Author Archive

Review: Recently developed novel cross-linking reactions

Fumi Nagatsugi and Shuhei Imoto talk about recently developed novel cross-linking reactions in this emerging area.

This short review focuses on the crosslinking reactions using modified ONs (synthetic oligonucleotides) to react natural bases in duplexes and describes their recent work on the development of selective cross-linking reactions.

To have a good overview of the latest developments in cross-linking reactions to target genes using modified oligonucleotides download this review.

Induced cross-linking reactions to target genes using modified oligonucleotides
Fumi Nagatsugi and Shuhei Imoto
Org. Biomol. Chem., 2011, 9, 2579-2585
DOI: 10.1039/C0OB00819B

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Delivery of fullerenes into liposomes – OBC Cover Issue 8

Atsushi Ikeda and colleagues describe in this paper, which is the outside cover of OBC Issue 8, how the addition of small amounts of lipids bearing a π-moiety can help the migration of hydrophobic C70 into the hydrophilic liposome surface.
The delivery of fullerenes C70 into liposomes could have interesting applications in drug delivery. 

Read more about the mechanism of how fullerenes are incorporated into the lipid structures in this article which is free to access for 6 weeks!

Formation and regulation of fullerene-incorporation in liposomes under the phase transition temperature
Atsushi Ikeda, Yoshihiko Kawai, Jun-ichi Kikuchi, Motofusa Akiyama, Eiji Nakata, Yoshihiro Uto and Hitoshi Hori
Org. Biomol. Chem., 2011, 9, 2622-2627
DOI: 10.1039/C0OB01030H

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HOT: Self-calibrating ratiometric viscosity sensors

Alterations in fluid viscosity at the cellular and organismal level can lead to different disorders and diseases such as Alzheimer’s, diabetes, hypertension, infarction and others. This is why, in recent years, there has been an increasing interest in the development of new methods to measure fluid viscosity.

Scientists at University of California, San Diego, and University of Georgia have now developed self-calibrating fluorescent sensors that can be used  for ratiometric measurements of viscosity by covalent linking a reference fluorophore (donor) with a molecular rotor (acceptor). They also present an application of these dyes for the detection of changes of the membrane viscosity in a liposome model and they show that shorter linker length produces a more viscosity sensitive dye.

You can now read this HOT article which is free to access until 26th April. Both the referees and the Editorial Office ranked it as very significant.

Synthesis and evaluation of self-calibrating ratiometric viscosity sensors
Hyung-Jo Yoon, Marianna Dakanali, Darcy Lichlyter, Willy M. Chang, Karen A. Nguyen, Matthew E. Nipper, Mark A. Haidekker and Emmanuel A. Theodorakis
Org. Biomol. Chem.
DOI: 10.1039/C0OB01042A

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Matthew Fuchter and his OBC article on Psammaplin A around the world

Matthew Fuchter‘s research on Psammaplin A has proven to be very well received by the public all over the world.
Dr Fuchter and his team at Imperial College in London, published a new way of making psammaplin A which has the potential to inspire novel anti-cancer drugs (OBC Issue 3).

You can see below some of the links highlighting this story.

From the Editorial Office, we would like to congratulate Matthew and his group for a very successful paper and a very promising research.

The article is now free to access for 4 weeks. Don’t miss out and read it now.

New synthetic strategies towards psammaplin A, access to natural product analogues for biological evaluation
Matthias G. J. Baud, Thomas Leiser, Franz-Josef Meyer-Almes and Matthew J. Fuchter
Org. Biomol. Chem., 2011, 9, 659-662
DOI: 10.1039/C0OB00824A, Communication

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Review: Green oxidations of furans

Georgios Vassilikogiannakis and colleagues at University of Crete, Greece, have written a very interesting emerging area on green oxidations of furans.

The reactivity of furans with the first excited state of molecular oxygen, known as singlet oxygen, was unearthed in 1967.  More than 40 years later, Vassilikogiannakis et al. tell us about how this work begun, how it evolved and where we are now.

They focus on how altering the position of a pendant hydroxyl group in the furan substrate can lead to different cascade reactions that result in the synthesis of different products. The icing of the cake: this chemistry is green chemistry as the oxidant is non-toxic, leaves no toxic residues, and the reactions are atom efficient.

If you want to find out more, download this OBC review now.

Green oxidations of furans—initiated by molecular oxygen—that give key natural product motifs
Tamsyn Montagnon, Dimitris Noutsias, Ioanna Alexopoulou, Maria Tofi and Georgios Vassilikogiannakis
Org. Biomol. Chem., 2011,
DOI: 10.1039/C0OB00952K, Emerging Area

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Review: Chemical and biological studies of lipoteichoic acid

Can LTA (lipoteichoic acids) be considered to be “the (endo)toxin of Gram-positive bacteria”?

Richard R. Schmidt, Ulrich Zahringer and their groups have become one of the leading teams in LTAs research. They have synthesised different types of LTAs and tested their biological activities against different receptors of the innate immune system.

They summarise part of their results and those of different groups working on the area in this comprehensive OBC review.  Download it now.

Chemical synthesis of bacterial lipoteichoic acids: An insight on its biological significance
Richard R. Schmidt, Christian M. Pedersen, Yan Qiao and Ulrich Zähringer
 Org. Biomol. Chem., 2011, 9, 2040-2052
DOI: 10.1039/C0OB00794C, Perspective

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OBC will be in Crete to attend ESOC 2011

Are you planning on going to ESOC 2011 this coming summer?

ESOC 2011 is the 17th European Symposium of Organic Chemistry that will be held in Crete, Greece, from 10th to 15th July 2011.

This well established conference will provide a forum for broad scientific and technological exchange
among researchers from Europe and elsewhere. The conference will emphasize on new achievements in
the following fields:

– Total Synthesis of Natural Products
– Catalysis in Organic Synthesis
– New Methods in Organic Synthesis
– Medicinal Chemistry
– Bioorganic Chemistry & Chemical Biology
– Supramolecular Chemistry
– Synthesis of Functional Materials
– Physical Organic Chemistry

The program will include an outstanding line up of invited speakers.
Keep up to date with the latest program information on the website http://www.esoc2011.com/

Organic & Biomolecular Chemistry will be there and it is one of the supporters of this meeting. If you are thinking of attending this conference and spending a week of your summer in sunny Crete, drop us an e-mail – it would be great to meet you! OBC will have a stand so feel free to come along!

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Review: Hybrid bidentate phosphorus ligands for asymmetric catalysis

Jeroen Wassenaar and Joost N. H. Reek identify optimal chiral catalysts for asymmetric hydrogenation.

Take a look at this perspective that gives a brief overview of different classes of phosphine ligands, with a focus on mixed phosphine ligands, incorporating a second coordinating group such as an amine, thiol, phosphite or phosphoramidite.

Hybrid bidentate phosphorus ligands in asymmetric catalysis: Privileged ligand approach vs. combinatorial strategies
Jeroen Wassenaar and Joost N. H. Reek
Org. Biomol. Chem., 2011, 9, 1704-1713
DOI: 10.1039/C0OB00732C

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Review: Cleavage of RNA phosphodiester bonds by small molecular entities

RNA molecules play a key role in several fundamental cellular events, serving both as a carrier of genetic information and as a catalyst, and hence, RNA has received increasing interest both as a chemotherapeutic agent and as a target of chemotherapy.

RNA is a polymer constructed from monomeric nucleosides by 3′,5′-phosphodiester bonds. In order to understand the chemical behaviour of RNA, the kinetics and mechanisms of the cleavage of RNA phosphodiester bonds have received extensive interest.

In this review, Harri Lonnberg at University of Turku in Finland, writes about the major mechanistic
findings and achievements concerning the cleavage of RNA by small molecules and ions and their significance for the development of efficient and biologically applicable artificial catalysts for RNA hydrolysis.

Read more here.

Cleavage of RNA phosphodiester bonds by small molecular entities: a mechanistic insight
Harri Lönnberg
Org. Biomol. Chem., 2011, 9, 1687-1703
DOI: 10.1039/C0OB00486C

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HOT: NAS vs. Pd mediated coupling – who is the winner?

When facing the synthesis of highly electron deficient monoaryl, di-aryl and bis-diaryl acetonitriles, Christopher Gorman and his research group at North Carolina State University look at two different methods: Nucleophilic aromatic substitution (NAS) and palladium-mediated coupling.

In their search for the most efficient method, they show that palladium-mediated coupling is more efficient than nucleophilic aromatic substitution for cyano-containing, electron deficient molecules. They further show that choice of solvent, base and supporting ligand has a large effect on the yield of this coupling.

Read all of this in this HOT article that is free to access until the 31st March.

Overcoming challenges in the palladium-catalyzed synthesis of electron deficient ortho-substituted aryl acetonitriles
Molly C. Brannock, William J. Behof, Gregory Morrison and Christopher B. Gorman
Org. Biomol. Chem., 2011
DOI: 10.1039/C0OB00903B

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