Isothiocyanates as H2S Donors Triggered by Cysteine: Reaction Mechanism and Structure and Activity Relationship

Yi Lin; Xin Yang; Yuyun Lu; Dong Liang; Dejian Huang

doi:10.1021/acs.orglett.9b02117

Isothiocyanates as H₂S Donors Triggered by Cysteine: Reaction Mechanism and Structure and Activity Relationship

Org Lett. 2019 Aug 2;21(15):5977-5980. doi: 10.1021/acs.orglett.9b02117. Epub 2019 Jul 18.

Authors

Yi Lin¹, Xin Yang¹, Yuyun Lu¹, Dong Liang², Dejian Huang^{1

3}

Affiliations

¹ Food Science and Technology Programme, Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543 , Singapore.
² Food Chemistry and Molecular Sensory Science , Technische Universität München , Lise-Meitner-Straße 34 , 85354 Freising , Germany.
³ National University of Singapore (Suzhou) Research Institute , 377 Lin Quan Street , Suzhou Industrial Park , Jiangsu 215123 , China.

PMID: 31318571
DOI: 10.1021/acs.orglett.9b02117

Abstract

Isothiocyanates are reported as H₂S donors, yet the mechanisms are not clear. Herein, we reported that isothiocyanates (ITCs, R-NCS) rapidly formed adducts with cysteine. These adducts underwent intramolecular cyclization followed by releasing organic amine R-NH₂ and raphanusamic acid (RA) as major products with formation of H₂S and 2-carbylamino-4,5-dihydrothiazole-4-carboxylic acids as minor products. The ratios of the two groups of products are dependent on the R groups which have strong impact on H₂S releasing rates.

Publication types

Research Support, Non-U.S. Gov't