Food Science and Technology Programme, Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543 , Singapore.
Food Chemistry and Molecular Sensory Science , Technische Universität München , Lise-Meitner-Straße 34 , 85354 Freising , Germany.
Org Lett. 2019 Aug 2;21(15):5977-5980. doi: 10.1021/acs.orglett.9b02117. Epub 2019 Jul 18.
Isothiocyanates are reported as HS 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-NH and raphanusamic acid (RA) as major products with formation of HS 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 HS releasing rates.
异硫氰酸酯被报道为 HS 供体，但机制尚不清楚。在此，我们报道异硫氰酸酯（ITC，R-NCS）可与半胱氨酸快速形成加合物。这些加合物进行分子内环化，随后释放有机胺 R-NH 和萝卜硫素（RA）作为主要产物，并形成 HS 和 2-碳氨酰基-4,5-二氢噻唑-4-羧酸作为次要产物。这两组产物的比例取决于 R 基团，R 基团对半胱氨酸释放速率有很大的影响。
