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.
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 | DataSheet | Size | AVAILABILITY | Price | Qty |
|---|
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
- 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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