July 2012 – Organic & Biomolecular Chemistry Blog

Archive for July, 2012

Issue 32 now published: Lythracea alkaloids and core-substituted naphthalenediimides on the covers

26 Jul 2012

Issue 32 is now published, read it here today!

The front cover of this issue (right) highlights the work of E. Peter Kündig et al. who present the total syntheses of the Lythracea alkaloids (+)-vertine and (+)-lythrine, which is the first reported total synthesis of (+)-lythrine.

Asymmetric synthesis of (+)-vertine and (+)-lythrine
Laëtitia Chausset-Boissarie, Roman Àrvai, Graham R. Cumming, Laure Guénée and E. Peter Kündig
DOI: 10.1039/C2OB25880C

The inside cover (left) is courtesy of Sheshanath V. Bhosale et al. whose Emerging area review provides an update on the progress in the field of core-substituted naphthalenediimides from 2010, covering supramolecular chemistry, sensors, photo-induced electron transport in artificial photosystems, and solar cell applications.

Recent progress of core-substituted naphthalenediimides: highlights from 2010
Sheshanath V. Bhosale, Sidhanath V. Bhosale and Suresh K. Bhargava
DOI: 10.1039/C2OB25798J

Both of these articles will free to access for the next 6 weeks so take a look and let us know your thoughts by commenting below.

Missed our 10th anniversary themed issue for OBC? Well after reading this week’s issue have a look at the 68 articles that made up our 10th birthday issue here….

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Organic: A mechanism-based fluorescence transfer assay for examining ketosynthase selectivity

23 Jul 2012

US scientists have developed a cheap and simple way to examine the selectivity of the ketosynthase domain found in polyketide synthases.

Polyketide synthases are multicomponent enzyme systems that make polyketide natural products. They have received attention from researchers hoping to harness their potential as a platform for generating new and improved therapeutics. But the field of polyketide engineering has faced a constant struggle to overcome often strict substrate selectivities of the critical biosynthetic enzymes.

The new fluorescence-based method is much simpler and cheaper than previously used radiolabelling techniques and should enable improved understanding of how these biosynthetic machines function.

A Mechanism-Based Fluorescence Transfer Assay for Examining Ketosynthase Selectivity
Gitanjeli Prasad, Lawrence S. Borketey, Tsung-Yi Lin and Nathan A. Schanrr
Org. Biomol. Chem., 2012, Accepted Manuscript
DOI: 10.1039/C2OB26008E

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Issue 31 online now, complete with mutant lipases & cyclic di-oxoguanidines

18 Jul 2012

Organic & Biomolecular Chemistry issue 31, it’s here and waiting to be read!

Secondary alcohols having bulky substituents on both sides of the hydroxy group are inherently poor substrates for most lipases. In a paper by Tadashi Ema et al., highlighted on this week’s front cover of OBC (right), the detailed rational design and creation of mutant lipases that display remarkably enhanced catalytic activity and enantioselectivity for poor substrates bearing bulky substituents on both sides of the hydroxy group is presented.

Redesign of enzyme for improving catalytic activity and enantioselectivity toward poor substrates: manipulation of the transition state
Tadashi Ema, Yasuko Nakano, Daiki Yoshida, Shusuke Kamata and Takashi Sakai
DOI: 10.1039/C2OB25614B

The inside front cover (left) highlights the Communication of Wen-Xiong Zhang and Zhenfeng Xi et al., presenting the first metal-free one-pot sequential coupling of various amines, carbodiimides and acyl dichlorides, providing a simple and straightforward path to cyclic di-oxoguanidines via an unexpected 2,2-dichloroimidazolidindione intermediate.

Metal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides
Fei Zhao, Yang Wang, Wen-Xiong Zhang and Zhenfeng Xi
DOI: 10.1039/C2OB25799H

Both of these featured articles are FREE to access for the next 6 weeks, why not have a read and let us know your thoughts by commenting below.

Also in this issue:

Emerging Area
Transition metal-catalyzed fluorination of multi carbon–carbon bonds: new strategies for fluorinated heterocycles
Guosheng Liu
DOI: 10.1039/C2OB25702E

Perspective
Discovery, application and protein engineering of Baeyer–Villiger monooxygenases for organic synthesis
Kathleen Balke, Maria Kadow, Hendrik Mallin, Stefan Saß and Uwe T. Bornscheuer
DOI: 10.1039/C2OB25704A

View the complete issue online now……

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OBC 10th anniversary art gallery

17 Jul 2012

With the 10th anniversary themed issue of OBC now online we thought we would share with you a couple of the other cover suggestions that were put forward by authors for this issue.

Below is the rather striking suggestion from Brimble et al. The tree and leaves represent nature, and its dew, superimposed with their spiroacetal-triazoles, drops into a pool of tablets representing the development of new therapeutic agents.

Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds
Jui Thiang Brian Kueh, Ka Wai Choi and Margaret A. Brimble
DOI: 10.1039/C2OB06802H

This second suggestion comes from Luh et al., featuring a decameric ladderphane in recognition of the 10 years that OBC has been published.

Double stranded polymeric ladderphanes with 16-π-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

Now you’ve seen the art, why not see the science? View the entire issue, featuring 68 articles from the breadth of OBC‘s scope by leaders in the field!

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Organic & Biomolecular Chemistry 10th anniversary themed issue now online: 68 great articles!

12 Jul 2012

The 10th anniversary issue of OBC has arrived! This celebratory issue contains a massive 68 articles of great science from investigators at the forefront of current research. View the entire issue here….

This nice front cover is courtesy of Eric H. Fort and Lawrence T. Scott who report the high reactivity of dimesitylbisanthene toward bay region air oxidation, leading to a bay region quinine. Fort and Scott say that “this finding signals a warning about the potential oxygen-sensitivity of hydrogenterminated carbon nanotubes; a single oxidation of this sort on the cylindrical rim of a growing carbon nanotube would preclude further elongation of the tube by the Diels–Alder cycloaddition/rearomatization protocol and would thereby terminate the growth.”

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

Also geared towards celebrating our 10th anniversary is this inside cover from Naoki Komatsu et al., which highlights their paper reporting on the optical enrichment of single-walled carbon nanotubes (SWNTs) with (n,m) other than those so far reported, together with their simultaneous separation according to their diameters by preferential extraction of commercial SWNTs with 2,6-pyridylene-bridged chiral diporphyrin nanotweezers.

Preferential extraction of left- or right-handed single-walled carbon nanotubes by use of chiral diporphyrin nanotweezers
Gang Liu, Tatsuki Yasumitsu, Li Zhao, Xiaobin Peng, Feng Wang, Ajoy K. Bauri, Shuji Aonuma, Takahide Kimura and Naoki Komatsu

In an issue packed with work from some of the best researches around there was always going to be a lot of HOT articles included, too many to list here. So, for the complete list of the HOT articles from this issue please have a look at our recent blog highlighting them.

Finally, the entire Organic & Biomolecular Chemistry team we would like to thank all of our Associate Editors, Editorial and Advisory Board members, authors and referees, without whom none of this past decade would have been possible, and we hope to work with you all to make the next 10 years even more successful.

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HOT articles from 10th anniversary themed issue of Organic & Biomolecular Chemistry

10 Jul 2012

After much anticipation the themed issue marking the 10th anniversary of Organic & Biomolecular Chemistry will be published this week, and it’s a bumper issue full of work from many at the forefront of current research who have continued contribute to the success of OBC over the past decade.

Ahead of the issue’s publication we have prepared a FREE collection of all the HOT articles that can be found within its covers, and considering all the talent that has contributed it is quite a big collection. These will all be free to access until the end of July.

Click here for the full list

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Meet the team at BOSS XIII

09 Jul 2012

I will shortly be attending the 13th Belgian Organic Synthesis Symposium (BOSS XIII) in Leuven, 15-20 July, and if you too are in attendance, I’ d love to meet you there!

Please let us know if you will also be in attendance and would like to arrange a meeting – simply email us at the OBC editorial office.

Dr Marie Cote, Oganic & Biomolecular Chemistry Deputy Editor

OBC is delighted to be a media partner of the conference, and there’s a lot to look forward to again on this 13th edition of the symposium:

Prof. Ben Feringa (University of Groningen, The Netherlands) is the Tetrahedron Chair 2012 awardee, and will give lectures all throughout the opening day on ‘Exploring chiral space in asymmetric catalysis’.
Prof. Illan Marek (Technion – Israel Institute of Technology) is the recipient of the 2012 Janssen Pharmaceutica Prize for Creativity in Organic Synthesis

Plenary lectures at the symposium will be given by :

Prof. Matthias Beller (University of Rostock, Germany)
Prof. Dale L. Boger (The Scripps research institute, La Jolla, USA)
Prof. Jan-Erling Backvall (Stockholm University, Sweden)
Prof. Karl Gademann (University of Basel, Switzerland)
Prof. Frank Glorius (University of Muenster, Germany)
Prof. Veronique Gouverneur (University of Oxford, UK)
Prof. Shu Kobayashi (University of Tokyo, Japan)
Professor Michael Krishe (University of Texas, Austin, USA)
Dr Emmanuel Lacote (ICSN – CNRS, France)
Prof. Istvan Marko (UCL, Belgium)
Prof. Gary A. Molander (University of Pennsylvania, USA)
Prof. Klaus Mueller (F. Hoffmann-La Roche, Switzerland)
Prof. Tobias Ritter (Harvard University, USA)
Prof. Scott Snyder (Columbia University, USA)
Prof. Paul A. Wender (Stanford University, USA)
Prof. Ming Hua Xu (Shanghai Institute of Materia Medica, PR China)

I look forward to meeting you in Leuven!

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Organic: Natural products with anti-inflammatory, sedative, and antispasmodic activities synthesised

09 Jul 2012

Scientists in Switzerland have carried out the asymmetric synthesis of the 12-membered lactone alkaloids (+)-vertine and (+)-lythrine (structurally related and possessing a range of bioactivities), which has so far proved a challenge.

Peter Kundig and his group employed a range of strategies and novel tactics to overcome the synthetic challenge, and the strain in the two diastereomeric 12-membered lactone alkaloids was ultimately overcome via Z-selective alkene metathesis.

Asymmetric synthesis of (+)-vertine and (+)-lythrine
Peter Kundig, Laetitia Chausset-Boissarie, Roman Arvai, Graham Cumming and Laure Guénée
DOI: 10.1039/C2OB25880C

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OBC issue 29 online now: radicals, ladderane lipids and Porphyrin–DNA conjugates

05 Jul 2012

Storming the castle on the cover of this week’s issue of OBC is the communication from Dustin H. Nouri and Dean J. Tantillo (winner of the 2012 NPR Lectureship) that presents quantum chemical calculations of a possible decomposition process for ladderane lipids. Nouri and Tantillo propose that hydrogen atom abstraction next to the ladderane core can lead to the opening of the cyclobutane rings that make up the ladderane substructure, and protonation leads directly to fragmentation.

Attack of radicals and protons on ladderane lipids: quantum chemical calculations and biological implications
Dustin H. Nouri and Dean J. Tantillo
DOI: 10.1039/C2OB25717C

This interesting inside cover (left) highlights the work of Gevorg Sargsyan and Milan Balaz, who report the synthesis, self-assembly, stability, and spectroscopic studies of short alternating non-self-complementary DNA sequences 5′-(dGdA)4 and 5′-(dAdG)4 with non-charged tetraarylporphyrins covalently linked to the 5′ position of deoxyadenosine or deoxyguanosine via a phosphate or amide linker.

Porphyrin–DNA conjugates: porphyrin induced adenine–guanine homoduplex stabilization and interduplex assemblies
Gevorg Sargsyan and Milan Balaz
DOI: 10.1039/C2OB25710F

These cover articles are free to accesss for 6 weeks. Also in this issue is this HOT article, which is free to access for 4 weeks:

Locking high energy 1D chain of dichloromethane molecules containing abnormally short Cl⋯Cl contacts of 2.524 Å inside organic crystals
Feng Zhou, Haoliang Fu, Wei Qiang Ong, Ruijuan Ye, Weixing Yuan, Yu-Jing Lu, Yan-Ping Huo, Kun Zhang, Haibin Su and Huaqiang Zeng

Read the complete issue here….

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