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Triisopropylsilane tips

Manufactured by Thermo Fisher Scientific
Sourced in United States

Triisopropylsilane (TIPS) is a widely used silylating agent in organic synthesis. It is a colorless, volatile liquid with a characteristic odor. TIPS is commonly employed as a protecting group for alcohols and other hydroxyl-containing functional groups during synthetic reactions.

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8 protocols using triisopropylsilane tips

1

Synthetic Peptide Protocol Using Grubbs' Catalyst

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Trifluoracetic acid (TFA), N,N-diisopropylethylamine (DIPEA), O-(6-chloro-1-hydrocibenzotrizol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HCTU), dichloroethane, first-generation Grubbs' reagent, phenol, triisopropylsilane (TIPS), and diethyl ether were purchased from Acros, TCI, Adamas. All Fmoc-protected amino acids were bought from GL Biochem Shanghai Co. Ltd. Rink amide resin (loading 0.15 mmol/g) was purchased from Tianjin Nankai Hecheng S&T Co., Ltd. Dichloromethane (DCM), dichloroethane (DCE), N,N-dimethylformamide (DMF), and acetonitrile used were bought from Sinopharm Chemical Reagent Co. Ltd. Peptides were analyzed and purified by reverse phase high-performance liquid chromatography (HPLC) (RP-HPLC, Shimadzu) using C18 column. The solvent systems were buffer A (0.1% TFA in CH3CN) and buffer B (0.1% TFA in water). High-resolution mass spectra (HR-MS) were measured on a Waters Xevo G2 QTOF mass spectrometer. Circular dichroism data were recorded using a JASCO J-820 spectropolarimeter (JASCO Corp., Ltd).
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2

Solid-Phase Peptide Synthesis Protocol

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2-Chlorotrityl resin, O-benzotriazole-N,N,N,N′-tetramethyl-uronium-hexafluoro-phosphate (HBTU), and Fmoc-protected amino acids were purchased from GL Biochem (Shanghai, China) Ltd. All solvents were purchased of analytical grade from Merck. Piperidine, trifluoroacetic acid (TFA), N,N-diisopropyl ethyl amine (DIPEA), and triisopropyl silane (TIPS) were from Acros (Milan, Italy). Sodium dihydrogen phosphate and disodium hydrogen phosphate were from BDH AnalaR (Milan, Italy). High-purity Milli-Q-water (MQ water) with a resistivity greater than 18 MΩ·cm was obtained from an in-line Millipore RiOs/Origin system.
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3

Peptide Synthesis and Characterization

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The following reagents were purchased from commercial vendors (Fisher Scientific (Waltham, MA, USA) or Sigma Aldrich (St. Louis, MO, USA)) and used without further purification: guanosine (Fisher Scientific), p-toluenesulfonic acid (Fisher Scientific), 2,2-dimethoxypropane (Fisher Scientific), acetone, (Fisher Scientific), 2,2,6,6,-tetramethyl-1-piperidinyloxyl (Fisher Scientific), [bis(acetoxy-iodo]benzene (Fisher Scientific), dimethylformamide (Fisher Scientific), Fmoc-Phe wang resin (Fisher Scientific), N,N,N′,N′-tetremethyl-O-(1H-benzotriazol-1-yl)uranium hexafluorophosphate (HBTU) (TCI America, Tokyo, Japan), fluorenylmethyloxycarbonyl (Fmoc) protected amino acids (Chem-Impex Int., Inc., Wood Dale, IL, USA), N-methylmorpholine (Fisher Scientific), dichloromethane (Fisher Scientific), N,N′-diisopropylcarbodiimide (DIC) (Fisher Scientific), ethyl cyano(hydroxylmino)acetate (Oxyma Pure) (Sigma Aldrich), trifluoroacetic acid (TFA) (Fisher Scientific), triisopropylsilane (TIPS) (Fisher Scientific), diethyl ether (Fisher Scientific), acetonitrile (Fisher Scientific), alpha-cyano-4-hydroxycinnamic acid (CHCA) (Ricca Chemical, Arlington, TX, USA), 4% uranyl acetate solution (Electron Microscopy Sciences). All water used to prepare assembly solutions was 18.2 MΩ ultrapurified water.
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4

Synthesis and Evaluation of Cabazitaxel-PEG Conjugates

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Cabazitaxel and PEG-NHS were purchased from LC Laboratories (Woburn, MA). PEG3000-Cholesterol was purchased from Biochempeg (Watertown, MA). Human recombinant MMP-2 protein was obtained from Millipore Sigma (Burlington, MA). α,γ-Di-tert-butyl glutamate, and triphosgene were purchased from Alfa Aesar(Haverhill, MA). N,N-Diisopropylethylamine (DIPEA), trifluoroacetic acid (TFA), triethylamine, triisopropylsilane (TIPS), HATU, HCTU, and piperidine were ordered from Fisher Scientific (Hampton, NH). Peptides were synthesized by United BioSystems (Herndon, VA). C4–2 cell line was purchased from the American Type Culture Collection (Rockville, MD).
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5

Synthesis and Characterization of c(RGDfC) Peptide

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Ultrapure water (Mili-Q, r > 18 MΩ·cm) was used in all the experiments. Acetonitrile (ACN), acetic acid (AcOH), dicholoromethane (DCM), diethyl ether (Et2O), dimethylformamide (DMF), chloroform (CHCl3), and methanol (MeOH) were obtained from Sigma-Aldrich (Saint-Quentin Fallavier, France) and were used without further purification.
The synthesis of c(RGDfC) peptide required N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) (Iris Biotech GmbH, Germany) and acetic anhydride (Sigma-Aldrich, Saint-Quentin Fallavier, France), and N–methylmorpholine (NMM), N–methylpyrrolidinone (NMP), N,N-diisopropylethylamine (DIPEA), piperidine and tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (Alfa Aesar, Haverhill, MA, USA) as reagents. Fmoc–L–Asp–OAll, Fmoc–Gly–OH, Fmoc–L–Arg(Pbf)–OH, Fmoc–L–Cys (Trt)–OH, Fmoc–D–Phe–OH and 2CTC resin (2-chlorotrityl chloride resin, 100–200 mesh, 1.0–2.0 mmol/g loading) were obtained from Iris Biotech GmbH (Marktredwitz, Germany). Trifluoroacetic acid (TFA) was purchased from Sigma-Aldrich (Saint-Quentin Fallavier, France) and triisopropylsilane (TIPS) from Alfa Aesar (Haverhill, MA, USA).
The synthesis of DSPE-PEG5000-c(RGDfC) required DSPE-PEG5000-Mal (≥95%, Biochempeg Scientific Inc., Watertown, MA, USA), and phosphate-buffered saline (pH 7.4) and 1 kDa dialysis membrane (Sigma-Aldrich, Saint-Quentin Fallavier, France).
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6

High-Throughput SrtA Inhibition Assay

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𝛽-LG, tris (hydroxymethyl) aminomethane (Tris) hydrochloride, TC, QC, BR, CUR, resazurin, agar, methanol (MeOH), ethanol (EtOH), sodium dodecyl sulfate (SDS), hydrochloric acid (HCl), Mueller—Hinton broth (MHB), and dimethylsulfoxide (DMSO) were purchased from Merck (Castle Hill, NSW, Australia). Propylene glycol liquid (USP) was purchased from the Melbourne Food Ingredient Depot (Melbourne, VIC, Australia). Triton X-100, CaCl2 and NaCl were purchased from Chem-Supply (Gillman, SA, Australia). Triisopropylsilane (TIPS) was purchased from Alfa Aesar (Tewksbury, MA, USA). The SrtAΔN59 enzyme was expressed and purified as previously described [4 (link)]. Dulbecco’s modified eagle medium (DMEM), fetal bovine serum (FBS), and penicillin/streptomycin were purchased from Thermo Fisher Scientific (Scoresby, VIC, Australia). PEX, INDO, MASTO, the quenched fluorescent resonance energy transfer (FRET) peptide (Abz-LPETGK(Dnp)-NH2), and Gly3-amide peptides were synthesized as previously described [9 (link)]. The bacterial library used herein consisted of S. aureus (ATCC25923), MRSA (ATCC43300), E. coli (ATCC25922), and P. aeruginosa (ATCC27853).
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7

Bacterial Strain Procurement and Reagents

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The bacterial strains (methicillin-sensitive S. aureus (MSSA) ATCC 25923, methicillin-resistant Staphylococcus aureus (MRSA) ATCC43300, E. coli ATCC 25922, and P. aeruginosa ATCC 27853) were obtained from the American Type Culture Collection (Manassas, VA, USA). All amino acids and Rink amide-4-methylbenzhydrylamine (MBHA) resin (0.54 mmol/g) were obtained from Mimotopes (Melbourne, VIC, Australia). Ethyl (hydroxyimino)cyanoacetate (Oxyma Pure) and N,N′-diisopropylcarbodiimide (DIC) were obtained from Chem-Impex International (Wood Dale, IL, USA). Triisopropylsilane (TIPS) was obtained from Alfa Aesar (Massachusetts, VA, USA). Dulbecco’s Modified Eagle Medium (DMEM), fetal bovine serum (FBS), and penicillin/streptomycin were obtained from Thermo Fisher Scientific (Scoresby, VIC, Australia). Acetonitrile (MeCN), cetyltrimethylammonium bromide (CTAB, 99%), N,N-dimethylformamide (DMF; peptide synthesis grade), dimethyl sulfoxide (DMSO), ethanol (EtOH), methanol (MeOH), Mueller–Hinton broth (MHB), tetraethyl orthosilicate (TEOS, reagent grade 98%), trifluoroacetic acid (TFA), 3-(trihydroxysilyl)propyl methylphosphonate (THMP, 90%), and all other reagents were purchased from Merck (Castle Hill, NSW, Australia).
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8

Peptide Synthesis with Fmoc Chemistry

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Ultrapure water (Milli-Q, ρ >18 MΩ⋅cm) was used in all the experiments. Acetonitrile (ACN), dichloromethane (DCM), dimethylformamide (DMF) and ethanol (EtOH) were obtained from Sigma-Aldrich and were used without further purification. The synthesis of all peptides required N,N,N′,N′-Tetramethyl-O-(1H-benzotriazol-1yl)uronium hexafluorophosphate (HBTU) (Iris Biotech GmbH, Germany), acetic anhydride and piperidine (Sigma-Aldrich, Germany) and N-methylmorpholine (NMM), Nmethylpyrrolidinone (NMP) (Alfa Aesar, Haverhill, MA, USA) as reagents. Fmoc-L-Cys (Trt)-OH, Fmoc-L-Lys(Boc)-OH, Fmoc-L-Gly-OH, Fmoc-L-Thr(tBu)-OH and Fmoc-L-Arg(Pbf)-OH were obtained from Iris Biotech GmbH (Germany). Fmoc-L-Ala-Wang resin (100-200 mesh), Fmoc-L-Arg(Pbf)-Wang resin (100-200 mesh) and Fmoc-L-Asn(Trt)-OH were obtained from Novabiochem (Germany). Trifluoroacetic acid (TFA) was purchased from Sigma Aldrich (Germany) and triisopropylsilane (TIPS) from Alfa Aesar (Haverhill, MA, USA).
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