Monthly Archives: April 2006

Facing up to fullerenes

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The environmental impact of nanotechnology is the cause of much debate – some of it quite heated. Are nanoparticles dangerous – will nanobots prey on our bodies as well as our minds, and how long before the Earth is overrun with grey goo? Well, we simply don’t know. The extreme visions of a famed novelist and a future king may not be the best indicators, but a lot more research needs to be done before we can even start answering such questions.

I was intrigued (and a little amazed), therefore, to read a recent article by Bethany Halford in Chemical and Engineering News about the use of buckminsterfullerene (C-60) in cosmetics. As she points out, there is some evidence that C-60 might not be the benign little soccer ball we all know and love.

I decided to visit the website of one C-60-containing product, Zelens Day Cream, and see what they had to say for themselves:

Zelens creams uniquely contain Fullerene C60, an extremely powerful anti-oxidant, for which its three discoverers received the Nobel Prize for Chemistry in 1997.

Hum… it was actually 1996, but who’s counting?

In the pharmaceutical industry, Fullerene C60 is expected to play a major part in the fight against Alzheimer’s, Parkinson’s, Aids and many other diseases in which oxidation plays an important role.

A universal cure-all? Is there anything “Fullerene C60” can’t do? Seriously now, just how much of an impact is C60 making in the pharmaceutical industry? Has the early hype turned into future hope? I didn’t think it had, but please, let me know if I’m wrong about this…

The creams arise out of Dr Lens’ extensive research in the field of skin cancer, reflected in the many papers by him published in leading medical journals.

A search on Thomsons’ ISI Web of Science for Dr Marko B Lens indicates that he has published 16 papers.

Anyway, I’m not likely to become acquainted with this product, because at more than 130 GBP for a 30 mL jar, I couldn’t face it. How about you?

Stuart

Stuart Cantrill (Associate Editor, Nature Nanotechnology)

Mind if I cut in?

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There are a number of papers that have described catalytic asymmetric C-H insertion reactions (see a recent review on catalytic intramolecular C-H aminations by Davies & Long), but there are only a few examples of asymmetric O-H insertion reactions. In the ASAP section of the Journal of the American Chemical Society, Maier & Fu reported the first “effective” method for catalytic enantioselective insertions into O-H bonds.

The authors showed that in the presence of copper and a chiral bisazaferrocene ligand, various alcohols reacted with methyl alpha-diazo-alpha-phenylacetate, yielding alpha-alkoxy esters (the best yields and ee were achieved using methanol, 2-trimethylsilylethanol, or para-methoxybenzyl alcohol). They further explored the scope of the reaction involving 2-trimethylsilylethanol and demonstrated that they could isolate a range of alpha-diazo-alpha-arylacetates in high yields and ee – since the trimethylsilylethyl group can be easily removed using boron trifluoride diethyl etherate, the authors could also obtain enantiomerically pure alpha-hydroxy esters in high yields and ee.

Joshua

Joshua Finkelstein (Associate Editor, Nature)