930466
HMP-alkyne
≥95%
Synonym(s):
4-Hydroxy-3-(hydroxymethyl)-N-(prop-2-yn-1-yl)benzenesulfonamide
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About This Item
Empirical Formula (Hill Notation):
C10H11NO4S
Molecular Weight:
241.26
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
description
Application: Chemoproteomics
Quality Level
Assay
≥95%
form
powder or chunks
storage temp.
−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
InChI key
FINAVIKBDSCNKL-UHFFFAOYSA-N
Application
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)
Other Notes
Profiling the proteome-wide selectivity of diverse electrophiles
A quantitative thiol reactivity profiling platform to analyze redox and electrophile reactive cysteine proteomes
Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells
A Chemoproteomic Platform To Assess Bioactivation Potential of Drugs
Inhibition of Zinc-Dependent Histone Deacetylases with a Chemically Triggered Electrophile
Reversibility of Covalent Electrophile-Protein Adducts and Chemical Toxicity
A quantitative thiol reactivity profiling platform to analyze redox and electrophile reactive cysteine proteomes
Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells
A Chemoproteomic Platform To Assess Bioactivation Potential of Drugs
Inhibition of Zinc-Dependent Histone Deacetylases with a Chemically Triggered Electrophile
Reversibility of Covalent Electrophile-Protein Adducts and Chemical Toxicity
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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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
Bengt H Gless et al.
The Journal of organic chemistry, 83(17), 10525-10534 (2018-08-07)
The one-pot synthesis and modification of cyclic peptides through a self-cleaving on-resin protocol is described. We apply Dawson's MeDbz linker to achieve direct intramolecular peptide cyclization by thioesterification followed by S → N acyl shift. This native chemical ligation approach
Yide He et al.
Talanta, 134, 468-475 (2015-01-27)
In this work, we present a two-step labeling approach for the efficient tagging with lanthanide-containing complexes. For this purpose, derivatization of the cysteine residues with an alkyne group acting as linker was done before the DOTA complex was introduced using
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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