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907243

Sigma-Aldrich

Methyl (4-bromobenzoyl)-L-cysteinate

≥95%

Synonym(s):

Chemoselective thiol probe for detection of electrophilic metabolites, Cysteine thiol probe, Pharmacophore probe for electrophilic natural products

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About This Item

Empirical Formula (Hill Notation):
C11H12BrNO3S
CAS Number:
1947408-74-3
Molecular Weight:
318.19
UNSPSC Code:
12352101

Assay

≥95%

form

powder

storage temp.

2-8°C

Application

Methyl (4-bromobenzoyl)-L-cysteinate is a chemoselective thiol probe for detection of electrophilic metabolites. As it is often difficult to isolate low-abundance natural products from extracts, metabolities with bioactivity or therapeutic potential may be missed. Castro-Falcón, et al developed a reactivity-guided approach using thiolate probes to discover electrophilic natural products - a cysteine-based probe and thiophenol-based probe. Both consist of
  • A chemoselective reagent for covalent reactivity with a pharmacophore,
  • A conspicuous UV/VIS or mass spectrometric (MS) tag,
  • A linker between the tag and reagent. Methyl (4-bromobenzoyl)-L-cysteinate contains a bromine MS tag and phenyl bromide UV tag that was demonstrated to chemoselectively label enone-, β-lactam-, and β-lactone-based natural products.

Complementarily, a thiophenol probe (cat# 125237) with a chlorine MS tag and phenyl chloride UV tag labeled epoxide-based natural products. These probes can be used in diverse extracts (bacterial, fungal, plant) to chemically faciliate access to high-value metabolites.

Other Notes

Thiol Probes To Detect Electrophilic Natural Products Based on Their Mechanism of Action

Thiol-Based Probe for Electrophilic Natural Products Reveals That Most of the Ammosamides Are Artifacts

Neolymphostin A Is a Covalent Phosphoinositide 3-Kinase (PI3K)/ Mammalian Target of Rapamycin (mTOR) Dual Inhibitor That Employs an Unusual Electrophilic Vinylogous Ester

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

907243-100MG:
907243-BULK:
907243-VAR:

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Daniela Reimer et al.
Journal of natural products, 80(1), 126-133 (2017-01-06)
To date, 16 members of the ammosamide family of natural products have been discovered, and except for ammosamide D each of these metabolites is characterized by an unusual chlorinated pyrrolo[4,3,2-de]quinoline skeleton. Several ammosamides have been shown to inhibit quinone reductase
Gabriel Castro-Falcón et al.
ACS chemical biology, 11(8), 2328-2336 (2016-06-14)
New methods are urgently needed to find novel natural products as structural leads for the development of new drugs against emerging diseases such as cancer and multiresistant bacterial infections. Here we introduce a reactivity-guided drug discovery approach for electrophilic natural
Gabriel Castro-Falcón et al.
Journal of medicinal chemistry (2018-11-02)
Using a novel chemistry-based assay for identifying electrophilic natural products in unprocessed extracts, we identified the PI3-kinase/mTOR dual inhibitor neolymphostin A from Salinispora arenicola CNY-486. The method further showed that the vinylogous ester substituent on the neolymphostin core was the

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