your Organic & Biomolecular Chemistry submission is just:

Communications: 12 days
Papers: 19 days

What is more, from submission to publication of the fully edited version of your manuscript (including time for author revisions) it takes on average:

Communications: 36 days
Papers: 49 days

This is based on all articles sent out to referees in the period January–June 2015. Articles that did not pass an initial assessment have not been included in this calculation.



Want to know more about OBC and the benefits of publishing your work with us?

Want to experience the same service as your colleagues that publish with us?

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OBC call for papers: Multivalent Biomolecular Recognition themed issue

Organic & Biomolecular Chemistry is delighted to announce a call for paper for its latest themed issue on: Multivalent Biomolecular Recognition

Guest Editors: Prof.  Mihail Barboiu (Institut Européen des Membranes, France),  Prof. Olof Ramström (KTH – Royal Institute of Technology, Sweden) and Prof. Stéphane Vincent (University of Namur, Belgium)

Submission Deadline: 15th July 2015

From the guest-editors:

The understanding and control of multivalent biomolecular interactions has become one of the key frontiers of chemistry and biology. This issue will cover important findings and advances in the field, in order to:
1. Develop functional sugar decorated nanoplatforms (nanoparticles, nanostructured surfaces, vesicles, microarrays, etc.).
2. Understand the biomolecular mechanisms by exploring their synergistic adaptive interactions with biomolecules, in order to accurately control the chemical/biological responses.

The inspiration for this issue comes partly from our membership of the EU-funded Dynamic Interactive Nanosystems ITN Marie Curie DYNANO Network (see http://www.dynano.eu ). We hope that colleagues from the Network will participate but are also very welcoming to contributors who have not (yet) joined our association.

Research in OBC is published as communications (for urgent work – up to 5 pages in length) or full papers. There is also the opportunity to write a Perspective or Review article for the issue, and if you would be interested in this please let us know. All submissions will be subject to rigorous peer review to meet the usual high standards of OBC.

The deadline for submissions to the themed issue is 15th July 2015, although submissions before this date are of course welcomed.

Manuscripts can be submitted using the RSC’s online submissions service. Please clearly mark that the manuscript is submitted for the themed issue on ‘Multivalent Biomolecular Recognition’.

Please would you inform the editorial office by e-mail as soon as possible if you plan to submit to the issue and whether your contribution will be original research or a review-type article. We would like to have a list of authors who intend to contribute as soon as possible.

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Winners at the 2014 RSC Organic Division Poster Symposium

Congratulations to the winners at the 2014 RSC Organic Division Poster Symposium, held on 01 December 2014 at the Royal Society of Chemistry, Burlington House, London.

The symposium, supported by headline sponsor F. Hoffmann-La Roche Ltd, provided a fantastic opportunity for final year organic chemistry PhD students to showcase their research and network with their peers, leading academics, and industrial chemists.

Organic & Biomolecular Chemistry was delighted to offer a front cover artwork opportunity to the winner of the First Prize, as well as a 1-year personal subscription to the journal to the winner of the Industry Prize.

First Prize

Sonja Kuschel, University of Manchester (Supervisor: Professor David Leigh). Poster title: Towards man-made ribosomes: Nanomachines for sequential peptide synthesis

Runners Up Prizes

Antony Burton, University of Bristol (Supervisor: Professor Derek Woolfson). Poster title: Installing Catalytic Activity into a de novo Designed Protein Structure

Sarah Walker, Heriot-Watt University (Supervisor: Dr Ai-Lan Lee). Poster title: Development of Pd(II)-catalysed oxidative Heck reactions and CH functionalisations

Industry Prize (selected by the industrial delegates)

Antoine Maruani, University College London (Supervisors: Professor Stephen Caddick and Dr Vijay Chudasama). Poster title: A Novel Class of Tuneable reagents for Selective Dual Modification of Proteins

Participants’ Prize (selected by the students)

Owen Davis, Imperial College London (Supervisor: Dr James Bull). Poster title: Synthesis and Functionalisation of Highly Substituted Oxetanes: Molecular Scaffolds for Drug Discovery

The event was also supported by: AstraZeneca, Evotec, Johnson Matthey Catalysis and Chiral Technologies, Pfizer Neusentis, Takeda, UCB and Vertex Pharmaceuticals.

Winners (left to right): Sonja Kuschel, Owen Davis, Sarah Walker, Antony Burton, Antoine Maruani (© MPP Image Creation / Royal Society of Chemistry)

With the judges and organising committee (left to right): Dr Andrew Thomas, Dr Anne Horan, Professor Jonathan Clayden, Mr Owen Davis, Professor Rob Field, Mrs Sonja Kuschel, Professor Julian Blagg, Miss Sarah Walker, Professor Stuart Conway, Mr Antony Burton, Mr Antoine Maruani, Dr David Rees, Dr Sarah Rook, Professor Sue Gibson, Miss Charlotte Still (© MPP Image Creation / Royal Society of Chemistry)

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Take 1…minute for chemistry in health

Can you explain the importance of chemistry to human health in just 1 minute? If you’re an early-career researcher who is up to the challenge, making a 1 minute video could win you £500.

The chemical sciences will be fundamental in helping us meet the healthcare challenges of the future, and we are committed to ensuring that they contribute to their full potential. As part of our work in this area, we are inviting undergraduate and PhD students, post-docs and those starting out their career in industry to produce an original video that demonstrates the importance of chemistry in health.

We are looking for imaginative ways of showcasing how chemistry helps us address healthcare challenges. Your video should be no longer than 1 minute, and you can use any approach you like.

The winner will receive a £500 cash prize, with a £250 prize for second place and £150 prize for third place up for grabs too.

Stuck for inspiration? Last year’s winning video is a good place to start. John Gleeson’s video was selected based on the effective use of language, dynamic style, creativity and its accurate content.

The closing date for entries to be submitted is 30 January 2015. Our judging panel will select the top five videos. We will then publish the shortlisted videos online and open the judging to the public to determine the winner and the runners up.

For more details on how to enter the competition and who is eligible, join us at the Take 1… page.

Good luck!

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