Organic & Biomolecular Chemistry Blog

Open the treasure of Free Radical Chemistry with this OBC Cover article.

Carl Schiesser takes us through the evolution of Free Radical Chemistry in this very original and well written paper that highlights results from the Beckwith “golden era”.
Join us in this trip from the “Dark Ages” of Free Radical Chemistry to the Post-Renaissance period.  The paper will be free to access until 14th April.

Apart from taking us on a very pleasant journey through the evolution of radical chemistry, the authors also determine the rate constant data and Arrhenius parameters for a series of substituted hexenyl radicals of differing electronic and steric demand.

This paper will be included in the special issue on ‘Free Radical Chemistry’ in memory of Athel Beckwith that will be published in Spring. Keep an eye on it!

Treasures from the Free Radical Renaissance Period – Miscellaneous hexenyl radical kinetic data
Athelstan L. J. Beckwith and Carl H. Schiesser
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00708K, Paper

Trying to treat interdependent  diseases can be tricky, but not when one drug is capable of dealing with both.

Overproduction of angiotensin II by the angiotensin converting enzyme (ACE) leads to hypertension, which is associated with cardiovascular diseases such as high blood pressure, heart failure, coronary artery disease and kidney failure.  Hypertension has also been shown to play a role in oxidative stress, the imbalance of oxidants and antioxidants.  A drug that could treat both conditions would be of serious value to the medical community, and now researchers from the Indian Institute of Sciences have just synthesised a compound that shows the potential for doing just that.

Bhaskar Bhuyan and Govindasamy Mugesh synthesised several selenium analogues of the common ACE inhibitor, Captopril and demonstrated that not only were they capable of enzyme inhibition but also acted as antioxidants, scavenging peroxynitrite – the highly reactive intermediate known to cause cellular damage.

Read the full article online here – it’s free to access for 6 weeks!

Synthesis, characterization and antioxidant activity of angiotensin converting enzyme inhibitors
Bhaskar J. Bhuyan and Govindasamy Mugesh
Org. Biomol. Chem., 2011, 9, 1356-1365
DOI: 10.1039/C0OB00823k

Cyclophanes have been used as molecular systems in host-guest complexations due to their ability to encapsulate other molecules through various non-covalent interactions.
Cyclophanes  can be rationally designed by choosing the right components, similar to  Lego® bricks. However, the features of these ‘lego bricks’ required to build the desired cyclophanes with the requisite biomolecular recognition properties have not been widely explored.

Now, Danaboyina Ramaiah and colleagues at NIIST in India have revealed some of the features to bear in mind when designing cyclophanes. They concluded by saying that  that the cavity size and its rigidity, the aromatic surface and nature of bridging units dictate the stability of the supramolecular complex and thereby govern the biomolecular recognition properties of cyclophanes.

You can now download this article, which is free to access until mid-March.

Study of cavity size and nature of bridging units on recognition of nucleotides by cyclophanes
Prakash P. Neelakandan, Paramjyothi C. Nandajan, Baby Subymol and Danaboyina Ramaiah
Org. Biomol. Chem., 2011, 9, 1021-1029
DOI: 10.1039/C0OB00673D, Paper

Are you concerned about your choice of functional? Losing sleep over computing costs? Then look no further than OBC!

This article by Jonathan Goodman and Luis Simón, highlighted on the cover of OBC Issue 3, discusses the relative merits of twelve different DFT functionals for the geometry optimisation of organic transition state structures.

They concluded that despite more sophisticated (and therefore costly) functionals being available, B3LYP and related functionals are still capable of predicting transition states with an acceptable level of accuracy.

The full article is currently free to access until March – download it today for an end to your functional troubles!

How reliable are DFT transition structures? Comparison of GGA, hybrid-meta-GGA and meta-GGA functionals
Luis Simón and Jonathan M. Goodman
Org. Biomol. Chem., 2011, 9, 689-700
DOI: 10.1039/C0OB00477D, Paper

Gangadhar J. Sanjayan and his team at the National Chemical Laboratory in Pune, India, write about the development of conformationally constrained unnatural aromatic amino acids in this communication that is the cover of OBC Issue 2.

The strategy described within the paper will be useful for the construction of oligomers displaying novel molecular architectures with unique conformations, distinct from those classically observed.

Download this paper free to access for a limited period of time.

Congratulations to the authors for a beautiful cover and their interesting research.

Conformationally rigid aromatic amino acids as potential building blocks for abiotic foldamers
Veera V. E. Ramesh, Arup Roy, Kuruppanthara N. Vijayadas, Amol M. Kendhale, Panchami Prabhakaran, Rajesh Gonnade, Vedavati G. Puranik and Gangadhar J. Sanjayan
Org. Biomol. Chem., 2011, 9, 367-369
DOI: 10.1039/C0OB00593B, Communication

A collaboration between research groups in UK, Spain and Italy led by Steven Nolan reveals the mechanism of the Au (I) catalysed formation of substituted indenes.

Read the conclusions of this mechanistic and computational study in this free to access until mid-January paper that is the inside cover of OBC Issue 1 2011.

Enjoy it!

A combined mechanistic and computational study of the gold(I)-catalyzed formation of substituted indenes
Pierrick Nun, Sylvain Gaillard, Albert Poater, Luigi Cavallo and Steven P. Nolan
Org. Biomol. Chem., 2011, 9, 101-104
DOI: 10.1039/C0OB00758G

Svetlana B Tsogoeva and colleagues at University of Erlagen-Nuremberg review the recent advances on the most successful C-C formation reactions using chiral BINOL phosphates as Bronsted acid catalysts.

Read this review, which is free to access until the end of the year, to find out more about these very popular Bronsted acid catalysts.

Toshihiro Ihara and colleagues at Kumamoto University demonstrate a quick reversible photocircularization of an anthracene-modified oligodeoxyribonucleotide conjugate and provide an example of its analytical application.

‘ The oligonucleotide conjugate was reversibly circularized through photodimerization of the antracenes attached on both ends. This process would be potentially useful as a probe reaction with high specificity and sensitivity’ say the authors on the description of their cover.

Read the article free to access until the end of November

Reversible circularization of an anthracene-modified DNA conjugate through bimolecular triplex formation and its analytical application
Pelin Arslan, Akinori Jyo and Toshihiro Ihara
Org. Biomol. Chem., 2010, 8, 4843-4848
DOI: 10.1039/C0OB00282H