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Merck

930466

Sigma-Aldrich

HMP-alkyne

≥95%

Synonym(e):

4-Hydroxy-3-(hydroxymethyl)-N-(prop-2-yn-1-yl)benzenesulfonamide

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About This Item

Empirische Formel (Hill-System):
C10H11NO4S
Molekulargewicht:
241.26
MDL-Nummer:
UNSPSC-Code:
12352101
NACRES:
NA.22

Beschreibung

Application: Chemoproteomics

Qualitätsniveau

Assay

≥95%

Form

powder or chunks

Lagertemp.

−20°C

SMILES String

OCC1=C(O)C=CC(S(NCC#C)(=O)=O)=C1

InChI

1S/C10H11NO4S/c1-2-5-11-16(14,15)9-3-4-10(13)8(6-9)7-12/h1,3-4,6,11-13H,5,7H2

InChIKey

FINAVIKBDSCNKL-UHFFFAOYSA-N

Anwendung

HMP-alkyne is a probe that can be used to photochemically label tryptophans. A method was developed using cysteine-reactive compounds including this one to allow for unbiased analysis of proteomic data in quantitative applications (Zanon et al. 2021). The method uses light or heavy labeling with the isotopically labelled desthiobiotin azide (isoDTB) tag for mass spectrometry analysis (Zanon et al. 2020). Analysis then uses the isotopic tandem orthogonal proteolysis activity-based protein profiling (isoTOP-ABPP) workflow (Weerapana et al. 2010, Backus et al. 2016)

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Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Profiling the proteome-wide selectivity of diverse electrophiles
Zanon P R A, et al.
ChemRxiv : the preprint server for chemistry (2021)
Zarko V Boskovic et al.
ACS chemical biology, 11(7), 1844-1851 (2016-04-12)
Unbiased binding assays involving small-molecule microarrays were used to identify compounds that display unique patterns of selectivity among members of the zinc-dependent histone deacetylase family of enzymes. A novel, hydroxyquinoline-containing compound, BRD4354, was shown to preferentially inhibit activity of HDAC5
De Lin et al.
Chemical research in toxicology, 21(12), 2361-2369 (2009-06-24)
The biotin-tagged electrophiles 1-biotinamido-4-(4'-[maleimidoethylcyclohexane]-carboxamido)butane (BMCC) and N-iodoacetyl-N-biotinylhexylenediamine (IAB) have been used as model electrophile probes in complex proteomes to identify protein targets associated with chemical toxicity. Whereas IAB activates stress signaling and apoptosis in HEK293 cells, BMCC does not. Cysteine
A H El-Khatib et al.
Journal of mass spectrometry : JMS, 52(8), 543-549 (2017-06-04)
1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) derivatives are applied in quantitative proteomics owing to their ability to react with different functional groups, to harbor lanthanoides and hence their compatibility with molecular and elemental mass spectrometry. The new DOTA derivatives, namely Ln-MeCAT-Click and Ln-DOTA-Dimedone
Rui Sun et al.
Chemical research in toxicology, 30(10), 1797-1803 (2017-09-30)
Reactive metabolites (RM) formed from bioactivation of drugs can covalently modify liver proteins and cause mechanism-based inactivation of major cytochrome P450 (CYP450) enzymes. Risk of bioactivation of a test compound is routinely examined as part of lead optimization efforts in

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