Domino reactions for the synthesis of various α-substituted nitro alkenes
Stefania Fioravanti, Lucio Pellacani and Maria Cecilia Vergari
DOI: 10.1039/C1OB06260C
As with all our cover articles, this one is free to access for 6 weeks – so why not take a look?
Welcome to OBC Issue 2, 2012
On the cover this week is the work of Tamas Martinek et al. at the University of Szeged (Hungary), reporting a tunable H12 helix –> H18 helix transition not previously observed for foldamers.
Combining traditional methods for peptide folding (ECD, DOSY-NMR) and molecular modeling to investigate the folding and self-assembly of peptide mimics, the authors show that foldamer sequences constructed using trans-ABHC and β3-hSer residues produce β-H18 helix in a solvent- and concentration-dependent way.
‘These observations strongly support the view that foldameric helix refolding is promoted by higher-order packing of the helices in protic solvent’, say the authors.
Self-association-driven transition of the β-peptidic H12 helix to the H18 helix
Éva Szolnoki, Anasztázia Hetényi, Tamás A. Martinek, Zsolt Szakonyi and Ferenc Fülöp
Org. Biomol. Chem., 2012, 10, 255-259
DOI: 10.1039/C1OB06627G
View the rest of Issue 2 here
Welcome to Issue 1 of OBC, 2012!
On the front cover we have an article from Brian Stolz and team on the synthesis of enantioenriched γ-quaternary cycloheptenones, with potential for the preparation of non-natural analogs of cycloheptanoid natural products.
Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems
Nathan B. Bennett, Allen Y. Hong, Andrew M. Harned and Brian M. Stoltz
DOI: 10.1039/C1OB06189E
On the inside front cover is an article from Robert Stockman and coworkers. They report the synthesis of an advanced intermediate, an azaspirocyclic aldehyde, in the route to halichlorine developed by Clive and coworkers, shortening the synthetic route by 15 steps.
Combining two-directional synthesis and tandem reactions: a short formal synthesis of halichlorine
Camille Gignoux, Annabella F. Newton, Alexandre Barthelme, William Lewis, Marie-Lyne Alcaraz and Robert A. Stockman
DOI: 10.1039/C1OB06380D
Incredibly 2012 will be our 10th year of publication and we would like to thank all our authors, referees, readers and Board members for their support over the last decade. Read the Editorial introduction to the next volume from Chair Jeffrey Bode and Editor Richard Kelly for the changes we’ve seen and what we have to look forward to in the coming year.
On the front cover of our last 2011 issue is work from Alessandro Volonterio and colleagues developing a multi-component one-pot synthetic route to novel glyco-hydantoin conjugates, which may be used as synthons for glyco-pseudopeptides.
Three-component, one-pot sequential synthesis of glyco-hydantoin conjugates
Maria Cristina Bellucci, Alessandra Ghilardi and Alessandro Volonterio
DOI: 10.1039/C1OB06312J
On the inside front cover is work from Stefan Matile and colleagues, applying principles from green and red fluorescent proteins from jellyfish and corals to develop the properties of core-substituted naphthalenediimide and perylenediimide fluorophores. Some these newly synthesized fluorophores are able to cover all primary colours upon pH changes, and as such may find practical use in naked-eye sensing arrays.
Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core
Andrea Fin, Irina Petkova, David Alonso Doval, Naomi Sakai, Eric Vauthey and Stefan Matile
DOI: 10.1039/C1OB05702B
View the rest of Issue 24 here
The article from Ahmed M. Zaed and Andrew Sutherland reporting the first total synthesis of clavaminol A, C and H features on the front cover of Issue 23. Clavaminols are 2-amino-3-alkanols recently isolated from the Mediterranean ascidian Clavelina phlegraea (see cover) and have an unusual stereochemistry of (2R,3S). Despite this they still show some cytotoxic activity.
Total synthesis of clavaminol A, C and H
Ahmed M. Zaed and Andrew Sutherland
DOI: 10.1039/C1OB06060K
On the inside front cover is work from Michael Harmata and coworkers on the synthesis of benzothiazines for use as fluorescent sensors. The fluorescent 7-amino-2,1-benzothiazines were prepared using the palladium-catalyzed reaction of 4-amino-2-chlorobenzaldehydes with a sulfoximine or the reaction of 7-fluoro-2,1-benzothiazines with amines.
Benzothiazines in organic synthesis. Synthesis of fluorescent 7-amino-2,1-benzothiazines
Nattawut Yongpruksa, Siddharth Pandey, Gary A. Baker and Michael Harmata
DOI: 10.1039/C1OB06051A
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
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:
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.
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
On the cover of Issue 19 is an article from Ference Fülöp and colleagues from the University of Szeged and the University of Valencia.
They have developed a synthetic route to fluorinated β-aminocyclohexene or cyclohexane esters from a bicyclic β-lactam via selective hydroxylation and hydroxy–fluorine exchange. Despite the potential of fluorinated cyclic amino acids for medicinal chemistry applications, only a handle of other fluorinated derivatives have been reported so far.
This article is part of a forthcoming Organic & Biomolecular Chemistry web theme issue on Foldamer Chemistry – check back soon for related articles.
Regio- and diastereoselective fluorination of alicyclic β-amino acids
Loránd Kiss, Enikő Forró, Santos Fustero and Ferenc Fülöp
Org. Biomol. Chem., 2011, 9, 6528-6534, Advance Article
DOI: 10.1039/C1OB05648D
Welcome to Issue 18 of OBC!
On the cover is illustrated a Perspective article by Qian Wang and colleagues at the University of South Carolina, USA, which highlights some of the recent progress in the chemical modifications of bionanoparticles, finding uses as biosensors, electronic nanodevices, drug delivery agents and vaccine carriers, amongst others.
This cover article is FREE to access for a period of 6 weeks. Why not take a look now?
Altering the landscape of viruses and bionanoparticles
L. Andrew Lee, Huong Giang Nguyen and Qian Wang
Org. Biomol. Chem., 2011, DOI: 10.1039/C1OB05700F
