NO2-Alkyne

NO2-alkyne is a linear C-nucleophile based chemoselective probe for detecting sulfenylated proteins.

Highlights:

  • Carbon nucleophile consisting of a (phenylsulfonyl)nitromethane warhead coupled to an alkyne moiety by a 4-atom spacer
  • (phenylsulfonyl)nitromethane group selectively and irreversibly reacts with sulfenic acid to give a stable thioether adduct (t1/2 = 5 days in 5 mM DTT)
  • Alkyne group can then be detected using azide-bearing tags by standard click chemistry
  • Shows >40-fold enhanced reactivity (compared to dimedone) towards a peptide based small molecule sulfenic acid model

Mild oxidation can convert the sulfhydryl group of cysteine residues on proteins to cysteine-sulfenic acid derivatives (Cys-SOH). Protein sulfenylation is a post-translational modification that is relevant to redox signaling. NO2-alkyne shows more than 40-fold enhanced reactivity (compared to dimedone) towards a peptide based small molecule sulfenic acid model.

From the laboratory of Kate Carroll, PhD, The Scripps Research Institute.

Catalog Number Product Size AVAILABILITY Price Qty
EST029
NO2-Alkyne, 10mg
10mg In stock
Regular Price:$205.00
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EST030
NO2-Alkyne, 25mg
25mg In stock
Regular Price:$513.00
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EST031
NO2-Alkyne, 50mg
50mg In stock
Regular Price:$820.00
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EST032
NO2-Alkyne, 100mg
100mg In stock
Regular Price:$1,538.00
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Specifications

Product Type: Small Molecule
Name: 1-((nitromethyl)sulfonyl)-3-(pent-4-yn-1-yloxy)benzene (NO2-alkyne)
Chemical Formula: C12H13NO5S
Molecular Weight: 283.3
Format: White Solid
Purity: >98%, HPLC
Solubility: Stock solution in DMSO (up to 500 mM), then dilute to appropriate concentration in aqueous buffer with final DMSO concentration <5%
Stability: >6 months at -30C
Spectral Information: 1H-NMR (400 MHz, CDCl3): δ 7.52 - 7.55 (m, 2H), 7.42 - 7.45 (m, 1H), 7.27 - 7.32 (m, 1H), 5.62 (s, 2H), 4.15 (t, 2H, J = 6.1 Hz); 2.43 (dt, 2H, J1 = 7.0 Hz, J2 = 2.6 Hz); 2.04 (p, 2H, J = 6.3 Hz), 2.01 (t, 1H, J = 2.7 Hz); 13C-NMR (in CDCl3, 100 Mhz): δ 159.8, 136.8, 131.0, 122.8, 121.5, 114.2, 90.4, 83.1, 69.5, 67.0, 28.0, 15.2. LR-MS, m/z for C12H13NO5S; Calculated: 283.30; Observed: 284.0 (M++1).
Storage: Room temperature for short-term, -30C for long term storage (light sensitive)
Shipped: Dry ice

Provider
From the laboratory of Kate Carroll, PhD, The Scripps Research Institute.
References
  1. Gupta, V. and Carroll, K. S.; Rational design of reversible and irreversible cysteine sulfenic acid-targeted linear C-nucleophiles, Chem. Commun., 52 (2016) 3414-3417.

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