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6 protocols using anhydrous solvents

1

Isotopic Labeling of Biomolecules

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Triethyl orthoformate, ethyl cyanoacetate, diethyl malonate, sodium metal, lithium aluminum hydride solution, triethylamine, potassium persulfate, silver nitrate, and 15N2-urea were obtained from Sigma-Aldrich (St. Louis, MO). Potassium perruthenate, paraformaldehyde, N-tert-butyldimethylsilyl-N-methyltrifluoroacetamide + 1% tert-butyldimetheylchlorosilane (MTBSTFA + 1% TBDMCS), reagent grade solvents, and anhydrous solvents were purchased from Fisher Scientific (Pittsburgh, PA). 15N2-Orotic acid, 2H4-thymine, DMSO-d6, and methanol-d4 were purchased from Cambridge Isotope Laboratory (Cambridge, MA). 2H4-5-methylcytosine and 2H2-cytosine were obtained from CDN Isotopes (Quebec, Canada). 15N2-uracil was purchased from Euriso-top (Saint-Aubin, France).
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2

Synthesis of Sunitinib Analogs

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All solvents and reagents were obtained from commercial suppliers and used without further purification. Anhydrous solvents were bought from Fisher Scientific GmbH (Austria) over molecular sieves. Sunitinib was purchased from LC Laboratories®, Nϵ‐allyloxycarbonyl‐l‐lysine from Chem‐Impex International, Inc., and morpholin‐4‐yl‐acetic acid from Activate Scientific GmbH.
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3

Synthesis of Substituted Pyridines

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4-amino-3-hydroxypyridine and 4-amino-3-methoxypyridine were purchased from Astatech (cat# 22383 and 35474). Anhydrous solvents were purchased from Acros Organics. All other chemicals were purchased from Sigma.
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4

Perovskite Solar Cell Fabrication

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Unless otherwise stated, all materials were purchased from Sigma-Aldrich or Alfa Aesar and used as received. Perovskite films and devices were fabricated using PbI2 and PbBr2 (99.99% purity) purchased from TCI, organic halide salts were purchased from GreatCell Solar, and cesium iodide (99.99% purity) was purchased from Alfa Aesar. The poly(triaryl amine) (PTAA) was purchased from Sigma-Aldrich. The PC61BM was purchased from Solenne. The bathocuproine (BCP; sublimed grade, 99.99% purity) was purchased from Sigma-Aldrich. All the anhydrous solvents were purchased from Acros Organics.
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5

Sourcing of Organic Reagents and Solvents

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All organic reagents were used as received from Sigma-Aldrich (St. Louis, Missouri, USA), Acros Organics (Geel, Belgium) and Fluka (Buchs, Switzerland). Solvents were purchased from Acros Organics, Pro-Labo (Tokyo, Japan), Fluka, and Sigma-Aldrich. Anhydrous solvents were obtained from Acros Organics.
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6

NanoBRET Assay for CBH-001 Evaluation

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All solvents were purchased of HPLC grade from commercial suppliers (Sigma, Thermo Fisher) and used without further purification. Anhydrous solvents were purchased from Acros Organics and stored under a nitrogen atmosphere with activated molecular sieves. CBH-001 was purchased from Enamine. NanoBRET 590 SE, NanoBRET™ Nano-Glo® Detection System and CellTiter-Glo® Luminescent Cell Viability Assay was purchased from Promega.
Reaction progress was monitored by TLC (Thin Layer Chromatography) and LC-MS. For the silica gel TLC, aluminium plates coated with 0.25 mm 60F254 silica gel (Merck) were used and visualized with UV light at l = 254 nm or l = 365 nm.
1H NMR spectra were recorded using a Bruker Avance 400 MHz spectrometer (400 MHz) and the deuterated solvent stated. Chemical shifts (δ) are quoted in parts per million (ppm) and referenced to the residual solvent peak. Multiplicities are denoted as singlet (s), doublet (d), triplet (t), quartet (q) and quintet (p) and derivatives thereof and multiplets (m). (br) denotes a broad resonance peak.
Coupling constants are recorded as Hz and rounded to the nearest 0.1 Hz. Spectra were analysed using MestreNova 14. Compound names were generated using ChemBioDraw Ultra v19.0 systematic naming.
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