Directing Biosynthesis V

22-24 March 2017 at the University of Warwick, UK

Don’t miss the fifth edition of this highly successful international natural products and chemical biology conference at the University of Warwick. Keynote speakers include Wilfred van der Donk, Janet Smith, John Verderas, Joern Piel and many more.

Oral abstract submission is now open!

Closing date 9 October 2016: submit abstracts online here.

This conference will cover aspects of natural product synthesis and development with emphasis on…

  • Biosynthesis of cell walls – targets for antimicrobials
  • Pathway engineering
  • Enzymology and structural biology
  • Natural products discovery – a response to AMR
  • Chemical ecology

Posters and exhibitors also welcome. Contact events@rsc.org for more information.

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OBC Call for Papers – Polycyclizations in Synthesis and Biosynthesis themed issue

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

Polycyclizations in Synthesis and Biosynthesis

Guest Editors: Michel Gagné (University of North Carolina at Chapel Hill, USA), Rong-Jie Chein (Academia Sinica, Taiwan) and Dean Tantillo (University of California Davis, USA)

Deadline for Submission: 1 February 2017

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 research on the development of new polycyclization reactions including new reagents and catalysts, applications to total synthesis and/or diversity-oriented synthesis, and experimental and/or theoretical mechanistic studies on polycyclizations in synthesis or biosynthesis.










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 Polycyclizations in Synthesis and Biosynthesis.

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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Engineering artificial metalloenzymes for applications in photoredox catalysis

Synthetic methodologies to control the selectivity and specificity of catalytic reactions remain the subject of intense research due to the importance of chiral compounds in pharmaceuticals, agrochemicals and functional materials. Homogenous catalysis takes advantage of weak interactions between the substrate, catalyst and groups distal to the active site to impart selectivity. Such features are ubiquitous in enzymes which display exceptionally high levels of stereochemical control and activity. In order to exploit the advanced capabilities of such enzymes for selective catalytic transformations, researchers have linked transition metal catalysts with different biological scaffolds–proteins, peptides, DNA–to create artificial metalloenzymes.

Since their inception in the late 1970’s, artificial metalloenzymes have emerged as a vibrant area of research with numerous examples of a variety of catalytic transformations reported alongside creative methods for incorporating the transition metal complex into the biomolecular scaffold. Key to their design is the ‘second coordination sphere’ provided by the biological scaffold where supramolecular interactions within the active site contribute to the rate and enantioselectivity of the system.

Prof. Thomas Ward and Prof. Oliver Wenger of the University of Basel have recently reported a novel biotin-streptavidin system equipped with an anchored photosensitizer capable of undergoing electron transfers between the biotinylated electron donor and ruthenium(II)-labeled streptavidin.

In the past, studies of the luminescent properties of biotinylated d6 metal complexes, common in photoredox catalysis, have been carried out for the purposes of cell imaging and ruthenium and rhenium complexes have been employed in the elucidation of electron tunneling pathways of various proteins. The application of phototriggered electron transfers to ruthenium photosensitizers, up until this point, had not yet been realized and this recent discovery demonstrates a significant advancement within this field.

This new biotin-streptavidin artificial metalloenzyme contains a ruthenium catalyst and photosensitizers embedded within the biotin binding pocket of streptavidin through covalent interactions with non-native cysteine residues. Their performance in various electron transfer studies demonstrates their potential to behave as advanced photoredox catalysts and given the diversity of reactions amenable to photoredox processes, these novel artificial metalloenzymes will provide unique opportunities within selective catalysis.

To find out more see:

Light-driven electron injection from a biotinylated triarylamine donor to [Ru(diimine)3]2+-labeled streptavidin
Sascha G. Keller, Andrea Pannwitz, Fabian Schwizer, Juliane Klehr, Oliver S. Wenger and Thomas R. Ward
DOI: 10.1039/C6OB01273F


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 prize winner at CRSI National Symposium

Congratulations to the OBC poster prize winner at the 2016 CRSI National Symposium!

We were pleased to present the OBC poster prize to Mr. K. Rajasekhar from the group of T. Govindaraju at the Jawaharlal Nehru Centre for Advanced Scientific Research, Bangalore. Mr. K. Rajasekhar presented his work on ‘Rationally designed peptidomimetic modulators of AB toxicity and related oxidative stress in Alzheimer’s disease’ on which he also recently published a Feature Article in Chemical Communications.


The 19th CRSI National Symposium in Chemistry is the most important annual chemistry symposium in India and took place from 14-16 July 2016 at the University of North Bengal (NBU), India.


Read K. Rajasekhar’s recent Feature article in ChemComm:

Function and toxicity of amyloid beta and recent therapeutic interventions targeting amyloid beta in Alzheimer’s disease
K. Rajasekhar, Malabika Chakrabarti and T. Govindaraju
Chem. Commun., 2015,51, 13434-13450

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RSC Organic Division Poster Symposium 2016

Headline sponsored by F. Hoffmann-La Roche, Ltd.

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 5 December 2016.

Abstract submission is now open!

The closing date for abstract submissions is Monday 3 October 2016. 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, and a ‘selected by Industry’ prize. 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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Past and present methodologies for the synthesis and functionalization of heterocycles and their impact on drug discovery

Heterocycles play a central role in modern drug design and this is reflected in the fact that they are present within the majority of marketed drugs. Their prevalence in medicine is not unexpected as heterocycles are the core elements of natural bioactive molecules and medicinal chemistry is centred around simulating the biological effects elicited by these privileged scaffolds.

Advances in organic synthesis are critical to the drug discovery process. The breadth of available synthetic methodologies related to heterocycle functionalization represents an almost endless source of innovation for the medicinal chemist. What is interesting however is the bias within the pharmaceutical industry toward relatively few reaction types. But why are certain methodologies favoured and what has been the long term impact?

Numerous reviews and analyses have been published wherein the types of chemical reactions used by the pharmaceutical industry over the past 30-50 years have been assessed and it has been established that of the current, most frequently used synthetic reactions—for example, amide bond formation, Suzuki-Miyaura cross-coupling, SNAr—none were discovered within the past 20 years.1 Increase in available commercial reagents, robustness and chemoselectivity has only amplified medicinal chemists’ preference for these reaction types.

The integration of new, ground-breaking methodologies in heterocycle synthesis such as ring-closing metathesis, C–H activation, multi-component reactions, photoredox catalysis etc. has been slow and this reliance on a select few reaction types has resulted in an overpopulation of a small amount of chemical space. Granted, underlying reasons for selected routes in a medicinal chemistry program are complex and the constant pressure to produce, maintain timelines, follow regulations and remain competitive is valid. However, this approach has not necessarily translated into an increase in FDA approved drugs. It’s fair to question whether or not such a practise is fully exploiting the vast toolbox of synthetic methodology available to medicinal chemists which could lead to new, diverse chemical space and new opportunities to tackle issues presently facing the pharmaceutical industry.

In a recently published OBC review as part of the themed collection on Contemporary Synthesis in Drug Discovery, scientists from Pfizer outline recent developments from both industry and academia in heterocycle synthesis and functionalization within the context of drug discovery. The purpose of this and other reviews is to help raise awareness and even popularize novel synthetic methodologies within the pharmaceutical industry. This is likely to be of greater impact in drug discover if more industrial-academic partnerships were to collaborate in the development of novel synthetic approaches toward medicinally relevant heterocycles. Regardless, advancements in synthetic chemistry are intertwined with the development of interesting molecular designs and transformative medicines.

1. Alexandria P. Taylor, Ralph P. Robinson, Yvette M. Fobian, David C. Blakemore, Lyn H. Jones and Olugbeminiyi Fadeyi, Org. Biomol. Chem.2016, 14, 6611–6637


To find out more see:

Contemporary Synthetic Chemistry in Drug Discovery OBC Themed Collection

Modern advances in heterocyclic chemistry in drug discovery
Alexandria P. Taylor, Ralph P. Robinson, Yvette M. Fobian, David C. Blakemore, Lyn H. Jones and Olugbeminiyi Fadeyi
DOI: 10.1039/C6OB00936K


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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Prize winners at the Southampton Supramolecular Chemistry Conference

Congratulations to all the prize winners at the Southampton Supramolecular Chemistry Conference 2016.

We were pleased to present prizes to these winners:

Valentina Santolini (Imperial College London) - ChemSocRev Talk Prize

Daniel Cornwell (York University) – Organic & Biomolecular Chemistry Talk Prize

Chris Taylor (Sheffield University) - ChemComm Poster Prize

The conference took place at University of Southampton on 24th June 2016.
It was focused on early career researchers working within Supramolecular Chemistry.  The conference was a great opportunity for PhDs and postdocs to present their research and network with their peers and leaders within this field.
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‘Microbial protein targets: towards understanding and intervention’ meeting

Hosted by The British Society of Parasitology in collaboration with the Royal Society of Chemistry

Microbial protein targets: towards understanding and intervention

14–16 September 2016, Durham, UK

This symposium will bring together leading expertise in protein structure determination, biochemical characterization and chemical biology to explore the most recent advances in the understanding of protein function and inhibition in microbial pathogens – both bacteria and parasites.

An exciting line-up of speakers will present their recent work in the area. Some of the confirmed speakers are:

  • Chris Abell University of Cambridge, UK
  • Gerald Spaeth Institut Pasteur, Paris, France
  • Ed Tate Imperial College London, UK
  • Maria Marco-Martin GSK Tres Contos, Spain

Take advantage of this opportunity to showcase your work alongside leaders in the field and submit an abstract for an oral or poster presentation today. Through generous sponsorship from the RSC Chemical Biology Interface Division and the BSP there are bursaries available for early career researchers to support their participation at this meeting.

The oral abstract deadline has just been extended until 15 July 2016, and poster abstracts are welcome until 5 August 2016. For more information and to register please visit the conference webpage.

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New Editorial and Advisory Board Members

A warm welcome to Géraldine Masson, Govindasamy Mugesh, Gonçalo Bernardes and Ratmir Derda

We are very pleased to welcome two new members to our Organic & Biomolecular Chemistry Editorial Board and two new members to our Advisory Board – Dr Géraldine Masson (Institut de Chimie des Substances Naturelles, France) and Professor Govindasamy Mugesh (Indian Institute of Science, Bangalore, India), and Dr Gonçalo Bernardes (University of Cambridge, UK) and Dr Ratmir Derda (University of Alberta, Canada).

Géraldine Masson received her PhD in 2003 from the Joseph Fourier University, (France), under the supervision of Dr. Sandrine Py and Prof. Yannick Vallée. In the years 2003–2005 she was a Marie Curie postdoctoral research fellow with Prof. Jan van Maarseveen and Prof. Henk Hiemstra at the University of Amsterdam (Holland). In 2005, she joined the Institut de Chimie des Substances Naturelles (CNRS, France) as Chargé de Recherche and was promoted to Director of Research 2nd class in 2014. Her group’s research activities are directed toward the development of new organocatalytic enantioselective reactions and novel synthetic methodologies, and photoredox catalysis and their application in the synthesis of diverse natural and unnatural molecules displaying biologically activities.


Mugesh received his B.Sc. (1990) and M.Sc. (1993) degrees from the University of Madras and Bharathidasan University, respectively. He obtained his Ph.D. (1998) at the Indian Institute of Technology, Bombay. He was an Alexander von Humboldt Fellow at the Technical University, Braunschweig, Germany and a Skaggs postdoctoral fellow at the Scripps Research Institute, La Jolla, USA. Mugesh is an author of more than 120 publications in international peer reviewed journals. He received several awards and recognitions, which include: J. C. Bose National Fellowship, Government of India (2016); Asian Rising Star Commemorative Plaque, Asian Chemical Congress (2013), Fellow, Royal Society of Chemistry (FRSC, 2013), Shanti Swarup Bhatnagar Prize (2012), Fellow, The National Academy of Sciences, India (2012), AstraZeneca Excellence in Chemistry Award (2012); Fellow, Indian Academy of Sciences (2012); Swarnajayanti Fellowship, Government of India (2006-07).

His research interests include:

  • chemistry of thyroid hormone metabolism,
  • development of novel therapeutics for endothelial dysfunction and neurodegenerative diseases, and
  • nanomaterials for biological applications.

Gonçalo Bernardes graduated in Chemistry from the University of Lisbon in 2004 and soon moved to the University of Oxford where he completed his D.Phil. in 2008 under the supervision of Prof. Ben Davis. He was then awarded a Marie-Curie Fellowship to perform postdoctoral studies with Prof. Peter H. Seeberger. After a short period in Portugal working as a Group Leader at Alfama Lda., Gonçalo moved to the ETH Zürich to join the lab of Prof. Dario Neri. Gonçalo started his independent research career in 2013 at the Department of Chemistry, University of Cambridge after being awarded a prestigious Royal Society University Research Fellowship. Simultaneously, he founded a pioneering research unit in Chemical Pharmacology at the Instituto de Medicina Molecular in Lisbon. Despite his early age, he has published >50 papers and 5 patents. He has picked many accolades during his research career such as the European Young Chemist Award – Silver Medal in 2014, and more recentlythe Chem Soc Rev Emerging Investigator Lectureship 2016 and the RSC Harrison–Meldola Memorial Prize. For his efforts in translational research, Gonçalo was distinguished by the Portuguese Ministry of Health (MH) of Portugal for relevant services to Public Health and Medicine.

He now spends his time between his labs in Cambridge and Lisbon, directing a research program at the interface of chemistry and biology with a focus on the development of novel chemoselective reactions for the modification of biomolecules, and their use to understand and influence human disease.

Ratmir Derda received his undergraduate degree in Physics from Moscow Institute of Physics and Technology in 2001 and Ph.D. in Chemistry from the University of Wisconsin-Madison in 2008, under the supervision of Laura L. Kiessling. From 2008 to 2011, he was a postdoctoral researcher at Harvard University working under the supervision of George M. Whitesides and Donald E. Ingber. He joined University of Alberta in 2011 as an Assistant Professor in Chemistry and the Principal Investigator at the Alberta Glycomics Centre.

The Derda Lab centers on the development and mechanistic investigation of chemical transformations of genetically-encoded substrates. We employ genetically-encoded chemical libraries to attack unsolved problems in molecular recognition to aid the discovery of new therapeutics, biomaterials and molecular diagnostics.


Find some of their most recent RSC publications below or find out more about the other members of our Editorial and Advisory Boards here.


Catalytic, highly enantioselective, direct amination of enecarbamates
Audrey Dumoulin, Claudia Lalli, Pascal Retailleau and Géraldine Masson
Chem. Comm. , 2015, 51 , 5383-5386, DOI: 10.1039/C4CC08052A, Communication

One pot and selective intermolecular aryl- and heteroaryl-trifluoromethylation of alkenes by photoredox catalysis
Aude Carboni, Guillaume Dagousset, Emmanuel Magnier and Géraldine Masson
Chem. Comm. , 2014, 50 , 14197-14200, DOI: 10.1039/C4CC08052A, Communication

Insights into the catalytic mechanism of synthetic glutathione peroxidase mimetics
Debasish Bhowmick and Govindasamy Mugesh
Org. Biomol. Chem. , 2015, 13, 10262-10272, DOI: 10.1039/C5OB01665G, Review Article

Introduction of a catalytic triad increases the glutathione peroxidase-like activity of diaryl diselenides
Debasish Bhowmick and Govindasamy Mugesh
Org. Biomol. Chem., 2015, 13, 9072-9082, DOI: 10.1039/C5OB01294E, Paper

Iminoboronates are Efficient Intermediates for Selective, Rapid and Reversible N-Terminal Cysteine Functionalisation
Hélio Faustino, Maria José Silva, Luis F. Veiros, Gonçalo J. L. Bernardes and Pedro M. P. Gois
Chem. Sci., 2016, Accepted Manuscript, DOI: 10.1039/C6SC01520D, Edge Article

Natural product modulators of transient receptor potential (TRP) channels as potential anti-cancer agents
Tiago Rodrigues, Florian Sieglitz and Gonçalo J. L. Bernardes
Chem. Soc. Rev., 2016, Advance Article, DOI: 10.1039/C5CS00916B, Tutorial Review

Phage-displayed macrocyclic glycopeptide libraries
Simon Ng and Ratmir Derda
Org. Biomol. Chem., 2016, 14, 5539-5545, DOI: 10.1039/C5OB02646F, Communication

Heat-enhanced peptide synthesis on Teflon-patterned paper
Frédérique Deiss, Yang Yang, Wadim L. Matochko and Ratmir Derda
Org. Biomol. Chem., 2016, 14, 5148-5156, DOI: 10.1039/C6OB00898D, Paper

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Fluorescent nucleosides provide flexibility in fine-tuning photophysical properties

The ubiquity of radioisotope-based bioprobes is being challenged by their nonradioactive counterparts. In recent years, they have gained significant popularity in life sciences due to major advances in available detection methods and enhanced analytical performance. Many would argue that radioactive labels offer superior results in experiments that require high sensitivity and resolution but their safe handling, stability and the proper disposal of radioactive materials limit speed and convenience of use.

The newest generation of fluorescent and chemifluorescent probes promise greater flexibility and versatility for a range of applications and the development of fully automated instrumentations and powerful imaging systems provide high throughput solutions to meet the increasing demands of the modern lab.

Unique photophysical properties can be incorporated into small biomolecules to generate fluorescent bioprobes. Fluorescently labeled nucleosides have distinct advantages over other synthetic molecules due to inherent fluorescence and minimal steric disruptions, and they can be tuned e.g. to form unusual base-pair preferences. They form noncovalent, highly specific duplexes with a complementary nucleic acid strand and are used to detect a defined DNA or RNA target sequence.

In a recent publication from the group of Yoshio Saito of Nihon University, the development of a novel nucleoside-based bioprobe containing a 3-deaza-2’-deoxyadenosine skeleton was reported. It behaves as an indicator for adenosine-cytosine base pair formation in oligodeoxynucleotide (ODN) duplexes by monitoring base-pair induced protonation. The probe displays distinct changes in its absorption and fluorescence activity as a result of its protonation state. In this way, the group is able to clearly discriminate cytosine from other bases on complementary strands based on absorption and fluorescence spectra.

The development of new biomarkers is providing insight to various genetic disorders, disease susceptibility, cancer predisposition and medication response. When fluorescent bioprobe imaging is coupled with genetic analytical techniques, such as single nucleoside polymorphism (SNP)-typing, the two synergize and provide a much more complete view than either one alone.

To find out more see:

Design and synthesis of a novel fluorescent benzo[g]imidazo[4,5-c]quinoline nucleoside for monitoring base-pair-induced protonation with cytosine: distinguishing cytosine via changes in the intensity and wavelength of fluorescence
Shogo Siraiwa, Azusa Suzuki, Ryuzi Katoh and Yoshio Saito
DOI:10.1039/C6OB00494F


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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