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8 protocols using triethylsilane

1

Hydrosilylation of Nitro Compounds

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All the reagents and solvents were purchased from commercial companies and were used as received without further purification. Poly(methylhydro)siloxanes (PMHS I, 1700–3200 g mol−1), palladium hydroxide on carbon (30 wt% loading), silver acetate (99.0%), 4-nitrophenol (≥99.0%), sodium borohydride (≥99.0%), toluene (anhydrous, 99.8%), tetrahydrofuran (99.9%), ethyl ether (≥99.0%), calcium sulfate (drierite, 8 mesh), triethylsilane (99%) were purchased from Sigma-Aldrich. N-Methyl-aza-2,2,4-trimethylsilacyclopentane was purchased from Gelest. Celite and sodium sulfate (≥99.0%) were purchased from EMD Chemicals. Experiments referring to compounds II and III were performed under N2 protection either in an N2 glovebox or using a Schlenk line.
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2

Peptide Synthesis of GLP-1 and GLP-2 Analogs

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The GLP-1 analog liraglutide was acquired commercially (Hørsholm Pharmacy). Native GLP-1, native GLP-2, and the GLP-2 analog teduglutide were prepared by automated solid-phase peptide synthesis (SPPS) using the Fmoc/tBu strategy on pre-loaded PHB TentaGel resin (Rapp polymere GmbH, Tuebingen, Germany). The couplings were performed using Fmoc-Nα-protected amino acids, N,N-diisopropylcarbodiimide and ethyl cyanoglyoxylate-2-oxime (oxyma) in N,N-dimethylformamide (Iris Biotech GmbH, Marktredwitz, Germany) for 2 × 2 h. The N-deprotections were performed using 40% piperidine in N-methyl-2-pyrrolidione (Iris Biotech GmbH, Marktredwitz, Germany) for 3 min followed by 20% piperidine in N-methyl-2-pyrrolidione for 17 min. Finally, the peptide was simultaneously side-chain deprotected and released from the solid support by a TFA cocktail containing trifluoro acetic acid (TFA) (Iris Biotech GmbH, Marktredwitz, Germany), triethylsilane (Sigma–Aldrich, Brøndby, Denmark), and H2O (95/2.5/2.5) as scavengers for 2 h. The peptide was precipitated by the addition of diethylether (Sigma–Aldrich, Brøndby, Denmark). The peptide was purified by RP-HPLC and identified by LC-MS. The final products were obtained with >95% purity.
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3

Perovskite Solar Cell Fabrication

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The SnO2 colloidal dispersions, featuring a particle size of 3–5 nm and diluted with 15% water, were obtained from Alfa Aesar. Meanwhile, flourine–doped tin oxide (FTO) with a Rsheet of 15 Ω/sq, thickness of 600 nm, and a light transmittance of >85% was procured from Beijing Huamin New Material Technology Co., Ltd., Beijing, China. Lead iodide (PbI2), MAI, FAI, MACl, MABr, and Spiro-OMeTAD were sourced from Xi’an Shuoyuan Optoelectronic Technology Co., Ltd., Xian, China, and supporting reagents such as K2SO4, triethylsilane, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), chlorobenzene (CB), 4-tert-butylpyridine (TBP), anhydrous isopropanol (IPA), and lithium bisfluoromethane sulfonamide (Li-TFSI) were purchased from Sigma Aldrich Co., Ltd., St. Louis, MO, USA. Artemisinin was also procured from Sigma.
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4

Solid-Phase Peptide Synthesis with Fmoc-Lys(Boc) Wang Resin

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The Fmoc-Lys(Boc) Wang resin, Acetonitrile (CH3CN), acetic anhydride, N, N-dimethylformamide (DMF), diethyl ether, 2,6-Lutidine, and triethylsilane (TES) were purchased from Sigma-Aldrich (Steinheim, Germany). N-hydroxybentrizol (HOBt) and 3-hydroxytriazolo[4,5-b]pyridine (HOAt) were purchased from Advanced Biotech Italia (Milan, Italy). All the Fmoc protected amino acids (AA), (E)-(((1-Cyano-2-ethoxy-2-oxyethylene)amino)oxy)tri(pyrrolidine-1-yl)phosphonium hexafluorophosphate(V) (PyOxim), 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), and N,N,N′,N′-Tetramethyl-O-(1H-benzotriazole-1-yl)uronium hexafluorophosphate (HBTU), were purchased from Novabiochem (Merck KGaA, Darmstadt, Germany). Trifluoroacetic acid (TFA), N-methyl-2-pyrrolidone (NMP), piperidine, N, N-Diisopropylethylamine (DIPEA), and Dichloromethane were purchased from Biosolve Chimie (Valkenswaard, The Netherlands).
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5

Quantification of Grape Polyphenols

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L-Glutathione (reduced), glutathione oxidized, L-methionine, trans-2-hexenal, acetonitrile, sodium borohydride (NaBH4), ethanol, N-(tert-butoxycarbonyl)-L-cysteine (Boc-Cys-OH), triethylamine, sodium sulfate, triethylsilane, trifluoroacetic acid, 4-methylpent-3-en-2-one (mesityl oxide), mesityl oxide-d10, sodium carbonate, acetic acid, hydrochloric acid, (+)-catechin, (−)-epicatechin, (−)-epicatechin gallate, procyanidin B1 and procyanidn B2 were obtained from Sigma-Aldrich (St. Louis, MO, USA). Diethyl ether, pyridine, dichloromethane, 1,4-dioxane, pentane and ethyl acetate were obtained from Merck (Darmstadt, Germany). Formic acid (LC-MS, Fluka), methanol (LC-MS, Chromasolv, Sigma-Aldrich) and ultra-pure water of Milli Q gradient (EMD Millipore, Billerica, MA, USA) were used for chromatography. For grape grinding under cryogenic conditions (−196 °C) a M20 mill from IKA (Staufen, Germany) was used.
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6

Solid-Phase Peptide Synthesis

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N-α-Fmoc–protected amino acids, Rink Amide MBHA resin (0.078 mmol/g loading), and benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (PYBOP) were purchased from Novabiochem (San Diego, CA, USA). Dimethylformamide (DMF), 1,2-dichloromethane (DCM), N,N-diisopropylethylamine (DIPEA), trifluoroacetic acid (TFA), triisopropylsilane (TIS), triethylsilane (TES), piperidine, and 5(6)-carboxytetramethylrhodamine (TAMRA) were purchased from Sigma-Aldrich (St. Louis, MO, USA). n-Hexane and diethyl ether were purchased from Daejung (Siheung, Gyeonggi, Korea).
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7

Solid-Phase Peptide Synthesis Methodology

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Acetic acid, acetone, acetonitrile, Fmoc protected Amino acids, Bis-Boc-aminooxy acetic acid (Aoa), Dichloromethane (DCM), N,N-Diisopropylethylamine (DIPEA), N,N-dimethylformamide (DMF), Ethyl cyano(hydroxyimino)acetate (Oxyma Pure), Methanol, Rink-Amide MBHA resin, Triethylamine (TEA), Triethylsilane (TES), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoro phosphate (HBTU) were purchased from Merck Millipore (Burlington, MA, USA). Diethyl ether, Trifluoroacetin acid (TFA) were purchased from Biosolve (Valkenswaard, Holland). 2-Proponal for HPLC (aldehyde and ketone free) was purchased from PanReac AppliChem (Darmstadt, Germany). Ethanol was purchased from Carlo Erba (Milan, Italy). N-Methyl-2-pyrrolidone (NMP) was purchased from Iris Biotech GmbH (Marktredwitz, Germany).
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8

Solid-Phase Peptide Synthesis Protocol

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The solid support resin Rink Amide MBHA, the Fmoc protected amino acids, the coupling reagents 2-(1H - Benzotriazole-1-yl) −1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU), ethyl cyano(hydroxyimino)acetate (oxyma pure), N,N-diisopropylethylamine (DIEA), triethylsilane (TES), N,N-dimethylformamide (DMF) and piperidine were from 10.13039/100009945Merck KGaA, (Darmstadt, Germany). Trifluoroacetic acid (TFA), diethyl ether and dichloromethane (DCM) were from Biosolve (Leenderweg, Valkenswaard, Netherlands). Acetonitrile was from Carlo Erba (Milan, Italy). N-methyl-2-pyrrolidone (NMP) was purchased by Iris Biotech GmbH (Halle, Germany).
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