Archive for the ‘Cover articles’ Category

Asymmetric catalytic Mannich-type reaction of hydrazones using Zn(II) complexes on the cover of OBC issue 13

The cover of this week’s OBC features work from Min Shi et al. at Shanghai Institute of Organic Chemistry and Texas Tech University, who have used chiral zinc(II)–imidazoline–phosphine complexes in a novel catalytic system for the asymmetric Mannich-type difluorination of hydrazones with difluoroenoxysilanes.

Asymmetric catalytic Mannich-type reaction of hydrazones with difluoroenoxysilanes using imidazoline-anchored phosphine ligand–zinc(II) complexes
Zhiliang Yuan, Liangyong Mei, Yin Wei, Min Shi, Padmanabha V. Kattamuri, Patrick McDowell and Guigen Li
Org. Biomol. Chem., 2012, 10, 2509-2513
DOI: 10.1039/C2OB07022G

Read the full Communication; it is FREE to access for the next 6 weeks.

This issue also contains:

A Perspective review article: On a so-called “kinetic anomeric effect” in chemical glycosylation, by Ian Cumpstey

as well as the HOT article:

Synthesis and protein binding studies of a peptide fragment of clathrin assembly protein AP180 bearing an O-linked β-N-acetylglucosaminyl-6-phosphate modification
Mark E. Graham, Robin S. Stone, Phillip J. Robinson and Richard J. Payne

If you liked these why not have a look at the rest of the issue here

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Room temperature syntheses of substituted beta-fluorofurans on the cover of OBC issue 12

On the cover this week is work by Roman Dembinski et al. at Oakland University and Eastern Illinois University, highlighting facile synthetic methods for the preparation of 3-fluorofurans, 3-bromo-4-fluorofurans, and 3-fluoro-4-iodofurans in good yields and at room temperature.

Read all about the synthetic sequences employed: this article will be FREE to access for a period of 6 weeks.

Room temperature syntheses of entirely diverse substituted β-fluorofurans
Yan Li , Kraig A. Wheeler and Roman Dembinski
Org. Biomol. Chem., 2012, 10, 2395-2408
DOI: 10.1039/C1OB06693E

Also in this issue, take a look at a hot article by Taku Shoji et al. presenting  novel developments in the field of donor-acceptor chromophores, which can be synthesised using the [2+2] cycloaddition-cycloreversion (CA/CR) reaction; or read a timely Perspective showcasing recent advancement in the stereoselective synthesis of 2-C-branched sugar analogs, by Torsten Linker et al., and much more!

View the full issue here

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Coupling of unactivated aldehydes and Anticancer activity of oleanolic acid derivatives on the cover of OBC issue 11

Welcome to OBC issue 11, 2012 

Oscar Navarro and colleagues at the University of Hawaii at Manoa have used well-defined (N-heterocyclic carbene)–Ag(I) complexes for the A3 reaction, thereby allowing for the coupling of unactivated aldehydes at room temperature with very short reaction times. This work is featured on OBC‘s outside front cover, showcasing a scheme of the reaction depicted in their article over a picture of the coast of Lanikai, in Hawaii.

Well-defined (N-heterocyclic carbene)–Ag(I) complexes as catalysts for A3 reactions
Ming-Tsz Chen, Brant Landers and Oscar Navarro 
DOI: 10.1039/C2OB06900H 

The inside front cover illustrates work by Barbara Bednarczyk–Cwynar et al. at Poznan University of Medical Sciences, Poland, who highlight the strong cytotoxic activity on KB, MCF-7 and HeLa cell lines of novel A-ring or/and C-ring modified methyl oleanolate derivatives.

Anticancer effect of A-ring or/and C-ring modified oleanolic acid derivatives on KB, MCF-7 and HeLa cell lines
Barbara Bednarczyk–Cwynar, Lucjusz Zaprutko, Piotr Ruszkowski and Bogusław Hładoń
DOI: 10.1039/C2OB06923G

Interested? Why not read both communications, they are FREE to access for the next 6 weeks.

 

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Collagen triple helices and click chemisry on the cover of OBC issue 10

Welcome to OBC issue 10!

OBC‘s cover this week features work by Helma Wennemers et al. at the University of Basel (Switzerland), who have used click chemistry to introduce moieties as sterically demanding as monosaccharides into the Yaa position of collagen model peptides, and studied the effect of different triazolyl derivatives as well as the configuration of the functionalized proline residue on the thermal stability of the collagen triple helices.

Conformational stability of collagen triple helices functionalized in the Yaa position by click chemistry

Roman S. Erdmann and Helma Wennemers
Org. Biomol. Chem., 2012, 10, 1982-1986
DOI: 10.1039/C2OB06720J

As with all of our cover articles, it will be FREE to access for the next 6 weeks

This article is part of OBC‘s web-themed issue on Foldamer Chemistry – View the full collection of articles here

The issue also contains:

three ‘Hot Articles’

and that’s just a taster… we hope you enjoy the whole issue!

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Chameleons and catalysis on the cover of the latest issue of OBC

The colourful images on our covers are from Andrew C. Benniston and Ming-Hua Xu et al.

Andrew Benniston (University of Newcastle) together with colleagues from Istanbul Technical University and Hacettepe University, Turkey have created a series of colour-responsive fluorescent fluorene-fused benzoquinones with potential for use as reactive oxygen species sensors.  One of the compounds synthesised exhibits ‘chameleon-like’ behaviour switching from red to blue fluorescence on reduction, and reverts back to red on reaction with ROSs.

Colour-responsive fluorescent oxy radical sensors
Baris Yucel, Bahar Sanli, Huseyin Akbulut, Suheyla Ozbey and Andrew C. Benniston
DOI: 10.1039/C2OB06825G

Ming-Hua Xu and colleagues at Shanghai Institute of Materia Medica have designed a structurally simple new class of chiral sulfur–olefin hybrid ligands – N-cinnamyl sulfinamides – for use in asymmetric catalysis. The ligands where tested in rhodium-catalyzed asymmetric 1,4-addition reactions, converting aryl boronic acids to α,β-unsaturated carbonyl compounds with up to 99% yield and 98% ee.

Design of N-cinnamyl sulfinamides as new sulfur-containing olefin ligands for asymmetric catalysis: achieving structural simplicity with a categorical linear framework
Shen-Shuang Jin, Hui Wang, Ting-Shun Zhu and Ming-Hua Xu
DOI: 10.1039/C2OB06723D

This issue also contains a review on the recognition properties of imidazole derivatives by Franscico Otón et al. and a hot article from Luis Simón and Jonathan Goodman on hydrogen-bond stabilization in oxyanion holes, showing that the 3D arrangement, rather than planar arrangement, of H-bonds stabilises oxyanion holes.

View the issue

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Multivalent scFvs, mitomycin C stereochemistry, peptide dendrimers and NET ligands in Issue 8

On the cover of Issue 8 we have two cancer-related articles from Jacquelyn Gervay-Hague (University of California Davis) on multivalent single chain variable fragments with increased tumor-associated antigen affinity and from Federico Gago (Universidad de Alcalá) modelling the binding of mitomycin C and analogues to DNA.

A general chemical synthesis platform for crosslinking multivalent single chain variable fragments
Joan G. Schellinger, Avinash Kudupudi, Arutselvan Natarajan, Wenjun Du, Sally J. DeNardo and Jacquelyn Gervay-Hague
DOI: 10.1039/C0OB01259A

Rationale for the opposite stereochemistry of the major monoadducts and interstrand crosslinks formed by mitomycin C and its decarbamoylated analogue at CpG steps in DNA and the effect of cytosine modification on reactivity
Juan A. Bueren-Calabuig, Ana Negri, Antonio Morreale and Federico Gago
DOI: 10.1039/C1OB06675G

The issue also contains a review from Jean-Louis Reymond and Tamis Darbre on combinatorial libraries of peptide and glycopeptide dendrimers and hot papers on creating (D)-sugars from (L)-amino acids from Paul Clarke and stilbazolium dimers as NET ligands from James N. Wilson.

View the issue

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Synthesising ureas from CO2, recognition of oxoanions and cross-metathesis for heterocycles in Issue 7

The cool images on this week’s cover are from Giuseppe Resnati, NFMLab, and James C. Anderson, UCL.

Resnati and colleagues have conducted an NMR study of phosphate oxoanion binding of a 2-iodo-imidazolium receptor with charge assisted halogen bonding, finding a surprisingly strong binding constant for phosphate anions, their work is highlighted on the outside front cover.

2-Iodo-imidazolium receptor binds oxoanions via charge-assisted halogen bonding
Massimo Cametti, Kari Raatikainen, Pierangelo Metrangolo, Tullio Pilati, Giancarlo Terraneo and Giuseppe Resnati
DOI: 10.1039/C1OB06524F

On a completely different topic, Anderson and Moreno have been using CO2 to produce ureas at ambient conditions, using 12- and 14- electron titanium imido complexes:

Synthesis of ureas from titanium imido complexes using CO2 as a C-1 reagent at ambient temperature and pressure
James C. Anderson and Rafael Bou Moreno
DOI: 10.1039/C1OB06576A

As well as these the issue also contains a review from Tim Donohoe on olefin cross-metathesis for heterocycle synthesis and plenty of other hot articles, take a look…

Hot articles in this issue:

Some cyclization reactions of 1,3-diphenylbenzo[e][1,2,4]triazin-7(1H)-one: preparation and computational analysis of non symmetrical zwitterionic biscyanines
Theodosia A. Ioannou, Panayiotis A. Koutentis, Harry Krassos, Georgia Loizou and Daniele Lo Re
DOI: 10.1039/C1OB06622F

Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation
B. V. Subba Reddy, Prashant Borkar, J. S. Yadav, P. Purushotham Reddy, A. C. Kunwar, B. Sridhar and René Grée
DOI: 10.1039/C1OB06489D

Chemoenzymatic synthesis of a mixed phosphine–phosphine oxide catalyst and its application to asymmetric allylation of aldehydes and hydrogenation of alkenes
Derek R. Boyd, Mark Bell, Katherine S. Dunne, Brian Kelly, Paul J. Stevenson, John F. Malone and Christopher C. R. Allen
DOI: 10.1039/C1OB06599H

James C. Anderson and Rafael Bou Moreno
Org. Biomol. Chem., 2012, 10, 1334-1338
DOI: 10.1039/C1OB06576A

Certain 12- and 14- electron titanium imido complexes

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Issue 6 online – including water-binding aquafoldamers, fluorinated probes and glycosylated 5-hydroxylysine

On the outside front cover of this week’s issue is a hot article from Huaiqing Zhao, National University of Singapore, et al. on a series of water-binding aquafoldamers with potential use in recognizing topologically diverse larger water clusters and as synthetic water channels. This article is part of our forthcoming themed issue on Foldamer Chemistry.

Synthesis, structural investigation and computational modelling of water-binding aquafoldamers
Huaiqing Zhao, Wei Qiang Ong, Xiao Fang, Feng Zhou, Meng Ni Hii, Sam Fong Yau Li, Haibin Su and Huaqiang Zeng
DOI: 10.1039/C1OB06609A

The inside front cover is work from Jonathan Guimond-Tremblay, Université Laval, et al. on the synthesis of three monofluorinated dimyristoylphosphatidylcholine derivatives for use as probes in 19F NMR studies to study the effects of drugs and peptides on model membranes.

Synthesis and properties of monofluorinated dimyristoylphosphatidylcholine derivatives: Potential fluorinated probes for the study of membrane topology
Jonathan Guimond-Tremblay, Marie-Claude Gagnon, Jozy-Ann Pineault-Maltais, Vanessa Turcotte, Michèle Auger and Jean-François Paquin
DOI: 10.1039/C2OB06570C

The issue also includes a review on the synthesis of glycosylated (2S,5R)-hydroxylysine from Margaret Brimble and coworkers and a hot article from Valentina Cerulli et al., on a highly diastereoselective Ugi multicomponent reaction

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Issue 5 just published – gold-mediated modification of oligosaccharides and easy access to cinnamonitriles on the covers

On the outside front cover a communication from Chi-Ming Che and Man-Kin Wong et al. is highlighted, showing their method for gold-mediated bifunctional modification of oligosaccharides via a three-component coupling reaction.

Gold-mediated bifunctional modification of oligosaccharides via a three-component coupling reaction
Karen Ka-Yan Kung, Gai-Li Li, Lan Zou, Hiu-Chi Chong, Yun-Chung Leung, Ka-Hing Wong, Vanessa Kar-Yan Lo, Chi-Ming Che and Man-Kin Wong
DOI: 10.1039/C1OB06429K

On the inside front cover is an article from Brindaban C. Ranu et al. on copper catalysed cyanation of styrenyl bromides to give functionalized cinnamonitriles with preserved stereochemistry.

Hydroxyapatite-supported Cu(I)-catalysed cyanation of styrenyl bromides with K4[Fe(CN)6]: an easy access to cinnamonitriles
Debasree Saha, Laksmikanta Adak, M. Mukherjee and Brindaban C. Ranu
DOI: 10.1039/C1OB06467C

View the rest of the issue including a review on squaraine dyes in photodynamic therapy

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Calixarene octopi on the cover of Issue 4

This rather tropical cover image illustrates work from Yan-Song Zheng and colleagues on amphiphilic calixarenes.  They have shown that when amphiphilic calix[4]arene and carboxylic acids such as naproxen and ibuprofen interact the direction of the branched substituents can be reversed, changing the shape and size of the calixarene micelles from solid to hollow or linear.  They liken this change in shape to an octopus engulfing fish!

Read the paper free for 6 weeks:

Effect of carboxylic acid on micelles of a neutral amphiphilic dendro-calix[4]arene
Hong Huang, Dong-Mi Li, Weizhou Wang, Yi-Chang Chen, Khalid Khan, Song Song and Yan-Song Zheng
DOI: 10.1039/C1OB06358H

View the rest of the issue here

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