Organic & Biomolecular Chemistry Blog

Welcome to OBC Issue 16, 2013!

This week’s front cover highlights the work of Atsushi Ikeda and co-workers at the Nara Institute of Science and Technology, Japan. They developed a photo-triggerable drug carrier based on cleavage of PEG lipids by photosensitiser fullerene derivatives. This interesting methodology has the potential to facilitate the development of novel liposomal drug carriers for use in biomedical research.

A photo-triggerable drug carrier based on cleavage of PEG lipids by photosensitiser-generated reactive singlet oxygen
Chikako Komeda, Atsushi Ikeda, Jun-ichi Kikuchi, Norihiro Ishida-Kitagawa, Hisashi Tatebe, Kazuhiro Shiozaki and Motofusa Akiyama
DOI: 10.1039/c2ob27199k

On the inside front cover is the work of Francisco Santoyo-Gonzalez and collegues at the University of Granada, Spain. They report an easy vinyl sulfone functionalisation of ferrocene derivatives which facilitates the preparation of a variety of versatile ferrocenylation reagents. Their methodology allows the facile preparation of a variety of conjugates and bioconjugates derivatives under mild conditions.

Vinyl sulfone-based ferrocenylation reagents: applications in conjugation and bioconjugation
Alicia Megia-Fernandez, Fernando Hernandez-Mateo and Francisco Santoyo-Gonzalez
DOI: 10.1039/c3ob27209e

Both articles can be read for free for the next 6 weeks!

Welcome to OBC Issue 15, 2013!

The outside front cover highlights a research article by Volonterio et al. in Milan describing an efficient multi-component domino process for the synthesis of peptide-urea and glyco-urea–peptide conjugates. This novel one-pot reaction allows the synthesis of a wide array of structurally diverse peptide-sugar conjugates in high yield and in a regioselective manner, from easily accessible starting materials, under mild conditions. Glycopeptides play an important role in biology and medicine and are indispensable tools for probing biological process.  The possibility to obtain libraries of peptide-sugar conjugates, containing enzymatically more stable linkages, makes a highly-significant impact in the field of drug discovery research.

Multi-component synthesis of peptide–sugar conjugates
Maria Cristina Bellucci, Giancarlo Terraneo and Alessandro Volonterio
DOI: 10.1039/C3OB27176E

On the inside front cover is the result of a collaboration from scientists at the University of Cagliari, Florence and Southampton. Caltagirone and co-workers report the synthesis and characterisation of a new family of bis-ureidic receptors (L1–L6). The ¹H NMR, absorption, luminescence properties, as well as the X-ray structure of system L6, and ion-binding behaviour have been studied in detail and theoretical calculations have helped to explain the binding properties observed. These findings provide insight in the development of new colorimetric and luminescent flexible anion probes. 

A new family of bis-ureidic receptors for pyrophosphate optical sensing
Claudia Caltagirone, Carla Bazzicalupi, Francesco Isaia, Mark E. Light, Vito Lippolis, Riccardo Montis, Sergio Murgia, Martina Olivaria and Giacomo Piccia
DOI: 10.1039/ C3OB27244C

Both articles can be read for free for the next 6 weeks!

This week front cover highlights a perspective article by Sebastian Fabritz et al. from the Kolmar group at Darmstadt University of Technology on cube-octameric silsesquioxanes. These small compact and highly symmetric nanoparticles have recently attracted increased attention as scaffold for tailor-made bioconjugates. The low toxicity, combined with solubility in aqueous systems and a half-life sufficient for in vivo studies make these structures attractive targets for a number of applications, among them drug delivery, tumor diagnostics and therapy.

Bioconjugation on cube-octameric silsesquioxanes
Sebastian Fabritz, Sebastian Hörner, Olga Avrutina and Harald Kolmar
DOI: 10.1039/c2ob26807h

On the inside front cover is the work of Jian-Mei Lu and co-workers describing an effective alternative method for the synthesis of diarylmethane derivatives, which utilises a readily available N-heterocyclic carbene–palladium(II)–1-methylimidazole complex. This efficient catalyst allowed the Suzuki–Miyaura coupling of benzylic chlorides with arylboronic acids or potassium phenyltrifluoroborate in neat water under mild conditions.

N-Heterocyclic carbene–palladium(II)–1-methylimidazole complex catalyzed Suzuki–Miyaura coupling of benzylic chlorides with arylboronic acids or potassium phenyltrifluoroborate in neat water
Yun Zhang, Meng-Ting Feng and Jian-Mei Lu
DOI: 10.1039/c3ob27353a 

Both articles can be read for free for the next 6 weeks!

Issue 9 of Organic & Biomolecular Chemistry is out now. Why not take a break, put your feet up with a can of your favourite drink and browse all the great content.

This week’s front cover highlights the work of Simon E. Lewis and colleagues at the University of Bath who demonstrate the applicability of Baddeley’s “aliphatic Friedel–Crafts” procedure to a range of saturated hydrocarbon substrates, and discuss its mechanism with the aid of DFT modelling data.

Aliphatic C–H activation with aluminium trichloride–acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons
Catherine L. Lyall, Mario Uosis-Martin, John P. Lowe, Mary F. Mahon, G. Dan Pantoş and Simon E. Lewis
DOI: 10.1039/C2OB26765A

On the inside front cover is the work of Lei Zhou and co-workers at Sun Yat-Sen University who describe a general synthesis of 2-substituted benzofurans and indoles through a CuBr-catalyzed coupling–allenylation–cyclization sequence.

Benzofuran and indole synthesis via Cu(I)-catalyzed coupling of N-tosylhydrazone and o-hydroxy or o-amino phenylacetylene
Tiebo Xiao, Xichang Dong and Lei Zhou
DOI: 10.1039/C2OB26867A

Both articles can be read for free for the next 6 weeks!

Issue 8 of Organic & Biomolecular Chemistry has landed and has brought clouds of chemistry along with it.

The front cover highlights the work of Goran Angelovski and colleagues who report the preparation and characterization of two novel macrocyclic gadolinium pH sensitive smart contrast agents appended with a phosphonate pendant arm and either an aliphatic or aromatic linker.

Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin
Sandip M. Vibhute, Jörn Engelmann, Tatjana Verbić, Martin E. Maier, Nikos K. Logothetis and Goran Angelovski
DOI: 10.1039/C2OB26555A

On the inside cover is the HOT article by Maggie He and Jeffrey W. Bode, which we have previously blogged about, highlighting their efforts in isolating a single bullvalene structure from a dynamic mixture of 852 isomers and their computational & network mapping investigations.

E pluribus unum: isolation, structure determination, network analysis and DFT studies of a single metastable structure from a shapeshifting mixture of 852 bullvalene structural isomers
Maggie He and Jeffrey W. Bode
DOI: 10.1039/C2OB26954F

Both of these cover articles are free to access for 6 weeks.

Also in this week’s issue: 1 Emerging area review, 3 Communications & 14 Articles.

Download the issue today!

Welcome to this week’s issue of Organic & Biomolecular Chemistry!

On the front cover:

M. Cepeda and co-workers explore the solution phase behaviour of β-cyclodextrin/alkyltrimethylammonium bromide mixtures, varying the surfactant alkyl chain length from hexyl (C₆) to octadecyl (C₁₈).

Competition between surfactant micellization and complexation by cyclodextrin
M. Cepeda, R. Daviña, L. García-Río, M. Parajó, P. Rodríguez-Dafonte and M. Pessêgo
DOI: 10.1039/C2OB26318A

On the inside cover:

Jasmin Mecinović and colleagues describe how hydroxylamine acts as an oxygen nucleophile in the substitution reaction with benzothiazole-2-sulfonamides in aqueous media.

Hydroxylamine as an oxygen nucleophile: substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides
Jos J. A. G. Kamps, Roman Belle and Jasmin Mecinović
DOI: 10.1039/C2OB26929E

Don’t forget, both of these cover articles are free to access for the next 6 weeks!

Get your hands on the rest of the great content in this issue HERE, and why not have a look at some of the latest published articles not yet in an issue.

This week in Organic & Biomolecular Chemistry we are bringing you: 1 Emerging Area review, 4 Communications and 18 articles full of interesting chemistry. Visit the issue and get it all!

On the front cover:
Andreea R. Schmitzer and coworkers present the first example of a benzimidazolium-based artificial transmembrane chloride transporter and a synthetic calcium ionophore that can regulate intracellular calcium concentrations in bacteria.

Benzimidazolium-based synthetic chloride and calcium transporters in bacterial membranes
Claude-Rosny Elie, Audrey Hébert, Mathieu Charbonneau, Adam Haiun and Andreea R. Schmitzer
DOI: 10.1039/C2OB26966J

On the inside cover:
Noriho Kamiya and colleagues at Kyushu University assess how the spatial arrangement of the avidin–biotin interaction between protein building blocks affects the formation of a protein supramolecular complex.

Protein supramolecular complex formation by site-specific avidin–biotin interactions
Yutaro Mori, Rie Wakabayashi, Masahiro Goto and Noriho Kamiya
DOI: 10.1039/C2OB26625C

Go to the issue now…..

Welcome one and all as we take a look inside issue 5 of Organic & Biomolecular Chemistry!

Between its covers this week we have 2 Emerging area reviews on the enantioselective synthesis of helicenequinones and -bisquinones, and asymmetric trienamine catalysis: new opportunities in amine catalysis; 2 Communications and 16 articles, including a HOT article on the synthesis of polysubstituted furanonaphthoquinones (free to access for 4 weeks).

On the front cover:
This week’s cover is highlighting the work of Irene Izzo and colleagues at Università degli Studi di Salerno. Izzo et al. highlight the potential of cyclopeptoids as phase transfer catalysts, reporting the syntheses, binding affinities and catalytic abilities of 5 cyclohexapeptoids and comparing them with well-known phase-transfer catalysts.

Cyclopeptoids: a novel class of phase-transfer catalysts
Giorgio Della Sala, Brunello Nardone, Francesco De Riccardis and Irene Izzo
DOI: 10.1039/C2OB26764K

On the inside front cover:
Highlighted here is the work of Christopher J. Schofield and co-workers who report the success design of inhibitors that have the dual-action of binding to prolyl hydroxylase active sites and simultaneously depleting iron levels in cells by inducing the binding of a second iron ion at the active site.

Dual-action inhibitors of HIF prolyl hydroxylases that induce binding of a second iron ion
Kar Kheng Yeoh, Mun Chiang Chan, Armin Thalhammer, Marina Demetriades, Rasheduzzaman Chowdhury, Ya-Min Tian, Ineke Stolze, Luke A. McNeill, Myung Kyu Lee, Esther C. Y. Woon, Mukram M. Mackeen, Akane Kawamura, Peter J. Ratcliffe, Jasmin Mecinović and Christopher J. Schofield
DOI: 10.1039/C2OB26648B

Issue 4 of Organic & Biomolecular Chemistry is now online; find it HERE

This rather green and leafy cover image is courtesy of Kazuya Kikuchi and co-workers at Osaka University who have developed a new mechanism for a reversible dual “OFF–ON–OFF” pH sensor with the influence from a suitably located carboxylic acid group.

pH Induced dual “OFF–ON–OFF” switch: influence of a suitably placed carboxylic acid
Kalyan K. Sadhu, Shin Mizukami, Akimasa Yoshimura and Kazuya Kikuchi
DOI: 10.1039/C2OB26630J

Highlighted on the inside cover of this issue is the work of J. Carlos Menéndez and colleagues who have developed an efficient method for the synthesis of trans-2-aryl-4-arylamino-tetrahydroquinolines from 3,5-disubstituted anilines, vinyl ethers and aromatic aldehydes.

Diastereoselective, multicomponent access to trans-2-aryl-4-arylamino-1,2,3,4-tetrahydroquinolines via an AA′BC sequential four-component reaction and their application to 2-arylquinoline synthesis
Pascual Ribelles, Vellaisamy Sridharan, Mercedes Villacampa, Mª Teresa Ramos and J. Carlos Menéndez
DOI: 10.1039/C2OB26754C

Both articles are free to access for the next 6 weeks