Scissoring the lipids

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 today. The method is now being developed to explore the possibility of creating a tuberculosis (TB) vaccine.

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 .

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.

More information: Nature Chemistry (2014), DOI: 10.1038/nchem.2010

add to favorites email to friend print save as pdf

Related Stories

Potential new drug for tuberculosis

Aug 05, 2013

A new drug capable of inhibiting growth of Mycobacterium tuberculosis is reported this week in Nature Medicine. The findings may improve therapeutic options for the treatment of drug resistant tuberculosis (TB). ...

Sugar synthesis hits the sweet spot

May 06, 2011

A new strategy for synthesizing the kind of complex molecules that certain bacteria use to build their protective cell walls has been developed by Akihiro Ishiwata and Yukishige Ito from the RIKEN Advanced ...

Chemists find a way to escape from flatland

Jun 09, 2014

(Phys.org) —A new method for coupling together secondary and tertiary boronic esters to aromatic compounds which preserves the 3-D shape of the boronic ester is described by researchers from the University ...

Recommended for you

NY and NJ say they will require Ebola quarantines

7 hours ago

The governors of New Jersey and New York on Friday ordered a mandatory, 21-day quarantine for all doctors and other arriving travelers who have had contact with Ebola victims in West Africa.

WHO: Mali case may have infected many people

11 hours ago

The World Health Organization says a toddler who brought Ebola to Mali was bleeding from her nose during her journey on public transport and may have infected many people.

Two US nurses are declared cured of Ebola

12 hours ago

Two American nurses were declared cured of Ebola on Friday, and one was healthy enough to leave the hospital and meet President Barack Obama for a hug.

User comments