Acyl chlorides

Manufactured by Merck Group

Sourced in United States, United Kingdom

Acyl chlorides are a class of organic compounds that are widely used in chemical synthesis. They are characterized by the presence of a carbonyl group bonded to a chlorine atom. Acyl chlorides are highly reactive and can participate in various organic reactions, such as acylation, esterification, and amidation, making them valuable intermediates in the production of a wide range of chemical products.

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3 protocols using acyl chlorides

Lipid Nanoparticle Synthesis and Characterization

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Amines, epoxides, acyl chlorides, TEA were purchased from Sigma Aldrich (Burlington, Massachusetts, USA), Tokyo Chemical Industry (TCI, Tokyo, Japan) and Ambeed (Arlington Heights, Illinois, USA). Alanine transaminase (ALT) colorimetric activity assay kit (#700260) and aspartate aminotransferase (AST) colorimetric activity assay kit (#701640) were purchased from Cayman Chemical (Ann Arbor, Michigan, USA). 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), 1,2-dimyristoyl-rac-glycero-3-methoxypolyethylene glycol-2000 (DMG-PEG 2000) and cholesterol were obtained from Avanti Polar Lipids (Alabaster, Alabama, USA). DLin-MC3-DMA and SM-102 were purchased from MedChem Express (Monmouth Junction, New Jersey, USA). Cas9 mRNA (5moU) was purchased from TriLink (San Diego, California, USA). Highly modified sgRNA target mouse TTR (guide No. G211) was chemically synthesized by AxoLabs (Kulmbach, Bayern, Germany) based on the previous publication^{43 (link)}. Anhydrous DCM, porcine liver esterase, amiloride hydrochloride, chlorpromazine, genistein, methyl-beta-cyclodextrin and TTR siRNAs (#NM_013697, siRNA IDs: SASI_Mm01_00076059, SASI_Mm01_00076060 and SASI_Mm01_00076061) were purchased from Sigma Aldrich (Burlington, Massachusetts, USA).

Han X., Xu J., Xu Y., Alameh M.G., Xue L., Gong N., El-Mayta R., Palanki R., Warzecha C.C., Zhao G., Vaughan A.E., Wilson J.M., Weissman D, & Mitchell M.J. (2024). In situ combinatorial synthesis of degradable branched lipidoids for systemic delivery of mRNA therapeutics and gene editors. Nature Communications, 15, 1762.

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Enzymatic Synthesis of Divinyl Adipate

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Novozym 435 lipase ([9001‐62‐1], derived from Candida antarctica and immobilized on an acrylic macroporous resin, solvents, pyridine, and acyl chlorides were purchased from Sigma‐Aldrich (Gillingham, UK), except for divinyl adipate [4074‐90‐2] which was purchased from TCI America. All chemicals were used as received.

Taresco V., Suksiriworapong J., Creasey R., Burley J.C., Mantovani G., Alexander C., Treacher K., Booth J, & Garnett M.C. (2016). Properties of acyl modified poly(glycerol‐adipate) comb‐like polymers and their self‐assembly into nanoparticles. Journal of Polymer Science. Part A, Polymer Chemistry, 54(20), 3267-3278.

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Solid-Phase Synthesis of Perfluoroalkylated Peptides

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Peptides were synthesized using standard solid-phase peptide synthesis techniques on an automated CSBio Synthesizer, model number CS136. Amino acids were obtained from Anaspec (Fremont, CA). DIC and Oxyma pure were obtained from ThermoFischer Sciences (Waltham, MA) and BAChem (Bubendorf, Switzerland), respectively. Dimethylformamide, dichloromethane, diisopropylethylamine, and 4-methylpiperidine were obtained and used without further purification from VWR. Synthesis was conducted on a rink amide resin on MBHA support (EMD Millipore, Billerica Massachusetts) at 0.5 mM scale. The perfluoroalkane tails were added on-resin via the Schotten-Baumann reaction. Acyl chlorides were obtained from Sigma-Aldrich. Acyl chloride (300 μL) was dissolved in 10 mL of solvent system-dried chloroform along with 600 μL of diisopropyl ethyl amine. The solution was directly added to a fritted shaker vessel along with the peptide on-resin and agitated for 30–45 min. The addition was repeated until ninhydrin test was negative. The peptide was cleaved from resin support in a solution of 95% trifluoroacetic acid, 2.5% water, and 2.5% triisopropyl silane over 3 h and precipitated in cold ether stored at −20 °C. The precipitate was purified using reverse-phase HPLC. Overall yield was typically 40%– 50%.

Preslar A.T., Tantakitti F., Park K., Zhang S., Stupp S.I, & Meade T.J. (2016). 19F Magnetic Resonance Imaging Signals from Peptide Amphiphile Nanostructures Are Strongly Affected by Their Shape. ACS nano, 10(8), 7376-7384.

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