Ethanedithiol

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester (DBCO-NHS), N-Hydroxysuccinimide (NHS), barium hydroxide, and ethanedithiol were purchased from Sigma Aldrich. 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), (succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate) (SMCC), NHS-PEG4-Azide, and Phosphate buffered saline (PBS, 137 mM NaCl, 2.7 mM KCl, 10 mM phosphate buffer, pH 7.4) were purchased from Thermo Fisher Scientific. The carboxylated silica beads (3 μm) were purchased from Microspheres-Nanospheres. Biotin-modified reverse primer, BsaI-restriction site included forward primer and other DNA oligonucleotides (see sequences in Supplementary Table 1) were purchased from Integrated DNA Technologies (IDT). The pET-26b (+) plasmid was received from EMD Millipore Sigma. All synthetic peptides were purchased from GenScript. Noxa BH3 peptide was purchased from Anaspec. (See sequences in Supplementary Table 2).

Unless otherwise stated, ACS reagent grade chemicals and solvents were purchased from Sigma-Aldrich and used without further purification. Tetrahydrofuran was collected from a dry solvent system and used immediately thereafter. Allyl glycidyl ether was purchased from TCI-America, Inc., degassed by freeze–pump–thaw, and distilled onto butylmagnesium chloride (Sigma-Aldrich), where it was stirred for 10 min at 0 °C and distilled to a buret for use. Potassium naphthalenide was prepared from potassium metal and recrystallized naphthalene in dry THF and allowed to stir with a glass-coated stir bar for 24 h at room temperature before use. Triethylsilane and tris(pentafluorophenyl)borane were purchased from Gelest. 2,2-Dimethoxy-2-phenylacetophenone (99%), eugenol, ethane dithiol, ethylene oxide (99.5%+), and poly(ethylene oxide) were purchased from Sigma-Aldrich. Deuterated solvents for NMR were purchased from Cambridge Isotope Laboratories, Inc.