I'm About to Make Something Cool

Spring break is approaching, and that means projects are around the corner. First up for discussion on this blog is the project for my synthesis class. I will be synthesizing N_ε-2-(2-(2-methoxyethoxy)ethoxy)acetyl- L-Lysine-N-carboxyanhydride (see figure). [1]
I like long names for chemical species whose synthesis is actually relatively easy.[2] The only precautions are anhydrous conditions for the recrystallization of your final product and a step that needs to be done under inert atmosphere. And all the other QC controls, like not sneezing into the solution container.

The choice isn't random. The professor of the synthesis lab wants to use the N-carboxyanhydride as a monomer for poly(N_ε-2(2-(2-methoxyethoxy)ethoxy)acetyl-lysine). This homopolypeptide is α-helical in water at ambient temperature. If I remember correctly, he wants to use it as a chiral medium for other compounds in his work. Though that isn't the only application of such a polymer, as reading [1] shows.

All the products are white solids or clear oils, so the synthesis will be boring to view. But it will empower me with the ability to say: "Yes, I did a synthesis. Yes, I hated it. That's why I'm a physical chemist".


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[1] Bellomo, E.; Davidson, P.; Imperor-Clerc, M.; Deming, T. J. Am. Chem. Soc. 2004, 126, 9101-9105. DOI: 10.1021/ja047932d
[2] See the supplemental materials to Bellemo et al. above.