A Woman Obsessed with Chirality

Thanks for the thalidomide article. It is funny because I had sent away for one of the original articles on the topic of the racemization of thalidomide after I did a search a few weeks ago and it also came today.

Testa, B.; Carrupt, P. A.; Gal, J. Chirality 5: 105-111 (1993)

It says...."In thalidomide, teratogenic activity on mice and rats was reported to reside in the (-)-S-enantiomer, but racemization was seemingly overlooked. Indeed, the compound was found to racemize with relative ease (residual enantiomeric excess of 2/3 after 5 days in DMF or 80% DMF at room temperature) Studies under biomimetic conditions yielded a half-life of racemization of 2.5 hours in phosphate buffer at pH 7.4 and 37oC, with serum albumin marketly accelerating the reaction. In fact, thalidomide isolated from the plasma of rabbits 2 h after i.v. injection was completely racemized.......Such results have generated a lively debate, the consensus being that it is practically impossible to demonstrate stereoselectivity in any in vivo biological effect of thalidomide."

I saw the normal myth being spread in a recent text book. I don't mean to be preachy because god knows I spread the myth myself. I wrote to the author via email, but he never got back to me.

There is another article on thalidomide in Lncet 339:365, 1992 which I am going to get a hold of.

So the guy who wrote the little web blurb was right.

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