Author Archive

HOT – From the lab to industry:A real-life story

Drug design and discovery in a research lab is already a very challenging task. It involves knowledge, intensive research, resources, a bit of luck and a lot of time. However, eureka moments do happen and when they happen it feels great.

However, the story does not finish there. One thing is the synthesis of a new drug in a lab (mg scale) but being able to scale that up to the multigram (or kilogram if you are lucky) scale in a non-expensive and safe manner that can be implemented in industry, well… THAT is the biggest challenge!

In this paper, Xiaohu Deng and colleagues at Johnson & Johnson Pharmaceutical Research and Development in San Diego, describe the ‘ideal synthesis’ of a CCK1/CCK2 dual receptor antagonist on a multi-gram scale, without protecting groups and in an environmentally friendly way.

This is an example of how academic research is translated into industrial applications.

Both the referees and the editorial office found this paper very interesting and selected it as a HOT article, which means it is free to access for 4 weeks! Download it now.

Protecting-group-free synthesis of a dual CCK1/CCK2 receptor antagonist
Jing Liu, Xiaohu Deng, Anne E. Fitzgerald, Zachary S. Sales, Hariharan Venkatesan and Neelakandha S. Mani
Org. Biomol. Chem., 2011, Advance Article
DOI:
10.1039/C0OB01004A, Paper

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Discover the treasure of free radical chemistry – OBC Cover

Open the treasure of Free Radical Chemistry with this OBC Cover article.

Carl Schiesser takes us through the evolution of Free Radical Chemistry in this very original and well written paper that highlights results from the Beckwith “golden era”.
Join us in this trip from the “Dark Ages” of Free Radical Chemistry to the Post-Renaissance period.  The paper will be free to access until 14th April.

Apart from taking us on a very pleasant journey through the evolution of radical chemistry, the authors also determine the rate constant data and Arrhenius parameters for a series of substituted hexenyl radicals of differing electronic and steric demand.

This paper will be included in the special issue on ‘Free Radical Chemistry’ in memory of Athel Beckwith that will be published in Spring. Keep an eye on it!

Treasures from the Free Radical Renaissance Period – Miscellaneous hexenyl radical kinetic data
Athelstan L. J. Beckwith and Carl H. Schiesser
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00708K, Paper

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HOT: Design of sophisticated supramolecular receptors

Molecular self-assembly is an area of research that has spectacularly grown during the last two decades. The design of macromolecules that can adopt specific shapes and can act as receptors or host other molecules through non-covalent interactions has attracted particular attention.

One of the most popular building blocks in self assembly is calixarenes.  However, although calix-[4]-arenes have been widely studied in the field of molecular recognition, calix-[6]-arenes have not received as much attention due to the flexibility of their skeleton. The design of calix-[6]-arenes is still a challenging task.

In this paper, Stephane Le Gac, Ivan Jabin and co-workers take advantage of the versatility of the calix[6]arene functionalization together with the flexibility of its skeleton to create additional host-guest and host-host interactions. The resulting supramolecular receptors are unique since these additional interactions are reminiscent of intra-protein interactions in biological receptors.

If you want to find out more about these unique supramolecular receptors, download this HOT paper which is free to access until 23rd March.

Allosterically driven self-assemblies of interlocked calix[6]arene receptors
Stéphane Le Gac, Jean-François Picron, Olivia Reinaud and Ivan Jabin
Org. Biomol. Chem., 2011
DOI: 10.1039/C0OB01020K

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OBC Editorial Board Members announcement

We are delighted to welcome Professor Kenichiro Itami (Nagoya University) and Professor Qi-Lin Zhou (Nankai University) to the Organic & Biomolecular Chemistry Editorial Board.

Ken Itami studied chemistry at Kyoto University and received his PhD in 1998 under the guidance of Prof Yoshihiko Ito. He also had the pleasure to work as a predoctoral researcher in the group of Prof Jan-E Backvall at Uppsala University, Sweden. He began his academic career at Kyoto University as an Assistant Professor (with Prof Jun-ichi Yoshida) and then he moved to Nagoya University to become an Associate Professor (with Prof Ryobi Noyori). In 2008 he was promoted to full professor.

The main emphasis of his research is on the development of new synthetic methods, strategies and concepts to solve challenging synthetic problems. Some of his group’s research projects include new reaction and catalyst for C-H bond transformation, programmed chemical synthesis, biologically active molecules and natural products, optoelectronic materials and nanocarbon materials.

Qi-Lin Zhou received his PhD degree in December 1987 working for Prof. Yao-Zeng Huang. He has also worked with many very well respected chemists such as Prof. Zheng-Hua Zhu at the Institute of Fine Chemicals, East China University of Science and Technology, Shanghai, Professor Klaus Muellen  at the Max-Planck Institute of Polymer Science, Professor Andreas Pfaltz at Basel University in Switzerland and Professor Michael Doyle at Trinity University in Texas. In 1996 he moved back to China as Professor of chemistry at the Institute of Fine Chemicals, East China University of Science and Technology and in 1999 he decided to take another Professorship at the State Key Laboratory of Elemento-organic Chemistry in Nankai University.

His main areas of research focus on the development of new synthetic methods, organometallic chemistry directed towards organic synthesis, asymmetric catalysis and the synthesis of biologically active natural and unnatural products.

From the editorial office and on behalf of the Editorial and Advisory Board we wanted to welcome both of them and wish them an enjoyable time working with us.

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Review: Se and Te in organic chemistry

Take a look at this review to find out more about the latest developments in chalcogenophene chemistry.

Undoubtedly, the interest for selenium and tellurium incorporated to organic substrate has been increasing in the past few years. Moreover, the incorporation of selenium and tellurium in heterocyclic compounds may provide a solution their biological toxicity.

In this review, Cristiano Rhodena and Gilson Zeni from Rio Grande do Sul, Brazil, revisit different aspects of seleno- and tellurophenes chemistry, including their reactivity and applications in the field of heterocycles.

New development of synthesis and reactivity of seleno- and tellurophenes
Cristiano R. B. Rhoden and Gilson Zeni
Org. Biomol. Chem., 2011, 9, 1301-1313
DOI: 10.1039/C0OB00557F

And if you are interested in this one, you may also be interested in this other:

Tellurium: an element with great biological potency and potential
Lalla Aicha Ba, Mandy Döring, Vincent Jamier and Claus Jacob
Org. Biomol. Chem., 2010, 8, 4203-4216
DOI: 10.1039/C0OB00086H, Emerging Area

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Multicomponent reactions and multi-catalytic cascade processes

This highly topical emerging area is the inside cover of OBC Issue 5.

Dhevalapally B. Ramachary and Sangeeta Jain at University of Hyderabad, India, believe in the development of different ways of producing chemical products that have an influence in our every day life in a more sustainable way, producing less waste and involving less money.

They believe that organic synthesis can be made much more efficient by designing processes in which multiple catalysts operate sequentially in “one-pot” with multiple components.

In this review, Ramachary and Jain describe the first systematic efforts toward the development of sequential one-pot combinations of multi-component reactions (MCRs) and multi-catalysis cascade (MCC) reactions.

If you want to read about this emerging area, ‘click’ here to read all of this in one pot!

Free to access for 6 weeks!

Sequential one-pot combination of multi-component and multi-catalysis cascade reactions: an emerging technology in organic synthesis
Dhevalapally B. Ramachary and Sangeeta Jain
Org. Biomol. Chem., 2011, 9, 1277-1300
DOI: 10.1039/C0OB00611D

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HOT: Biosynthetic pathway for 7-deazapurines

Deazapurines are bicyclic heterocycles derived from purine where one nitrogen atom is replaced by a carbon. Although they have been widely studied in recent years, the mechanistic understanding of the biosynthesis of 7-deazapurines has always been intriguing.

There is a question that inevitably arise when looking at the biosynthetic pathway of deazapurines: Where does N-7 go? 

Now, Professor Moody and his group at University of Nottingham have solved this mystery by using a doubly labelled purine-adenine and following it up by NMR spectroscopy and mass spectrometry.
Their conclusions are supported and support a recent study published in Biochemistry.

If you want to find out more about the fate of this nitrogen and the mechanistic understanding of the biosynthesis of deazapurines, read this HOT paper which is free to access until 16th March.

7-Deazapurine biosynthesis: NMR study of toyocamycin biosynthesis in Streptomyces rimosus using 2-13C-7-15N-adenine
Ugo Battaglia, Jed E. Long, Mark S. Searle and Christopher J. Moody
Org. Biomol. Chem., 2011
DOI: 10.1039/C0OB01054E

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HOT: Highly selective formation of lantibiotic conjugates

Lantibiotics (and there is no spelling mistake) are a potential new class of antibiotics for clinical applications and food preservation. Their drawback is however their inability to penetrate the outer membranes of Gram-negative bacteria.

John Vederas and colleagues, at University of Alberta in Canada, try to overcome this problem by developing new ‘siderophores – transporters’ able to deliver lantibiotics to the targeted bacteria.

If you want to find out more about what happened next and the scope and limitation of siderophore-mediated drug transport for the development of new antibiotics download this HOT article which is free to access until 8th March.

Chemical synthesis and biological evaluation of gallidermin-siderophore conjugates
Sabesan Yoganathan, Clarissa S. Sit and John C. Vederas
Org. Biomol. Chem., 2011
DOI: 10.1039/C0OB00846J

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HOT: Aryl azides go with the flow

Organic azides are considered to be amongst the most hazardous chemicals and therefore not amongst the most popular within  synthetic chemistry communities. In organic chemistry they are commonly used as a way to introduce an amine group, which makes them key compounds for synthetic chemists.

Steven Ley, Ian Baxendale and their group at University of Cambridge, describe in these back to back papers the development of a flow process for the synthesis of alkyl and aryl azides in high conversions. One of the key features of this flow procedure is the introduction of a new monolithic triphenylphosphine reagent that allows the use of triphenylphosphine in flow to provide high purity products without the need of further purification steps.

They also describe a general protocol for the in-line purification of the intermediates. They incorporate the azide synthesis and purification process into a multistep flow sequence to generate a collection of aminocyanotriazoles in a fully automated fashion.

Now you can read these very interesting and HOT papers which are free to access until the 8th March.

Download both papers here.

Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent
Catherine J. Smith, Christopher D. Smith, Nikzad Nikbin, Steven V. Ley and Ian R. Baxendale
Org. Biomol. Chem., 2011
DOI: 10.1039/C0OB00813C

A fully automated, multistep flow synthesis of 5-amino-4-cyano-1,2,3-triazoles
Catherine J. Smith, Nikzad Nikbin, Steven V. Ley, Heiko Lange and Ian R. Baxendale
Org. Biomol. Chem., 2011
DOI: 10.1039/C0OB00815J

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Perspective: Multivalent inhibitors of lectins

Sebastien G. Gouin and his team at University of Nantes, France, review some of the important structural features in the synthesis of multivalent glycoconjugates for a tight binding with specific lectins.

Read this review on multivalent inhibitors of lectins from a different and very interesting point of view: how the scaffold influences potency.

Insights in the rational design of synthetic multivalent glycoconjugates as lectin ligands
David Deniaud, Karine Julienne and Sébastien G. Gouin
Org. Biomol. Chem., 2011, 9, 966-979
DOI: 10.1039/C0OB00389A, Perspective

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