New Editorial Board Chair

Introducing the new Editorial Board Chair for Organic & Biomolecular Chemistry, Professor Andrei Yudin

Prof. Andrei YudinWe are delighted to announce that Professor Andrei Yudin has become the Chair of the Editorial Board for Organic & Biomolecular Chemistry.

For the past 3 years Andrei has been handling manuscripts for OBC as an Associate Editor, but with his move to his new role he will no longer be handling manuscripts himself.

The previous Chair, Professor Jeff Bode, passed over the reins to Andrei at the begining of 2015, and this brings his time on the OBC Editorial Board to a close. Professor Paolo Scrimin’s time on the Editorial Board has also drew to a close at the end of 2014. We would all like to thank both Jeff and Paolo for the many years of service and the invaluable contributions they have made in helping to guide the journal.

About Andrei:

Professor Andrei Yudin obtained his B.Sc. degree at Moscow State University and his Ph.D. degree at the University of Southern California under the direction of Professors G. K. Surya Prakash and George A. Olah. He subsequently took up a postdoctoral position in the laboratory of Professor K. Barry Sharpless at the Scripps Research Institute. In 1998, he started his independent career at the University of Toronto. He received early tenure, becoming an Associate Professor in 2002, and received an early promotion to the rank of a Full Professor in 2007.

Amongst Professor Yudin’s awards are the CSC Award in Combinatorial Chemistry, the 2004 Amgen New Faculty Award, the 2010 CSC Merck-Frosst Therapeutic Center Award, the 2010 Rutherford Medal of the Royal Society of Canada, the 2011 University of Toronto Inventor of the Year Award, and the 2015 Bernard Belleau Award in Medicinal Chemistry. Professor Yudin is a Fellow of the Royal Society of Canada.

Andrei’s Homepage: http://www.chem.utoronto.ca/wp/yudinlab/

Andrei also maintains a science blog – Amphoteros – that aims to illuminate the ongoing synthetic and chemical biology efforts in his lab and to discuss general advances in science, both from the past and present.

Below is his blog following our Editorial Board meeting at the end of last year.

Some news from London

Posted on November 20, 2014

Over the past several days I have been in London, England, where I attended the Fall Board Meeting of Organic and Biomolecular Chemistry. Richard Kelly, the Managing Editor of this RSC publication, has put this meeting together in the Mayfair district of London. Jeff Bode (ETH, Zurich) is stepping down as the Board Chairman and I will be taking over his responsibilities from January 2015. I have to tip my hat off to Jeff for his leadership over the past several years. I have thoroughly enjoyed my role of one of the Associate Editors. The difference now will be that I am no longer going to handle manuscripts, but will instead oversee some strategic areas for growth and improvement. I think this will be very exciting. Earlier this week, I had a lot of fun together with Jeff as well as Ashraf Brik of Ben Gurion University, Margaret Brimble of the University of Aukland, Tony Davis of the University of Bristol, Jonathan Clayden of the University of Manchester, Pauline Chiu of the University of Hong Kong, and Paolo Scrimin of the University of Padova. Unfortunately, Jin-Quan Yu of Scripps was not able to make it to this meeting. Along with Margaret and I, Jin-Quan is one of OBC’s Associate Editors.

In terms of chemistry, I actually wanted to share something that relates to the work of Margaret Brimble (she flew in all the way from New Zealand to meet us). Margaret brought along some exciting news: NNZ-2566, a molecule developed as part of a collaboration between her lab and Neuren Pharma, was recently approved by the FDA, which has granted orphan drug designation to NNZ-2566 for treatment of Fragile X Syndrome. This tripeptide also demonstrates neuroprotective efficacy in models of traumatic brain injury such as concussion. Evidently, the U.S. Army is very interested in NNZ-2566, although not much is known about the mechanism of action of this exciting compound. What I found remarkable is that the tripeptide is orally bioavailable. The C-methyl proline residue makes this molecule considerably more stable than the corresponding non-methylated congener. The methyl group really “messes up” with the nearby amide bond, which apparently drives the logD down and improves the pharmacological profile of NNZ-2566. I have always thought that there is something special about C-methylproline…

http://www.neurenpharma.com/irm/content/nnz-2566-in-rett-syndrome.aspx?RID=330

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HOT Organic & Biomolecular Chemistry articles

The following Organic & Biomolecular Chemistry articles have all been recommened by the reviewers of the articles as being particularly interesting or particularly significant research. These have all been made free to access until 15th February 2015. The order they appear in the list holds no special meaning or ranking.

Cationic azacryptands as selective three-way DNA junction binding agents
Jana Novotna, Aurelien Laguerre, Anton Granzhan, Marc Pirrotta, Marie-Paule Teulade-Fichou and David Monchaud  
DOI: 10.1039/C4OB01846J, Paper

C4OB01846J GA


Efficient merging of copper and photoredox catalysis for the asymmetric cross-dehydrogenative-coupling of alkynes and tetrahydroisoquinolines
Inna Perepichka, Soumen Kundu, Zoë Hearne and Chao-Jun Li  
DOI: 10.1039/C4OB02138J, Paper

C4OB02138J GA


A peptide topological template for the dispersion of [60]fullerene in water
S. Bartocci, D. Mazzier, A. Moretto and M. Mba  
DOI: 10.1039/C4OB02102A, Communication
From themed collection Supramolecular Chemistry in Water

C4OB02102A GA


6-Substituted 1,2-benzoxathiine-2,2-dioxides are isoform-selective inhibitors of human carbonic anhydrases IX, XII and VA
Muhammet Tanc, Fabrizio Carta, Andrea Scozzafava and Claudiu T. Supuran  
DOI: 10.1039/C4OB02155J, Communication

C4OB02155J GA


Artificial metalloenzymes for the diastereoselective reduction of NAD+ to NAD2H
Tommaso Quinto, Daniel Häussinger, Valentin Köhler and Thomas R. Ward  
DOI: 10.1039/C4OB02071E, Communication
From themed collection Supramolecular Chemistry in Water

C4OB02071E GA

 


Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing π-extended diarylacetylene motifs
Sara De Ornellas, John M. Slattery, Robert M. Edkins, Andrew Beeby, Christoph G. Baumann and Ian J. S. Fairlamb  
DOI: 10.1039/C4OB02081B, Communication

C4OB02081B GA


One-pot quadruple/triple reaction sequence: a useful tool for the synthesis of natural products
K. Kashinath and D. Srinivasa Reddy  
DOI: 10.1039/C4OB02143F, Perspective

C4OB02143F GA


 

Indole-based novel small molecules for the modulation of bacterial signalling pathways
Nripendra Nath Biswas, Samuel K. Kutty, Nicolas Barraud, George M. Iskander, Renate Griffith, Scott A. Rice, Mark Willcox, David StC. Black and Naresh Kumar  
DOI: 10.1039/C4OB02096K, Paper

C4OB02096K GA


Carbocycles from donor–acceptor cyclopropanes
Huck K. Grover, Michael R. Emmett and Michael A. Kerr  
DOI: 10.1039/C4OB02117G, Review Article

C4OB02117G GA


Synthesis of isoxazolidine-containing uridine derivatives as caprazamycin analogues
Mayumi Yamaguchi, Akira Matsuda and Satoshi Ichikawa  
DOI: 10.1039/C4OB02142H, Paper

C4OB02142H GA


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What are your colleagues reading in Organic & Biomolecular Chemistry?

The articles below are the most read Organic & Biomolecular Chemistry articles in July, August and September 2014.

Marine natural products-inspired phenylmethylene hydantoins with potent in vitro and in vivo antitumor activities via suppression of Brk and FAK signaling
Asmaa A. Sallam, Mohamed M. Mohyeldin, Ahmed I. Foudah, Mohamed R. Akl, Sami Nazzal, Sharon A. Meyer, Yong-Yu Liu and Khalid A. El Sayed 
DOI: 10.1039/C4OB00553H

Watsonianone A–C, anti-plasmodial β-triketones from the Australian tree, Corymbia watsoniana
Anthony R. Carroll, Vicky M. Avery, Sandra Duffy, Paul I. Forster and Gordon P. Guymer 
DOI: 10.1039/C2OB26931G

Pyridostatin analogues promote telomere dysfunction and long-term growth inhibition in human cancer cells
Sebastian Müller, Deborah A. Sanders, Marco Di Antonio, Stephanos Matsis, Jean-François Riou, Raphaël Rodriguez and Shankar Balasubramanian 
DOI: 10.1039/C2OB25830G

Synthesis, characterization and biological evaluation of carboranylmethylbenzo[b]acridones as novel agents for boron neutron capture therapy
A. Filipa F. da Silva, Raquel S. G. R. Seixas, Artur M. S. Silva, Joana Coimbra, Ana C. Fernandes, Joana P. Santos, António Matos, José Rino, Isabel Santos and Fernanda Marques 
DOI: 10.1039/C4OB00644E

Organic synthetic transformations using organic dyes as photoredox catalysts
Shunichi Fukuzumi and Kei Ohkubo 
DOI: 10.1039/C4OB00843J

Copper-catalysed direct radical alkenylation of alkyl bromides
Xu Zhang, Hong Yi, Zhixiong Liao, Guoting Zhang, Chao Fan, Chu Qin, Jie Liu and Aiwen Lei 
DOI: 10.1039/C4OB00813H

Metal-free oxidative olefination of primary amines with benzylic C–H bonds through direct deamination and C–H bond activation
Liang Gong, Li-Juan Xing, Tong Xu, Xue-Ping Zhu, Wen Zhou, Ning Kang and Bin Wang 
DOI: 10.1039/C4OB01025F

Recent advances in trifluoromethylation of organic compounds using Umemoto’s reagents
Cai Zhang 
DOI: 10.1039/C4OB00671B

An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones
Venkatachalam Rajeshkumar, Selvaraj Chandrasekar and Govindasamy Sekar 
DOI: 10.1039/C4OB01564A

Amino acid chirons: a tool for asymmetric synthesis of heterocycles
Priyanka Singh, Krishnananda Samanta, Sanjit Kumar Das and Gautam Panda 
DOI: 10.1039/C4OB00943F

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HOT Organic & Biomolecular Chemistry articles

The following Organic & Biomolecular Chemistry articles have all been recommened by the reviewers of the articles as being particularly interesting or particularly significant research. These have all been made free to access until 31st December 2014. The order they appear in the list holds no special meaning or ranking.

Catalytic asymmetric desymmetrization approaches to enantioenriched cyclopentanes
Madhu Sudan Manna and Santanu Mukherjee  
DOI: 10.1039/C4OB01649A, Perspective

C4OB01649A GA


Corrin-based chemosensors for the ASSURED detection of endogenous cyanide
Felix Zelder and Lucas Tivana  
DOI: 10.1039/C4OB01889C, Perspective


An efficient synthetic route to 1,3-bis(arylethynyl)isobenzofuran using alkoxybenzocyclobutenone as a reactive platform
Kenta Asahina, Suguru Matsuoka, Ryosuke Nakayama and Toshiyuki Hamura  
DOI: 10.1039/C4OB02012J, Communication

C4OB02012J GA


Cationic azacryptands as selective three-way DNA junction binding agents
Jana Novotna, Aurelien Laguerre, Anton Granzhan, Marc Pirrotta, Marie-Paule Teulade-Fichou and David Monchaud  
DOI: 10.1039/C4OB01846J, Paper

C4OB01846J GA


An efficient reagent for covalent introduction of alkynes into proteins
Jie Zhang, Dejun Ma, Dawei Du, Zhen Xi and Long Yi  
DOI: 10.1039/C4OB01873G, Communication

C4OB01873G GA


Efficient merging of copper and photoredox catalysis for the asymmetric cross-dehydrogenative-coupling of alkynes and tetrahydroisoquinolines
Inna Perepichka, Soumen Kundu, Zoë Hearne and Chao-Jun Li  
DOI: 10.1039/C4OB02138J, Paper

C4OB02138J GA


Naphthalene diimides as red fluorescent pH sensors for functional cell imaging
Filippo Doria, Marco Folini, Vincenzo Grande, Graziella Cimino-Reale, Nadia Zaffaroni and Mauro Freccero  
DOI: 10.1039/C4OB02054E, Paper

C4OB02054E GA

A peptide topological template for the dispersion of [60]fullerene in water
S. Bartocci, D. Mazzier, A. Moretto and M. Mba  
DOI: 10.1039/C4OB02102A, Communication
C4OB02102A GA

6-Substituted 1,2-benzoxathiine-2,2-dioxides are isoform-selective inhibitors of human carbonic anhydrases IX, XII and VA
Muhammet Tanc, Fabrizio Carta, Andrea Scozzafava and Claudiu T. Supuran  
DOI: 10.1039/C4OB02155J, Communication
C4OB02155J GA

The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions
Steffen Glöckner, Duc N. Tran, Richard J. Ingham, Sabine Fenner, Zoe E. Wilson, Claudio Battilocchio and Steven V. Ley  
DOI: 10.1039/C4OB02105C, Paper
From themed collection Recent Advances in Flow Synthesis and Continuous Processing
C4OB02105C GA
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Winners at the 2014 RSC Organic Division Poster Symposium

Congratulations to the winners at the 2014 RSC Organic Division Poster Symposium, held on 01 December 2014 at the Royal Society of Chemistry, Burlington House, London.

The symposium, supported by headline sponsor F. Hoffmann-La Roche Ltd, provided a fantastic opportunity for final year organic chemistry PhD students to showcase their research and network with their peers, leading academics, and industrial chemists.

Organic & Biomolecular Chemistry was delighted to offer a front cover artwork opportunity to the winner of the First Prize, as well as a 1-year personal subscription to the journal to the winner of the Industry Prize.

First Prize

Sonja Kuschel, University of Manchester (Supervisor: Professor David Leigh). Poster title: Towards man-made ribosomes: Nanomachines for sequential peptide synthesis

Runners Up Prizes

Antony Burton, University of Bristol (Supervisor: Professor Derek Woolfson). Poster title: Installing Catalytic Activity into a de novo Designed Protein Structure

Sarah Walker, Heriot-Watt University (Supervisor: Dr Ai-Lan Lee). Poster title: Development of Pd(II)-catalysed oxidative Heck reactions and CH functionalisations

Industry Prize (selected by the industrial delegates)

Antoine Maruani, University College London (Supervisors: Professor Stephen Caddick and Dr Vijay Chudasama). Poster title: A Novel Class of Tuneable reagents for Selective Dual Modification of Proteins

Participants’ Prize (selected by the students)

Owen Davis, Imperial College London (Supervisor: Dr James Bull). Poster title: Synthesis and Functionalisation of Highly Substituted Oxetanes: Molecular Scaffolds for Drug Discovery

The event was also supported by: AstraZeneca, Evotec, Johnson Matthey Catalysis and Chiral Technologies, Pfizer Neusentis, Takeda, UCB and Vertex Pharmaceuticals.

Winners (left to right): Sonja Kuschel, Owen Davis, Sarah Walker, Antony Burton, Antoine Maruani (© MPP Image Creation / Royal Society of Chemistry)

With the judges and organising committee (left to right): Dr Andrew Thomas, Dr Anne Horan, Professor Jonathan Clayden, Mr Owen Davis, Professor Rob Field, Mrs Sonja Kuschel, Professor Julian Blagg, Miss Sarah Walker, Professor Stuart Conway, Mr Antony Burton, Mr Antoine Maruani, Dr David Rees, Dr Sarah Rook, Professor Sue Gibson, Miss Charlotte Still (© MPP Image Creation / Royal Society of Chemistry)

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Take 1…minute for chemistry in health

Can you explain the importance of chemistry to human health in just 1 minute? If you’re an early-career researcher who is up to the challenge, making a 1 minute video could win you £500.

The chemical sciences will be fundamental in helping us meet the healthcare challenges of the future, and we are committed to ensuring that they contribute to their full potential. As part of our work in this area, we are inviting undergraduate and PhD students, post-docs and those starting out their career in industry to produce an original video that demonstrates the importance of chemistry in health.

We are looking for imaginative ways of showcasing how chemistry helps us address healthcare challenges. Your video should be no longer than 1 minute, and you can use any approach you like.

The winner will receive a £500 cash prize, with a £250 prize for second place and £150 prize for third place up for grabs too.

Stuck for inspiration? Last year’s winning video is a good place to start. John Gleeson’s video was selected based on the effective use of language, dynamic style, creativity and its accurate content.

The closing date for entries to be submitted is 30 January 2015. Our judging panel will select the top five videos. We will then publish the shortlisted videos online and open the judging to the public to determine the winner and the runners up.

For more details on how to enter the competition and who is eligible, join us at the Take 1… page.

Good luck!

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A new reagent for click bioconjugation

A recent communication in Organic and Biomolecular Chemistry reports the synthesis of a new reagent for the introduction of alkynes into proteins; a key step for click bioconjugation. The new diazonium reagent was prepared in a one-pot synthesis from commercially available 4-ethynylaniline.

Having optimized bioconjugation in a tyrosine containing small molecule, the new diazonium reagent was then used to covalently label proteins. Fluorescence labelling of protein surface tyrosine residues was achieved under mild conditions (pH 8.0) by reaction of the protein with the diazonium reagent and subsequent reaction with an azide-containing fluorescent compound. The new diazonium reagent was also used to achieve protein PEGylation; a strategy that could be employed to improve protein stability and reduce immunogenicity.

The new diazonium reagent can facilitate bioconjugation in a range of proteins and could be a useful addition to the biochemist’s toolbox.

Read the full article:
An efficient reagent for covalent introduction of alkynes into proteins
Jie Zhang, Dejun Ma, Dawei Du, Zhen Xi and Long Yi
Org. Biomol. Chem., 2014, DOI: 10.1039/C4OB01873G

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HOT Organic & Biomolecular Chemistry articles

The following Organic & Biomolecular Chemistry articles have all been recommened by the reviewers of the articles as being particularly interesting or particularly significant research. These have all been made free to access until 30th November. The order they appear in the list holds no special meaning or ranking.

Design strategies for bioorthogonal smart probes
Peyton Shieh and Carolyn R. Bertozzi
DOI: 10.1039/C4OB01632G, Review Article

bioorthogonal smart probes


Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride: stereocontrolled and regiocontrolled access to 1,2,3-trifunctionalized cyclobutanes
Florian Hernvann, Gloria Rasore, Valérie Declerck and David J. Aitken
DOI: 10.1039/C4OB01383B, Paper

Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride


Towards novel efficient and stable nuclear import signals: synthesis and properties of trimethylguanosine cap analogs modified within the 5′,5′-triphosphate bridge
Malgorzata Zytek, Joanna Kowalska, Maciej Lukaszewicz, Blazej A. Wojtczak, Joanna Zuberek, Aleksandra Ferenc-Mrozek, Edward Darzynkiewicz, Anna Niedzwiecka and Jacek Jemielity
DOI: 10.1039/C4OB01579G, Paper

trimethylguanosine cap analogs


Catalytic asymmetric synthesis of the pentacyclic core of (−)-nakadomarin A via oxazolidine as an iminium cation equivalent
Nobuya Tsuji, Michael Stadler, Naoya Kazumi, Tsubasa Inokuma, Yusuke Kobayashi and Yoshiji Takemoto
DOI: 10.1039/C4OB01678E, Communication

atalytic asymmetric synthesis of the pentacyclic core of (−)-nakadomarin A


Short and efficient synthesis of fluorinated δ-lactams
Thomas J. Cogswell, Craig S. Donald, De-Liang Long and Rodolfo Marquez
DOI: 10.1039/C4OB01547A, Paper

synthesis of fluorinated δ-lactams


An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones
Venkatachalam Rajeshkumar, Selvaraj Chandrasekar and Govindasamy Sekar
DOI: 10.1039/C4OB01564A, Paper

 I2-catalyzed synthesis of isatins


5-Nitroindole oligonucleotides with alkynyl side chains: universal base pairing, triple bond hydration and properties of pyrene “click” adducts
Sachin A. Ingale, Peter Leonard, Haozhe Yang and Frank Seela
DOI: 10.1039/C4OB01478B, Paper

5-Nitroindole oligonucleotides with alkynyl side chains


Cross-strand histidine–aromatic interactions enhance acyl-transfer rates in beta-hairpin peptide catalysts
M. Matsumoto, S. J. Lee, M. R. Gagné and M. L. Waters
DOI: 10.1039/C4OB01754D, Paper

 Cross-strand histidine–aromatic interactions enhance acyl-transfer rates in beta-hairpin peptide catalysts


The asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines via two sequential tandem ring-closure/N-debenzylation processes
Stephen G. Davies, Ai M. Fletcher, Emma M. Foster, Ian T. T. Houlsby, Paul M. Roberts, Thomas M. Schofield and James E. Thomson
DOI: 10.1039/C4OB01737D, Paper

asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines


Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents
Louis C. Morrill, Daniel G. Stark, James E. Taylor, Siobhan R. Smith, James A. Squires, Agathe C. A. D’Hollander, Carmen Simal, Peter Shapland, Timothy J. C. O’Riordan and Andrew D. Smith
DOI: 10.1039/C4OB01788A, Paper

Organocatalytic Michael addition–lactonisation of carboxylic acids

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Cyanide test for cassava

Hamish Crawford writes about an Organic & Biomolecular Chemistry article for Chemistry World

A new sensing system that changes colour to indicate if a cassava-based foodstuff is safe to eat by checking for hydrogen cyanide has been devised by researchers in Switzerland and Mozambique.

Cassava, an edible root that grows well in poor conditions, is the third largest source of calories for people in the tropics. However, as a self-defence mechanism against attack from pests and predators, cassava releases hydrogen cyanide upon damage to its cells. Sun-drying, fermentation and other traditional processing techniques can successfully eliminate the hydrogen cyanide but it may remain and cause a variety of illnesses, including tropical ataxic neuropathy and epidemic spastic paraparesis, if pre-consumption treatment is substandard…..

Read the full article in Chemistry World»


Read the original journal article in Organic & Biomolecular Chemistry – it’s free to access until 4 December:
Corrin-based chemosensors for the ASSURED detection of endogenous cyanide
Felix Zelder and Lucas Tivana
DOI: 10.1039/C4OB01889C

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Diversification of a Multicomponent Reaction

Arun Ankush Tanpure, a graduate student at IISER Pune, India, writes on a recent OBC article

The Ugi reaction was one of the very first multicomponent reactions exploited to develop chemical libraries, which further extended to combinatorial, solid phase and flow synthesis for evolving new lead structures of active agents. Implementing the Ugi reaction in combination with other organic reactions enlarges the chemical diversity of possible products.

Researchers at Vrije University Brussel, led by Steven Ballet, have made a step forward by executing a one-pot Ugi-Huisgen tandem reaction and found an alternative high atom economy pathway for the synthesis of conformationally constrained, amino-triazoloazepinone-containing di- and tripeptides.

Strategically, they have used an unconventional azide containing acid, and alkyne amine along with traditional aldehydes and isocyanides. By using equimolar reactants with very mild reaction conditions, they were able to observe total conversion to the linear Ugi-compounds equipped with azide and alkyne functionality. Furthermore, they have cyclised the resulting compounds into the respective triazoles, by performing a catalyst-free Huisgen cycloaddition reaction in a sealed tube.

Variation in substitution patterns and tolerance of a large array of aldehydes in this methodology will open a new avenue for the synthesis of various building blocks to be used in peptidomimetics with a wide range of applications.

Find out more in their Communication:

Efficient synthesis of conformationally constrained, amino-triazoloazepinone-containing di- and tripeptides via a one-pot Ugi–Huisgen tandem reaction
T. M. A. Barlow, M. Jida, D. Tourwéa and S. Ballet
DOI: 10.1039/C4OB01381F

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