A chemoselective probe for protein sulfenylation
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WYneC

Item No. 42009

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(triphenylphosphoranylidene)-5-hexyn-2-one
CAS Number
74763-44-3
Synonyms
  • Wittig-alkyne C
Molecular Formula
C24H21OP
Formula Weight
356.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mlEthanol: Sparingly soluble: 1-10 mg/ml
SMILES
O=C(CCC#C)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
InChi Code
InChI=1S/C24H21OP/c1-2-3-13-21(25)20-26(22-14-7-4-8-15-22,23-16-9-5-10-17-23)24-18-11-6-12-19-24/h1,4-12,14-20H,3,13H2
InChi Key
GZOJNGHPVJJRIK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $109

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    25 mg

    $231

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    50 mg

    $409

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    Product Description

    WYneC is a chemoselective probe for the detection of sulfenylated proteins in live cells.1,2 It is selective for a sulfenylated dipeptide over sulfinic acid- or sulfonic acid-containing dipeptides, reduced glutathione (GSH), glutathione disulfide (GSSG), and S-nitrosoglutathione (GSNO), as well as cysteine sulfinic acid and glutathione sulfonic acid, in cell-free assays.1 WYneC also selectively binds to C64,82S glutathione peroxidase 3 (GPX3) containing a sulfenic acid at Cys36 over C64,82S GPX3 containing a reduced thiol, sulfinic acid at Cys36, or an intramolecular disulfide bond in cell-free assays. It binds to sulfenylated proteins in live cells and can then be conjugated to azide-containing fluorescent probes for detection.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shi, Y., Fu, L., Yang, J., et al. Wittig reagents for chemoselective sulfenic acid ligation enables global site stoichiometry analysis and redox-controlled mitochondrial targeting. Nat. Chem. 13(11), 1140-1150 (2021).

    2. He, J.-X., Fei, Z.-C., Fu, L., et al. A modification-centric assessment tool for the performance of chemoproteomic probes. Nat. Chem. Biol. 18(8), 904-912 (2022).