Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Review | Regular issue | Vol 102, No. 6, 2021, pp.1061-1082
Published online, 9th November, 2020
DOI: 10.3987/REV-20-943
■ Systematic Search for Transition States in Complex Molecules: Computational Analyses of Regio- and Stereoselective Interflavan Bond Formation in Flavan-3-ols

Daisuke Urabe* and Keisuke Fukaya

*Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan

Abstract

This review describes our recent work on a systematic search for transition states in transformations of complex molecules. The method features a combination of a conformational search method using constrained models to create a large library of transition-state candidates, and subsequent density functional theory (DTF)-based transition state calculations for the candidates. The method is applicable to calculation of transition states for inter- and intramolecular interflavan bond formation in flavan-3-ols to reproduce experimental results for highly regio- and stereoselective C-C bond formation. The specific roles of van der Waals interactions in the transition states can be visualized by NCIPLOT mapping to show the importance of weak but attractive interactions for selective interflavan bond formation.