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Highlights in Chemical Science

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Do I know you, sugar?


31 October 2006

A molecule that can recognise carbohydrates could further the fight against infections.

The carbohydrate-containing compound lipid A is found in certain bacteria and can cause septic shock, a serious condition that may lead to organ failure and death. Ben Miller at the University of Rochester, New York, US, said molecules that selectively bind lipid A could be used to diagnose infection or to treat septic shock.

'Molecular recognition of carbohydrates is a challenging problem,' said Miller. 'Carbohydrates look a lot like bulk solvent, and are more complex than other biopolymers because they have a lot of branching points.' Despite these problems Miller and his University of Rochester co-workers succeeded in designing a molecule, called TW545, that recognises lipid A.

TW545 molecule
The molecule TW545 (above) can recognise a carbohydrate-containing bacterial toxin

Miller describes TW545 as a 'stepping stone' towards new strategies for molecular recognition of carbohydrates. He is particularly interested in using carbohydrate-binding molecules for diagnostic purposes. Many proteins relevant to human health contain carbohydrate groups, said Miller, so molecules that recognise these could be put to good medical use.

Whether TW545 itself will find medical use is uncertain. Miller admits that its synthesis is too lengthy to be practical. Anthony Davis, professor of supramolecular chemistry at the University of Bristol, UK, added that TW545 has only been tested on lipid A, and may bind a variety of other molecules too. 'Unless it is selective, it's doubtful if it could ever be much use,' said Davis.

Nevertheless, Davis called Miller's early results 'very encouraging' and said that there is plenty of scope for tuning the system.

Daničle Gibney

References

K M Bucholtz, P C Gareiss, S G Tajc and B L Miller, Org. Biomol. Chem., 2006, 4, 3973 
DOI: 10.1039/b610727c