Organic & Biomolecular Chemistry Blog

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

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

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

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

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

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

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

Take a look at this review to find out more about the latest developments in chalcogenophene chemistry.

Undoubtedly, the interest for selenium and tellurium incorporated to organic substrate has been increasing in the past few years. Moreover, the incorporation of selenium and tellurium in heterocyclic compounds may provide a solution their biological toxicity.

In this review, Cristiano Rhodena and Gilson Zeni from Rio Grande do Sul, Brazil, revisit different aspects of seleno- and tellurophenes chemistry, including their reactivity and applications in the field of heterocycles.

New development of synthesis and reactivity of seleno- and tellurophenes
Cristiano R. B. Rhoden and Gilson Zeni
Org. Biomol. Chem., 2011, 9, 1301-1313
DOI: 10.1039/C0OB00557F

And if you are interested in this one, you may also be interested in this other:

Tellurium: an element with great biological potency and potential
Lalla Aicha Ba, Mandy Döring, Vincent Jamier and Claus Jacob
Org. Biomol. Chem., 2010, 8, 4203-4216
DOI: 10.1039/C0OB00086H, Emerging Area

Sebastien G. Gouin and his team at University of Nantes, France, review some of the important structural features in the synthesis of multivalent glycoconjugates for a tight binding with specific lectins.

Read this review on multivalent inhibitors of lectins from a different and very interesting point of view: how the scaffold influences potency.

Insights in the rational design of synthetic multivalent glycoconjugates as lectin ligands
David Deniaud, Karine Julienne and Sébastien G. Gouin
Org. Biomol. Chem., 2011, 9, 966-979
DOI: 10.1039/C0OB00389A, Perspective