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Key Documents

907243

Sigma-Aldrich

Methyl (4-bromobenzoyl)-L-cysteinate

≥95%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C11H12BrNO3S
Numero CAS:
Peso molecolare:
318.19
Codice UNSPSC:
12352101

Saggio

≥95%

Forma fisica

powder

Temperatura di conservazione

2-8°C

Applicazioni

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.

Prodotti correlati

N° Catalogo
Descrizione
Determinazione del prezzo

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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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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