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Safety Information

930466

Sigma-Aldrich

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:
MFCD34704580
UNSPSC Code:
12352101
NACRES:
NA.22

description

Application: Chemoproteomics

Quality Level

100

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

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930423

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930431

SuTEx1-alkyne, ≥95%

930458

OxMet2-alkyne

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)
Romain Tessier et al.
Angewandte Chemie (International ed. in English), 59(27), 10961-10970 (2020-04-02)
Current approaches to introduce terminal alkynes for bioorthogonal reactions into biomolecules still present limitations in terms of either reactivity, selectivity, or adduct stability. We present a method for the ethynylation of cysteine residues based on the use of ethynylbenziodoxolone (EBX)
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
Ping Yu et al.
Nucleosides, nucleotides & nucleic acids, 40(7), 754-766 (2021-06-29)
We report herein comprehensive investigations of alkylation/sulfur exchange reactions of sulfur-containing substrates including nucleosides such as s2U, m5s2U, s4U, s2A and s2T-incorporated DNA enable by comprehensive screenings of the reagents (2a-2h). It has been proven that iodoacetamide (2a) displays the
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