Organic & Biomolecular Chemistry Blog

Véronique Gouverneur and colleagues at University of Oxford, UK,  have designed an excellent avenue to generate 18F-labelled molecules via traceless Staudinger ligation.

This OBC HOT article is free to access until the end of the year. The referees rated it as very significant and the authors say that this novel prosthetic group 18F-radiochemistry may find numerous applications in the context of peptide 18F-labelling as the new functionality installed upon ligation is the native amide bond.

This article is part of the fluorine chemistry web themed issue that will be published on line in December. Watch out for it and if you want us to let you know when it is published contact us.

The traceless Staudinger ligation for indirect 18F-radiolabelling
Laurence Carroll, Sophie Boldon, Romain Bejot, Jane E. Moore, Jérôme Declerck and Véronique Gouverneur
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00564A , Paper

Piet Herdewijn from the Catholic University of Leuven, Belgium, and colleagues have designed a series of leaving groups that are compatible with HIV-1 reverse transcriptase (an enzyme that synthesises DNA from RNA).

The manuscript has been highlighted in Highlights on Chemical Biology and it is also a OBC Hot article which will be free to access until the end of the year.

Tha referees said that it was a VIP paper that made a very important contribution to the field.

Read more here

3-Phosphono-L-alanine as pyrophosphate mimic for DNA synthesis using HIV-1 reverse transcriptase
Shiqiong Yang, Mathy Froeyen, Eveline Lescrinier, Philippe Marlière and Piet Herdewijn
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00554A , Paper

Daniel Häussinger, Marcel Mayor and co-workers at University of Basel in Switzerland look at the physical organic aspects of push-pull biaryls and their dynamic conformational interchange for the preparation of bulk organic materials that will display non-linear optical activities.

Two main physical properties are crucial for a strong nonlinear optic response: a large hyperpolarizability of the chromophore and a noncentrosymmetric centre.

In this HOT paper, the authors describe the rotational barriers for atropisomer interconversion in a series of cyclophane derivatives functionalized with complementary electron donating/withdrawing substituents. The referees said that it was a very significant paper in the fied.

You can now read it for free until the end of the year.

Racemisation dynamics of torsion angle restricted biphenyl push-pull cyclophanes
Jürgen Rotzler, Heiko Gsellinger, Markus Neuburger, David Vonlanthen, Daniel Häussinger and Marcel Mayor
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00650E, Paper

Rajeev Menon and Martin Banwell at the Australian National University in Camberra have identified a novel and highly efficient Au (I) catalysed intramolecular Michael addition reaction that is a key step towards the first total synthesis of crassifolone and dihydrocrassifolone.

These two natural products can be extracted from the wood of the tree Myoporum Crassifolium that grows in Noumea, New Caledonia.  So now there is no need to go to this paradisiac beach to get these two natural products – you just need to get the white lab coat and safety googles on and go to the lab! 🙂

‘This unprecedent reaction may represent a useful new protocol for the construction of other terpenoids incorporating an annulated furan core’, say the authors of the paper.

Read it free to access until next year!

Total syntheses of the furanosesquiterpenes crassifolone and dihydrocrassifolone via an Au(I)-catalysed intramolecular Michael addition reaction
Rajeev S. Menon and Martin G. Banwell
Org. Biomol. Chem., 2010, 8, 5483-5485
DOI: 10.1039/C0OB00487A

Taifo Mahmud and colleagues at Oregon State and Shanghai Jiao Tong Universities present their results on the role of ValB in validamycin biosynthesis and facilitate the development of new tools for the production of carbohydrate mimetics in this HOT and very significant (as rated by the referees) paper.

You can now read this HOT paper which is free to access until the 14th of December and leave your comments on our blog.

Nucleotidylation of unsaturated carbasugar in validamycin biosynthesis
Jongtae Yang, Hui Xu, Yirong Zhang, Linquan Bai, Zixin Deng and Taifo Mahmud
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C0OB00475H