Archive for the ‘Uncategorized’ Category

What are your colleagues reading in Organic & Biomolecular Chemistry?

The articles below are some of the most read Organic & Biomolecular Chemistry articles in April, May and June 2017.

Review Articles:

Design and synthesis of analogues of natural products
Martin E. Maier
DOI: 10.1039/C5OB00169B

Transition-metal catalyzed valorization of lignin: the key to a sustainable carbon-neutral future
Markus D. Kärkäs, Bryan S. Matsuura, Timothy M. Monos, Gabriel Magallanes and Corey R. J. Stephenson
DOI: 10.1039/C5OB02212F

Selective chemical labeling of proteins
Xi Chen and Yao-Wen Wu
DOI: 10.1039/C6OB00126B

Site-selective incorporation and ligation of protein aldehydes
Richard J. Spears and Martin A. Fascione
DOI: 10.1039/C6OB00778C

1,3-Dipolar cycloadditions of azomethine imines
Carmen Nájera, José M. Sansano and Miguel Yus
DOI: 10.1039/C5OB01086A

Organocatalytic synthesis of axially chiral atropisomers
P. Renzi
DOI: 10.1039/C7OB00908A

The application of design of experiments (DoE) reaction optimisation and solvent selection in the development of new synthetic chemistry
Paul M. Murray, Fiona Bellany, Laure Benhamou, Dejan-Krešimir Bučar, Alethea B. Tabor and Tom D. Sheppard
DOI: 10.1039/C5OB01892G

Recent advances in the synthesis and application of fluorescent α-amino acids
Alexander H. Harkiss and Andrew Sutherland
DOI: 10.1039/C6OB01715K

Communications & Papers:

Amidation of unactivated ester derivatives mediated by trifluoroethanol
Christopher G. McPherson, Nicola Caldwell, Craig Jamieson, Iain Simpson and Allan J. B. Watson
DOI: 10.1039/C7OB00593H, Communication

A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
Jakov Ivkovic, Christian Lembacher-Fadum and Rolf Breinbauer D
OI
: 10.1039/C5OB01838B, Communication

A protocol for amide bond formation with electron deficient amines and sterically hindered substrates
Maria E. Due-Hansen, Sunil K. Pandey, Elisabeth Christiansen, Rikke Andersen, Steffen V. F. Hansen and Trond Ulven
DOI: 10.1039/C5OB02129D, Communication

A NHC-catalyzed 1,3-dipolar cycloaddition reaction of allyl ketones with azides: direct access to 1,4,5-trisubstituted 1,2,3-triazoles
Huijun Yuan, Lili Zhang, Zhantao Liu, Yang Liu, Jian Wang and Wenjun Li
DOI: 10.1039/C7OB00906B, Communication

A novel off–on fluorescent probe for sensitive imaging of mitochondria-specific nitroreductase activity in living tumor cells
Bo Huang, Wen Chen, Yong-Qing Kuang, Wei Liu, Xian-Jun Liu, Li-Juan Tang and Jian-Hui Jiang
DOI: 10.1039/C7OB00781G, Communication

FeCl3 catalysed 7-membered ring formation in a single pot: a new route to indole-fused oxepines/azepines and their cytotoxic activity
K. Shiva Kumar, Meesa Siddi Ramulu, Bandari Rajesham, N. Praveen Kumar, Vani Voora and Rama Krishna Kancha
DOI: 10.1039/C7OB00715A,Paper

Copper-catalyzed oxidative decarboxylative coupling of α-keto acids and sulfoximines
Chaleena Pimpasri, Ladawan Sumunnee and Sirilata Yotphan
DOI: 10.1039/C7OB00776K, Paper

Tf2NH-catalyzed formal [3 + 2] cycloaddition of oxadiazolones with ynamides: a simple access to aminoimidazoles
Yingying Zhao, Yancheng Hu, Xincheng Li and Boshun Wan
DOI: 10.1039/C7OB00701A, Communication

Cyclic dipeptide based cell-penetrating peptidomimetics for effective DNA delivery
Chilakapati Madhu, Chandrashekhar Voshavar, K. Rajasekhar and Thimmaiah Govindaraju
DOI: 10.1039/C7OB00167C, Communication

Synthesis, properties, and crystal structures of π-extended double [6]helicenes: contorted multi-dimensional stacking lattice
Takao Fujikawa, Nobuhiko Mitoma, Atsushi Wakamiya, Akinori Saeki, Yasutomo Segawa and Kenichiro Itami
DOI: 10.1039/C7OB00987A, Paper

Urotensin-II peptidomimetic incorporating a non-reducible 1,5-triazole disulfide bond reveals a pseudo-irreversible covalent binding mechanism to the urotensin G-protein coupled receptor
Salvatore Pacifico, Aidan Kerckhoffs, Andrew J. Fallow, Rachel E. Foreman, Remo Guerrini, John McDonald, David G. Lambert and Andrew G. Jamieson
DOI: 10.1039/C7OB00959C, Paper

Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis
Vishal M. Sheth, Bor-Cherng Hong and Gene-Hsiang Lee
DOI: 10.1039/C7OB00473G, Communication

Asymmetric synthesis of CF3-containing tetrahydroquinoline via a thiourea-catalyzed cascade reaction
Yuanyuan Zhu, Boyu Li, Cui Wang, Zhenghao Dong, Xiaoling Zhong, Kairong Wang, Wenjin Yan and Rui Wang
DOI: 10.1039/C7OB01013C, Communication

Palladium-catalyzed Suzuki–Miyaura coupling of amides by carbon–nitrogen cleavage: general strategy for amide N–C bond activation
Guangrong Meng and Michal Szostak
DOI: 10.1039/C6OB00084C, Paper

Ru(II)-Catalyzed annulation of benzamidines and alkynes by C–H/N–H activation: a facile synthesis of 1-aminoisoquinolines
P. P. Kaishap, G. Duarah, D. Chetia and S. Gogoi
DOI: 10.1039/C7OB00389G, Paper

2,2,2-Trifluoroethanol as a solvent to control nucleophilic peptide arylation
Diana Gimenez, Anica Dose, Nicholas L. Robson, Graham Sandford, Steven L. Cobb and Christopher R. Coxon
DOI: 10.1039/C7OB00295E, Communication

Regioselective 6-endodig iodocyclization: an accessible approach for iodo-benzo[a]phenazines
Sonu Kumar, Mohammad Mujahid and Akhilesh K. Verma
DOI: 10.1039/C7OB00671C, Paper

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Poster prize winners at the 11th Symposium on Biorelevant Chemistry

Congratulations to the poster prize winners at the Symposium on Biorelevant Chemistry!

Organic & Biomolecular Chemistry are please to present prizes to these winners:

Ryotaro Yamada (Nagoya University, Graduate School of Science, Department of Chemistry)
Title: Probing auxin signaling with synthetic auxin-engineered receptor pair

Kieko Senda (Nagoya University, Graduate School of Science, Department of Chemistry)
Title: Photostable fluorescent nanoparticles encapsulating a NIR phospha-rhodamine dye

Organised by the Chemical Society of Japan, the Symposium on Biorelevant Chemistry took place from the 7th – 9th September 2017.

The winners receiving their prizes from Philippa Hughes (Executive Editor, Royal Society of Chemistry)

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Organic & Biomolecular Chemistry partners with Publons

Organic & Biomolecular Chemistry has partnered with Publons (a third-party reviewer recognition service) so you can keep a record of every review you complete.

We really value your reviewing and editorial contributions and want to ensure you get more recognition for them.

How it works
When you submit a review to a participating journal you will be asked if you want to opt in to Publons, you can then instantly start building your verified peer review and editorial record to showcase the full extent of your contributions and influence in your field. Publons tracks your reviews without compromising reviewer anonymity, by default, only the year of the review and the journal title will be shown on reviewer profiles for our journals.

Read more about the partnership on our news pages

For more information about Publons, visit publons.com/benefits/researchers

 

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Diversity-oriented synthesis of biaryl-containing macrocycles

Developing efficient protocols for the synthesis of macrocycle-containing molecules has been a longstanding challenge in chemistry. In a recent OBC publication, collaborative efforts between Prof. Tomás Torroba of the University of Burgos and Prof. Luis Miranda of Universidad Nacional Autónoma de México have resulted in a diversity oriented synthetic strategy for the synthesis of biaryl-containing macrocycles.

Macrocyclic structures have utility in many different areas of chemistry and have significant applications in medicine due to their broad range of biological activities. Compared to small molecules, macrocycles offer unique functional advantages in terms of selectivity and potency as their cyclic framework enables a high degree of structural preorganization such that key functional groups can interact across extended binding pockets without a major loss of entropy. Moreover, macrocycles display favourable drug-like properties such as improved solubility, lipophilicity, membrane penetration and stability.

Of interest are peptide macrocycles containing an endo aryl-aryl bond which constitute an important class of biologically active macrocyclic natural products. In terms of established synthetic approaches, two strategies have been commonly implemented 1) construction of the biaryl unit followed by a cyclization and 2) ring closure through the formation of the aryl-aryl bond.

These routes are limited however by the synthesis of the peptide backbone which typically requires challenging multi-step sequences.

To circumvent this issue, Torobba and Miranda proposed a sequence combining a Ugi four component reaction (Ugi-4CR) with a Suzuki-Miyaura cross-coupling for rapid access to the desired macrocycles in a diversity oriented approach. This synthetic strategy is composed of four steps: 1) Ugi-4CR using two bifunctional building blocks, the mono-Boc protected diamine and iodine containing carboxylic acid; 2) Boc cleavage; 3) a second Ugi-4CR involving a MIDA protected boron-containing carboxylic acid and finally 4) Suzuki-Miyaura cross-coupling-based macrocyclization.

After optimisation, the synthesis of a small collection of biaryl-containing macrocycles was carried out with good overall yields (35-65% isolated yield) and their cytotoxicity evaluated against eight human cancer cell lines.

The ease with which this synthetic sequence can be reproduced in combination with their preliminary biological results will no doubt open doors for the future evaluation of larger collections of this class of biaryl-containing macrocycles and in determining their full potential in drug discovery.

To find out more see:

Diversity-oriented synthesis and cytotoxic activity evaluation of biaryl-containing macrocycles
Karell Pérez-Labrada, Marco A. Cruz-Mendoza, Alejandra Chávez-Riveros, Eduardo Hernández-Vázquez, Tomás Torroba and Luis D. Miranda
DOI: 10.1039/C6OB02726A


Victoria Corless is currently completing her Ph.D. in organic chemistry with Prof. Andrei Yudin at The University of Toronto. Her research is centred on the synthesis of kinetically amphoteric molecules which offer a versatile platform for the development of chemoselective transformations with particular emphasis on creating novel biologically active molecules.

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