Alkyne-phenol

• CAT Number: I045460
• CAS Number: 1694495-59-4
• Molecular Formula: C13H15NO2
• Molecular Weight: 217.26
• Purity: ≥95%
• Synonyms: N-[2-(4-hydroxyphenyl)ethyl]pent-4-ynamide
• InChI: InChI=1S/C13H15NO2/c1-2-3-4-13(16)14-10-9-11-5-7-12(15)8-6-11/h1,5-8,15H,3-4,9-10H2,(H,14,16)
• InChIKey: CQZJBJSXQYZLEX-UHFFFAOYSA-N
• SMILES: C#CCCC(=O)NCCC1=CC=C(C=C1)O

Alkyne-phenol (Alk-Ph) is a clickable ascorbate peroxidase 2 (APEX2) probe. Alkyne-phenol substantially improves APEX-labeling efficiency in intact yeast cells, as it is more cell wall-permeant than APEX2 substrate biotin-phenol (BP). Alkyne-phenol also facilitates the identification of APEX-labeling sites, allowing the unambiguous assignment of membrane topology of mitochondrial proteins[1]. Alkyne-phenol is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Yeast cells expressing Su9-APEX2 are incubated with each probe at 2.5 mM final concentration for half an hour, and the labeling reaction is initiated by the addition of 1 mM H2O2. Alkyne-phenol is the most reactive APEX2 substrate for labeling the yeast proteome[1].
APEX2-mediated Alkyne-phenol labeling in the yeast mitochondria is more effective at probe concentrations above 1 mM[1]. Alkyne-phenol enables proteomic profiling in the mitochondrial matrix of intact yeast cells with exceptionally high specificity (94%), and offers higher coverage than the traditional APEX2 substrate biotin-phenol (BP)[1].

Reference

[1]. Li Y, et al. A Clickable APEX Probe for Proximity-Dependent Proteomic Profiling in Yeast. Cell Chem Biol. 2020;27(7):858-865.e8.
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