Author Archive

HOT: new N-spiro quaternary ammonium salt phase-transfer catalysts from tartaric acid

Mario Waser et al. have designed new N-spiro quaternary ammonium salt-based catalysts from tartaric acid-derived TADDOLs.  The new catalysts catalyse the asymmetric α-alkylation of glycine Schiff bases in good yields and up to 93% ee.

Design, synthesis, and application of tartaric acid derived N-spiro quaternary ammonium salts as chiral phase-transfer catalysts
Mario Waser, Katharina Gratzer, Richard Herchl and Norbert Müller
DOI: 10.1039/C1OB06573D

This article is part of a joint ChemComm & OBC web theme issue on Organocatalysis.

Keep checking this page as further articles are added to the web theme issue.

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Perspective: Development and utilization of non-coding RNA–small molecule interactions

Wesleigh Georgianna and Douglas Young review the possibilities for small molecule regulation of non-coding RNA covering:

  • miRNA
  • siRNA
  • RNA aptamers
  • riboswitches
  • ribozymes

Download the article to find out more about regulating this novel target:

Development and utilization of non-coding RNA–small molecule interactions
Wesleigh E. Georgianna and Douglas D. Young
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB06324C

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HOT: Increased affinity of LewisX mimics for DC-SIGN

The binding of two α-fucosylamide-based mimics of LewisX to DC-SIGN ECD (Dendritic Cell-Specific ICAM-3 Grabbing Nonintegrin extracellular domain) using STD NMR and docking studies has been investigated by Pedro M. Nieto and coworkers.  The mimics are shown to bind in a similar way to LewisX, through the fructose moiety and in a multi-modal fashion, but with increased affinity due to the aromatic moiety.

Insights into molecular recognition of LewisX mimics by DC-SIGN using NMR and molecular modelling
Cinzia Guzzi, Jesús Angulo, Fabio Doro, José J. Reina, Michel Thépaut, Franck Fieschi, Anna Bernardi, Javier Rojo and Pedro M. Nieto
Org. Biomol. Chem., 2011, 9, 7705-7712
DOI: 10.1039/C1OB05938F

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On the cover: a fluorescent probe for cyclin A and C-nitrosation of minoxidil

On the outside front cover of this issue we have a hot communication from José L. Mascareñas and M. Eugenio Vázquez on the design of a peptide fluorescent sensor for cyclin A, a key protein in cycle cycle regulation.

Rational design of a cyclin A fluorescent peptide sensor
Elena Pazos, Miguel Pérez, Hugo Gutiérrez-de-Terán, Mar Orzáez, Tatiana Guevara, José L. Mascareñas and M. Eugenio Vázquez
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB06009K

The image on the inside front cover depicts work from Julio Casado et al. on minoxidil – a treatment for hair loss and high blood pressure.  They have investigated C-nitrosation at the C-5 position of the pyrimidine ring, which is 7 times more likely to occur than in phenol, and conclude that the resultant N-nitrosominoxidil could be harmful to minoxidil users.

Aromatic C-nitrosation of a bioactive molecule. Nitrosation of minoxidil
Mario González-Jiménez, Jorge Arenas-Valgañón, Emilio Calle and Julio Casado
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05686G

View the rest of the issue, including reviews on the photo-dehydro-Diels–Alder reaction and synthetic approaches to lantibiotics

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On the cover: perspective on cation-pi interactions in asymmetric synthesis and alloxazine–cyclodextrin conjugates for sulfoxidations

On the outside cover of Issue 21 we have a hot perspective article from Shinji Yamada and John S. Fossey describing nitrogen cation-π interactions in asymmetric synthesis and summarises the areas where these interactions play an important role.

Areas covered:

  • Iminium–π interactions
  • Pyridinium–π interactions
  • Imidazolium, thiazolium and related structure–π interactions

Nitrogen cation–π interactions in asymmetric organocatalytic synthesis
Shinji Yamada and John S. Fossey
Org. Biomol. Chem., 2011, 9, 7275-7281
DOI: 10.1039/C1OB05228D

The inside cover highlights work from Radek Cibulka and Tomas Kraus et al. who have used four alloxazine–cyclodextrin conjugates as catalysts for enantioselective oxidation of prochiral sulfides to sulfoxides.  Their method avoids the problems of overoxidation to sulfones that sometimes occur when transition metal catalysts are used, and provides better enantioselectivity (up to 77% ee) than other sulfoxidation organocatalysts.

Alloxazine–cyclodextrin conjugates for organocatalytic enantioselective sulfoxidations
Viktor Mojr, Miloš Buděšínský, Radek Cibulka and Tomáš Kraus
Org. Biomol. Chem., 2011, 9, 7318-7326
DOI: 10.1039/C1OB05934C

Both articles are free to access for the next 6 weeks.

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HOT: Investigating polymorphism in quadruplexes without the need for sequence modification

This hot article from John O. Trent et al. at the University of Louisville describes a method for using size exclusion chromatography (SEC) to determine polymorphism in G-quadruplexes.  Current methods for investigating polymorphism rely on modification at either the 3′ or 5′ ends of the sequence, shortening or lengthening putative loop regions to try to produce an enriched configuration to study. But this manipulation of the equilibrium may result in the creation of unnatural species that are not present in vivo.

Trent’s method allows the separation and analysis of quadruplex species without any of the above modifications and has been demonstrated successfully in ten promoter sequences:

Polymorphism and resolution of oncogene promoter quadruplex-forming sequences
M. Clarke Miller, Huy T. Le, William L. Dean, Patrick A. Holt, Jonathan B. Chaires and John O. Trent
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05891F

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Self-cleaving DNAzymes on the cover of Issue 20

On the cover of this month’s issue we have an article from David M. Perrin and colleagues from the University of British Columbia, Canada.

In order to expand the repertoire of side chain functionality in DNAzymes Perrin and coworkers have explored the use of the phenol group, which is characteristic of the tyrosine side chain found in many active sites of protein enzymes. They have used a phenol-modified 2′-deoxyuridine triphosphate to produce a modified DNA library, which was then used to select DNAzymes capable of self cleaving in the presence of Mg2+ and Zn2+.  The most active DNAzyme, Dz11-17PheO, has an activity of 0.2 min-1.

A divalent metal-dependent self-cleaving DNAzyme with a tyrosine side chain
Curtis H. Lam, Christopher J. Hipolito, Marcel Hollenstein and David M. Perrin
Org. Biomol. Chem., 2011,
DOI: 10.1039/C1OB05359K, Paper

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Two new Associate Editors for OBC

We are delighted to announce the appointment of two new Associate Editors, Professor Jin-Quan Yu and Professor Andrei Yudin, to handle manuscripts for OBC.

Professor Jin-Quan Yu has worked at the Scripps Research Institute since July 2007, where his research centres around the discovery of novel reactions based on C-H activation.  Prior to this he held an Assistant Professorship at Brandeis University and has also worked at the University of Cambridge where he received his PhD under the supervision of Professor Jonathan B. Spencer.

Jin-Quan Yu has received numerous awards throughout his career, most recently the 2012 Mukaiyama Award, the 2012 Arthur C. Cope Scholar Award, and the 2011 Novartis Early Career Award. He has authored over 85 publications to date, many of which have been highlighted in the scientific press.

Professor Andrei Yudin obtained his B.Sc. degree at Moscow State University and his Ph.D. degree at the University of Southern California under the direction of Professors G. K. Surya Prakash and George A. Olah. He subsequently took up a postdoctoral position in the laboratory of Professor K. Barry Sharpless at the Scripps Research Institute. In 1998, he started his independent career at the University of Toronto. He received early tenure, becoming an Associate Professor in 2002, and received an early promotion to the rank of a Full Professor in 2007.

Amongst Professor Yudin’s awards are the CSC Award in Combinatorial Chemistry, the 2004 Amgen New Faculty Award, the 2010 CSC Merck-Frosst Therapeutic Center Award, the 2010 Rutherford Medal of the Royal Society of Canada, and the 2011 University of Toronto Inventor of the Year Award.

The appointment of the two Associate Editors to the OBC Board means that authors now have a choice of submission routes when sending their articles to the journal. Using our online submission system, authors can choose for their articles to be handled by either Professor Yu, Professor Yudin (from October), or a Publishing Editor at the Cambridge Editorial office. More details on the submission procedures for OBC can be found in the journal’s guidelines.

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Perspective: heterocycle synthesis via tandem copper cross-coupling reactions

Yunyun Liu and Jie-Ping Wan from Jiangxi Normal University in China review recent research progress in heterocycle syntheses using tandem reactions initiated by copper-catalysed coupling transformations.

Areas they include are:

  • Reactions initiated by C–N coupling
  • Reactions initiated by C–O coupling
  • Reactions initiated by C–S coupling
  • Reactions involving a double C–X coupling process

Our sister journal Chemical Society Reviews has just published a themed issue on cross-coupling reactions – why not take a look?

Tandem reactions initiated by copper-catalyzed cross-coupling: A new strategy towards heterocycle synthesis
Yunyun Liu and Jie-Ping Wan
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05769C

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HOT: colloidal gold functionalised with carbohydrate mimics for selectin binding

Sabine Schlecht and colleagues from the Free University of Berlin have designed a series of sulfated cyclic and acyclic amino alcohols bound to colloidal gold nanoparticles for use as multivalent selectin binding agents.  The carbohydrate mimics were chosen to act as simplified analogs of the sLex unit found in biological selectin ligands, and demonstrated extremely high binding affinities towards L- and P-selectin and no cytotoxicity.

To read the details of this well conducted study download the article – it’s free to access for 4 weeks:

Multivalent interaction and selectivities in selectin binding of functionalized gold colloids decorated with carbohydrate mimetics
Meike Roskamp, Sven Enders, Fabian Pfrengle, Shahla Yekta, Vjekoslav Dekaris, Jens Dernedde, Hans-Ulrich Reissig and Sabine Schlecht
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05583F

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