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Scissoring the lipids: New strategy of disconnecting molecules may lead to tuberculosis vaccine

Date:
July 28, 2014
Source:
University of Bristol
Summary:
A new strategy that enables molecules to be disconnected essentially anywhere, even remote from functionality, is described by researchers in a new article. The method is now being developed to explore the possibility of creating a tuberculosis (TB) vaccine. The organic synthesis strategy involves a new method for combining smaller fragments together in which there is no obvious history in the product of their genesis.

A new strategy which enables molecules to be disconnected essentially anywhere, even remote from functionality, is described by researchers from the University of Bristol in Nature Chemistry. The method is now being developed to explore the possibility of creating a tuberculosis (TB) vaccine.

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The organic synthesis strategy, developed by Professor Varinder Aggarwal and Dr Ramesh Rasappan in the School of Chemistry, involves a new method for combining smaller fragments together in which there is no obvious history in the product of their genesis.

The paper describes not only this new strategy, but also its application to the shortest known synthesis, just 14 steps, of hydroxyphthioceranic acid, a key component of the cell wall lipid of the virulent mycobacterium tuberculosis.

Professor Aggarwal said: "Tuberculosis bacteria (TB) have an extraordinary thick lipid coat which acts as an impenetrable waxy barrier to cytotoxic agents, making it especially challenging to combat. Vaccination would be an ideal solution against TB and the lipid coat has been identified as a potential antigen. This requires the synthesis of the complex lipid which is composed of a disaccharide sugar core along with the complex chiral lipid, hydroxyphthioceranic acid."

In a collaborative project funded by the Gates Foundation, the method is now being scaled up to explore the possibility of creating a TB vaccine based on the cell wall sulfolipid.


Story Source:

The above story is based on materials provided by University of Bristol. Note: Materials may be edited for content and length.


Journal Reference:

  1. Ramesh Rasappan, Varinder K. Aggarwal. Synthesis of hydroxyphthioceranic acid using a traceless lithiation–borylation–protodeboronation strategy. Nature Chemistry, 2014; DOI: 10.1038/nchem.2010

Cite This Page:

University of Bristol. "Scissoring the lipids: New strategy of disconnecting molecules may lead to tuberculosis vaccine." ScienceDaily. ScienceDaily, 28 July 2014. <www.sciencedaily.com/releases/2014/07/140728113359.htm>.
University of Bristol. (2014, July 28). Scissoring the lipids: New strategy of disconnecting molecules may lead to tuberculosis vaccine. ScienceDaily. Retrieved November 27, 2014 from www.sciencedaily.com/releases/2014/07/140728113359.htm
University of Bristol. "Scissoring the lipids: New strategy of disconnecting molecules may lead to tuberculosis vaccine." ScienceDaily. www.sciencedaily.com/releases/2014/07/140728113359.htm (accessed November 27, 2014).

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