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Paper | Special issue | Vol 82, No. 2, 2010, pp.1203-1215
Published online, 20th August, 2010
DOI: 10.3987/COM-10-S(E)31
Autocatalysis and Organocatalysis with Kemp’s Triacid Compounds

Dariush Ajami, Seiji Kamioka, Aaron C. Sather, Richard J. Hooley, and Julius Rebek, Jr.*

*Department of Chemistry, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, U.S.A.

Abstract

Synthetic structures capable of autocatalysis based on molecular recognition – self-replication – were introduced nearly 20 years ago. These systems involved neither informational oligomers such as nucleic acids nor conditions that are generally regarded as prebiotic, but they revealed how self-complementary molecules could act as templates for their own formation and helped define the structure of minimalist replicators. Recent expansions in the field of organocatalysis raise the possibility that a synthetic structure might behave as an autocatalyst and function as a chemical catalyst for other reactions. We show here that these properties can be engineered into a single synthetic structure: the compound can selectively accelerate its own formation and catalyzes hydrogenation reactions of nitrostyrene. It is likely that a wide variety of synthetic structures can be modified for autocatalysis and organocatalysis.