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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Nanoscale engineering of wound beds

A collagen-binding peptide with applications in wound healing has been developed by scientists in the US. The peptide is able to invade the strands of collagen, forming a strong and stable non-covalent bond at room temperature. Pendant drug molecules could be attached to the peptide and anchored at the wound site to aid wound healing…

Read the full article at Chemistry World, or read the OBC paper:

Peptides that anneal to natural collagen in vitro and ex vivo
Sayani Chattopadhyay, Christopher J. Murphy, Jonathan F. McAnulty and Ronald T Raines
DOI: 10.1039/C2OB25190F

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Reminder: Don’t forget the first Organic & Biomolecular Chemistry International Symposium

The first ever Organic & Biomolecular Chemistry International Symposium starts next week!

 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

Each of these one-day meetings feature a selection of lectures covering organic and bioorganic chemistry by some of the world’s leading international scientists, including:

Professor Jeffrey Bode (ETH Zürich, Switzerland): Amide Bond Formation: Taking N-O for an Answer

Professor Dirk Trauner (Ludwig Maximilian University Munich, Germany): Exploring the Limits of Biomimetic Synthesis

Professor Andrei Yudin (University of Toronto, Canada): Amphoteric Molecules – A Powerful Platform for Reaction Discovery

Plus many leading scientists from each of the host organisations!

The symposium is ABSOULUTELY FREE and NO REGISTRATION is needed so you can just turn up on the day, making it perfect for students as well!

For more information please see the symposium website.

We look forward to seeing you there!

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Chiral recognition of carbon nanoforms & 3-alkyl enol mimic inhibitors on the cover of OBC issue 18

We are pleased to present to you OBC issue 18, 2012

Emilio M. Pérez and Nazario Martín present an Emerging area article providing an overview of some of the few successful examples of chiral recognition of carbon nanoforms, highlighting their common features with the aim of helping to develop general trends for the design of new generations of hosts.

Chiral recognition of carbon nanoforms
Emilio M. Pérez and Nazario Martín
Org. Biomol. Chem., 2012, 10, 3577–3583
DOI: 10.1039/C2OB07159B

The inside front cover illustrates work by Concepción González-Bello and co-workers at Universidad de Santiago de Compostela and University of Newcastle upon Tyne, who synthesised several 3-alkylaryl mimics of the enol intermediate in the the reversible dehydration reaction of 3-dehydroquinic acid, which is catalysed by type II dehydroquinase, to investigate the effect on the inhibition potency of replacing the oxygen atom in the side chain by a carbon atom.

Synthesis of 3-alkyl enol mimics inhibitors of type II dehydroquinase: factors influencing their inhibition potency
Beatriz Blanco, Antía Sedes, Antonio Peón, Heather Lamb, Alastair R. Hawkins, Luis Castedo and Concepción González-Bello
Org. Biomol. Chem., 2012, 10, 3662–3676
DOI: 10.1039/C2OB07081B

                            Both of these articles are free to access for 6 weeks so get your hands on them today!                              

Also in this issue:

A perspective by María Paz Muñoz covering the progress in transition metal-catalysed intermolecular reaction of allenes with oxygen nucleophiles, analysing the intermolecular metal-catalysed reaction of allenes using palladium, iridium, rhodium, ruthenium, gold and platinum, in the presence of alcohols, water or carboxylic acids, and the mechanistic implications of these processes depending on the metal used.

Transition metal-catalysed intermolecular reaction of allenes with oxygen nucleophiles: a perspective María Paz Muñoz
Org. Biomol. Chem., 2012,
DOI: 10.1039/C2OB07128B
 
The HOT article :
A convenient biomimetic synthesis of optically active putative neurotoxic metabolites of MDMA (“ecstasy”) from R-(−)- and S-(+)-N-methyl-α-methyldopamine precursors
Claire-Marie Martinez, Anne Neudörffer and Martine Largeron
DOI: 10.1039/C2OB25245G

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HOT: Biomimetic synthesis of optically active MDMA (ecstasy) metabolites

In this HOT paper Martine Largeronand co-workers at CNRS-Université Paris Descartes report the first total synthesis of S-(+)-HHMA in 45% overall yield (six steps) and 99% ee. Along with their previously reported method for making R-(−)-HHMA, Largeron et al. go on to prepare large amounts of optically active thioether conjugates viaa straightforward one-pot electrochemical procedure. This new availability of optically active thioether conjugates allows future studies into their exact role in the neurotoxic effects of MDMA to be carried out.

MDMA, also known as “ecstasy”, is a psychoactive drug with selective neurotoxic potential toward brain serotonin neurons. Despite intensive research, the precise mechanism by which MDMA selectively damages brain neurons in most species remains unknown. One hypothesis is that MDMA neurotoxicity may at least partially be a consequence of its metabolism. In particular, O-demethylenated MDMA metabolites such as N-methyl-α-methyldopamine (HHMA) have been postulated to serve as precursors for toxic catechol–thioether conjugates.

As MDMA enantiomers have different pharmacological properties, it is reasonable to predict that the thioether conjugates of the HHMA enantiomers similarly display distinct neurotoxicity profiles. However, such studies have yet to be carried out because HHMA exists as a pair of enantiomers so its thioether conjugates exist as a mixture of diastereoisomers and current analytical and semipreparative methodologies for the diastereoisomeric separation of HHMA thioether conjugates only furnish small quantities of both diastereoisomers. Now, thanks to this work by Largeron et al. such studies can be undertaken.

 

  • As with all our HOT articles it is free to access for the next 4 weeks!

 A convenient biomimetic synthesis of optically active putative neurotoxic metabolites of MDMA (“ecstasy”) from R-(−)- and S-(+)-N-methyl-α-methyldopamine precursors
Claire-Marie Martinez, Anne Neudörffer and Martine Largeron
Org. Biomol. Chem., 2012,
DOI: 10.1039/C2OB25245G

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Promiscuous enantioselective lactamase activity on the cover of OBC issue 17

This week’s OBC cover highlights the work of Aurelio Hidalgoand co-workers at the Center for Molecular Biology, whose paper describes the promiscuous enantioselective (−)-γ-lactamase activity in Pseudomonas fluorescensesterase I. In the paper Aurelio Hidalgoet al. show how the introduction of a mutation to the wild esterase improved the reaction turnover without affecting the enantioselectivity. Read the paper to find out more…..

This paper is FREE to access for the next 6 weeks, so why not take a look at it.

Promiscuous enantioselective (−)-γ-lactamase activity in the Pseudomonas fluorescensesterase I
Leticia L. Torres, Anna Schließmann, Marlen Schmidt, Noella Silva-Martin, Juan A. Hermoso, José Berenguer, Uwe T. Bornscheuer and Aurelio Hidalgo
Org. Biomol. Chem., 2012, 10, 3388-3392
DOI: 10.1039/C2OB06887G

Also in this issue:

 A review:

 Making expensive dirhodium(II) catalysts cheaper: Rh(II) recycling methods
Nuno R. Candeias, Carlos A. M. Afonso and Pedro M. P. Gois
Org. Biomol. Chem., 2012, 10, 3357-3378
DOI: 10.1039/C2OB06731E

A HOT article:

Copper-mediated domino synthesis of pyrimido[4,5-b]carbazolones via Ullmann N-arylation and aerobic oxidative C–H amidation
Devanga K. Sreenivas, Nagarajan Ramkumar and Rajagopal Nagarajan
Org. Biomol. Chem., 2012, 10, 3417-3423
DOI: 10.1039/C2OB07179G

 View the entire issue HERE

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HOT: Copper-mediated domino synthesis with Ullmann N-arylation and aerobic oxidative C–H amidation

Rajagopal Nagarajan and colleagues at University of Hyderabad have synthesized a series of pyrimido[4,5-b]-carbazolone derivatives using cascade Ullmann N-arylation and aerobic oxidative C–H amidation reactions that allow the assembly of readily accessible building blocks into diverse (heteroarylannulated) pyrimido[4,5-b]carbazolones with the aid of CuBr as a catalyst without any additives or ligands.

An attractive feature of this synthetic approach is that it not only provides a new approach for constructing pyrimido[b]carbazoles but also offers an efficient method for preparation of synthetically and medicinally important hetero-arylated carbazoles.

For all the details of their investigation simply CLICK HERE. This HOT article is FREE to access for 4 weeks!

What are your thoughts on this paper? Why not share them by leaving a comment below.

Copper-mediated domino synthesis of pyrimido[4,5-b]carbazolones via Ullmann N-arylation and aerobic oxidative C–H amidation
Devanga K. Sreenivas, Nagarajan Ramkumar and Rajagopal Nagarajan
Org. Biomol. Chem., 2012,
DOI: 10.1039/C2OB07179G

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There’s still time to join ICPOC21!

Good news!

There’s still a chance to submit your oral abstract to ICPOC21: 21st IUPAC International Conference on Physical Organic Chemistry to be held 9 – 13 September 2012 at Durham University.

The Scientific Committee is currently reviewing all submissions, and has agreed to accept contributions up to Friday 13 April to allow for the Easter holiday break.

Why join ICPOC21?

This meeting is organised by the Organic Division of the RSC on behalf of IUPAC. In addition to outstanding plenary sessions, there will be three parallel sessions over the five days comprising invited lectures and contributed talks, as well as poster sessions.

Key topics that will be covered in the meeting include:

• Physical underpinnings
• Mechanism and Catalysis
• Supramolecular and Systems Chemistry

A broad range of scientists from across the whole community who share a quantitative perspective on chemistry will be there, providing an opportunity to discuss and celebrate the current status, development, and the future of physical organic chemistry.

Make sure you are one of them! Don’t miss the oral abstract submission deadline – 13 April

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Take a stroll down memory lane with Organic & Biomolecular Chemistry on our 10th anniversary

In our continued countdown to Organic & Biomolecular Chemistry‘s 10th anniversary issue we have had a look back at some of the art work that has appeared on our covers through the years. Below are the front covers of issue 1 and the work that featured on them for each year since the inception of OBC. What’s your favourite?

These stylish old school covers (right) were originally seen in 2003 & 2004 on volumes 1 & 2 respectively.

Volume 3:
Free: New chiral anion mediated asymmetric chemistry
Jérôme Lacour and Richard Frantz
Org. Biomol. Chem., 2005, 3, 15–19
DOI: 10.1039/B413554G

Volume 4:
Free: Artificial ribonucleases
Teija Niittymäki and Harri Lönnberg
Org. Biomol. Chem., 2006, 4, 15–25
DOI: 10.1039/B509022A

Volume 5:
Free: Synthesis of protein–polymer conjugates
Karina L. Heredia and Heather D. Maynard
Org. Biomol. Chem., 2007, 5, 45–53
DOI: 10.1039/B612355D

Volume 6:
Free:
Metallo-nucleosides: synthesis and biological evaluation of hexacarbonyl dicobalt 5-alkynyl-2′-deoxyuridines
Craig D. Sergeant et al.

Org. Biomol. Chem., 2008, 6, 73–80
DOI: 10.1039/B713371E

Volume 7:
Free:
Chemical approach toward efficient DNA methylation analysis
Akimitsu Okamoto
Org. Biomol. Chem., 2009, 7, 21–26
DOI: 10.1039/B813595A

Volume 8:
Free:
Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
Stuart J. Conway et al.

Org. Biomol. Chem., 2010, 8, 66–76
DOI: 10.1039/B913399B

Volume 9:
Free:
Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts
Thomas C. Nugent, Mohammad Shoaib and Amna Shoaib
Org. Biomol. Chem., 2011, 9, 52–56
DOI: 10.1039/C0OB00822B

Volume 10:
Free:
Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems
Nathan B. Bennett et al.

Org. Biomol. Chem., 2012, 10, 56–59
DOI: 10.1039/C1OB06189E

All of these articles are FREE to access so if you missed them the first time round why not have a read now. In fact, why not have a look at the whole of the issue? All the content from each issue 1 is now FREE to access so dive in and enjoy:

Volume: 1 2 3 4 5 6 7 8 9 10

  • Do you have a favourite cover from our 10 years? Why not share it with us by leaving a comment below.

 

  •  Interested in having your work featured on a cover? Submit your work to us and show us your artwork.

 

  •  Missed our other 10th anniversary posts? Take a look here for some of our top cited work.
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Top ten most accessed articles in February

This month sees the following articles in Organic & Biomolecular Chemistry that are in the top ten most accessed:

Imidazole derivatives: A comprehensive survey of their recognition properties
Pedro Molina, Alberto Tárraga and Francisco Otón
Org. Biomol. Chem., 2012, 10, 1711-1724
DOI: 10.1039/C2OB06808G

Copper(I)–amine metallo-organocatalyzed synthesis of carbo- and heterocyclic systems
Benjamin Montaignac, Victor Östlund, Maxime R. Vitale, Virgnie Ratovelomanana-Vidal and Véronique Michelet
Org. Biomol. Chem., 2012, 10, 2300-2306
DOI: 10.1039/C2OB06449A

Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions
Laurence Burroughs, Paul A. Clarke, Henrietta Forintos, James A. R. Gilks, Christopher J. Hayes, Matthew E. Vale, William Wade and Myriam Zbytniewski
Org. Biomol. Chem., 2012, 10, 1565-1570
DOI: 10.1039/C1OB06798B

Facile synthesis of 4-substituted 3,4-dihydrocoumarins via an organocatalytic double decarboxylation process
Shiyong Peng, Lei Wang, Haibing Guo, Shaofa Sun and Jian Wang
Org. Biomol. Chem., 2012, 10, 2537-2541
DOI: 10.1039/C2OB25075F

On a so-called “kinetic anomeric effect” in chemical glycosylation
Ian Cumpstey
Org. Biomol. Chem., 2012, 10, 2503-2508
DOI: 10.1039/C2OB06696C

Olefin cross-metathesis for the synthesis of heteroaromatic compounds
Timothy J. Donohoe, John F. Bower and Louis K. M. Chan
Org. Biomol. Chem., 2012, 10, 1322-1328
DOI: 10.1039/C2OB06659A

Fluorogenic sensing of CH3CO2 and H2PO4 by ditopic receptor through conformational change
Nisar Ahmed, Vangaru Suresh, Bahareh Shirinfar, Inacrist Geronimo, Amita Bist, In-Chul Hwang and Kwang S. Kim
Org. Biomol. Chem., 2012, 10, 2094-2100
DOI: 10.1039/C2OB06994F

A selective fluorescent turn-on NIR probe for cysteine
Xin-Dong Jiang, Jian Zhang, Xiangmin Shao and Weili Zhao
Org. Biomol. Chem., 2012, 10, 1966-1968
DOI: 10.1039/C2OB07046D

Chemical generation of o-quinone monoimines for the rapid construction of 1,4-benzoxazine derivatives
Naganjaneyulu Bodipati and Rama Krishna Peddinti
Org. Biomol. Chem., 2012, 10, 1958-1961
DOI: 10.1039/C2OB06681E

Construction of highly functional α-amino nitriles via a novel multicomponent tandem organocatalytic reaction: a facile access to a-methylene γ-lactams
Feng Pan, Jian-Ming Chen, Zhe Zhuang, Yin-Zhi Fang, Sean Xiao-An Zhang and Wei-Wei Liao
Org. Biomol. Chem., 2012, 10, 2214-2217
DOI: 10.1039/C2OB07112F

Why not take a look at the articles today and blog your thoughts and comments below.

Fancy submitting an article to Organic & Biomolecular Chemistry? Then why not submit to us today or alternatively email us your suggestions.

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