OrgSyn 50 Conference 27th – 28th February 2017

OrgSyn 50 – Developments in Organic Chemistry

Fluorochem invite you to join them from 27-28 February 2017 in Manchester, UK to celebrate their 50-year milestone in helping support research and supplying intermediates for R&D worldwide.

During the two days there will be 13 outstanding lectures covering a broad range of subjects. Fluorochem are delighted to have attracted a high calibre of speakers to this event and want to ensure people don’t miss out on a unique opportunity to appreciate the remarkable standard of current research being undertaken in the UK. Join them for tales of the unexpected; from fluorination to feedstock, cascades to catalysis and nanoscale to nature. Learn about the latest in cancer research and engage in topics such as rotaxanes, urea function and digitising chemistry.

Introducing an outstanding line up of speakers which includes:

For more information and to register please visit the website.

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Poster prize winners at the 10th Symposium on Biorelevant Chemistry

Congratulations to the two poster prize winners at the 10th Symposium on Biorelevant Chemistry!

We were pleased to present prizes to these winners:

Yuuma Shisaka (Nagoya University) – Molecular BioSystems Poster Prize
Title: ‘Interaction Analysis of Hemoprotein HasA with Captured Synthetic Metal Complexes and Its Specific Receptor HasR from Pseudomonas Aeruginosa

Yuki Imakura (University of Tokyo) – Organic & Biomolecular Chemistry Poster Prize
Title: ‘Design of long-lived hyperpolarized probes based on T1 relaxation mechanism’

Organized by the Chemical Society of Japan, the Biorelevant Chemistry Symposium took place from 7-9 September 2016 in Kanazawa, Japan and was attended by a total of 430 delegates.

From left to right: Professor Hisakazu Mihara (Tokyo Institute of Technology, Chair of the Division of Biofunctional Chemistry, Chemical Society of Japan), Professor Nobutaka Fujieda (Osaka University, Poster award committee co-chair), Mr Yuuma Shisaka (Nagoya Univerisity, Molecular BioSystems award winner), Mr Yuki Imakura (Nagoya Univerisity, OBC award winner), Professor Kenji Yokoyama (Tokyo University of Technology, Chair of the Division of Biotechnology, Chemical Society of Japan), Professor Asanuma Hiroyuki (Nagoya University, Poster award committee chair), Professor Masato Saito (Osaka University, Poster award committee co-chair).

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An efficient second-generation total synthesis of Aplyronine A

The importance of natural products in health and medicine is enormous owing to their diverse biological activities and their role as a basis for drug development. Endeavours in total synthesis have attracted some of the most talented organic chemists–providing intellectual and creative outlets–and have been central to the evolution and technical development of organic synthesis.

In the early 1990’s, Professor Hideo Kigoshi of the University of Tsukuba reported the first total synthesis of the marine macrolide Aplyronine A which is still a highly desirable synthetic target due to its potent and unique biological properties.

In collaboration with Professor Ichiro Hayakawa of Okayama University, the group has recently published a highly efficient second-generation total synthesis of Aplyronine A which requires fewer synthetic steps and boasts an improved overall yield. Issues with poor stereoselectivity, regioselectivity and isomerization were overcome through the optimization of a Ni/Cr-mediated coupling.

As shown in the retrosynthetic pathway below, Aplyronine A was obtained from 10, the same intermediate used in the first generation synthesis however, instead of the Julia coupling between ketone and sulfone-containing fragments, the macrolactone 11 was cyclized via an intramolecular Ni/Cr-mediated coupling. This modification drastically reduced the number of unwanted byproducts obtained from the Julia coupling and eliminated the need to employ a modified Yamaguchi lactonization which had resulted in the formation of an undesired 26-membered lactone that required an additional isomerization to yield the desired product. Precursor 11 was constructed through an intermolecular esterification between carboxylic acid 12 and alcohol 13 which were each prepared through asymmetric Ni/Cr-mediated couplings. In the case of the carboxylic acid, route efficiency was further enhanced as this strategy resulted in the simultaneous formation of the C14–C15 (E)-trisubstituted double bond and the C13 stereogenic center through the use of a chiral ligand.

In addition to establishing an efficient synthetic pathway to Aplyronine A, the Ni/Cr-mediated coupling has significant potential in the preparation of structurally diverse derivatives which may result in enhanced biological activity and the discovery of a novel lead.

The popularity of natural products as synthetic targets will continue as they provide unparalleled inspiration for drug leads and the synthesis of non-natural compounds. Strategies to develop concise and efficient synthetic routes are significantly important not only in terms of their utility in medicine but in the downstream application of novel synthetic methodologies developed during the process of their total synthesis.

To find out more see:

Second generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions
Ichiro Hayakawa, Keita Saito, Sachiko Matsumoto, Shinichi Kobayashi, Ayaka Taniguchi, Kenichi Kobayashi, Yusuke Fujii, Takahiro Kanekob and Hideo Kigoshi
DOI: 10.1039/C6OB02241C


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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Halogen bonding in anion recognition and sensing

As part of an ongoing research programme in host-guest supramolecular chemistry, Professor Paul Beer of Oxford University has been developing methods for the synthesis of interlocking molecular architectures based on halogen bond donor motifs.

Halogen bonding interactions—the noncovalent, attractive interaction between an electron deficient halogen (X) and a Lewis base (B)—are slowly becoming more prevalent as a complimentary alternative to more commonly used binding interactions. Since its discovery in the late 1960’s, anion recognition chemistry has developed from an interesting area of academic research to a pillar of supramolecular chemistry. In recent years, there has been dramatic advancements within the field that have resulted in a number of practical applications such as organocatalysis involving ion complexation, ion extraction from mixtures and the development of sensory devices and molecular switches.

Anions play fundamental roles in a large number of biological, chemical, medicinal and environmental processes and nature’s binders typically complex anions through intricate networks of electrostatic interactions. The ability to mimic the selectivity of biological systems in artificial settings has been a longstanding challenge in this field.

In a recent OBC publication, the Beer group successfully synthesized two mono-cationic and two dicationic halogen and hydrogen bonding rotaxane anion recognition systems (see figure) and successfully demonstrated the enhanced binding affinity and selectivity of the dicationic halogen bonding analogue relative to its hydrogen bond-containing counterpart. In addition, the dicationic halogen bonding system displayed an enhanced preference for binding to bromine anions over other halides, nitrate and dihydrogen phosphate oxoanions. NMR binding studies reveal that the enhanced strength and selectivity of halide recognition is the result of chelated charge assisted halogen bonding interactions in the dicationic system. This study elegantly demonstrates efforts in exploiting the XB chelate effect to improve anion binding affinity and selectivity. Halogen bonding is still an emerging area of research however, examples such as this highlight its utility as a complementary mode of binding when compared to other more established interactions and will no doubt lead to an evolution in anion receptor design.


To find out more see:

Chelated charge assisted halogen bonding enhanced halide recognition by a pyridinium-iodotriazolium axle containing [2]rotaxane
Alexander E. Hess and Paul D. Beer
DOI: 10.1039/C6OB01851C


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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Congratulations to Ben Feringa

Inaugural OBC Chair wins 2016 Nobel Prize in Chemistry

The prestigious Nobel Prize in Chemistry 2016 was awarded jointly to Jean-Pierre Sauvage, Sir J. Fraser Stoddart and Bernard L. Feringa for their outstanding contributions to the design and synthesis of molecular machines. Many congratulations to all of them!


Ben Feringa has not only significantly influenced our journal as the  inaugural Chair of Organic & Biomolecular Chemistry from 2003 to 2007, but he has also so far published an impressive 40 manuscripts in OBC since it’s launch. We would like to mark this special occasion by highlighting only a few of them here:


Bacterial patterning controlled by light exposure
Willem A. Velema, Jan Pieter van der Berg, Wiktor Szymanski, Arnold J. M. Driessen and Ben L. Feringa

Mild Ti-mediated transformation of t-butyl thio-ethers into thio-acetates
Thomas C. Pijper, Jort Robertus, Wesley R. Browne and Ben L. Feringa

Silanization of quartz, silicon and mica surfaces with light-driven molecular motors: construction of surface-bound photo-active nanolayers
Gábor London, Gregory T. Carroll and Ben L. Feringa

Chiral separation by enantioselective liquid-liquid extraction
Boelo Schuur, Bastiaan J. V. Verkuijl, Adriaan J. Minnaard, Johannes G. de Vries, Hero J. Heeres and Ben L. Feringa

Catalytic asymmetric conjugate addition of dialkylzinc reagents to α,β-unsaturated sulfones
Pieter H. Bos, Beatriz Maciá, M. Ángeles Fernández-Ibáñez, Adriaan J. Minnaard and Ben L. Feringa

Copper-free ‘click’: 1,3-dipolar cycloaddition of azides and arynes
Lachlan Campbell-Verduyn, Philip H. Elsinga, Leila Mirfeizi, Rudi A. Dierckx and Ben L. Feringa

A redesign of light-driven rotary molecular motors
Michael M. Pollard, Auke Meetsma and Ben L. Feringa

Photoresponsive dithienylethene-urea-based organogels with “reversed” behavior
Masako Akazawa, Kingo Uchida, Jaap J. D. de Jong, Jetsuda Areephong, Marc Stuart, Giuseppe Caroli, Wesley R. Browne and Ben L. Feringa

Rhodium/phosphoramidite-catalyzed asymmetric arylation of aldehydes with arylboronic acids
Richard B. C. Jagt, Patrick Y. Toullec, Johannes G. de Vries, Ben L. Feringa and Adriaan J. Minnaard

Enantioselective synthesis of β2-amino acids using rhodium-catalyzed hydrogenation
Rob Hoen, Theodora Tiemersma-Wegman, Barbara Procuranti, Laurent Lefort, Johannes G. de Vries, Adriaan J. Minnaard and Ben L. Feringa


If you are interested please find a full list of his OBC articles here.

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International Chemical Biology Society (ICBS) – 5th Annual Conference

Meet our Deputy Editor James Anson

Organic & Biomolecular Chemistry (OBC) is pleased to support the 2016 annual meeting of the International Chemical Biology Society.  The conference aims to provide a forum for chemical biologists to speak of their work and discuss important scientific problems and to promote exchange between emerging and established scientists.

This international conference has a balanced program of speakers from all disciplines in chemical biology ranging from infectious diseases to natural products to epigenetics and many more.  This year the speakers include:

  • Laura Kiessling (University of Wisconsin-Madison) – Us Versus Them: Microbial Glycans as Cellular ID Cards
  • Kai Johnsson (École PolytechniqueFédérale de Lausanne) – Expanding Protein Function Through Synthetic Chemistry
  • Junying Yuan (Harvard Medical School) – Regulation of Inflammation and Cell Death by RIPK1
  • Ulrike Eggert (Molecular BioSystems Editorial Board, King’s College London) – A Chemical Approach to Understanding Cell Division
  • Tapas Kundu (Jawaharlal Nehru Centre for Advanced Scientific Research, Bangalore) – Small Molecule Modulators of Histone Acetyltransferases: Implications in Disease Biology
  • Emily Balskus (Harvard University) – Chemical Discovery in the Human Microbiota

… and many more. For more information and to register please visit the website.


Meet the team:

James Anson (Deputy Editor of OBC, Natural Product Reports, MedChemComm and Molecular BioSystems) will be attending the event. He would love to hear about your research and meet with our readers, authors and referees. Please do get in touch with James if you would like to arrange a meeting in advance.

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The development of novel diagnostic tools in the treatment of infectious diseases

Antibiotic resistance has become a major clinical issue in recent decades and is one of the greatest health problems of our time. Tuberculosis (TB) has been present for thousands of years and according to WHO is globally, one of the leading causes of death from a curable infectious disease. The advent of the antibiotic era represented a major breakthrough for those suffering from TB however the spread of multi-drug resistant strains, which have propagated due to incorrect drug use, prescription errors or low patient compliance has become a major threat to disease control. In order to mitigate this, new drugs and diagnostic tools are desperately needed.

A collaborative study between Peter Woodruff of the University of Southern Maine and Benjamin Swarts of Central Michigan University has looked at in vivo nuclear imaging as a non-invasive means of diagnosing TB as well as disease monitoring and treatment response in real time. This means that vital information regarding disease progression that is complimentary to other forms of diagnosis can be quickly attained.

Current imaging methods rely on radiotracers to provide information on host inflammatory response to the infection however there can be some inaccuracy due to a lack of specificity in cellular uptake. An attractive alternative are radiolabeled analogues of antimycobacterial compounds which specifically label the desired bacteria and can provide in vivo imaging.

In the past, the disaccharide trehalose and its analogues have been applied to study metabolic mechanisms of mycobacteria and provide a means to design specifc probes for the mycobacteria induced infections. In this current publication, the researchers successfully developed a robust and concise synthetic route to access a number of fluorinated trehalose (FDTre) analogues using a rapid chemoenzymatic process followed by a simple purification by ion exchange chromatography. This drastic improvement compared to previously reported synthetic routes, which require lengthy reaction times and often result in low recovery, makes this new route highly desirable as well as compatible with timescale required for radiolabel synthesis. In addition, the authors demonstrated the ability of their FDTre analogues to be successfully recognized and taken up through trehalose transporter pathways in M. smegmatis and pathogenic mycobacteria, allowing for FDTre accumulation within cells.

Further investigations are still required to overcome remaining hurdles such as the cost associated with synthesis, assessment of uptake efficiencies at concentrations closer to in vivo radiotracer concentrations as well as evaluation of the speficity of the FDTre radioprobes. Regardless, the methodology established in this study provides an exceptional platform for the development of a new class of nuclear imaging probes to help treat multi-drug resistant TB and other mycobacterial infections.



To find out more see:

Deoxyfluoro-D-trehalose (FDTre) analogues as potential PET probes for imaging mycobacterial infection
Sarah R. Rundell, Zachary L. Wagar, Lisa M. Meints, Claire D. Olson, Mara K. O’Neill, Brent F. Piligian, Anne W. Poston, Robin J. Hood, Peter J. Woodruff and Benjamin M. Swarts
DOI: 10.1039/C6OB01734G


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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Top 10 Reviewers for Organic & Biomolecular Chemistry

In celebration of Peer Review Week, with the theme around Recognition for Review – we would like to highlight the top 10 reviewers for Organic & Biomolecular Chemistry in 2016, as selected by the editor for their significant contribution to the journal.

Name Institution
Professor Dean Tantillo University of California, Davis
Reviewer has requested to remain anonymous.
Dr Alakananda Hajra Visva-Bharati
Dr Concepcion Gonzalez-Bello CIQUS, Universidad de Santiago de Compostela
Dr Hiroshi Matsubara Osaka Prefecture University
Professor Jonathan Clayden University of Bristol
Dr Zhiyi Liu Houston Methodist Research Institute
Dr Rob Young GlaxoSmithKline
Dr Marco Di Antonio University of Cambridge
Dr Koji Hirano Osaka University

















We would like to say a massive thank you to these reviewers as well as the Organic & Biomolecular Chemistry Editorial and Advisory Boards and all of the Organic Chemistry and Chemical Biology community for their continued support of the journal, as authors, reviewers and readers.

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OBC Call for Papers – Macrocycles with bio-related applications

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

Macrocycles with bio-related applications

Guest Editors: Spiros Liras (Pfizer, USA), Andrei Yudin and Conor Scully (University of Toronto, Canada)

Deadline for Submission: 15 January 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

The special issue will serve as a forum to disseminate the latest findings in the burgeoning field of macrocycles. This will include studies aimed at new ways of constructing macrocycles, efforts to understand their biological activity, and new approaches to deciphering conformational profiles using state of the art spectroscopic methods. The issue is aimed at a broad audience comprising synthetic, medicinal, and biological chemists

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 beforehand. 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 Macrocycles with bio-related applications.

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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OBC Call for Papers – Biocatalysis: Natural and biologically inspired synthetic enzymes

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

Biocatalysis: Natural and biologically inspired synthetic enzymes

Guest Editors: Scott Silverman and Douglas Mitchell (University of Illinois at Urbana-Champaign, USA)

Deadline for Submission: 15 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

Biocatalysis includes a range of topics related to catalysis by molecules obtained or derived from biology. This issue will cover the following topics:

1. Study of naturally occurring biological catalysts (protein enzymes and ribozymes)
2. Protein engineering and directed evolution, including computational tools
3. Metabolic engineering for synthetic chemistry
4. Development of synthetic biologically inspired catalysts, including small-molecule catalysts

















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 beforehand. 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 Biocatalysis: Natural and biologically inspired synthetic enzymes.

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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