A molecular library of antibiotics inspired by marine natural products

There is a need to develop new antibiotics to combat the emergence of antibiotic resistant bacterial pathogens. In bacteria, polyamine analogues can compete with natural polyamines to affect key cellular processes. Taking inspiration from the antibacterial properties of bromotyrosine-derived alkaloids isolated from the marine sponge (Subarea ianthelliformis), a recent paper reports the synthesis and antibacterial activity of a library of 39 new ianthelliformisamine analogues.

The library was synthesised by combining 3-phenylacrylic acid derivatives with Boc-protected polyamines. The antibacterial activities of the library compounds were tested in vitro using standard techniques. Some synthetic ianthelliformisamine analogues were more potent against gram positive and gram negative bacteria than their parent natural products.

To find out more read:

Syntheses of a library of molecules on marine natural product ianthelliformisamines platform and their biological evaluations
Faiz Ahmed Khan, Saeed Ahmad, Naveena Kodipelli, Gururaj Shivange and Roy Anindya
DOI: 10.1039/C3OB42537A, Paper;

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Q4 Top Ten most accessed Organic & Biomolecular Chemistry articles

During October, November and December, the following articles were the Top Ten most accessed:

A coumarin-based fluorescent probe for biological thiols and its application for living cell imaging
Lingliang Long, Liping Zhou, Lin Wang, Suci Meng, Aihua Gong, Fengyi Du and Chi Zhang
Org. Biomol. Chem., 2013,11, 8214-8220
DOI: 10.1039/c3ob41741g; Download PDF

Bifunctional primary amine-thioureas in asymmetric organocatalysis
Olga V. Serdyuk, Christina M. Heckel and Svetlana B. Tsogoeva
Org. Biomol. Chem., 2013,11, 7051-7071
DOI: 10.1039/c3ob41403e; Download PDF

To be or not to be metal-free: trends and advances in coupling chemistries
Rick Arneil D. Arancon, Carol Sze Ki Lin, Carolina Vargas and Rafael Luque
Org. Biomol. Chem., 2014,12, 10-35
DOI: 10.1039/c3ob41768a; Download PDF

Synthetic applications of arylboronic acid via an aryl radical transfer pathway
Guobing Yan, Minghua Yang and Xiangmei Wu
Org. Biomol. Chem., 2013,11, 7999-8008
DOI: 10.1039/c3ob41851k; Download PDF

Synthetic applications of photoredox catalysis with visible light
Yumeng Xi, Hong Yi and Aiwen Lei
Org. Biomol. Chem., 2013,11, 2387-2403
DOI: 10.1039/c3ob40137e; Download PDF

Analysis of the reactions used for the preparation of drug candidate molecules
John S. Carey, David Laffan, Colin Thomson and Mike T. Williams
Org. Biomol. Chem., 2006,4, 2337-2347
DOI: 10.1039/b602413k; Download PDF

N-heterocyclic carbene-catalyzed reactions of C–C unsaturated bonds
Xiang-Yu Chen and Song Ye
Org. Biomol. Chem., 2013,11, 7991-7998
DOI: 10.1039/c3ob41469h; Download PDF

Copper-catalyzed redox-neutral C–H amination with amidoximes
Hui Chen and Shunsuke Chiba
Org. Biomol. Chem., 2014,12, 42-46
DOI: 10.1039/c3ob41871e; Download PDF

Recent trends in Pd-catalyzed remote functionalization of carbonyl compounds
Ivan Franzoni and Clément Mazet
Org. Biomol. Chem., 2014,12, 233-241
DOI: 10.1039/c3ob42050g; Download PDF

Maximising multivalency effects in protein–carbohydrate interactions
Roland J. Pieters
Org. Biomol. Chem., 2009,7, 2013-2025
DOI: 10.1039/b901828j; Download PDF

If you have any thoughts or comments on any of these articles, please post them in the comment box below!

Do you have an article that you would like to submit to OBC? Why not submit to us here today?

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT Organic & Biomolecular Chemistry articles for March – updated throughout the month

A computational and experimental study of O-glycosylation. Catalysis by human UDP-GalNAc polypeptide:GalNAc transferase-T2
Hansel Gómez, Raúl Rojas, Divya Patel, Lawrence A. Tabak, José M. Lluch and Laura Masgrau
Org. Biomol. Chem., 2014, Advance Article, DOI: 10.1039/C3OB42569J

A computational and experimental study of O-glycosylation. Catalysis by human UDP-GalNAc polypeptide:GalNAc transferase-T2

Free to access until 25th April


Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation
Catarina Carvalho, David Siegel, Martyn Inman, Rui Xiong, David Ross and Christopher J. Moody
Org. Biomol. Chem., 2014, Advance Article, DOI: 10.1039/C3OB42258E

Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation

Free to access until 25th April


Diastereoselective Ireland–Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins
Stephen G. Davies, Ai M. Fletcher, James A. Lee, Paul M. Roberts, Myriam Y. Souleymanou, James E. Thomson and Charlotte M. Zammit  
Org. Biomol. Chem., 2014, Advance Article, DOI: 10.1039/C4OB00274A

Diastereoselective Ireland–Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins

Free to access until 25th April


Biomimetic total synthesis of (±)-yezo’otogirin A
Hiu C. Lam, Kevin K. W. Kuan and Jonathan H. George  
Org. Biomol. Chem., 2014,12, 2519-2522, DOI: 10.1039/C4OB00186A

Biomimetic total synthesis of (±)-yezo'otogirin A

Free to access until 25th April


Anti-cooperative ligand binding and dimerisation in the glycopeptide antibiotic dalbavancin
Mu Cheng, Zyta M. Ziora, Karl A. Hansford, Mark A. Blaskovich, Mark S. Butler and Matthew A. Cooper  
Org. Biomol. Chem., 2014,12, 2568-2575, DOI: 10.1039/C3OB42428F

Anti-cooperative ligand binding and dimerisation in the glycopeptide antibiotic dalbavancin

Free to access until 25th April


Fructose controlled ionophoric activity of a cholate–boronic acid
James R. D. Brown, Inmaculada C. Pintre and Simon J. Webb  
Org. Biomol. Chem., 2014,12, 2576-2583, DOI: 10.1039/C4OB00165F

Fructose controlled ionophoric activity of a cholate–boronic acid

Free to access until 25th April


Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases
B. P. Rempel and S. G. Withers  
Org. Biomol. Chem., 2014,12, 2592-2595, DOI: 10.1039/C4OB00235K

Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases

Free to access until 25th April


Acyclic CB[n]-type molecular containers: effect of solubilizing group on their function as solubilizing excipients
Ben Zhang, Peter Y. Zavalij and Lyle Isaacs
Org. Biomol. Chem., DOI: 10.1039/C3OB42603C, Paper
Free to access until 21st April


Out-Basicity of 1,8-bis(dimethylamino)naphthalene: the experimental and theoretical challenge
Valery A. Ozeryanskii, Alexander F. Pozharskii, Alexander S. Antonov and Alexander Filarowski
Org. Biomol. Chem., DOI: 10.1039/C3OB41986J, Paper
Free to access until 21st April


Carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins: highly enantioselective and chemoselective access to a chiral benzylmethyl center
Shuang Yang, Shou-Fei Zhu, Na Guo, Song Song and Qi-Lin Zhou
Org. Biomol. Chem., DOI: 10.1039/C4OB00018H, Communication
Free to access until 5th April


Making Fe(BPBP)-catalyzed C–H and C=C oxidations more affordable
Vital A. Yazerski, Peter Spannring, David Gatineau, Charlotte H. M. Woerde, Sara M. Wieclawska, Martin Lutz, Henk Kleijn and Robertus J. M. Klein Gebbink
Org. Biomol. Chem., DOI: 10.1039/C3OB42249F, Paper
Free to access until 5th April


Chromane helicity rule – scope and challenges based on an ECD study of various trolox derivatives
Marcin Górecki, Agata Suszczyńska, Magdalena Woźnica, Aneta Baj, Michał Wolniak, Michał K. Cyrański, Stanisław Witkowski and Jadwiga Frelek
Org. Biomol. Chem., DOI: 10.1039/C3OB42376J, Paper
Free to access until 5th April


Reaction pathways and free energy profiles for cholinesterase-catalyzed hydrolysis of 6-monoacetylmorphine
Yan Qiao, Keli Han and Chang-Guo Zhan
Org. Biomol. Chem., DOI: 10.1039/C3OB42464B, Paper
Free to access until 10th April

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Chemistry in Water

We are delighted to share with you the second of a series of collections of recent themed issues and articles on the topic of water. Here we have assembled some of the ground-breaking research and transformative reviews related to the chemistry in water – highlighting the importance and versatility of water as a medium in chemistry – from across our journals. Read all these articles for free until 21 April 2014!

We are delighted to share with you a series of collections of recent books, themed issues and articles on the topic of water. These four collections – one per month – demonstrate different aspects of water: its chemistry, its wide use in reactions and as a solvent, its relationship with energy and sustainability, as well as with human health and the environment. 

Image (c) Shutterstock

Here, in our second collection, we have assembled some of the ground-breaking research and transformative reviews related to the chemistry in water – highlighting the importance and versatility of water as a medium in chemistry – from across our journals. 

Professor Rafael Luque, winner of the RSC 2013 Environment, Sustainability and Energy Division Early Career Award, welcomes this timely and topical collection. “For a more sustainable future, we need to develop benign chemical protocols,” he notes. “Conducting chemical processes in water is a significant step towards this goal. This high profile collection includes articles from leading scientists in the field with varying topics – from materials synthesis to organocatalysis, synthetic organic chemistry and heterogeneous catalysis – that we hope can provide a starting point for young researchers, as well as key references to stimulate further research in the field.” 

“This year, as the IPCC prepares to release the final contributions to their Fifth Assessment Report on climate change, it is timely to consider the role of chemistry in addressing global challenges, such as food, water, raw materials and energy,” remarks Professor Lesley Yellowlees, President of the Royal Society of Chemistry. “This collection from our journals shares the latest research from scientists around the world, aiming to tackle these challenges. Featuring original research and commentary by leaders in the field, we hope that you will find this high-quality collection engaging, inspirational and informative.” 

You can read all of these articles for free until 21 April 2014! We truly hope you enjoy this collection. 

We have already published an article collection on the chemistry of water.  In the next couple of months, we will be publishing collections on water in energy, health and the environment. 

Did you know that the RSC has put together a webpage on Water, which brings together information on activities for scientists, policymakers, educators and young people? Take a look today… 


Reviews and Perspectives 

In water, on water, and by water: mimicking nature’s aldolases with organocatalysis and water
Nobuyuki Mase and Carlos F. Barbas, III
Org. Biomol. Chem., 2010,8, 4043-4050GA?id=C3CS60025D
DOI: 10.1039/C004970K, Perspective 

Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis
Manoj B. Gawande, Vasco D. B. Bonifácio, Rafael Luque, Paula S. Branco and Rajender S. Varma
Chem. Soc. Rev., 2013,42, 5522-5551
DOI: 10.1039/C3CS60025D, Review Article

Olefin metathesis in aqueous media
Jasmine Tomasek and Jürgen Schatz
Green. Chem., 2013,15, 2317-2338
DOI: 10.1039/C3GC41042K, Critical Review 

Green chemistry oriented organic synthesis in water
Marc-Olivier Simon and Chao-Jun Li
Chem. Soc. Rev., 2012,41, 1415-1427
DOI: 10.1039/C1CS15222J, Tutorial Review
From themed collection Green Chemistry 

sp2 C–H bond activation in water and catalytic cross-coupling reactions
Bin Li and Pierre H. Dixneuf
Chem. Soc. Rev., 2013,42, 5744-5767 GA?id=C0SM01072C
DOI: 10.1039/C3CS60020C, Review Article 

Stimulus responsive core-shell nanoparticles: synthesis and applications of polymer based aqueous systems
Olivier J. Cayre, Nelly Chagneux and Simon Biggs
Soft Matter, 2011,7, 2211-2234
DOI: 10.1039/C0SM01072C, Review Article 

Alkynes as an eco-compatible “on-call” functionality orthogonal to biological conditions in water
Nick Uhlig and Chao-Jun Li
Chem. Sci., 2011,2, 1241-1249
DOI: 10.1039/C1SC00164G, Minireview GA?id=C1SC00164G 

Anion binding in water at lanthanide centres: from structure and selectivity to signalling and sensing
Stephen J. Butler and David Parker
Chem. Soc. Rev., 2013,42, 1652-1666
DOI: 10.1039/C2CS35144G, Tutorial Review
From themed collection Alfred Werner Nobel Prize 100 year celebration 

Prebiotic chemistry in eutectic solutions at the water–ice matrix
César Menor-Salván and Margarita R. Marín-Yaseli
Chem. Soc. Rev., 2012,41, 5404-5415
DOI: 10.1039/C2CS35060B, Tutorial Review
From themed collection Prebiotic Chemistry


Original research articles 

An in-water, on-water domino process for synthesis
Philip Norcott, Calan Spielman and Christopher S. P. McErlean
Green. Chem., 2012,14, 605-609
DOI: 10.1039/C2GC16259H, Communication 

Highly efficient iron(0) nanoparticle-catalyzed hydrogenation in water in flow
Reuben Hudson, Go Hamasaka, Takao Osako, Yoichi M. A. Yamada, Chao-Jun Li, Yasuhiro Uozumi and Audrey Moores
Green. Chem., 2013,15, 2141-2148
DOI: 10.1039/C3GC40789F, Paper 

Water as an additive to enhance the ring opening of naphthalene
Qian Wang, Honglei Fan, Suxiang Wu, Zhaofu Zhang, Peng Zhang and Buxing Han
Green. Chem., 2012,14, 1152-1158 GA?id=C1OB05735A
DOI: 10.1039/C2GC16554F, Paper 

Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon
Francisco Alonso, Yanina Moglie, Gabriel Radivoy and Miguel Yus
Org. Biomol. Chem., 2011,9, 6385-6395
DOI: 10.1039/C1OB05735A, Paper 

An organocatalytic highly efficient approach to the direct synthesis of substituted carbazoles in water
Pradeep Kumar Jaiswal, Soumen Biswas, Shivendra Singh and Sampak Samanta
Org. Biomol. Chem., 2013,11, 8410-8418
DOI: 10.1039/C3OB42034E, Paper 

GA?id=C1GC15726D 

Near-critical water, a cleaner solvent for the synthesis of a metal–organic framework
Ilich A. Ibarra, Peter A. Bayliss, Eduardo Pérez, Sihai Yang, Alexander J. Blake, Harriott Nowell, David R. Allan, Martyn Poliakoff and Martin Schröder Green Chem., 2012,14, 117-122
DOI: 10.1039/C1GC15726D, Paper 

Stille couplings in water at room temperature
Guo-ping Lu, Chun Cai and Bruce H. Lipshutz
Green Chem., 2013,15, 105-109
DOI: 10.1039/C2GC36042J, Paper 

DNA-based asymmetric organometallic catalysis in water
Jens Oelerich and Gerard Roelfes
Chem. Sci., 2013,4, 2013-2017
DOI: 10.1039/C3SC00100H, Edge Article 

Pyridinium-based tripodal chemosensor in visual sensing of AMP in water by indicator displacement assay (IDA)
Kumaresh Ghosh, Sk Sarfaraj Ali, Avik Ranjan Sarkar, Asmita Samadder, Anisur Rahman Khuda-Bukhsh, Ioannis D. Petsalakis and Giannoula Theodorakopoulos
Org. Biomol. Chem. , 2013, 11, 5666-5672
DOI: 10.1039/C3OB40833G, Paper 

GA?id=C2GC16240G 

Design, synthesis, and solution behaviour of small polyamines as switchable water additives
Sean M. Mercer, Tobias Robert, Daniel V. Dixon, Chien-Shun Chen, Zahra Ghoshouni, Jitendra R. Harjani, Soran Jahangiri, Gilles H. Peslherbe and Philip G. Jessop
Green Chem. , 2012,14, 832-839
DOI: 10.1039/C2GC16240G, Paper 

In situ generation of bioreducible and acid labile nanogels/microgels simply via adding water into the polymerization system
Zhong-Kai Wang, Long-Hai Wang, Jiao-Tong Sun, Li-Fen Han and Chun-Yan Hong
Polym. Chem., 2013, 4, 1694-1699
DOI: 10.1039/C2PY21058D, Paper 

Template-directed synthesis of multi-component organic cages in water
Artur R. Stefankiewicz, Mark R. Sambrook and Jeremy K. M. Sanders
Chem. Sci., 2012,3, 2326-2329
DOI: 10.1039/C2SC20347B, Edge Article 

Tuning the catalytic activity of L-proline functionalized hydrophobic nanogel particles in water
Annhelen Lu, Dafni Moatsou, Deborah A. Longbottom and Rachel K. O’Reilly
Chem. Sci., 2013,4, 965-969
DOI: 10.1039/C2SC21300A, Edge Article 

GA?id=C3SC51547H 

Gold nanoparticles stabilized by an amphiphilic pillar[5]arene: preparation, self-assembly into composite microtubes in water and application in green catalysis
Yong Yao, Min Xue, Zibin Zhang, Mingming Zhang, Yong Wang and Feihe Huang
Chem. Sci., 2013,4, 3667-3672
DOI: 10.1039/C3SC51547H, Edge Article 

Water-controlled synthesis and single-crystal structural transformations of a cyanide-bridged W(IV)–Ni(II) molecular wheel complex and 3D networks
Dao-Peng Zhang, Li-Fang Zhang, Guo-Ling Li and Zhong-Hai Ni
Chem. Comm., 2013,49, 9582-9584
DOI: 10.1039/C3CC46063K, Communication 

Oxidation of water by a nonhaem diiron(IV) complex via proton-coupled electron transfer
Dong Wang and Lawrence Que
Chem. Comm., 2013,49, 10682-10684
DOI: 10.1039/C3CC46391E, Communication
From themed collection Biological oxidation reactions: mechanisms and design of new catalysts 

Enantioselective Friedel–Crafts reactions in water catalyzed by a human telomeric G-quadruplex DNA metalloenzyme
Changhao Wang, Yinghao Li, Guoqing Jia, Yan Liu, Shengmei Lu and Can Li
Chem. Comm., 2012,48, 6232-6234
DOI: 10.1039/C2CC31320K, Communication 

Enhanced imine synthesis in water: from surfactant-mediated catalysis to host–guest mechanisms
Kamel Meguellati, Ali Fallah-Araghi, Jean-Christophe Baret, Abdeslam El Harrak, Thomas Mangeat, Carlos M. Marques, Andrew D. Griffiths and Sylvain Ladame
Chem. Comm., 2013,49, 11332-11334
DOI: 10.1039/C3CC46461J, Communication
Open Access 

A method for increasing permeability in O2/N2 separation with mixed-matrix membranes made of water-stable MIL-101 and polysulfone
Harold B. Tanh Jeazet, Claudia Staudt and Christoph Janiak
Chem. Comm., 2012,48, 2140-2142
DOI: 10.1039/C2CC16628C, Communication 

Cu(OTf)2-catalysed Ritter reaction: efficient synthesis of amides from nitriles and halohydrocarbons in water
Gui-Rong Qu, Yan-Wei Song, Hong-Ying Niu, Hai-Ming Guo and John S. Fossey
RSC Adv., 2012,2, 6161-6163
DOI: 10.1039/C2RA20941A, Communication 

GA?id=C3RA40833G 

Recyclable NaHSO4 catalyzed alkylation of tert-enamides with indoles or amines in water: facile construction of pharmaceutically analogous bis-alkaloid scaffolds
Xue-Qiang Chu, Shun-Yi Wang and Shun-Jun Ji
RSC Adv., 2013,3, 8380-8387
DOI: 10.1039/C3RA40833G, Paper 

Efficient microwave-assisted preparation of squaric acid monoamides in water
Carlos López, Manuel Vega, Elena Sanna, Carmen Rotger and Antoni Costa
RSC Adv., 2013,3, 7249-7253
DOI: 10.1039/C3RA41369A, Communication 

CuI/TBAB as a novel efficient catalytic system for Heck reaction in water
Yufang Wang, Qichao Yang, Li Yang, Jianxin Shi and Mingjie Zhang
RSC Adv., 2013,3, 21251-21255
DOI: 10.1039/C3RA44819C, Communication 

Highly efficient visible-light-induced photocatalytic hydrogenation of nitrobenzene to aniline in water
Weiming Wu, Rui Lin, Lijuan Shen, Ruowen Liang, Rusheng Yuan and Ling Wu
RSC Adv., 2013,3, 10894-10899
DOI: 10.1039/C3RA40935J, Paper 

Ruthenium catalysed one-pot synthesis of S-allyl and cinnamyl dithiocarbamates using allyl and cinnamyl acetates in water
Sabir Ahammed, Amit Saha and Brindaban C. Ranu
RSC Adv., 2012,3, 6329-6335
DOI: 10.1039/C2RA20856C, Paper 

GA?id=C3SC52357H 

Water-soluble multi-cage super tetrahedral uranyl peroxide phosphate clusters
Jie Qiu, Jie Ling, Laurent Jouffret, Rebecca Thomas, Jennifer E. S. Szymanowski and Peter C. Burns
RSC Adv., 2014,5, 303-310
DOI: 10.1039/C3SC52357H, Edge Article 

Mechanistic changes observed in heavy water for nitrate reduction reaction on palladium-modified Pt(hkl) electrodes
J. Souza-Garcia, E. A. Ticianelli, V. Climent and J. M. Feliu
Chem. Sci., 2012,3, 3063-3070
DOI: 10.1039/C2SC20490H, Edge Article 

Active and reusable Pd(II) organometallic catalyst covalently bonded to mesoporous silica nanospheres for water-medium organic reactions
Wenhan He, Fang Zhang and Hexing Li
Chem. Sci., 2011,2, 961-966
DOI: 10.1039/C0SC00652A, Edge Article 

Selective electrocatalytic reduction of carbon dioxide to formate by a water-soluble iridium pincer catalyst
Peng Kang, Thomas J. Meyer and Maurice Brookhart
Chem. Sci., 2013,4, 3497-3502
DOI: 10.1039/C3SC51339D, Edge Article

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Strengthening the Bonds Between Bases

Deoxyribonucleic acid (DNA) is one of the most famous molecules in the world. First isolated and identified by Freidrich Miescher in 1871,1 DNA is responsible for coding ‘genetic instructions’ in all known living organisms and viruses. DNA molecules consist of two long helical biopolymer chains wrapped around a common axis and held tightly together by intermolecular forces called hydrogen bonds and base-stacking interactions. Each biopolymer chain is made up of small units called nucleotides, which themselves consist of a sugar, a phosphate group, and one of four different nucleobases (guanine, adenine, thymine or cytosine, abbreviated to G, A, T and C respectively). The specific orders in which the nucleotides appear in a DNA strand is what allows for the storage of genetic information.

Figure 1. Modified deoxycytosine and deoxyguanosine forming four hydrogen bonds

Shorter, single strands of nucleotide residues bonded together are called oligonucleotides. They are capable of binding to another oligonucleotide strand (via the same intermolecular forces as found in full length DNA helices) if the other strand has the ‘complimentary’ order of nucleotides (cytosine and guanine exclusively bind with each other; as do adenine and thymine). Due to this property, they are used in areas such as genetic testing, gene therapy, DNA probes and forensics.

The binding of one strand to its complimentary strand can be strengthened by modifying the nucleobase, as long as the  modifications do not disrupt duplex formation. In particular, the nucleobase cytosine has several reported modifications2 which allow for additional hydrogen bonding (thus strengthening the binding of two strands). Unfortunately, a lot of the previously reported cytosine modifications have the drawback of long synthetic sequences necessary to make them.

In this paper, Sekine and co-workers report their modifications of cytosine nucleotides, and measure these new molecule’s binding affinities with guanine (the ‘complimentary’ base which cytosine hydrogen bonds with, Figure 1). As well as demonstrating an efficient synthetic route to their new cytosine derivatives, the authours prove that oligonucleotides which incorporate their modified cytosine residue show an increased binding affinity to the complimentary strands when compared with the unmodified, parent oligonucleotide. These promising results could lead to the design and synthesis of even better cytosine nucleotides inspired by the scaffold reported in this work, in turn leading to oligonucleotides which can perform better in DNA-recognition based tests.

To read more, see;

A new modified cytosine base capable of base pairing with guanidine using four hydrogen bonds
K. Yamada, Y. Masaki, H. Tsunoda, A. Ohkubo, K. Seio and M. Sekine,
Org. Biomol. Chem., 2014, DOI:10.1039/c3ob42420k. Download PDF

Free to access until 10th April

References

1 R. Dahm, “Discovering DNA: Friedrich Miescher and the early years of nucleic acid research” Human Genetics, 2008, 122, 565–81.
2 A. S. Wahba, A. Esmaeili, M. J. Damha, R. H. E. Hudson, Nucleic Acids Res., 2010, 38, 1048; S. Preus, K. Kilsa, L. M. Wilhelmsson, B. Albinsson, Phys. Chem. Chem. Phys., 2010, 12, 8881; A. Ohkubo, T. Sakaue, H. Tsunoda, K. Seio, M. Sekine, Chem. Lett., 2010, 39, 726.


Dr C. Liana AllenDr C. Liana Allen is currently a post-doctoral research associate in the group of Professor Scott Miller at Yale University, where she works on controlling the enantio- or regioselectivity of reactions using small peptide catalysts. Liana received her Ph.D. in organic chemistry at Bath University with Professor Jonathan Williams, where she worked on developing novel, efficient syntheses of amide bonds.

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Macrolactams bind to heat shock protein 90

Posted on behalf of Steve Moore, web writer for Organic & Biomolecular Chemistry

The heat shock protein 90 (Hsp90) has a key role in some oncogenic pathways and is a widely studied target for anti-cancer therapeutics. The search for small molecule inhibitors of Hsp90 is ongoing. The most potent in vitro inhibitor of Hsp90 is radicicol, a resorcylic acid lactone; however radicicol lacks activity in vivo, possibly because of the presence of readily metabolised functional groups.

In their search for new inhibitors of Hsp90, scientists from the University of Nottingham and the University of Sussex have synthesised a series of macrolactam radicicol analogues. A new synthetic route to N-methylated resorcylic acid macrolactams is described which permits convenient variation of ring size. Macrolactam binding to Hsp90 was demonstrated by isothermal calorimetry and conformational changes were observed in co-crystallization experiments with yeast Hsp90.

Synthesis of macrolactam analogues of radicicol and their binding to heat shock protein Hsp90
Bridie L. Dutton, Russell R. A. Kitson, Sarah Parry-Morris, S. Mark Roe, Chrisostomos Prodromou and Christopher J. Moody
Org. Biomol. Chem., 2014, DOI: 10.1039/C3OB42211A, Paper

Free to access until: 24th March Download PDF | Download HTML

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT Organic & Biomolecular Chemistry articles for February

Synthetic strategies toward hetidine and hetisine-type diterpenoid alkaloids
Amy M. Hamlin, Jessica K. Kisunzu and Richmond Sarpong
Org. Biomol. Chem., 2014, DOI: 10.1039/C3OB42541J

Free to access until 28th March


Oxenoids in organic synthesis
Yury Minko and Ilan Marek
Org. Biomol. Chem., 2014, DOI: 10.1039/C3OB42349B

Free to access until: 17th March 2014

 Oxenoids in organic synthesis


A concise formation of N-substituted 3,4-diarylpyrroles – synthesis and cytotoxic activity
Maxim Egorov, Bernard Delpech, Geneviève Aubert, Thierry Cresteil, Maria Concepcion Garcia-Alvarez, Pascal Collin and Christian Marazano
Org. Biomol. Chem., 2014, DOI: 10.1039/C3OB42309C

Free to access until: 17th March 2014

synthesis of N-substituted 3,4-diarylpyrroles


Enantioselective synthesis of α-halo-α-alkylmalonates via phase-transfer catalytic α-alkylation
Suckchang Hong, Minsik Kim, Myunggi Jung, Min Woo Ha, Myungmo Lee, Yohan Park, Mi-hyun Kim, Taek-Soo Kim, Jihoon Lee and Hyeung-geun Park
Org. Biomol. Chem., 2014, DOI: 10.1039/C3OB42107D

Free to access until: 17th March 2014

Enantioselective synthesis of α-halo-α-alkylmalonates via phase-transfer catalytic α-alkylation

Expand here to see the full list

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

How Much Peptide Does it Take to Kill a Bacteria?

Posted on behalf of Dr Liana Allen, guest web writer for Organic & Biomolecular Chemistry.

Antibiotics are drug compounds used to treat infections caused by bacteria, such as tuberculosis and some forms of meningitis. The processes involved in bacteria cell reproduction are highly complicated and many different targets along the biological pathway of bacterial cell replication have been identified as potential opportunities to disrupt bacterial growth. Antibacterial drugs can be described as ‘bactericidal’ if they kill the bacterial cells by inhibition of bacteria cell wall or cell membrane synthesis, or by interfering with an essential bacterial enzyme. Those which target bacterial protein synthesis can be described as ‘bacteriostatic’ as they stop bacteria from reproducing but otherwise do not harm them.

One specific mode of antibacterial action is interaction with DNA gyrase, which is an enzyme involved in the unwinding of double stranded DNA helices during DNA replication.1 DNA gyrase is an enzyme which is not present in humans, making it an especially good target for antibiotics. One way in which antibacterial molecules interact with DNA gyrase is through stabilization of a DNA-gyrase covalent complex which is formed during the DNA replication process. The result of this interaction is the release of ‘broken DNA’, which kills the organism. For this reason, antibacterial agents which behave in this way are referred to as DNA gyrase poisons.

Microcin B17 (MccB17) structure

Microcin B17 (MccB17)

Microcin B17 (MccB17) is a peptide which displays antibacterial action and is thought to act as a DNA gyrase poison, but unfortunately, the full MccB17 peptide is not a suitable drug candidate due to its poor physiochemical properties. MccB17 is particularly interesting as the mature peptide contains some unusual hetrocyclic units.

In this paper, Katrina A. Jolliffe, Richard J. Payne and colleagues aimed to investigate the structure-activity relationship of MccB17 in order to determine exactly which parts of the peptide are needed for the antibacterial action and to develop a simplified DNA gyrase poison which would be a good lead candidate for antibacterial drug discovery. Using their own synthetic methodology,2 they prepared a range of full length and truncated analogues of MccB17, then tested their abilities to act as DNA gyrase poisons. They then compared the results with a known, potent DNA gyrase poison, ciprofloxacin. Many of the prepared analogues showed activity very similar to the native peptide; however some of the truncated variants actually performed better in this test. These promising results now enable more detailed investigation into the mechanism of bactericidal action of MccB17. In a second series of experiments, the peptides were tested for their antibacterial activity against two strains of E. coli. In this test it was the full length native MccB17 which gave the best results, suggesting that, even though truncated analogues can still exhibit DNA gyrase poisoning activity, the full length sequence would still currently be needed for bactericidal activity in vivo.

To read more, see;

Synthesis of Full Length and Truncated Microcin B17 Analogues as DNA Gyrase Poisons
R. E. Thompson, F. Collin, A. Maxwell, K. A. Jolliffe and R. J. Payne,
Organic & Biomolecular Chemistry, 2014, DOI: 10.1039/C3OB42516A.

Free to access until 7th March

References
1 Gore, J., Bryant, Z., Stone, M. D., Nöllmann, M., Cozzarelli, N.R., Bustamante, C. Nature, 2006, 439, 100.
2 Thompson, R. E., Jolliffe, K. A., Payne, R. J., Org. Lett., 2011, 13, 680.


Dr C. Liana AllenDr C. Liana Allen is currently a post-doctoral research associate in the group of Professor Scott Miller at Yale University, where she works on controlling the enantio- or regioselectivity of reactions using small peptide catalysts. Liana received her Ph.D. in organic chemistry at Bath University with Professor Jonathan Williams, where she worked on developing novel, efficient syntheses of amide bonds.

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

Organic & Biomolecular Chemistry at conferences in 2014

A selection of conferences the journal will be attending in 2014

Dr Richard Kelly, Managing Editor

Dr Marie Cote, Deputy Editor

The Organic & Biomolecular Chemistry team will be attending a number of conferences in 2014 and we would be delighted to meet you there.

We’re also the team behind OBC’s sister journals MedChemComm, Natural Product Reports, and the latest addition to the portfolio, Toxicology Research, so we’ll happily discuss your interdisciplinary research work. In fact, many of our authors choose to publish their research across all of these titles.

Here are just some of the conferences where you can meet us in the coming months:


GRC marine natural products 2-7 March Ventura, CA, USA – Meet Rich

Society of Toxicology annual meeting 23-27 March Phoenix, USA – Meet Marie

National Organic Symposium Trust 11-14 April Agra, India – Meet Rich

ISMSC-9 7-11 June Shanghai, China – Meet Marie

GRC Bioorganic Chemistry 8-13 June Proctor Academy, USA – Meet Rich

BOSS XIV 13-18 July Louvain-la-Neuve, Belgium – Meet Marie

Fall ACS meeting 10-14 August San Francisco, USA – Meet Rich

Gregynog Young Chemists’ Workshop 10-12 September Gregynog, Wales – Meet Marie

EFMC-ISMC 7-10 September Lisbon, Portugal – Meet Rich

Eurotox 7-9 September Edinburgh, UK – Meet Marie

Let us know if you are planning on attending any of these meetings, as we would be happy to meet you there!

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)

HOT Organic & Biomolecular Chemistry articles for January

A highly selective chemodosimeter for fast detection and intracellular imaging of Hg2+ ions based on a dithiocarbamate–isothiocyanate conversion in aqueous ethanol
Suman Pal, Joydev Hatai, Mousumi Samanta, Alok Shaurya and Subhajit Bandyopadhyay  
Org. Biomol. Chem., 2014,12, 1072-1078
DOI: 10.1039/C3OB42108B

 Graphical abstract


Ethynylbenzenoid metabolites of Antrodia camphorata: synthesis and inhibition of TNF expression
Marco Buccini, Kathryn A. Punch, Belinda Kaskow, Gavin R. Flematti, Brian W. Skelton, Lawrence J. Abraham and Matthew J. Piggott  
Org. Biomol. Chem., 2014,12, 1100-1113
DOI: 10.1039/C3OB42333F

Free to access until 21st February 2014

Graphical abstract


Hypervalent iodine(III)-mediated cyclopropa(e)nation of alkenes/alkynes under mild conditions
Shaoxia Lin, Mengru Li, Zhiyong Dong, Fushun Liang and Jingping Zhang  
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C3OB42123F

Free to access until 21st February 2014

Graphical abstract

Expand here to see the full list

Digg This
Reddit This
Stumble Now!
Share on Facebook
Bookmark this on Delicious
Share on LinkedIn
Bookmark this on Technorati
Post on Twitter
Google Buzz (aka. Google Reader)