Thursday, April 05, 2007

Just try it.


Try googling "masamune effect". It has to be in quotes for this to work. I was looking for a specific reference and was too lazy to go to Web of Science right away. I got a good chuckle for my efforts, but little else.
Sorry I haven't blogged in a bit. I'm recovering from an unfortunate turn of events that I'd prefer not to post about, and my computer time's being eaten up by other things these days.

..when you're done with that, read the real references, if you're so inclined. (I did have to go outside of Google to find them, since this work is mentioned offhand in many more recent papers.)
(a)W. Choy, L. A. Redd III., S. Masamune, J. Org. Chem. 1983, 48, 1137-1139;
(b) S. Masamune, L. A. Reed III., J. T. Davis, W. Choy, J. Org. Chem. 1983, 48, 4441-4444.

Satoru Masamune, while a professor of chemistry at MIT, made many contributions to the field of chemical synthesis. These two papers describe some of his contributions to the Diels-Alder reaction, one of my adviser's favorites.
The Diels-Alder reaction is artistic (it can let us sculpt 3D molecules out of flat precursors), it's green (no waste atoms lying around after the reaction, with just a few exceptions), and chemists have gotten pretty good at controlling and predicting its power.

Back to Masamune's papers. This work describes a small reactant with a defined 3D structure, which reacts very well at low temperatures, catalyst-free (green again, low energy requirement) with a variety of partners. The best part about this reactant was that one could predict the 3D structure of the products for the reaction. Masamune surmised that this was made possible by hydrogen bonding interactions occurring over the course of the reaction. That's a strategy taken straight out of the enzyme's playbook.

I picked the picture because I've always been fascinated by those desk toys. If you could turn the magnet on and off at will, I think it's a pretty decent basic illustration of the concept of building 3D things from flat things.

*UPDATE 4/28/07. Apparently, "She Blinded Me with Science" is now the top hit when you try googling "masamune effect". Neat.

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3 Comments:

At 7:21 AM, Blogger Milo said...

I hope your unfortunate turn of events was not too terrible. It is amazing what will rock the boat when you are in the twilight of the graduate career.

 
At 11:35 AM, Blogger Excimer said...

From the Google...Using duel techs in which Frog physically attacks the Masamune effect still works. So use X-Slash and Spire...

Man, does that bring back memories.

 
At 10:44 AM, Anonymous Anonymous said...

if you had searchehd Masamune Diels Alder your reference would have appeared on the very top pf google... At least one of them.

i love google :)

 

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