Discovering Monoterpene Catalysis Inside Nanocapsules with Multiscale Modeling and Experiments

Pahima, Efrat and Zhang, Qi and Tiefenbacher, Konrad K. and Major, Dan T.. (2019) Discovering Monoterpene Catalysis Inside Nanocapsules with Multiscale Modeling and Experiments. Journal of the American Chemical Society, 141 (15). pp. 6234-6246 .

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Official URL: https://edoc.unibas.ch/75132/

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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.
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie > Synthesis of Functional Modules (Tiefenbacher)
UniBasel Contributors:Zhang, Qi and Tiefenbacher, Konrad Karl
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
Note:Publication type according to Uni Basel Research Database: Journal article
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edoc DOI:
Last Modified:09 Jun 2020 10:37
Deposited On:21 Feb 2020 13:03

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