A couple of months ago, Rory and Aiden and I agreed to try to post periodic entries about research published by Williams faculty, students, and alumni. A new blog category, Rephsearch, was created. As the scientist of the group, I was to cover the sciences (and math, I suppose). I was given EphBlog author status, which I test-drove with a silly entry about my son (What every Eph golfer needs?). And now I’m finally ready to offer my first bit of “rephsearch.”

Here are the citations, with links to the abstracts:
Green, enzymatic syntheses of divanillin and diapocynin for the organic, biochemistry, or advanced general chemistry laboratory, Nishimura, R.T.; Giammanco, C.H.; Vosburg, D.A. Journal of Chemical Education 2010, 87, 526-527.
A green, enantioselective synthesis of warfarin for the undergraduate organic laboratory, Wong, T.C.; Sultana, C.M.; Vosburg, D.A. Journal of Chemical Education 2010, 87, 194-195.

This pair of papers comes to us from Dave Vosburg ’97, who is an Assistant Professor of Chemistry at Harvey Mudd College. The papers’ common theme is green (i.e., environmentally benign) chemistry. In Dave’s words, “The general idea in these experiments is to apply environmentally friendly methods to the preparation of useful and recognizable molecules in an undergraduate setting.” He adds:

The warfarin that is used in rat poison and is prescribed as a blood-thinner (including to President Eisenhower) is racemic, or a mixture of the right- and left-handed forms. We adapted a new procedure that can selectively form either the right- or left-handed form selectively. Basically, in this experiment undergrads can easily make “better” warfarin than what you could get from a pharmacist. Sometimes my students ask if they can sell the warfarin that they make in this experiment, but they aren’t too sad when I tell them no. Faculty at several other schools have inquired with me about using this experiment, which is exciting.

Vanillin is extremely popular in foods and fragrances. Divanillin, a molecule formed by connecting two molecules of vanillin to each other, can enhance many of the flavoring properties of vanillin. There are a variety of ways to produce divanillin, including the use of rather toxic inorganic oxidants. A milder and greener procedure uses the enzyme horseradish peroxidase and dilute hydrogen peroxide. The reaction is performed in water, the only byproduct formed is water, and the product spectacularly crashes out of solution almost instantly. And it smells great, too.

Congrats to Dave for getting both of these papers published, and thanks to him for taking the time to discuss them with me!

Print  •  Email