ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway

Abstract

A general pathway was devised to synthesize ω-methylsulfanylalkyl glucosinolates, which represent an important class of structurally homogeneous plant secondary metabolites. The required thiofunctionalized hydroximoyl chlorides were obtained from the corresponding α,ω-nitroalkyl methylsulfide precursors, involving as the key-step, a nitronate chlorination strategy. A coupling reaction with 1-thio-beta-d-glucopyranose, followed by O-sulfation of the intermediate thiohydroximate and final deprotection of the sugar moiety afforded the target compounds.

Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

“…Additionally, such compounds could be used for the fluorescence detection of thioglucosidase‐producing bacteria. Owing to their interesting biological activities, natural GSLs have been the target of several total syntheses . Additionally, the syntheses of several artificial GSLs bearing unnatural or isotopically labeled aglycones and glucose units as well as α‐anomeric GSLs have been reported.…”

Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases

“…[11,19,20] GSLs as naturally occurring ITC-releasing molecules have therefore gained interest as intestinal formation of ITCs from GSLs is known to mediate the health beneficiary effects of Brassicales enriched dietary. [21][22][23] Considering their interesting biological activities, it is not surprising that natural [17,[24][25][26][27][28] as well as artificial GSLs have been synthesized including representatives bearing unnatural [17,28,29] or isotopically labeled [29][30][31][32][33] aglycones and glucose units as well as α-anomeric GSLs. [34,35] Furthermore, artificial GSLs have been designed to serve as myrosinase-responsive tool compounds in chemical biology.…”