OBC issue 36 online now!

Taking a sneak peek at some of the content in this week’s issue

It’s all getting a bit fruity on the cover of this week’s issue of OBC thanks to the work of Sungwoo Hong and co-workers from Korea Advanced Institute of Science and Technology. Hong et al. present the impressive catalytic effects of Fe(OTf)3 in the Pd(II)-catalyzed conjugate addition of arylboronic acids to chromones to give a variety of flavanones, which exclusively yield flavone analogs when of catalytic amounts of DDQ and KNO2 are added.

Synthetic approach to flavanones and flavones via ligand-free palladium(II)-catalyzed conjugate addition of arylboronic acids to chromones
Donghee Kim, Kyungrok Ham and Sungwoo Hong

The inside cover highlights the work of Alexander V. Butin and colleagues, who have developed a simple method for the transformation of furfural, a large-scale product from the processing of agricultural and forestry wastes, into the  potent pharmacologically active compounds indolo[3,2-c]quinolines and isocryptolepines.

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

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

Also of interest in this issue is the review:

Organic fluorine as a polypeptide building element: in vivo expression of fluorinated peptides, proteins and proteomes

from L. Merkel and N. Budisa who present the most recent advances in the field of protein biosynthesis using fluorinated amino acids.

Read the entire issue HERE today!

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Trojan horse tuberculosis treatment

A Chemistry World story on the OBC paper ‘Syntheses of mycobactin analogs as potent and selective inhibitors of Mycobacterium tuberculosis’

During the Trojan war, Greeks built a huge wooden horse, hid men inside it and left it outside the city of Troy. The Trojans, claiming it as a victory trophy, brought it into their city. That night, the Greek force crept out of the horse, opened the gates for the rest of the Greek army and they destroyed the city of Troy

The emergence of drug resistant bacterial strains has led to an urgent need for new antibiotic agents. Scientists in the US are utilising the iron uptake pathway of Mycobacterium tuberculosis as a ‘Trojan horse’ approach to tuberculosis treatment.

Marvin Miller at the University of Notre Dame and colleagues have synthesised analogues of iron scavenging compounds that contain a maleimide functional group for future drug conjugation. Miller explains that these compounds will be actively assimilated by the M. tuberculosis pathogen by the active iron transport system, but can also carry a lethal agent into the pathogen.

One of the challenges of synthesising drug conjugates is finding a suitable functional group to attach the drug to the conjugate. The maleimide functionalised mycobactin analogue synthesised by the team simplifies the synthetic route by reducing the need for protecting groups. Thiol-maleimide chemistry can then be used to attach the drug.

Derek Tan, an expert in rational drug design at the Memorial Sloan–Kettering Cancer Center, US, is enthusiastic about the work. He believes that the advantage of the maleimide functional group is that it can react with nucleophiles, which may already be present in a potential conjugate drug, as opposed to electrophiles, which generally need to be synthetically introduced into the conjugate drug. This maleimide–mycobactin analogue ‘will enable the future synthesis of a wider array of potential Trojan horse antibiotics’, says Tan.

Miller and co-workers found that the maleimide–mycobactin analogue displayed antibiotic activity against Mycobacterium tuberculosis, but it was inactive against a broad panel of Gram-positive and Gram-negative bacteria. ‘The use of siderophores [iron chelating compounds] to deliver antibiotics exclusively into a single type of bacteria (e.g., Mtb, P. aeruginosa, E. coli), could reduce the administration of broad-spectrum antibiotics, minimising exposure and therefore the development of drug resistance’ says Miller.

In the future, the team intends to use a rational approach for selecting drugs to attach to the maleimide–mycobactin analogue, starting with drugs that inhibit essential survival processes.

References
1. R E Juárez-Hernández, S G Franzblau and M J Miller, Org. Biomol. Chem., 2012, DOI: 10.1039/c2ob26077h

2. Chemistry World story by Alisa Becker

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Caffeine test to tell if decaf coffee really is decaffeinated

Graphical abstractScientists in Switzerland have synthesised a dye (3,4:3’,4’-bibenzo[b]thiophene-2,2’-disulfonate) that can be used as a sensitive and selective molecular probe for the fluorimetric detection of caffeine in water.

The system’s sensitivity and selectivity are higher than those of current synthetic caffeine sensors, so much so that caffeine can be detected in the sub-millimolar concentration range, the researchers claim. The team prepared sensor test strips on which a change in emission colour on addition of caffeine was easy to detect by the naked eye.

A ratiometric fluorescence sensor for caffeine
Nicolas Luisier, Albert Ruggi, Stephan N. Steinmann, Laurane Favre, Nicolas Gaeng, Clémence Corminboeuf and Kay Severin
DOI: 10.1039/C2OB26117K

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OBC issue 35 online now, read it today!

Issue 35 of Organic & Biomolecular Chemistry is now available online for you to access today!

On the front cover this weeks is the work of Chi-Ming Che and colleagues from The University of Hong Kong, who present a gold(I)/chiral Brønsted acid cooperative catalytic system for the efficient one-pot asymmetric synthesis of tetrahydroquinolines, with one or two chiral centres at different positions as well as highly divergent functional groups, from reaction of 2-aminobenzaldehydes or 2-aminophenones with alkynes.

Highly regio-, diastereo- and enantioselective one-pot gold/chiral Brønsted acid-catalysed cascade synthesis of bioactive diversely substituted tetrahydroquinolines
Xin-Yuan Liu, Ya-Ping Xiao, Fung-Ming Siu, Li-Chen Ni, Yong Chen, Lin Wang and Chi-Ming Che
DOI: 10.1039/C2OB25753J

The inside cover highlights the work of Prasat Kittakoop et al. on the isolation, characterization, and biological activities of a novel tricyclic polyketide, 2 of its biosynthetic congeners as well as austdiol, a known azaphilone, from the endophytic fungus Dothideomycete sp., which was isolated from the Thai medicinal plant, Tiliacora triandra.

A novel tricyclic polyketide and its biosynthetic precursor azaphilone derivatives from the endophytic fungus Dothideomycete sp
Sarath P. D. Senadeera, Suthep Wiyakrutta, Chulabhorn Mahidol, Somsak Ruchirawat and Prasat Kittakoop
DOI: 10.1039/C2OB25959A

Read this issue, and previous issues, today!

Do you have an image you think would look good on a cover? Why not let us know when you submit your work to us.

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OBC issue 34 now online

Forget the pot of gold at the end of the rainbow, this week it’s all about getting you hands on issue 34 of Organic & Biomolecular Chemistry and its technicoloured covers.

On the front cover Hidemitsu Uno, Ehime University, and colleagues have prepared potential selective near-infrared (NIR) dyes by the fusion of boron-dipyrromethene (BODIPY) chromophores. Uno et al. designed these π-fused bis-BODIPY chromophores to show intensive absorption and strong fluorescence in the near-infrared region and not to have any strong absorption in the visible region.

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

The inside cover from Xin-Dong Jiang, Henan University, and co-workers demonstrates the synthesis of a novel BODIPY from a 3,4,4a-trihydroxanthene-fused pyrrole, that is non-cytotoxic and so is suited to the labeling of living cells in the NIR region.

A NIR BODIPY dye bearing 3,4,4a-trihydroxanthene moieties
Xin-Dong Jiang, Ruina Gao, Yi Yue, Guo-Tao Sun and Weili Zhao

Also in this issue is a review by Liqun Jin and Aiwen Lei which presents insights into the elementary steps in Negishi coupling through kinetic investigations.

Read the complete issue here…. and as always the cover articles will be free to access for the next 6 weeks!

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OBC issue 33 now online: a tool for RNA conjugation and iodine cyclisations on the covers

Crack open this week’s issue over your coffee break and have a read…

On the front cover:

Strap yourself in with this week’s front cover highlighting the work of Ishwar Singh and co-workers who have developed a fast, strain promoted cycloaddition as a tool for RNA conjugation on the solid phase exploiting the cycloaddition of a series of RNA-cyclooctynes with both azide (strain-promoted azide–alkyne cycloaddition) and nitrile oxide dipoles (strain-promoted nitrile oxide–alkyne cycloaddition). Singh et al. say that the reaction is compatible with 2’-OMe blocking as well as with 2’-O-TBDMS protection on the ribose moieties of the sugar.

Fast RNA conjugations on solid phase by strain-promoted cycloadditions
Ishwar Singh, Colin Freeman, Annemieke Madder, Joseph S. Vyle and Frances Heaney
DOI: 10.1039/C2OB25628B

On the inside front cover:

Ming-Jung Wu and colleagues, National Sun Yat-sen University, have developed an efficient synthetic method to convert enynylpyrazoles to pyrazolo[1,5-a]pyridines and 6-iodopyrazolo[1,5-a]pyridines by gold-catalyzed cyclisation and iodinemediated cyclisation reactions, respectively. Wu et al. go on to demonstrate the synthetic utility of this by preparing a p38 kinase inhibitor.

Au(I)-catalyzed and iodine-mediated cyclization of enynylpyrazoles to provide pyrazolo[1,5-a]pyridines
Hung-Chou Wu, Chia-Wen Yang, Long-Chih Hwang and Ming-Jung Wu
DOI: 10.1039/C2OB25973G

Read both these articles for free for 6 weeks!

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

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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Top ten most accessed articles in June

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

Efficient iodine catalyzed three components domino reaction for the synthesis of 1-((phenylthio)(phenyl)methyl)pyrrolidin-2-one derivatives possessing anticancer activities
Gunasekar Ramachandran, Natesan S. Karthikeyan, Periyasamy Giridharan and Kulathu I. Sathiyanarayanan
Org. Biomol. Chem., 2012, 10, 5343-5346
DOI: 10.1039/C2OB25530H

A BODIPY-based colorimetric and fluorometric chemosensor for Hg(II) ions and its application to living cell imaging
Mani Vedamalai and Shu-Pao Wu
Org. Biomol. Chem., 2012, 10, 5410-5416
DOI: 10.1039/C2OB25589H

Copper-catalyzed domino coupling reaction: an efficient method to synthesize oxindoles
Jen-Chieh Hsieh, An-Yi Cheng, Jun-Hao Fu and Ting-Wei Kang
Org. Biomol. Chem., 2012, 10, 6404-6409
DOI: 10.1039/C2OB26110C

Asymmetric formal synthesis of schulzeines A and C
Jaebong Jang, Jong-Wha Jung, Jaeseung Ahn, Jaehoon Sim, Dong-Jo Chang, Dae-Duk Kim and Young-Ger Suh
Org. Biomol. Chem., 2012, 10, 5202-5204
DOI: 10.1039/C2OB25772F

Chiral quaternary phosphonium salts: a new class of organocatalysts
Dieter Enders and Thanh Vinh Nguyen
Org. Biomol. Chem., 2012, 10, 5327-5331
DOI: 10.1039/C2OB25823D

Total synthesis of indole-3-acetonitrile-4-methoxy-2-C-β-D-glucopyranoside. Proposal for structural revision of the natural product
Akop Yepremyan and Thomas G. Minehan
Org. Biomol. Chem., 2012, 10, 5194-5196
DOI: 10.1039/C2OB25821H

Enantioselective synthesis of 3,3′-dihydropyrryl-spirooxindoles via an organocatalytic three-component reaction
Wen-Tao Wei, Chun-Xia Chen, Rui-Jiong Lu, Jin-Jia Wang, Xue-Jing Zhang and Ming Yan
Org. Biomol. Chem., 2012, 10, 5245-5252
DOI: 10.1039/C2OB25629K

A convergent stereocontrolled total synthesis of (–)-terpestacin
Yehua Jin and Fayang G. Qiu
Org. Biomol. Chem., 2012, 10, 5452-5455
DOI: 10.1039/C2OB25940K

A cyanine based fluorophore emitting both single photon near-infrared fluorescence and two-photon deep red fluorescence in aqueous solution
Lu Wang, Jiefu Jin, Xishan Chen, Hai-Hua Fan, Billy King Fai Li, Kok-Wai Cheah, Ning Ding, Shenghong Ju, Wing-Tak Wong and Cong Li
Org. Biomol. Chem., 2012, 10, 5366-5370
DOI: 10.1039/C2OB25619C

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

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

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

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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