Inside Organic & Biomolecular Chemistry issue 41 – online now

An overview of this week’s issue of Organic & Biomolecular Chemistry

OBC issue 41 is now online, and ready for you to browse to your heart’s content. So what have we got for you this week? Well…

On the front cover:
A HOT paper by Hans-Wolfgang Klafki, Hans-Joachim Knölker and co-workers, who describe the synthesis of novel tripartite structures and extensive studies on their structure-activity relations in cell-based assays. They report, in detail, the effect of different lipophilic membrane anchors and spacers on the activity of tripartite structures carrying the prototype peptidic pharmacophore GL189.

Optimisation of BACE1 inhibition of tripartite structures by modification of membrane anchors, spacers and pharmacophores – development of potential agents for the treatment of Alzheimer’s disease
Philipp Linning, Ute Haussmann, Isaak Beyer, Sebastian Weidlich, Heinke Schieb, Jens Wiltfang, Hans-Wolfgang Klafki and Hans-Joachim Knölker

On the inside cover:
In this HOT perspective Helen E. Blackwell and colleagues at University of Wisconsin-Madison provide an overview of the use of chemical probes and techniques in quorum sensing research, highlighting throughout how the diversity of chemical techniques can complement biological approaches and ultimately lead to an improved understanding of bacterial quorum sensing.

Chemical methods to interrogate bacterial quorum sensing pathways
Thanit Praneenararat, Andrew G. Palmer and Helen E. Blackwell

As always both cover articles are free to access for the next 6 weeks.



Also in this issue of OBC is a HOT article that featured in Chemistry World recently:

Triterpenoids functionalized at C-2 as diagenetic transformation products of 2,3-dioxygenated triterpenoids from higher plants in buried wood
Gilles Schnell, Philippe Schaeffer, Estelle Motsch and Pierre Adam

For all this and much more, have a look at OBC issue 41 today.

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Biocatalysis: an article collection

A collection of high impact articles focusing on biocatalysis, from the RSC’s Catalysis Science & Technology, Green Chemistry, RSC Advances, Organic & Biomolecular Chemistry (OBC) and ChemComm

Beers, wines and cheeses are enjoyed around the world today and have been for millennia. In fact the practices of brewing and cheese-making pre-date recorded history so it is difficult to accurately determine when we first started using naturally occurring enzymes and microorganisms to create valuable (and in this case, tastier!) products.

Biocatalysts are of course used in far more diverse applications than the creation of food-stuffs, including in many organic syntheses and in the generation of fine chemicals. Due to their natural design, they can offer superior selectivity for particular products and have a far lower environmental impact than many traditional catalysts. Our knowledge and understanding of biocatalysts has increased dramatically in the last few decades, which has allowed us to develop biologically modified and biomimetic catalysts for a range of applications.

To keep you up to date with the latest advances in this rapidly expanding field we have collected together these high impact articles and made them free to access until the 31st October!

Click here for the full list of free articles

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OBC poster prize awarded at ICPOC-21

Congratulations to Michael J. Rawling, from the University of Strathclyde in Glasgow, who won the Organic & Biomolecular Chemistry poster prize at the 21st IUPAC  International Conference on Physical Organic Chemistry (ICPOC21 ) in Durham on 9th-13th September 2012.

His winning poster was entitled ‘Metal-Free Dihydroxylation of Alkenes’, presenting his work carried out in Prof. Nicholas Tomkinson‘s group.

Prof. Ian Williams presents Michael Rawling with his certificate. (Photo taken by Anne Horan)

Michael receives a one-year personal subscription to Organic & Biomolecular Chemistry, and a book of his choice from the RSC books catalogue. Thank you to Ian Williams, Professor of Theoretical Organic Chemistry at the University of Bath, for awarding the prize certificate.

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Molecular fossils: new compounds from 4900-year-old wood

Highlighting a HOT OBC article being featured in Chemistry World

If you dug up a wooden artefact, how could you tell what type of tree it came from? French chemists have identified unique molecules from an ancient piece of oak that could hold the key.

Pierre Adam and co-workers from the University of Strasbourg, France, used gas chromatography-mass spectrometry to identify triterpenoid molecules, which appear to be related to the natural product oleanane, in a 4900-year-old wood sample collected from river sediments. The discovered triterpenoids are unusual as they only have an oxygen-containing functional group at the C-2 position, while triterpenoids from living trees either have this at C-3 or both C-2 and C-3. This crucial difference could be due to chemical breakdown of the molecules by micro-organisms in the environment where the wood is buried.

The transformation is important, as the structure of the molecules identified today can be directly traced back to the natural molecules that existed in the living wood, so they can be linked.

Read the full article in Chemistry World

And read the OBC paper, highlighted as being HOT by the referees, for free here:
Triterpenoids functionalized at C-2 as diagenetic transformation products of 2,3-dioxygenated triterpenoids from higher plants in buried wood
Gilles Schnell, Philippe Schaeffer, Estelle Motsch and Pierre Adam
DOI: 10.1039/C2OB26191J

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OBC issue 40 now online!

An overview of this week’s issue of Organic & Biomolecular Chemistry

The cover of this week’s issue of OBC highlights the work of Florian Hollfelder and colleagues at University of Cambridge. This HOT paper from Hollfelder et al. presents kinetic and computational evidence that hydrolytic reactions of sulfonate esters proceed with a two-step mechanism involving a pentavalent intermediate for poorer leaving groups.

Kinetic and computational evidence for an intermediate in the hydrolysis of sulfonate esters
Ann C. Babtie, Marcelo F. Lima, Anthony J. Kirby and Florian Hollfelder
DOI: 10.1039/C2OB25699A

The inside cover features the work of Lechosław Latos-Grażyński and co-workers showing that a N-confused porphyrin undergoes controlled regionselective phosphorylations at the inner, outer or both carbon atoms of the inverted pyrrole ring.

Regioselective phosphorylation and thiophosphorylation of N-confused porphyrin: a route to hybrid carbaporphyrinoids
Norbert Grzegorzek, Lechosław Latos-Grażyński and Ludmiła Szterenberg
DOI: 10.1039/C2OB26019K

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

Also featuring in this issue are 2 more articles marked as being HOT be the referees:

Metal-free reactions of alkynes via electrophilic iodocarbocyclizations
Adeline Palisse and Stefan F. Kirsch
DOI: 10.1039/C2OB26508G

Highly enantioselective synthesis of Warfarin and its analogs catalysed by primary amine–phosphinamide bifunctional catalysts
Juan Dong and Da-Ming Du
DOI: 10.1039/C2OB26334C

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Top ten most accessed articles in July 2012

This month sees the following articles in Organic & Biomolecular Chemistry that are in the top ten most accessed:

Recent progress of core-substituted naphthalenediimides: highlights from 2010  
Sheshanath V. Bhosale, Sidhanath V. Bhosale and Suresh K. Bhargava  
Org. Biomol. Chem., 2012, 10, 6455-6468
DOI: 10.1039/C2OB25798J

A new N-imidazolyl-1,8-naphthalimide based fluorescence sensor for fluoride detection  
Junqi Wang, Lingyun Yang, Chen Hou and Haishi Cao  
Org. Biomol. Chem., 2012, 10, 6271-6274
DOI: 10.1039/C2OB25903F

Asymmetric organocatalytic diboration of alkenes  
Amadeu Bonet, Cristina Sole, Henrik Gulyás and Elena Fernández  
Org. Biomol. Chem., 2012, 10, 6621-6623
DOI: 10.1039/C2OB26079D

Transition metal-catalyzed fluorination of multi carbon–carbon bonds: new strategies for fluorinated heterocycles 
Guosheng Liu  
Org. Biomol. Chem., 2012, 10, 6243-6248
DOI: 10.1039/C2OB25702E

π-Fused bis-BODIPY as a candidate for NIR dyes  
Mitsunori Nakamura, Hiroyuki Tahara, Kohtaro Takahashi, Toshi Nagata, Hiroki Uoyama, Daiki Kuzuhara, Shigeki Mori, Tetsuo Okujima, Hiroko Yamada and Hidemitsu Uno  
Org. Biomol. Chem., 2012, 10, 6840-6849
DOI: 10.1039/C2OB25930C
 
Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and L-(−)-CCG-II  
Pradeep Kumar, Abhishek Dubey and Anand Harbindu  
Org. Biomol. Chem., 2012, 10, 6987-6994
DOI: 10.1039/C2OB25622C  
 
From biomass to medicines. A simple synthesis of indolo[3,2-c]quinolines, antimalarial alkaloid isocryptolepine, and its derivatives 
Maxim G. Uchuskin, Arkady S. Pilipenko, Olga V. Serdyuk, Igor V. Trushkov and Alexander V. Butin  
Org. Biomol. Chem., 2012, 10, 7262-7265
DOI: 10.1039/C2OB25836F  

Chiral phosphine-catalyzed asymmetric allylic alkylation of 3-substituted benzofuran-2(3H)-ones or oxindoles with Morita–Baylis–Hillman carbonates  
De Wang, Yuan-Liang Yang, Jia-Jun Jiang and Min Shi  
Org. Biomol. Chem., 2012, 10, 7158-7166
DOI: 10.1039/C2OB25694K  
 
Diverted organic synthesis (DOS): accessing a new, natural product inspired, neurotrophically active scaffold through an intramolecular Pauson–Khand reaction  
Goverdhan Mehta, Ramesh Samineni, Pabbaraja Srihari, R. Gajendra Reddy and Sumana Chakravarty  
Org. Biomol. Chem., 2012, 10, 6830-6833
DOI: 10.1039/C2OB26107C  
 
Asymmetric synthesis of (+)-vertine and (+)-lythrine 
Laëtitia Chausset-Boissarie, Roman Àrvai, Graham R. Cumming, Laure Guénée and E. Peter Kündig 
Org. Biomol. Chem., 2012, 10, 6473-6479
DOI: 10.1039/C2OB25880C  

Why not take a look at the articles today and blog your thoughts and comments below.

Fancy submitting an article to Organic & Biomolecular Chemistry? Then why not submit to us today or alternatively email us your suggestions.

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Highly enantioselective synthesis of Warfarin by primary amine–phosphinamide bifunctional catalysts

This paper is HOT as recommended by the referees, and is free to access for 4 weeks.

In this HOT article Juan Dong and Da-Ming Du, Beijing Institute of Technology, present a new organocatalytic enantioselective Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones.

The article features a new kind of bifunctional primary amine–phophinamide catalyst, which when applied to catalyze the Michael reaction of 4-hydroxycoumarin to α,β-unsaturated ketones lead to the synthesis of the important pharmaceutical product Warfarin.

Highly enantioselective synthesis of Warfarin and its analogs catalysed by primary amine–phosphinamide bifunctional catalysts

Juan Dong and Da-Ming Du
DOI: 10.1039/C2OB26334C

This article features as part of OBC‘s organocatalysis collection. If you liked this article why not have a look at the collection for other articles on organocatalysis….
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Metal-free reactions of alkynes via electrophilic iodocarbocyclizations

This review is HOT as recommended by the referees, and is free to access for 4 weeks.

Electrophilic cyclisations is an area of chemistry that is continually and rapidly growing and expanding. This Emerging area from Adeline Palisse and Stefan F. Kirsch, University of Wuppertal, highlights the recent progress in C–C bond-forming halocyclisations allowing the reaction of alkynes with carbon-nucleophiles.

Palisse and Kirsch focus on iodine electrophiles, and aim to show that these iodocyclisations with alkynes have become a very useful strategy to construct structures.  The review is roughly split into three major categories:
1)    malonates as nucleophilic
2)    arene nucleophiles
3)    olefins as nucleophiles

Read this Emerging Area today! Download it free by following the link below…

Metal-free reactions of alkynes via electrophilic iodocarbocyclizations
Adeline Palisse and Stefan F. Kirsch
DOI: 10.1039/C2OB26508G

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OBC issue 39 out now

An overview of this week’s issue of Organic & Biomolecular Chemistry

On the front cover of this issue of OBC Chun Liu and colleagues, at Dalian University of Technology, report a fast and efficient ligand-free protocol for the synthesis of N-heteroaryl substituted 9-arylcarbazolyl derivatives under aerobic and aqueous conditions using a palladium catalyst.

A highly efficient and aerobic protocol for the synthesis of N-heteroaryl substituted 9-arylcarbazolyl derivatives via a palladium-catalyzed ligand-free Suzuki reaction
Xiaofeng Rao, Chun Liu, Jieshan Qiu and Zilin Jin

The inside cover features the work of James D. White and co-workers, Oregon State University, describing the total synthesis of phorboxazole A, one of the most potent antitumor marine macrolide natural products with a challenging structure.

Total synthesis of the marine toxin phorboxazole A using palladium(II)-mediated intramolecular alkoxycarbonylation for tetrahydropyran synthesis
Punlop Kuntiyong, Tae Hee Lee, Christian L. Kranemann and James D. White

Also featuring in this issue are 4 Communications: 

Rationally-designed fluorescent lysine riboswitch probes
Pradeep Budhathoki, Lina F. Bernal-Perez, Onofrio Annunziata and Youngha Ryu

A novel copper-catalyzed reductive coupling of N-tosylhydrazones with H-phosphorus oxides

Lei Wu, Xiǎo Zhang, Qing-Qing Chen and An-Kun Zhou

Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes

Nandkishor Chandan, Amber L. Thompson and Mark G. Moloney

KI-catalyzed imidation of sp3 C–H bond adjacent to amide nitrogen atom

Zhi-Qi Lao, Wen-He Zhong, Qing-Hua Lou, Zhong-Jun Li and Xiang-Bao Meng

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Small molecule control of bacterial biofilms – a must read review by Christian Melander

This article is HOT as recommended by the referees, and is free to access for 4 weeks.

This HOT review from Christian Melander and colleagues at North Carolina State University presents a comprehensive overview of development of small molecules targeting bacterial biofilms through non-microbicidal mechanisms. Melander et al. discuss the varied approaches that are applied to the discovery of lead small molecules that mediate the development of biofilms. These are grouped as:

  • Compounds that modulate biofilms by targeting bacterial signalling pathways
  • Chemical library screening
  • Natural products and natural product analogues that possess anti-biofilm activity

This review is very timely and covers an important topic in addressing bacterial infections, as antibiotic resistance is an issue of ever increasing concern, and has been described as a must read.

Download it today by following the link below; it’s free to access for 4 weeks

Small molecule control of bacterial biofilms
Roberta J. Worthington, Justin J. Richards and Christian Melander
DOI: 10.1039/C2OB25835H

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