- Carmine, A.; Domoto, Y.; Sakai, N.; Matile, S. “Comparison of Lipoic and Asparagusic Acid for Surface-Initiated Disulfide-Exchange Polymerization” Chem. Eur. J. 2013, 19, 11558-11563
Bring it on: Organic chemistry on surfaces and in solution is not the same; this study offers a perfect example, with small changes (from 27 to 35°; see graphic) and big consequences. Strained cyclic disulfides from asparagusic, but not lipoic acid, are ideal for growing functional architectures directly on surfaces; for the substrate-initiated synthesis of cell-penetrating poly(disulfide)s in solution, exactly the contrary is true.