Organic & Biomolecular Chemistry Blog

Check out our Foldamer Chemistry web themed issue

03 May 2012

The Organic & Biomolecular Chemistry web theme issue focussing on the exciting area of foldamer chemistry is now available for you to access, with 21 articles for you to read, 4 of which have so far appeared on the covers of issues.

Here are some of the popular articles that others have been reading:

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
DOI: 10.1039/C1OB05648D

Conformational stability of collagen triple helices functionalized in the Yaa position by click chemistry
Roman S. Erdmann and Helma Wennemers
Org. Biomol. Chem., 2012, 10, 1982-1986
DOI: 10.1039/C2OB06720J

Stereoselective preparation of β,γ-methano-GABA derivatives
David J. Aitken, Ludovic Drouin, Sarah Goretta, Régis Guillot, Jean Ollivier and Marco Spiga
Org. Biomol. Chem., 2011, 9, 7517-7524
DOI: 10.1039/C1OB06095C

Design and synthesis of trans-3-aminopyran-2-carboxylic acid (APyC) and α/β-peptides with 9/11-helix
Gangavaram V. M. Sharma, Kodeti Srinivas Reddy, Shaik Jeelani Basha, Kondreddi Ravinder Reddy and Akella V. S. Sarma
Org. Biomol. Chem., 2011, 9, 8102-8111
DOI: 10.1039/C1OB06279D

To read the rest of this great web themed issue… CLICK HERE

What do you think if this area of chemistry? Do you have a favourite article from the collection?
Let us know your thoughts by leaving a comment below.

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HOT: Critical enzyme–substrate interactions in GlfT2-catalyzed mycobacterial galactan assembly

01 May 2012

By Marie Cote, Deputy Editor.

Todd L. Lowary and colleagues at the University of Alberta, Canada, have synthesised a series of UDP-galactofuranose analogs and used these analogs to examine enzyme–substrate binding interactions for the galactofuranosyltransferase enzyme GlfT2, a glycosyltransferase responsible for the formation of the galactan complex in M. tuberculosis and a potential drug target.

Critical hydrogen bonding interactions within the active site of the mycobacterial galactofuranosyltransferase GlfT2 are revealed and it is hoped the knowledge of these specific protein-carbohydrate interactions may be explored for the development of novel inhibitors.

Selected as ‘Hot’, this article will be FREE to access for the next 4 weeks.
Why not read it now and let us know what you think by leaving a comments below!

Synthetic UDP-galactofuranose analogs reveal critical enzyme–substrate interactions in GlfT2-catalyzed mycobacterial galactan assembly
Myles B. Poulin, Ruokun Zhou and Todd L. Lowary
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25159K, Paper

Todd L. Lowary’s OBC work is also highlighted in this C&EN news story ‘Determining Sugar Sequence Fidelity’

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OBC symposium concludes in Beijing

26 Apr 2012

By Richard Kelly.

The final day of the OBC symposium saw us arrive at Peking University.

Professor Lei Liu presenting at Peking University

The day opened with PKU head of organic chemistry Professor Zhenfeng Xi welcoming us to the institute, and this was followed by Andrei Yudin’s final presentation and then Professor Guanxin Liang from Nankai University showing a variety of natural product syntheses from his lab. The morning was rounded off by Dirk Trauner.

The first afternoon session showcased the work of Professors from two institutes in Beijing. Professor Lei Liu from Tsinghua University presented on protein synthesis while Professor Sanzhong Luo from the Institute of Chemistry, Chinese Academy of Sciences showed his latest research on asymmetric binary-acid catalysis.

The second afternoon session saw OBC Chair Jeffrey Bode giving another demonstration of his research into amide-forming reactions, and then Professor Zhi-Xiang Yu from Peking University gave an interesting overview of the potential power of computational chemistry in natural products synthesis.

Our visit to Beijing was a great way to finish this first OBC symposium and we’re very grateful to local organiser Professor Jianbo Wang and all of the speakers.

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OBC Symposium moves to Lanzhou University

26 Apr 2012

By Richard Kelly.

Following a successful first day in Shanghai, the OBC Symposium travelled to Lanzhou. On arrival we were greeted by a huge banner opposite the entrance. No one visiting the University would be in any doubt that OBC were in town!

The OBC symposium banner at the entrance to Lanzhou University

The day started with a welcome by Director of the State Key Laboratory of Applied Organic Chemistry at Lanzhou Professor Yongqiang Tu, which was followed by Dirk Trauner’s presentation on natural product synthesis. The morning was rounded-off by Professor Xiaoming Feng from Sichuan University, who guided us through his research on asymmetric catalysis using chiral N,N’-Dioxide ligands.

Professor Andrei Yudin at Lanzhou University

Following lunch Professor Hongbin Zhang from Yunnan University presented the syntheses of some bioactive alkaloids. Professor Tu then returned to the stage to continue the natural products synthesis theme by giving an overview of his work on syntheses which employ 1,2-migration reactions. Andre Yudin gave another overview of his work using amphoteric molecules and the final talk of the day was given by Professor Hanmin Huang from Lanzhou Institute of Chemical Physics, on C-C and C-N bond formation via C-H activation.

All in all it was a very enjoyable visit to Lanzhou. Our thanks go to Professor Tu for hosting us, Professor Wei Wang and his colleagues for local organisation and to all the speakers.

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Issue 19 online with quantum mechanical tunnelling & 2-substituted 3-bromopyrrolidines on the covers

24 Apr 2012

By James Anson.

On the front cover is this HOT Emerging Areaarticle from Peter R. Schreiner and co-workers (Justus-Liebig University, Germany) who discuss quantum mechanical tunnelling and provide an overview of the importance of tunnelling in organic chemical reactions.
Discussion includes:

a brief history of tunnelling
hydrogen tunnelling
carbon tunnelling
heteroatom tunnelling

Tunnelling control of chemical reactions – the organic chemist’s perspective
David Ley, Dennis Gerbig and Peter R. Schreiner
Org. Biomol. Chem., 2012, 10, 3781-3790
DOI: 10.1039/C2OB07170C

On the inside front cover is this Communication, from Ying-Yeung Yeung and colleagues at National University of Singapore, where a facile and highly enantioselective route to 2-substituted 3-bromopyrrolidines is presented. The authors demonstrate how these can be reached via the bromo-aminocyclisation of 1,2-disubstituted olefinic amides using amino-thiocarbamates as a catalyst. This is also part of our growing Organocatalysis web collection.

A highly enantioselective approach towards 2-substituted 3-bromopyrrolidines
Jie Chen, Ling Zhou and Ying-Yeung Yeung
Org. Biomol. Chem., 2012, 10, 3808-3811
DOI: 10.1039/C2OB25327E

Both of these cover articles will be free to access for the next 6 weeks.

Also in this issue:

A perspectiveby Alessandro Massi and Daniele Nanni:
Thiol–yne coupling: revisiting old concepts as a breakthrough for up-to-date applications

And 2 HOT articles that are still free to access for another 3 weeks

Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid
Mark C. Elliott et al.

Glycosylated diazeniumdiolate-based oleanolic acid derivatives: synthesis, in vitro and in vivo biological evaluation as anti-human hepatocellular carcinoma agents
Yihua Zhang et al.

View the entire issue HERE, it’s full of lots of great content!

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HOT: Glycosylated diazeniumdiolate-based oleanolic acid derivatives as therapeutic agents for human hepatocellular carcinoma

23 Apr 2012

By Marie Cote, Deputy Editor.

Following their earlier work on nitric oxide (NO) releasing oleanolic acid (OA) derivatives as therapeutic agents for human hepatocellular carcinoma (HCC) – the third leading cause of cancer death worldwide without effective chemotherapy – Prof. Yihua Zhang and coll. at the Center of Drug Discovery, China Pharmaceutical University (Nanjing, P.R. China) have designed a series of glycosylated diazeniumdiolate derivatives of oleanolic acid.

One of the coupounds has been found to selectively inhibit the proliferation of HCC in vivo but not that of non-tumor liver cells, with relatively low acute toxicity, and may be a promising drug candidate against HCC.

The authors also provide an in-depth analysis of the mechanisms underlying the action of this group of glycosylated diazeniumdiolate-based OA derivatives…

Want to know more? Why not read now, the article will be FREE to access to all for the next four weeks

Glycosylated diazeniumdiolate-based oleanolic acid derivatives: synthesis, in vitro and in vivo biological evaluation as anti-human hepatocellular carcinoma agents
Zhangjian Huang, Junjie Fu, Ling Liu, Yijun Sun, Yisheng Lai, Hui Ji, Edward E. Knaus, Jide Tian and Yihua Zhang
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB25252J, Paper

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Foldamer Chemistry web themed issue now published

23 Apr 2012

By James Anson.

Here Prof. Ferenc Fülöp, University of Szeged, gives a brief introduction to Organic & Biomolecular Chemistry‘s Foldamer Chemistry web themed issue:

The syntheses and structural and functional investigations of peptide oligomers that adopt designed compact conformations have become challenging tasks in recent decades. β-Amino acids, among them cyclic β-amino acids, find a broad range of use as building blocks for the preparation of modified analogues of biologically active peptides. The peptidomimetic approach in drug research is of significant potential. Since their discovery, the field of foldamers has come of age as a branch of chemistry, and synthetic self-organizing polymers have infiltrated almost all chemical disciplines, either as tools or as topics of fundamental science.

The interest in foldamers originated in the challenge to mimic the structural behaviour of biomolecules with synthetic sequences. This challenge was quickly answered: beautiful structures and programmable self-organization can be achieved with non-natural molecules. Various synthetic methodologies have led to novel building blocks becoming accessible, and a further source of diversity is the combination of different monomer types within a single sequence. Different amino acid homologues can be coupled in specific patterns (α,β-peptides, β,γ-peptides, etc.), all resulting in novel secondary structure patterns. Moreover, the coupling of aromatic building blocks with aliphatic monomers has been achieved, and short βαγ- and βαδ-peptide sequences have recently been described, which points to the practically limitless number of possible combinations. The building-up of higher-order structures from foldamers is a further great challenge and an important trend in the field. The diversity of peptidic foldamers is currently passing through a ramping-up process at all levels.

The present web themed issue covers the syntheses of β-amino acid monomers, and discusses the syntheses, structural investigations and applications of foldamers.

Click here to see all of the articles in the web themed issue

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HOT paper: Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid

20 Apr 2012

By James Anson.

In this HOT paper Mark C. Elliott and colleagues at Cardiff University present an investigation on the deprotonation and alkylation of 1-methylcyclohexa-2,5-diene-1-carboxylic acid under a range of conditions. The culmination of the investigation shows that deprotonation of 1-methylcyclohexa-2,5-diene-1-carboxylic acid with n-BuLi in the presence of TMEDA, followed by alkylation, offers a direct and highly diastereoselective route to the corresponding 4-substituted products in which the alkyl group introduced is transto the carboxylic acid.

Mark C. Elliott et al. comment that this result “complements previous findings of H. van Bekkum in which a 4-substituted benzoic acid is reductively alkylated and where, when any selectivity is observed, the alkyl group and the carboxylic acid are preferentially cis.”

Click here for the complete study…..

This HOT article will be FREE TO ACCESS for the next 4 weeks!

Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid
Nicholas J. Bennett, Mark C. Elliott, Natalie L. Hewitt, Benson M. Kariuki, Clare A. Morton, Steven A. Raw and Simone Tomasi
Org. Biomol. Chem., 2012
DOI: 10.1039/C2OB25211B

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Mannich reactions, carbon nanotubes & polymeric ladderphanes: a taste of what’s to come for Organic & Biomolecular Chemistry’s 10th anniversary issue

18 Apr 2012

By James Anson.

Our 10th anniversary themed issue is well under way, with many articles now published online. Here is just a taster of some of the hot articles that are included in the collection so far:

Development of strong Brønsted base catalysis: catalytic direct-type Mannich reactions of non-activated esters via a product-base mechanism
Yasuhiro Yamashita, Hirotsugu Suzuki and Shu Kobayashi
DOI: 10.1039/C2OB25522G

Facile air-oxidation of large aromatic hydrocarbon bay regions to bay region quinones: predicted oxygen-sensitivity of hydrogen-terminated carbon nanotubes
Eric H. Fort and Lawrence T. Scott
DOI: 10.1039/C2OB25208B

Double stranded polymeric ladderphanes with 16-p-electron antiaromatic metallocycle linkers
Hsin-Hua Huang, Chih-Gang Chao, Shern-Long Lee, Hung-Jen Wu, Chun-hsien Chen and Tien-Yau Luh
DOI: 10.1039/C2OB25114K

Solvent and substituent effects on aggregation constants of perylene bisimide p-stacks – a linear free energy relationship analysis
Zhijian Chen, Benjamin Fimmel and Frank Würthner
DOI: 10.1039/C2OB07131B

These 4 HOT artilces will be FREE to access for the next 4 weeks.

There are plenty more articles HERE, covering many different and interesting topics. Why not take a look, we’re sure you’ll find something you will like.

In the weeks to come we will be highlighting more of the hot articles that have been published for our 10th anniversary issue so watch this space!

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Organic & Biomolecular Chemistry Blog

Check out our Foldamer Chemistry web themed issue

HOT: Critical enzyme–substrate interactions in GlfT2-catalyzed mycobacterial galactan assembly

OBC symposium concludes in Beijing

OBC Symposium moves to Lanzhou University

Issue 19 online with quantum mechanical tunnelling & 2-substituted 3-bromopyrrolidines on the covers

HOT: Glycosylated diazeniumdiolate-based oleanolic acid derivatives as therapeutic agents for human hepatocellular carcinoma

Foldamer Chemistry web themed issue now published

HOT paper: Diastereoselective alkylation reactions of 1-methylcyclohexa-2,5-diene-1-carboxylic acid

Mannich reactions, carbon nanotubes & polymeric ladderphanes: a taste of what’s to come for Organic & Biomolecular Chemistry’s 10th anniversary issue

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