Author Archive

Review: Carbohydrate chemistry in drug discovery

Carbohydrates are the most diverse and one of the most important classes of biomolecules in nature. However, it is still difficult to find carbohydrate-based drugs in the market nowadays. The high polarity of this kind of drugs represents an issue for the pharmacological properties. Therefore, understanding and being able to modify these properties would help with the development of more ‘drug-like’ carbohydrate-based drugs.

In this review, M Carmen Galan and co-workers at University of Bristol, give and up-date on the latest advancements in carbohydrate chemistry and the role thy play in drug discovery.

If you want to find out more, download it now.

Carbohydrate chemistry in drug discovery
M. Carmen Galan, David Benito-Alifonso and Gregory M. Watt
Org. Biomol. Chem., 2011, 9, 3598-3610
DOI: 10.1039/C0OB01017K

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT: Switch on the rotaxane!

Rotaxanes are mechanically interlocked molecules with interesting physical and chemical properties. They have attracted much attention due to their potential applications in molecular electronics, smart materials and molecular machines.

In this HOT paper, Da-Hui Qu, He Tian and their research group at East China University of Science & Technology in Shanghai, synthesise a multi-state [2]rotaxane based on a crown ether. They introduce a dithienylethene (DTE) photochromic functional group that can be switched by pH, light or the combination of pH and light. This photochromic unit is responsible of the multi-mode alteration of intercomponent interactions such as energy transfer, electron transfer and charge transfer interactions.

This multi-state molecular shuttle has potential to construct multi-level molecular machines.

You can now read this article, which is free to download until 25th May, here.

The referees and the editorial office found it very interesting. We hope you like it too.

Altering intercomponent interactions in a photochromic multi-state [2]rotaxane
Hui Zhang, Xin-Xin Kou, Qiong Zhang, Da-Hui Qu and He Tian
Org. Biomol. Chem., 2011
DOI: 10.1039/C1OB05307H

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT: Novel efficient synthesis of functionalised naphthoquinones

Naphthoquinone derivatives have important pharmacological properties. They have been explored for their anti-inflammatory, antifungal and antitumor biological activities amongst many others. Therefore, efficient syntheses of naphthoquinines are of great interest.

In this paper, Jian Wang and his team at the National University of Singapore, have developed a new catalytic synthetic method for the preparation of chiral naphthoquinones with a novel chiral thiourea catalyst. They achieve excellent yields (94-99%) and excellent enantioselectivities (90-98% ee)

Read more about this new and very efficient synthesis in this HOT paper which is free to access until 14th May.

Enantioselective organocatalytic Michael-hemiketalization catalyzed by a trans-bifunctional indane thiourea catalyst
Yaojun Gao, Qiao Ren, Swee-Meng Ang and Jian Wang
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05404J

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Review: Mannich–Michael vs. aza-Diels–Alder approaches to piperidine derivatives

Andrew Whiting and colleagues at University of Durham and Merck Research Laboratories, question whether the mechanism of the aza-Diels–Alder reaction is step wise as opposed to concerted when using
oxygenated dienes.

This review explain the mechanistic details as well as scope of the reaction in future.

Mannich–Michael versus formal aza-Diels–Alder approaches to piperidine derivatives
P. Ricardo Girling, Takao Kiyoi and Andrew Whiting
Org. Biomol. Chem., 2011, 9, 3105-3121
DOI: 10.1039/C0OB00996B

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Review: The stimulating adventure of KRN 7000

Aline Banchet-Cadeddu and colleagues at Universite de Reims Champagne-Ardenne and Universite de Strasbourg, present an up-to-date library of analogues of KRN 7000,  a potent synthetic galactosylceramide that activate the invariant NKT immune cells.

They have collected recent breakthroughs done in crystallography and molecular modelling, and
related them to the available biological results.

This review will help the scientific community in their KRN research.

The stimulating adventure of KRN 7000
Aline Banchet-Cadeddu, Eric Hénon, Manuel Dauchez, Jean-Hugues Renault, Fanny Monneaux and Arnaud Haudrechy
Org. Biomol. Chem., 2011, 9, 3080-3104
DOI: 10.1039/C0OB00975J

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Ring-opening Radical Clock Reactions – OBC Issue 9 Cover

Why do certain DFT methods give good results for ring-opening reactions while others do not?

Gino DiLabio and Iain Mackie at University of Albaerta, in Canada, try to answer this question in this timely paper on radical clock reactions.

You can read it for free until the end of May.

This paper will be included in the special web themed issue on radical chemistry in memory of Athel Beckwith that will be published soon. Keep an eye on it!

Ring-opening radical clock reactions: many density functionals have difficulty keeping time
Iain D. Mackie and Gino A. DiLabio
Org. Biomol. Chem., 2011, 9, 3158-3164
DOI: 10.1039/C0OB01246G

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT: Effect of substituents on the stabilities of radicals

The effect of substituents on the thermodynamic stabilities of trisubstituted carbon-centered radicals is an interesting topic that has received limited attention in literature until now.

Now, Leo Radom and collaborators in Australia and Switzerland present in this paper a thorough computational study, which correlates with experimental data, of the stability of a very large series of multiply-substituted carbon-centered radicals. They look at the stabilization and interaction energies and the deviations from additivity of RSEs.

If you want to learn about the 14 conclusions they reach in this HOT article, download it now. It is free to access until 5th May.

This article will be included in the OBC special issue in memory of Athel Beckwith: Free Radical Chemistry. Coming soon.

Effect of substituents on the stabilities of multiply-substituted carbon-centered radicals
Ambili S. Menon, David J. Henry, Thomas Bally and Leo Radom
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05196B

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Hot: Glycosidase inhibitors with potential

Glycosidases are involved in a broad range of biological and pathological processes. The development of inhibitors of these enzymes that could potentially help with diseases such as type II diabetes mellitus, viral infections, cancer or hereditary enzyme deficiency diseases is one of the aims of Jose M Garcia Fernandez, Carmen Ortiz Mellet and their research groups in Spain.

In this paper, they prepare a library of sp2-iminosugar-type glycomimetics and they evaluate their glycosidase inhibition properties against a panel of commercial glycosidases. They actually got very interesting results that show the potential of this molecular diversity-oriented approach to identify suitable hits for further in cell and in vivo studies.

Read this HOT article now that is free to access until the 5th May.

Bicyclic (galacto)nojirimycin analogues as glycosidase inhibitors: Effect of structural modifications in their pharmacological chaperone potential towards β-glucocerebrosidase
Matilde Aguilar-Moncayo, M. Isabel García-Moreno, Ana Trapero, Meritxell Egido-Gabás, Amadeu Llebaria, José M. García Fernández and Carmen Ortiz Mellet
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05234A

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT:Modeling oxidative damage to peptide radicals

Richard O’Hair and colleagues use mass spectrometry (MS) as an analytical tool to study the mechanism of protein oxidation.

They say in the paper that the aims of their work are:

  1. To establish whether these peptide radicals react with oxygen in the gas phase to form peroxyl radicals and if so to examine the gas-phase chemistry of these peroxyl radicals
  2. To determine if the radicals NO. and NO2. can act as ‘radical scavengers’ of these peptide radicals and if so to establish whether the resultant adducts provide structural information on any migrations of the original peptide radical sites

If you want to find out whether they achieved these goals, download this HOT article which is free to access until 5th May.

This paper is part of the OBC collection of free radical chemistry papers in memory of Athel Beckwith that will be published soon. Watch this space!

Gas-phase ion-molecule reactions using regioselectively generated radical cations to model oxidative damage and probe radical sites in peptides
Christopher K. Barlow, Adam Wright, Christopher J. Easton and Richard A. J. O’Hair
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB01245A

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Review: Organic reactions mediated by electrochemically generated ArS+

Jun-ichi Yoshida and colleagues at Kyoto University, describe in this excellent review some of the reactions mediated by electrochemically generated ArS+.

This Perspective focuses on three main points:

  1. The electrochemical generation of ArS+ ions by oxidation of ArSSAr
  2. The applications of the obtained ArS+ pools in organic synthesis
  3. Catalysis by ArS+

It is a very complete and informative perspective that has captivated both the referees and the editorial office. Would you feel the same? Download it now and let us know.

Organic reactions mediated by electrochemically generated ArS+
Kouichi Matsumoto, Seiji Suga and Jun-ichi Yoshida
Org. Biomol. Chem., 2011, 9, 2586-2596
DOI: 10.1039/C0OB01070G

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)