Cysteine thiol probe

Cysteine Thiol Probe is a thiol-based probe designed to label electrophilic natural products. Cysteine Thiol Probe possesses each of the characteristics of an ideal pharmacophore probe, and has a chromophore. Cysteine Thiol Probe is capable of engaging enone-, β-lactam-, and β-lactone-based electrophilic metabolites[1][2].

Research Areas >> Others

Signaling Pathways >> Others >> Others

Cysteine Thiol Probe (Probe 1) reacts much more readily with β-lactam- and β-lactone-based electrophilic natural products, and its reactivity with epoxide-based electrophilic natural products is poor. And probe 2 reacts much faster with epoxide-containing natural products. This orthogonal reactivity allows them to be employed in extracts simultaneously. Since Cysteine Thiol Probe is brominated and probe 2 is chlorinated, the isotopic patterns of labeled natural products point toward their structural origin. Competition experiments using Cysteine Thiol Probe and 2 indicated that brominated Cysteine Thiol Probe reacted exclusively with the β-lactam in penicillin G and the β-lactone in salinosporamide A while chlorinated probe 2 alone reacted with the epoxide in salinamide A[1].

[1]. Castro-Falcón G, et al. Thiol Probes To Detect Electrophilic Natural Products Based on Their Mechanism of Action. ACS Chem Biol. 2016 Aug 19;11(8):2328-36.

[2]. Reimer D, et al. Thiol-Based Probe for Electrophilic Natural Products Reveals That Most of the Ammosamides Are Artifacts. J Nat Prod. 2017 Jan 27;80(1):126-133.