Discovering Monoterpene Catalysis Inside Nanocapsules with Multiscale Modeling and Experiments

Efrat Pahima, Qi Zhang, Konrad Tiefenbacher, Dan T. Major

Research output: Contribution to journalArticlepeer-review

32 Scopus citations


Large-scale production of natural products, such as terpenes, presents a significant scientific and technological challenge. One promising approach to tackle this problem is chemical synthesis inside nanocapsules, although enzyme-like control of such chemistry has not yet been achieved. In order to better understand the complex chemistry inside nanocapsules, we design a multiscale nanoreactor simulation approach. The nanoreactor simulation protocol consists of hybrid quantum mechanics-molecular mechanics-based high temperature Langevin molecular dynamics simulations. Using this approach we model the tail-to-head formation of monoterpenes inside a resorcin[4]arene-based capsule (capsule I). We provide a rationale for the experimentally observed kinetics of monoterpene product formation and product distribution using capsule I, and we explain why additional stable monoterpenes, like camphene, are not observed. On the basis of the in-capsule I simulations, and mechanistic insights, we propose that feeding the capsule with pinene can yield camphene, and this proposal is verified experimentally. This suggests that the capsule may direct the dynamic reaction cascades by virtue of π-cation interactions.

Original languageEnglish
Pages (from-to)6234-6246
Number of pages13
JournalJournal of the American Chemical Society
Issue number15
StatePublished - 17 Apr 2019

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.


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