Marie Cote, Deputy Editor – Page 4 – Organic & Biomolecular Chemistry Blog

Author Archive

Cyclocondensation reactions of the heterocyclic scaffold benzotriazinone lead to several highly coloured acenes

23 Jan 2012

In this OBC Hot Article, Panayiotis Koutentis and co-workers at the University of Cyprus show how 1,3-Diphenylbenzo[e][1,2,4]triazin-7(1H)-one reacts with various bisnucleophiles to give a variety of deeply coloured polyazaacenes, including two zwitterionic analogues.

Read the article to find out more about the preparation, mechanistic considerations and photophysical studies of these new heterocyclic ring systems derived from benzo[1,2,4]triazin-7-ones.

FREE to access for a period of 4 weeks!

Some cyclization reactions of 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: preparation and computational analysis of non symmetrical zwitterionic biscyanines
Theodosia A. Ioannou, Panayiotis A. Koutentis, Harry Krassos, Georgia Loizou and Daniele Lo Re
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06622F, Paper

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HOT: chemoenzymatic synthesis of a mixed phosphine–phosphine oxide organocatalyst and its applications

16 Jan 2012

This OBC Hot Article by Paul J. Stevenson and co-workers at Queens University (Belfast) and Celtic Catalysts Ltd (Dublin) highlights the chemoenzymatic synthesis of a Lewis basic phosphine–phosphine oxide organocatalyst from a cis-dihydrodiol metabolite of bromobenzene.

Of particular interest is the impressively facile Arbuzov [2,3]-sigmatropic rearrangement reaction that the team observed – a pivotal step for this synthesis.

Find out about the applications of this new catalyst…
Read the article for Free for the next 4 weeks…

Reference
Chemoenzymatic synthesis of a mixed phosphine–phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes
Derek R. Boyd, Mark Bell, Katherine S. Dunne, Brian Kelly, Paul J. Stevenson, John F. Malone and Christopher C. R. Allen
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06599H, Paper

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HOT: Aquafoldamers as synthetic water channels

11 Jan 2012

In this OBC Hot Paper Huaqiang Zeng and coworkers at the National University of Singapore have studied a series of water-binding aquafoldamers, illustrating their potential use for recognizing larger water clusters of diverse topologies and as synthetic water channels.

Read for free…
This article is part of our forthcoming themed issue on Foldamer Chemistry – visit this page to see the collection of articles grow.

Reference:
Synthesis, structural investigation and computational modelling of water-binding aquafoldamers
Huaiqing Zhao, Wei Qiang Ong, Xiao Fang, Feng Zhou, Meng Ni Hii, Sam Fong Yau Li, Haibin Su and Huaqiang Zeng
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06609A

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Meet the OBC team

03 Jan 2012

The OBC team will be attending a number of conferences in 2012 and we would be delighted to meet you.

Dr Marie Cote, Deputy Editor

Dr Richard Kelly, Managing Editor

Here are just some of the conferences where you can meet us in the coming months:

Zing conference on Natural Products Synthesis and Biosynthesis – 10-13 February, Lanzarote, Spain – Meet Marie
Gordon Research Conference on Marine Natural Products – 26 Feb.- 02 March, Ventura, USA – Meet Richard
Keystone sympoium on Addressing the Challenges of Drug Discovery – 19-23 March, Tahoe City, USA – Meet Marie
BTS Annual Congress 2012 – 25-28 March 2012, Warwick, UK – Meet Richard
OBC Symposia, touring Shanghai, Lanzhou and Beijing – 14-21 April, China – Full details coming soon… – Meet Richard
48th EUROTOX Congress – 17-20 June, Stockholm, Sweden – Meet Nicola Wise, Business Development Executive
Gordon Research Conference on Heterocyclic Compounds – 24-29 June, Salve Regina University, USA – Meet Marie
BOSS XIII – 13th Belgium Organic Synthesis Symposium – 15-20 July, Leuven, Belgium – Meet Marie
ASIATOX VI – 17-20 July, Sendai, Japan – Meet Richard
244th ACS National Meeting, 19-23 August, Philadelphia, USA – Meet Richard
ISMC 2012 – 22nd International Symposium on Medicinal Chemistry – 02-06 Sept., Berlin, Germany – Meet Marie
ICPOC 21 – 21st IUPAC International Conference on Physical Organic Chemistry – 09-13 Sept., Durham, UK – Meet Marie

Please let us know if you are planning on attending any of these meetings, as it would be lovely to meet you there!

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Squaraine dyes for photodynamic therapy: reviewing the latest developments

21 Dec 2011

Following our latest OBC Hot Article by Prof. Bradley D. Smith (available here), Squaraines are in the spotlight again in this review article by Danaboyina Ramaiah et al..

The Perspective highlights the recent developments of squaraines as PDT sensitizers, including:

Design principles
Squaraines as singlet oxygen generators
Squaraines as two-photon absorbing agents
Carrier systems for squaraine dyes
In vitro and in vivo studies of squaraine-PDT action

Timely and HOT, why not read this Perspective now – it will be FREE to access for the next 4 weeks

Squaraine dyes in PDT: from basic design to in vivo demonstration
Rekha R. Avirah, Dhanya T. Jayaram, Nagappanpillai Adarsh and Danaboyina Ramaiah
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06588B, Perspective

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Deep-red fluorescent, water-soluble, with rapid renal clearance…?

20 Dec 2011

Prof. Bradley D. Smith and coworkers at University of Notre Dame and Molecular Targeting Technologies, Inc. have modified squaraine rotaxanes with four large stopper groups that provide the much needed long-term, chemical stability in physiological solution. Combined with high quantum yields, excellent excitation/emission wavelength for in vivo analysis, good water-solubility, some of these new dyes undergo rapid renal clearance and very low tissue uptake in living mice, making them excellent fluorescent tracers.

As noted by the authors, the dendritic and polyionic structures of these dyes will also interest and inform the community of scientists who are trying to develop compounds that do not interact with biological surfaces.

A simple and novel approach – Read all the details here – This Hot Article will be free to access for the next 4 weeks

Water-soluble, deep-red fluorescent squaraine rotaxanes
Erin L. Cole, Easwaran Arunkumar, Shuzhang Xiao, Bryan A. Smith and Bradley D. Smith
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06783H, Communication

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HOT: Thiophosphonoacetate-modified oligoribonucleotides with RNA therapeutics in sight

16 Dec 2011

The groups of Marvin Caruthers (University of Colorado at Boulder, USA) and Michael Gait (Medical Research Council Centre, Cambridge, UK) describe a new chemical synthesis and biological properties of 2’-O-methyl oligoribonucleotides (ORNs) containing internucleotide linkages modified with phosphonoacetate (PACE) and thiophosphonoacetate (thioPACE) groups.

ThioPACE modifications were found to greatly improve the efficiency of cell uptake and the potency of a 2′-O-Me-ORN miRNA122 inhibitor, showing that this class of modifications has great potential for applications in RNA therapeutics research.

As with all our HOT Articles, this OBC article is FREE for you to access, for a period of 4 weeks.

Synthesis and biological activity of phosphonoacetate- and thiophosphonoacetate-modified 2′-O-methyl oligoribonucleotides
Richard N. Threlfall, Adrian G. Torres, Angelika Krivenko, Michael J. Gait and Marvin H. Caruthers
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06614E

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Perspective: Organofluoro nucleophiles for enantioselective organocatalytic fluorination

12 Dec 2011

‘While methods of electrophilic fluorination have been extensively developed to stereoselectively install fluorine atoms onto molecules, nucleophilic fluorination is a much less explored approach’, explains Associate Professor Choon-Hong Tan, from National University of Singapore.

In this concise review article, Choon-Hong and coll. highlight an emerging methodology of enatioselective C-C coupling via fluorocarbanion additions, which significantly expands the scope of enantio-enriched fluorine-containing compounds that can be synthesised. The recent advances in the application of organofluoro nucleophiles in organocatalysis are described.

Read all about this emerging methodology in the Perspective article, FREE to access for the next 4 weeks!

Enantioselective organocatalytic fluorination using organofluoro nucleophiles
Yujun Zhao, Yuanhang Pan, Sui-Boon Derek Sim and Choon-Hong Tan
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB05840A, Perspective

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HOT: Stereochemical diversity-oriented strategy for histamine receptor ligands synthesis

12 Dec 2011

In their quest to develop specific ligands for drug target proteins, Professor Satoshi Shuto and coll. have used a stereochemical diversity-oriented conformational restriction strategy to synthesize potent histamine H3 and/or H4 receptor ligands. Some of these cyclopropane-based analogs of histamine with a chiral cis- or trans-2,3-methanobutane backbone show remarkable antagonistic activity towards H3 and H4.

Interested in Medicinal Chemistry and curious about what conformational restriction strategies can do for you?

Then why not read this article, FREE to access for a period of four weeks

Cyclopropane-based stereochemical diversity-oriented conformational restriction strategy: Histamine H3 and/or H4 receptor ligands with the 2,3-methanobutane backbone
Mizuki Watanabe, Takaaki Kobayashi, Takatsugu Hirokawa, Akira Yoshida, Yoshihiko Ito, Shizuo Yamada, Naoki Orimoto, Yasundo Yamasaki, Mitsuhiro Arisawa and Satoshi Shuto
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06496G, Paper

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Tunable H12 helix → H18 helix transition on the cover of OBC Issue 2

09 Dec 2011

Welcome to OBC Issue 2, 2012

On the cover this week is the work of Tamas Martinek et al. at the University of Szeged (Hungary), reporting a tunable H12 helix –> H18 helix transition not previously observed for foldamers.

Combining traditional methods for peptide folding (ECD, DOSY-NMR) and molecular modeling to investigate the folding and self-assembly of peptide mimics, the authors show that foldamer sequences constructed using trans-ABHC and β³-hSer residues produce β-H18 helix in a solvent- and concentration-dependent way.

‘These observations strongly support the view that foldameric helix refolding is promoted by higher-order packing of the helices in protic solvent’, say the authors.

This OBC Communication will be FREE to access for the next 6 weeks:

Self-association-driven transition of the β-peptidic H12 helix to the H18 helix
Éva Szolnoki, Anasztázia Hetényi, Tamás A. Martinek, Zsolt Szakonyi and Ferenc Fülöp
Org. Biomol. Chem., 2012, 10, 255-259
DOI: 10.1039/C1OB06627G

View the rest of Issue 2 here

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