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Updated: Jul 20, 2025

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
Published on: March 6, 2019
Facile access to S-methyl dithiocarbamates with sulfonium or sulfoxonium iodide as a methylation reagent
Huiying Deng1, Lingling Xiang1, Zhijun Yuan1
1Artemisinin Research Center and The First Affiliated Hospital, Guangzhou University of Chinese Medicine, 12 Jichang Road, Guangzhou 510405, China. jingzhang@gzucm.edu.cn.
Abstract:
Efficient access to S-methyl dithiocarbamates was achieved with sulfonium or sulfoxonium iodide as a methylation reagent. This method is reliable for the synthesis of dithiocarbamates from primary or secondary amines, with sulfoxonium iodide demonstrating more robust methylation capability than sulfonium iodide. Moreover, it also enables facile access to S-trideuteromethyl dithiocarbamates via sulfoxonium metathesis between sulfoxonium iodide and DMSO-d6 with high yields.
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The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...

