In this reaction, the proton acts as the electrophile and water coming from the solvent attacks the sulfinyl group.
Not convinced yet? There are even crystal structures to prove it!
Download the article for free until 10th November
Studies on highly regio- and stereoselective hydration of 1,2-allenylic sulfoxides
Zhao Fang, Chao Zhou, Chunling Fu and Shengming Ma
Org. Biomol. Chem., 2010, 8, 4554-4561
DOI: 10.1039/C0OB00007H
The RSC currently presents around 60 prestigious Prizes and Awards annually to scientists in all the main chemical science disciplines allowing for the greatest range of scientists to be recognised for their work; individuals, teams and organisations working across the globe.
There are nine categories of awards including specific categories for Industry and Education so whether you work in business, industry, research or education recognition is open to everyone.
Our Prizes and Awards represent the dedication and outstanding achievements in the chemicals sciences and are a platform to showcase inspiring science to gain the recognition deserved.
Do you know someone who has made a significant contribution to advancing the chemical sciences? View our full list of Prizes and Awards and use the online system to nominate yourself or colleagues.
Bound to succeed for gene therapy
by David Barden
An all-in-one solution to improve gene therapy in vivo has been devised by US scientists.
Correcting the genetic code of malfunctioning cells, known as gene therapy, has enormous potential to cure diseases. However, two key challenges are getting the new DNA into the cell and tracking it once inside. Now a group led by Mark Woods at Oregon Health and Sciences University in Portland has shown that these two problems can be solved in one stroke, with clear benefits for the development of new gene therapy treatments.
DNA has a high negative charge, meaning that it is repelled by biological membranes such as cell walls. One way of getting it into a cell is to mask the charge by bundling it with a positively charged polymer. Tracking this process in real-time is highly desirable, says Woods and is currently done by attaching a contrast agent to the polymer – but this can fundamentally modify its properties, he says. Instead Woods and colleagues optimised the polymer so that it already contains a contrast agent, which they say will provide ‘a valuable addition to the gene therapy tool kit.’
Woods realised that a polymeric europium complex that they had previously developed as a contrast enhancer in magnetic resonance imaging (MRI) might also be suitable as a transfer agent as it had a high positive charge. Testing their complex out on a stretch of DNA encoding the well-known green fluorescent protein showed that it aided migration into cells. In addition, the binding of the complex to the DNA changed the contrast signal produced, ‘potentially providing a means of imaging the delivery and release of a gene,’ says Woods.
However, he adds, improvements to the transfer efficiency and contrast enhancement are needed before such complexes can be considered as gene therapy agents. Altering the lipophilicity of the polymer, adding copolymers to the chain, or adjusting the charge on the complex should afford routes to more effective agents, he suggests.
Peter van Zijl, an expert in MRI methodologies at Johns Hopkins University in Baltimore, US, says ‘This work constitutes another important step forward in the design of compounds that can function both as MRI contrast agents and gene delivery agents,’ adding that ‘this proof of principle will greatly stimulate future efforts to develop transfection agents that can report on their efficacy through MRI.’
Read the article and comment on the blog
Polymeric PARACEST MRI contrast agents as potential reporters for gene therapy
Yunkou Wu, Christiane E. Carney, Michael Denton, Elaine Hart, Piyu Zhao, Daniel N. Streblow, A. Dean Sherry and Mark Woods, Org. Biomol. Chem., 2010
DOI: 10.1039/c0ob00087f
Original story in Highlights of Chemical Biology
Seeberger and colleagues design carbohydrate-functionalized β-cyclodextrins (βCDs) and liposomes for hepatocyte-specific delivery.
Find out about the detection of hepatocyte binding and uptake in this free to access until October 8th OBC HOT article.
Design, synthesis and biological evaluation of carbohydrate-functionalized cyclodextrins and liposomes for hepatocyte-specific targeting
Gonçalo J. L. Bernardes, Raghavendra Kikkeri, Maha Maglinao, Paola Laurino, Mayeul Collot, Sung You Hong, Bernd Lepenies and Peter H. Seeberger
Org. Biomol. Chem., 2010, Advance Article
DOI: 10.1039/C0OB00372G , Paper
Ulrik Gether, Kristian Stromgaard and colleagues at University of Copenhagen explore the structure-activity relationships of the first small molecule inhibitor of PICK 1, a potential drug target against brain ischemia, pain and cocain addiction.
It is the inside cover of OBC Issue 19 and it will be free to access until October 19th.
Read it and try to PICK 1 comment!
Structure–activity relationships of a small-molecule inhibitor of the PDZ domain of PICK1
Anders Bach, Nicolai Stuhr-Hansen, Thor S. Thorsen, Nicolai Bork, Irina S. Moreira, Karla Frydenvang, Shahrokh Padrah, S. Brøgger Christensen, Kenneth L. Madsen, Harel Weinstein, Ulrik Gether and Kristian Strømgaard
Org. Biomol. Chem., 2010, 8, 4281-4288
DOI: 10.1039/C0OB00025F
Dan Pantos and co-workers at Cambridge University explore the ‘sergeants and soldiers’ behaviour where a chiral derivative, amino acid derivatives of naphtalene-diimides (NDIs), imposes its chirality on a structure formed out of achiral derivatives.
Supramolecular systems, nanotubes, C60… everything included in this very interesting paper, front cover of OBC Issue 19.
Reading it is a must (although not an order!) and commenting on it an option
Free to access until 19th October
The sergeants-and-soldiers effect: chiral amplification in naphthalenediimide nanotubes
Tom W. Anderson, Jeremy K. M. Sanders and G. Dan Pantoş
Org. Biomol. Chem., 2010, 8, 4274-4280
DOI: 10.1039/C0OB00027B
Can Deuterium act as a protecting group to prevent unwanted hydrogen atom transfers?
Mark Wood and colleagues have the answer here.
Reviewers were very impressed with it and we made it a HOT article.
Curious? Find out more! Free to access until the end of September.
Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generation of α-aminoalkyl radicals
Mark E. Wood, Sabine Bissiriou, Christopher Lowe, Andrew M. Norrish, Katell Sénéchal, Kim M. Windeatt, Simon J. Coles and Michael B. Hursthouse
Org. Biomol. Chem., 2010, Advance Article
DOI: 10.1039/C0OB00205D , Paper
David Leigh and co-workers talk about a macrocycle that contains both a hydrazone and a disulfide linkage.
Find out more about the synthesis, the structure and the different chemistry they perform on it in this very interesting paper.
Excellent reviews from the referees and thumbs up from the editorial office make it a HOT paper.
Free to access until the end of September.
Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions
Max von Delius, Edzard M. Geertsema, David A. Leigh and Alexandra M. Z. Slawin
Org. Biomol. Chem., 2010, Advance Article
DOI: 10.1039/C0OB00214C, Paper
Namboothiri and colleagues describe Rauhut-Curier (RC) reactions of aliphatic nitroalkenes and nitrodienes with enones and acrylates.
It has received very positive comments from the referees and the Editorial Office. What do you think?
As a HOT article, it will be free to access until September 26th.
Rauhut–Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes
Pramod Shanbhag, Pradeep R. Nareddy, Mamta Dadwal, Shaikh M. Mobin and Irishi N. N. Namboothiri
Org. Biomol. Chem., 2010, Advance Article
DOI: 10.1039/C0OB00062K , Paper
Thomas Nugent and co-workers talk about the top organocatalysts for cyclic ketones and discover a 2-picolylamine template which is a promising new organocatalyst for aqueous aldol reactions.
Do you want to read more? You can do it for free until early October here!
Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions
Thomas C. Nugent, M. Naveed Umar and Ahtaram Bibi
Org. Biomol. Chem., 2010, 8, 4085-4089
DOI: 10.1039/C0OB00049C
