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Molecules 2017, 22(1), 19; doi:10.3390/molecules22010019

Modeling of the Bioactivation of an Organic Nitrate by a Thiol to Form a Thionitrate Intermediate

1
Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8551, Japan
2
Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Shunichi Fukuzumi
Received: 22 November 2016 / Revised: 20 December 2016 / Accepted: 23 December 2016 / Published: 25 December 2016
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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Abstract

Thionitrates (R–SNO2) have been proposed as key intermediates in the biotransformation of organic nitrates that have been used for the clinical treatment of angina pectoris for over 100 years. It has been proposed and widely accepted that a thiol would react with an organic nitrate to afford a thionitrate intermediate. However, there has been no example of an experimental demonstration of this elementary chemical process in organic systems. Herein, we report that aryl- and primary-alkyl-substituted thionitrates were successfully synthesized by the reaction of the corresponding lithium thiolates with organic nitrates by taking advantage of cavity-shaped substituents. The structure of a primary-alkyl-substituted thionitrate was unambiguously established by X-ray crystallographic analysis. View Full-Text
Keywords: thionitrates; reactive intermediates; kinetic stabilization; organic nitrates; nitric oxide; biotransformation; X-ray crystallographic analysis thionitrates; reactive intermediates; kinetic stabilization; organic nitrates; nitric oxide; biotransformation; X-ray crystallographic analysis
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Sano, T.; Shimada, K.; Aoki, Y.; Kawashima, T.; Sase, S.; Goto, K. Modeling of the Bioactivation of an Organic Nitrate by a Thiol to Form a Thionitrate Intermediate. Molecules 2017, 22, 19.

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