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.

Product information

CAS Number: 1947408-74-3

Molecular Weight: 318.19

Formula: C11H12BrNO3S

Chemical Name: methyl (2R)-2-[(4-bromophenyl)formamido]-3-sulfanylpropanoate

Smiles: COC(=O)[C@H](CS)NC(=O)C1C=CC(Br)=CC=1

InChiKey: QLAHQHTYCQKQLI-VIFPVBQESA-N

InChi: InChI=1S/C11H12BrNO3S/c1-16-11(15)9(6-17)13-10(14)7-2-4-8(12)5-3-7/h2-5,9,17H,6H2,1H3,(H,13,14)/t9-/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 250 mg/mL (785.69 mM; Need ultrasonic).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

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.

References:

1. Castro-Falcon 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.

Products are for research use only. Not for human use.