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Mutant enzymes help break cocaine habit

02 Oct 2013

An enzyme modified to hydrolyse cocaine 1000 faster than it did before could form the basis of the first medicinal treatment for cocaine addiction. Not only can the enzyme swiftly chop cocaine into inactive metabolites but modification of the enzyme has not affected its selectivity towards other natural substrates.

A treatment for cocaine abuse could be on the horizon © Shutterstock

Cocaine is one the most widely used illegal drugs in the world. Unlike many other commonly abused substances, there are no proven medications available to treat cocaine addition. The health consequences of cocaine abuse are severe and addicts can cause significant societal problems. Finding an addiction treatment is therefore of the utmost importance.

Substrate selectivity of high-activity mutants of human butyrylcholinesterase
Chang-Guo Zhan et al.
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41713A

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Q2 Top 10 for Organic & Biomolecular Chemistry

13 Aug 2013

Please take a look at the top 10 most accessed Organic & Biomolecular Chemistry articles for the second quarter of 2013:

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

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
Org. Biomol. Chem., 2012, 10, 6299-6308
DOI: 10.1039/C2OB25614B

Recent advances in the synthesis of aromatic nitro compounds
Guobing Yan and Minghua Yang
Org. Biomol. Chem., 2013, 11, 2554-2566
DOI: 10.1039/C3OB27354G

Expeditious synthesis of bacterial, rare sugar building blocks to access the prokaryotic glycome
Madhu Emmadi and Suvarn S. Kulkarni
Org. Biomol. Chem., 2013, 11, 3098-3102
DOI: 10.1039/C3OB40615F

Transition metal-catalyzed functionalization of pyrazines
Nicolai I. Nikishkin, Jurriaan Huskens and Willem Verboom
Org. Biomol. Chem., 2013, 11, 3583-3602
DOI: 10.1039/C3OB40460A

New trends in bismuth-catalyzed synthetic transformations
Thierry Ollevier
Org. Biomol. Chem., 2013, 11, 2740-2755
DOI: 10.1039/C3OB26537D

Synthesis and biological evaluation of new paclitaxel analogs and discovery of potent antitumor agents
Kyriacos C. Nicolaou and Roman A. Valiulin
Org. Biomol. Chem., 2013, 11, 4154-4163
DOI: 10.1039/C3OB40654G

Manipulating non-innocent π-spacers: the challenges of using 2,6-disubstituted BODIPY cores within donor–acceptor light-harvesting motifs
Catherine Bonnier, Devin D. Machin, Omar Abdi and Bryan D. Koivisto
Org. Biomol. Chem., 2013, 11, 3756-3760
DOI: 10.1039/C3OB40213D

Bu₄NI-catalyzed decarboxylative acyloxylation of an sp³ C–H bond adjacent to a heteroatom with α-oxocarboxylic acids
Shuai Zhang, Li-Na Guo, Hua Wang and Xin-Hua Duan
Org. Biomol. Chem., 2013, 11, 4308-4311
DOI: 10.1039/C3OB40748A

Recent applications of arene diazonium salts in organic synthesis
Fanyang Mo, Guangbin Dong, Yan Zhang and Jianbo Wang
Org. Biomol. Chem., 2013, 11, 1582-1593
DOI: 10.1039/C3OB27366K

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Antigenic sugars identified for Chagas disease

24 Jul 2013

Scientists in the US and Spain have synthesised the combinations of sugars from the surface of the Chagas disease parasite that trigger the human immune response to it. This could help establish better diagnostic tests for the disease, and even a vaccine.

The triatomine beetles that transmit Chagas disease are known as kissing bugs because they tend to feed on people’s faces

Chagas disease is caused by the parasite Trypanosoma cruzi. The parasite is transmitted by contaminated food, blood transfusions and blood sucking beetles commonly known as kissing bugs. After a phase of acute local infection, the disease becomes chronic and can eventually lead to life-threatening heart and digestive system disorders. Already endemic in Latin America, Chagas disease is also becoming more of a health issue in Europe and the US with blood banks now screening for it.

Currently, Chagas diagnosis involves spotting the parasite during microscopic investigation of blood samples or checking to see if antibodies in blood samples of infected patients bind to a lysate of Chagas parasites, but these tests are not very sensitive. As treatment is only effective at the acute stage of infection, better diagnostics are highly desirable.

The surface of the parasite is garnished with unusual sugars, but until now it has not been clear which ones elicit antibodies to the parasite. Sugar chemist Katja Michael and glycobiologist Igor Almeida from the University of Texas at El Paso and colleagues have synthesised combinations of α-galactose sugars from the Chagas parasites’ surface to solve the mystery. Sera of blood samples from infected patients were added to fluorescent immunoassays of the different sugar combinations. The assay revealed the disaccharide Galα(1,3)–Galβ as the immunodominant glycotope on the parasite’s cell surface.

Read the full article in Chemistry World

Potential use of synthetic α-galactosyl-containing glycotopes of the parasite Trypanosoma cruzi as diagnostic antigens for Chagas disease
R A Ashmus et al
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB40887F

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Chemical Biology and Medicinal: Synthesis of a selective inhibitor of a fucose binding bacterial lectin from Burkholderia ambifaria

09 May 2013

Pathogen-associated lectins are considered to be attractive targets for the development of antiadhesive drugs. It is of great importance to design sugar-based derivatives able to selectively bind to specific pathogen-associated lectins with the aim of fighting bacterial infections without interfering with human lectins involved in physiological processes.

The stereoselective synthesis of the new fucose-based derivative 1, as the first example of glycomimetic selectively recognized by the fucose-binding lectin BambL from Burkholderia ambifaria is described.

Scientists in Italy report the first example of a synthetic ligand able to selectively bind, in the micromolar range, the pathogen-lectin BambL. BambL is a fucose-specific lectin from Burkholderia ambifaria, a bacterium member of the Burkholderia cepacia complex (BCC), a closely related group of Gram-negative bacteria responsible for cepacia syndrome in immunocompromised patients.

The fucose-based mimetic is therefore a promising candidate for the development of antibacterial agents against infection by B. ambifaria.

Synthesis of a selective inhibitor of a fucose binding bacterial lectin from Burkholderia ambifaria
Barbara Richichi, A Imberty, Emilie Gillon, Rosa Bosco, Ieva Sutkeviciute, Franck Fieschi and Cristina Nativi
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB40520F

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OBC Top 10 most accessed articles published in 2012 (Volume 10)

15 Apr 2013

Curious about which articles published in 2012 gathered most readership? Here are the Top 10 works your colleagues have been accessing in Organic & Biomolecular Chemistry:

A one-pot catalysis: the strategic classification with some recent examples
Nitin T. Patil, Valmik S. Shinde and Balakrishna Gajula
Org. Biomol. Chem., 2012, 10, 211-224
DOI: 10.1039/C1OB06432K

A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions
Peter A. Byrne, Kamalraj V. Rajendran, Jimmy Muldoon and Declan G. Gilheany
Org. Biomol. Chem., 2012, 10, 3531-3537
DOI: 10.1039/C2OB07074J

Imidazole derivatives: A comprehensive survey of their recognition properties
Pedro Molina, Alberto Tárraga and Francisco Otón
Org. Biomol. Chem., 2012, 10, 1711-1724
DOI: 10.1039/C2OB06808G

Enhanced reduction of C–N multiple bonds using sodium borohydride and an amorphous nickel catalyst
Shouxin Liu, Yihua Yang, Xiaoli Zhen, Junzhang Li, Huimin He, Juan Feng and Andrew Whiting
Org. Biomol. Chem., 2012, 10, 663-670
DOI: 10.1039/C1OB06471A

Strategies for the enantioselective synthesis of spirooxindoles
Nicolas R. Ball-Jones, Joseph J. Badillo and Annaliese K. Franz
Org. Biomol. Chem., 2012, 10, 5165-5181
DOI: 10.1039/C2OB25184A

Thiol–yne coupling: revisiting old concepts as a breakthrough for up-to-date applications
Alessandro Massi and Daniele Nanni
Org. Biomol. Chem., 2012, 10, 3791-3807
DOI: 10.1039/C2OB25217A

Small molecule control of bacterial biofilms
Roberta J. Worthington, Justin J. Richards and Christian Melander
Org. Biomol. Chem., 2012, 10, 7457-7474
DOI: 10.1039/C2OB25835H

Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions
Laurence Burroughs, Paul A. Clarke, Henrietta Forintos, James A. R. Gilks, Christopher J. Hayes, Matthew E. Vale, William Wade and Myriam Zbytniewski
Org. Biomol. Chem., 2012, 10, 1565-1570
DOI: 10.1039/C1OB06798B

Olefin cross-metathesis for the synthesis of heteroaromatic compounds
Timothy J. Donohoe, John F. Bower and Louis K. M. Chan
Org. Biomol. Chem., 2012, 10, 1322-1328
DOI: 10.1039/C2OB06659A

Selective N-alkylation of amines using nitriles under hydrogenation conditions: facile synthesis of secondary and tertiary amines
Takashi Ikawa, Yuki Fujita, Tomoteru Mizusaki, Sae Betsuin, Haruki Takamatsu, Tomohiro Maegawa, Yasunari Monguchi and Hironao Sajiki
Org. Biomol. Chem., 2012, 10, 293-304
DOI: 10.1039/C1OB06303K

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Organic: By-product of Teflon manufacture used to generate compounds for medicinal, agrichemical and materials sciences

05 Feb 2013

Scientists in Japan have used a by-product of Teflon manufacture to generate carbonyl compounds with trifluoromethyl groups. Organic molecules bearing a trifluoromethyl group have received much attention because of their unique physical and chemical properties, which are important in the fields of medicinal, agrichemical and materials sciences, say the researchers. Efficient ways of introducing CF₃ groups into target molecules are being sought. The nucleophilic trifluoromethylation of carbonyl compounds using a Ruppert–Prakash reagent – (trifluoromethyl)trimethylsilane – is a well-explored strategy. But, (trifluoromethyl)trimethylsilane is expensive to prepare and is prepared from ozone-depleting bromotrifluoromethane. Fluoroform – a by-product of Teflon manufacture – has emerged as a potential environmentally benign alternative to (trifluoromethyl)trimethylsilane. It is also non-toxic, cheap and available in large quantities.

Graphical Abstract

A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform
Hiroyuki Kawai, Zhe Yuan, Etsuko Tokunaga and Norio Shibata
Org. Biomol. Chem., 2013,
DOI: 10.1039/C3OB27368G

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Nanoscience: Using DNA origami as a scaffold to assemble uniform length carbon nanotubes

05 Dec 2012

Scientists in the US have developed a convenient, versatile method to organise discrete length single-walled carbon nanotubes (SWNT) into complex geometries using 2D DNA origami tiles. Constructing intricate geometric arrangements of components is one of the central challenges of nanotechnology. The origami scaffolds considered here, both rectangular and triangular, were used to organise the nanotubes: several arrangements of nanotubes were constructed, with defined tube lengths and inter-tube angles. This method allows for uniform tube lengths and positional precision, leading to the reliable assembly of SWNTs into well-structured arrays.

Graphical Abstract

DNA origami templated self-assembly of discrete length single wall carbon nanotubes
Zhao Zhao, Yan Liu and Hao Yan
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C2OB26942B

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Chemical biology and medicinal: New anticancer compounds

09 Nov 2012

Scientists in Canada have reported the anti-leukaemia activity of four new prodigiosin analogues in vitro in a cancer cell line and in vivo in a zebrafish model. Prodigiosin is the parent member of a family of tripyrrolic natural products isolated from bacteria.

Graphical Abstract

Investigations regarding the utility of prodigiosenes to treat leukemia
Deborah A. Smithen, A. Michael Forrester, Dale P. Corkery, Graham Dellaire, Julie Colpitts, Sherri A. McFarland, Jason N. Berman and Alison Thompson
Org. Biomol. Chem., DOI: 10.1039/C2OB26535D

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Organic: Anticancer compound’s analogues exhibit potent cytotoxicity against cancer cell lines

30 Oct 2012

Scientists in France and Lebanon had previously synthesised and evaluated the biological properties of a series of 1,1-diarylethylene analogues of isocombretastatin A-4, which is related to the natural combretastatin A-4, an antitumour agent. Now, they have studied the effects of structural modifications on the linker between the two aromatic rings of the isocombretastatin A-4 to better understand the structure-activity relationships associated with this series of 1,1-diarylethylene tubulin polymerisation inhibitors. The new compounds exhibit potent cytotoxicity against cancer cell lines.

Organic: Anticancer compound’s analogues exhibit potent cytotoxicity against cancer cell lines

Organic: Anticancer compound’s analogues exhibit potent cytotoxicity against cancer cell lines
Abdallah Hamze and Mouad Alami
Org. Biomol. Chem., 2012,
DOI: 10.1039/C2OB26253C

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Organic & Biomolecular Chemistry Blog

Author Archive

Mutant enzymes help break cocaine habit

Antigenic sugars identified for Chagas disease

Chemical Biology and Medicinal: Synthesis of a selective inhibitor of a fucose binding bacterial lectin from Burkholderia ambifaria

Organic: By-product of Teflon manufacture used to generate compounds for medicinal, agrichemical and materials sciences

Nanoscience: Using DNA origami as a scaffold to assemble uniform length carbon nanotubes

Chemical biology and medicinal: New anticancer compounds

Organic: Anticancer compound’s analogues exhibit potent cytotoxicity against cancer cell lines

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