CN-Alkyne

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

Highlights:

  • Carbon nucleophile consisting of a (phenylsulfonyl)acetonitrile warhead coupled to an alkyne moiety by a 4-atom spacer
  • (phenylsulfonyl)acetonitrile group selectively and reversibly reacts with sulfenic acid to give a thioether adduct (t1/2 = 20 min in 5 mM DTT)
  • Alkyne group can then be detected using azide-bearing tags by standard click chemistry
  • Shows >150-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. CN-alkyne shows more than 150-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
EST025
CN-Alkyne, 10mg
10mg Temporarily on hold
Regular Price:$205.00
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EST026
CN-Alkyne, 25mg
25mg Temporarily on hold
Regular Price:$513.00
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EST027
CN-Alkyne, 50mg
50mg Temporarily on hold
Regular Price:$820.00
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EST028
CN-Alkyne, 100mg
100mg Temporarily on hold
Regular Price:$1,538.00
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Specifications

Product Type: Small Molecule
Name: 2-((3-(pent-4-yn-1-yloxy)phenyl)sulfonyl)-acetonitrile (CN-alkyne)
Chemical Formula: C13H13NO3S
Molecular Weight: 263.3
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 7.59 ? 7.63 (m, 1H), 7.53 ? 7.58 (t, 1H, J = 8.0 Hz), 7.50 ? 7.52 (m, 1H), 7.27 ? 7.31 (m, 1H), 4.18 (t, 2H, J = 6.1 Hz); 4.07 (s, 2H), 2.44 (dt, 2H, J 1 = 7.0 Hz, J 2 = 2.6 Hz), 2.05 (p, 2H, J = 6.2 Hz), 2.01 (t, 1H, J = 2.7 Hz); 13C-NMR (in CDCl3, 100 Mhz): δ 159.9, 137.9, 131.1, 122.6, 121.1, 113.8, 110.6, 83.1, 69.5, 67.1, 45.9, 28.0, 15.3. LR-MS, m/z for C13H13NO3S; Calculated: 263.31; Observed: 264.1 (M++1).
Storage: Room temperature for short-term, -30C for long term storage.
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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