Organic & Biomolecular Chemistry Blog

Gold nanoparticles detect avian influenza

07 Oct 2013

This paper is HOT as recommended by the referees, and is free to access for 4 weeks.
Published on behalf of Steve Moore, Organic & Biomolecular Chemistry web science writer.

The influenza virus is capable of crossing from animals to humans. The health threat posed by influenza jumping the species barrier has been highlighted by recent outbreaks: N5N1 ‘bird flu’ in 2003/2004, H1N1 ‘swine flu’ in 2009 and avian H7N9 earlier this year. Current methods used for the detection of influenza are time consuming and may require trained analysts and specialised equipment. There is a need for a rapid diagnostic test to discriminate between human influenza and emerging animal strains.

This HOT article describes a gold nanoparticle-based colorimetric assay for the detection of influenza. Specificity was achieved by targeting the haemagglutanin (HA) surface glycoprotein. Human influenza binds preferentially to sialic acid α2,6 galactose sequences and avian influenza preferentially binds to sialic acid α2,3 galactose sequences. Gold nanoparticles were functionalised with trivalent α2,6-thio-linked sialic acid ligands and polyethylene glycol ligands. A solution of gold nanoparticles was used to detect HA virus surface glycoproteins and in the presence of human influenza virus a colour change was observed. The colour change was caused by the aggregation of the glycopeptide with the influenza virus and was detectable with the naked eye. Owing to the careful choice of ligands, this assay was able to discriminate between human and avian H5N1 influenza.

Glyconanoparticles for the plasmonic detection and discrimination between human and avian influenza virus
María J. Marín, Abdul Rashid, Martin Rejzek, Shirley A. Fairhurst, Stephen A. Wharton, Stephen R. Martin, John W. McCauley, Thomas Wileman, Robert A. Field and David A. Russell
Org. Biomol. Chem., 2013,11, 7101-7107
DOI: 10.1039/C3OB41703D

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Mutant enzymes help break cocaine habit

02 Oct 2013

By Aliya Anwar.

An enzyme modified to hydrolyse cocaine 1000 faster than it did before could form the basis of the first medicinal treatment for cocaine addiction. Not only can the enzyme swiftly chop cocaine into inactive metabolites but modification of the enzyme has not affected its selectivity towards other natural substrates.

A treatment for cocaine abuse could be on the horizon © Shutterstock

Cocaine is one the most widely used illegal drugs in the world. Unlike many other commonly abused substances, there are no proven medications available to treat cocaine addition. The health consequences of cocaine abuse are severe and addicts can cause significant societal problems. Finding an addiction treatment is therefore of the utmost importance.

Substrate selectivity of high-activity mutants of human butyrylcholinesterase
Chang-Guo Zhan et al.
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41713A

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OMCOS 17 poster prizes

26 Sep 2013

By James Anson.

Congratulations to Carla Obradors and Keisuke Nakamura who received poster prizes from OBC and Chemical Science at OMCOS 17 (17th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis).

Carla Obradors, from the group of Professor Antonio Echavarren at Institute of Chemical Research of Catalonia (ICIQ) won for a poster entitled “Role of the Counterion in Intermolecular Gold(I)-Catalyzed Cycloadditions“, while Keisuke Nakamura from the group of Professor Naoto Chatani at Osaka University presented a poster entitled “Nickel-Catalyzed Transformations Involving the Cleavage of a Carbon-Nitrogen Bond in Aniline Derivative“.

Both winners received a copy of Organometallic Chemistry, edited by Ian J S Fairlamb, Jason M Lynam. Their awards were presented by Chemical Science Associate Editor Matt Gaunt.

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RSC Organic Division Poster Symposium – Deadline for poster abstracts 02 October 2013

23 Sep 2013

By James Anson.

RSC Organic Division Poster Symposium: Deadline for poster abstracts 02 October 2013

The RSC Organic Division Poster Symposium is still accepting abstracts, but not for long. If you are a final year PhD student based in the UK/ROI and would like the opportunity to showcase your work to leading chemists in industry and academia, as well as your peers, make sure you submit your poster abstract by Wednesday 2^nd October.

The symposium will take place on Monday 2^nd December 2013, at The Chemistry Centre, Burlington House, London and there are several prizes available on the day. Alongside the £500 First Prize, there will also be a £500 “Selected by Industry” prize and two runners-up prizes of £250. And this year our headline sponsor, F. Hoffmann-La Roche are offering a further prize of a visit to their site in Basel, Switzerland, to the First and Industry prize winners.

Reasonable travel costs will be covered for the students who are selected to present at this meeting. If you would like to find out more about the symposium and submit an abstract, visit our symposium website

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

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HOT Organic & Biomolecular Chemistry articles for September

19 Sep 2013

By James Anson.

Disulfide bond reduction-triggered molecular hydrogels of folic acid–Taxol conjugates
Chengbiao Yang, Dongxia Li, Qianqi FengZhao, Lianyong Wang, Ling Wang and Zhimou Yang
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB40969D, Paper

The influence of G-quadruplex structure on DNA-based asymmetric catalysis using the G-quadruplex-bound cationic porphyrin TMPyP4·Cu
Michael Wilking and Ulrich Hennecke
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41366G, Paper

A highly active cyclometallated iridium catalyst for the hydrogenation of imines
Barbara Villa-Marcos, Weijun Tang, Xiaofeng Wu and Jianliang Xiao
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41150H, Paper

ω-Transaminase-catalyzed asymmetric synthesis of unnatural amino acids using isopropylamine as an amino donor
Eul-Soo Park, Joo-Young Dong and Jong-Shik Shin
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB40495A, Paper

Visible-light activatable organic CO-releasing molecules (PhotoCORMs) that simultaneously generate fluorophores
Ping Peng, Chaoming Wang, Zheng Shi, Valentine K. Johns, Liyuan Ma, Jeremiah Oyer, Alicja Copik, Robert Igarashi and Yi Liao
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41385C, Communication

The first asymmetric total synthesis of (+)-coriandrone A and B
Wenjing Wang, Jijun Xue, Tian Tian, Yingdong Jiao and Ying Li
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41497C, Communication

Convergent synthesis and cellular uptake of multivalent cell penetrating peptides derived from Tat, Antp, pVEC, TP10 and SAP
Gabriela A. Eggimann, Stefanie Buschor, Tamis Darbre and Jean-Louis Reymond
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41023D, Paper

Copper(II) chloride mediated (aza)oxindole synthesis by oxidative coupling of C_sp²–H and C_sp³–H centers: substrate scope and DFT study
Chandan Dey, Evgeny Larionov and E. Peter Kündig
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41254G, Paper

Histidine-functionalized water-soluble nanoparticles for biomimetic nucleophilic/general-base catalysis under acidic conditions
Geetika Chadha and Yan Zhao
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41485J, Paper

A one-pot coupling–addition–cyclocondensation sequence (CACS) to 2-substituted 3-acylpyrroles initiated by a copper-free alkynylation
Jan Nordmann and Thomas J. J. Müller
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41269E, Paper

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HOT – Novel copper-mediated cyclisations leading to diverse heterocyclic structures

17 Sep 2013

By Annabella Newton, RSC Blogs Writer.

Annabella Newton is an organic chemist and trainee patent attorney with Phillips Ormonde Fitzpatrick based in Melbourne, Australia.

In this HOT paper, Peter Kündig’s research team have developed a new mode of copper-mediated oxidative coupling allowing access to racemic (aza)oxindole structure in an efficient and atom-economic fashion.

Oxindoles are useful structures in organic chemistry as they are found ubiquitously in nature. Molecules bearing this motif have a range of interesting biological properties and new methods of their construction are always useful to the organic chemist.

Peter Kündig and his team at the University of Geneva have been looking into the asymmetric synthesis of these structures, employing palladium-catalysed intramolecular α-arylations of amide substrates.[1] During these studies, they discovered a novel and efficient route to access racemic 3,3,-disubstituted oxindoles which employed a copper-mediated radical reaction.[2] This reaction has also been applied to the racemic synthesis of aza-oxindoles.[3]

In this excellent account from Prof. Kündig, this methodology has been further explored. The substrate scope has been expanded leading to a range of oxindoles bearing a variety of aromatic, hetero- aromatic, allyl and heteroatom substituents in the 3-position. The reaction was also successfully performed on a large scale, with excellent yield and regioselectivity. In addition to this, some nifty DFT and computational studies confirm the proposed mechanism and regioselectivity.

Read the full article here.

Copper(II) chloride mediated (aza)oxindole synthesis by oxidative coupling of Csp2–H and Csp3–H centers: substrate scope and DFT study
Chandan Dey, Evgeny Larionov and E. Peter Kündig
Org. Biomol. Chem., 2013, DOI: 10.1039/c3ob41254g

[1] E. P. Kündig, T. M. Seidel, Y. X. Jia and G. Bernardinelli, Angew. Chem., Int. Ed., 2007, 46, 8484; Y. X. Jia, J. M. Hillgren, E. L. Watson, S. P. Marsden and E. P. Kündig, Chem. Commun., 2008, 4040.

[2] Y. X. Jia and E. P. Kündig, Angew. Chem., Int. Ed., 2009, 48, 1636.

[3] C. Dey and E. P. Kündig, Chem. Commun., 2012, 48, 3064.

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Chemical and Biological Therapeutic Approaches to Neurological Disorders II

16 Sep 2013

By James Anson.

There’s still time to register for the second one-day symposium on Chemical and Biological Therapeutic Approaches to Neurological Disorders, on Monday 23^rd September. The meeting will feature presentations and posters, from leading experts in academia and industry, about new developments in genetics, biochemistry, pathophysiology and medicinal chemistry relating to neurological disorders. A wide range of conditions will be discussed, including Alzheimer’s disease, epilepsy, schizophrenia, multiple sclerosis and Parkinson’s disease.

Neurological disorders are an increasingly important global public health problem, and the cause of much long-term suffering and disability. Currently available pharmaceuticals have been ineffective in curing many of these disorders and developing a deeper understanding of the nervous system is one of the major challenges facing scientists in the 21^st century. New research will hopefully contribute to the identification of better clinical biomarkers and medicines for diagnosis, monitoring and treatment of neurological disorders.

This one day symposium has been organised by the RSC’s Biotechnology Group with support from the Chemistry Biology Interface Division, and will be held at The Chemistry Centre, Burlington House, London. Speakers include:

Prof. Christopher Dobson, University of Cambridge
Prof. Ciaran Regan, University College Dublin
Prof. Lennart Bunch, University of Copenhagen
Prof. Peter Jenner, King’s College London
Prof. Stefan Przyborski, University of Durham
Dr. Jan Kehler, H. Lundbeck, A/S
Prof. Jonathan Corcoran, University College Dublin
Dr. Jan Passchier, Imanova Ltd.

If you would like to attend, please register here.

If you would like to find out more about this event, more information can be found on the RSC website.

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Hydrogel treatment targets tumours

27 Aug 2013

By Alessia Millemaggi.

Hydrogels of cancer drug taxol injected directly into tumours have been shown to be more effective at inhibiting tumour growth than intravenous taxol injections of four times the dosage.

Taxol is used to treat many forms of cancer, including breast, lung and ovarian cancer. Its administration is typically every three weeks by intravenous injection and it can take several hours to achieve the required dose.

Hydrogels have great potential to reduce the dosing frequency of chemotherapy. They can hold exceptionally high drug loadings that are released in a controlled and sustained manner. However, synthesising such hydrogels is complex, ultimately resulting in low yields.

Zhimou Yang and fellow researchers at Nankai University in China have successfully simplified the synthesis of taxol hydrogels. Their hydrogel contains taxol conjugated to folic acid. The folic acid facilitates tumour targeting as many cancer cells have folic acid receptors so the hydrogels will sustainably release their taxol cargo through ester bond hydrolysis at the site of cancer cells.

Read the full article on Chemistry World.

Disulfide bond reduction-triggered molecular hydrogels of Folic acid-Taxol conjugates
Chengbiao Yang et al.
DOI: 10.1039/C3OB40969D

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HOT Organic & Biomolecular Chemistry articles for August

23 Aug 2013

By Marie Cote, Deputy Editor.

Keep checking back this month to see new HOT articles that are recommended by our referees

Pd(0)-catalyzed benzylic arylation–oxidation of 4-methylquinazolines via sp3 C–H activation under air conditions
Dan Zhao, Min-Xue Zhu, Yue Wang, Qi Shen and Jian-Xin Li
Org. Biomol. Chem., 2013,11, 6246-6249
DOI: 10.1039/C3OB41488D, Communication

Major mechanistic differences between the reactions of hydroxylamine with phosphate di- and tri-esters
Michelle Medeiros, Eduardo H. Wanderlind, José R. Mora, Raphaell Moreira, Anthony J. Kirby and Faruk Nome
Org. Biomol. Chem., 2013,11, 6272-6284
DOI: 10.1039/C3OB40988K, Paper
From themed collection In Celebration of Andrew D. Hamilton’s Career in Chemistry

Novel synthesis of various orthogonally protected Cα-methyllysine analogues and biological evaluation of a Vapreotide analogue containing (S)-α-methyllysine
Souvik Banerjee, Walker J. Wiggins, Jessie L. Geoghegan, Catherine T. Anthony, Eugene A. Woltering and Douglas S. Masterson
Org. Biomol. Chem., 2013,11, 6307-6319
DOI: 10.1039/C3OB41282B, Paper

Synthesis of novel pyrazole-based heterocycles via a copper(II)-catalysed domino annulation
Márió Gyuris, László G. Puskás, Gábor K. Tóth and Iván Kanizsai
Org. Biomol. Chem., 2013,11, 6320-6327
DOI: 10.1039/C3OB41146J, Paper

Structure–activity studies of 4-phenyl-substituted 2′-benzoylpyridine thiosemicarbazones with potent and selective anti-tumour activity
Adeline Y. Lukmantara, Danuta S. Kalinowski, Naresh Kumar and Des R. Richardson
Org. Biomol. Chem., 2013,11, 6414-6425
DOI: 10.1039/C3OB41109E, Paper

Transport of macrocyclic compounds across phospholipid bilayers by umbrella-rotaxanes
Christine Chhun, Josée Richard-Daniel, Julie Kempf and Andreea R. Schmitzer
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41209A, Paper

Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity
Steven Gunawan and Christopher Hulme
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB40900G, Paper

Comparative in vitro studies of MR imaging probes for metabotropic glutamate subtype-5 receptor targeting
Sven Gottschalk, Jörn Engelmann, Gabriele A. Rolla, Mauro Botta, David Parker and Anurag Mishra
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41297K, Paper

Synthesis and biological evaluation of non-isomerizable analogues of Ala-tRNA^Ala
Denia Mellal, Matthieu Fonvielle, Marco Santarem, Maryline Chemama, Yoann Schneider, Laura Iannazzo, Emmanuelle Braud, Michel Arthur and Mélanie Etheve-Quelquejeu
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41206G, Paper

First synthesis of antitumoral dasyscyphin B
Ali Akhaouzan, Antonio Fernández, Ahmed I. Mansour, Esteban Alvarez, Ali Haidöur, Ramón Alvarez-Manzaneda, Rachid Chahboun and Enrique Alvarez-Manzaneda
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41290C, Paper

Open Access

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In Celebration of Andrew D. Hamilton’s Career in Chemistry

22 Aug 2013

By Marie Cote, Deputy Editor.

Professor Andrew D. Hamilton FRS

We are delighted to present an on-line collection of articles dedicated to Professor Andrew D. Hamilton FRS, on the occasion of his 60th birthday.

Students and colleagues past and present have come together to contribute over 40 communications, full papers, feature articles and perspectives of some of their latest work now published in ChemComm, OBC, MedChemComm and RSC Advances.

“An insight into the rise of a star in molecular recognition, ground breaking discoveries, and on a more light-hearted note, some fond reminiscences of research in Cambridge, Princeton, Pittsburgh, Yale and Oxford.”

Read the introductory Profile article by guest-editors Sam Thompson and Andrew J. Wilson, with the contribution of Sir Alan R. Battersby.

Access the full collection here

As a taster, the collection of articles includes:

Chemical approaches for detection and destruction of nerve agents
Dariush Ajami and Julius Rebek
Org. Biomol. Chem., 2013,11, 3936-3942
DOI: 10.1039/C3OB40324F

Diverse topologies in dynamic combinatorial libraries from tri- and mono-thiols in water: sensitivity to weak supramolecular interactions
Artur R. Stefankiewicz and Jeremy K. M. Sanders
Chem. Commun., 2013,49, 5820-5822
DOI: 10.1039/C3CC41158C

Peptides: minimal drug surrogates to interrogate and interfere with protein function
A. Cruz-Migoni, N. Fuentes-Fernandez and T. H. Rabbitts
Med. Chem. Commun., 2013,4, 1218-1221
DOI: 10.1039/C3MD00142C

A rotaxane host system containing integrated triazole C–H hydrogen bond donors for anion recognition
Nicholas G. White and Paul D. Beer
Org. Biomol. Chem., 2013,11, 1326-1333
DOI: 10.1039/C2OB27229F, Paper

Supramolecular hydrogels based on bola-amphiphilic glycolipids showing color change in response to glycosidases
Rika Ochi, Kazuya Kurotani, Masato Ikeda, Shigeki Kiyonaka and Itaru Hamachi
Chem. Commun., 2013,49, 2115-2117
DOI: 10.1039/C2CC37908B, Communication

Identification of a potent salicylic acid-based inhibitor of tyrosine phosphatase PTP1B
Sina Haftchenary, Daniel P. Ball, Isabelle Aubry, Melissa Landry, Vijay M. Shahani, Steven Fletcher, Brent D. G. Page, Andriana O. Jouk, Michel L. Tremblay and Patrick T. Gunning
Med. Chem. Commun., 2013,4, 987-992
DOI: 10.1039/C3MD00011G

and many more!

Why not have a look at the great cover artworks authors have created to illustrate their articles from the collection – click on the images to access the articles!