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2 protocols using n n diisopropylcarbodiimide dic

1

Synthesis and Characterization of Ferulic Acid Esters

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Ferulic acid (99%) and triphenyl phosphine (99%) were purchased from Sigma-Aldrich Japan Co., Ltd. p-Coumaric acid (>98.0%), sinapinic acid (>98.0%), oxalyl chloride (>98.0%), and diisopropyl azodicarboxylate (40% in toluene, ca. 1.9 mol L−1) were purchased from Tokyo Chemical Industry Co., Ltd. Methyl ricinoleate (>97.0%), acetic anhydride (>97.0%), N,N-dimethylaminopyridine (DMAP) (>99.0%), N,N′-diisopropylcarbodiimide (DIC) (>99.0%), pyridine (>99.5%, dehydrated), N,N-dimethylformamide (DMF) (>99.5%, dehydrated), sodium sulphate (Na2SO4) (>99.0%), and tetrahydrofuran (THF) (>99.5%, with stabilizer, for gel permeation chromatography (GPC) grade) were purchased from FUJIFILM Wako Pure Chemical Corporation. p-Toluenesulfonic acid monohydrate (>99.0%) and lithium hydroxide monohydrate (>99.0%) were purchased from KISHIDA CHEMICAL Co., Ltd. Toluene (>99.5%, dehydrated), dichloromethane (CH2Cl2) (>99.5%, dehydrated), and THF (>99.5%, dehydrated stabilizer free) were purchased from Kanto Chemical and purified on a Glass Contour Solvent Purification System (NIKKO HANSEN & Co., Ltd, Japan). Chloroform-d1 (99.8 atom % D with 0.03 vol% tetramethylsilane) was purchased from Kanto Chemical. These chemicals were used without further purification unless otherwise noted. 4-(Dimethylamino)pyridinium p-toluenesulfonate (DPTS) was synthesised according to the literature.43 (link)
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2

Peptide Synthesis with Diverse Reagents

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NovaSyn TGA resin (amine density of 0.2 mmol/g), Fmoc-Glu(Odmab)-OH, Fmoc-Asp(OtBu)-OH and Fmoc-Gly-OH were obtained from Novabiochem, Merck (Tokyo, Japan). N-[1-(Cyano-2-ethoxy-2-oxoethylideneaminooxy) dimethylamino (morpholino)] uronium hexafluorophosphate (COMU), Fmocβ-Ala-OH, Fmoc-Glu-OtBu, diisopropylethylamine (DIPEA), dichloromethane (DCM), 1-methyl-2-pyrrolidone (NMP), and piperidine were purchased from Watanabe Chemical (Tokyo, Japan).
Pyridine, N,N-dimethyl-4-aminoPyridine benzoic anhydride (DMAP) and N,N-diisopropylcarbodiimide (DIC) were obtained from Wako Pure Chemicals (Osaka, Japan). Boc-11-amino-3,6,9-trioxaundecanoic acid•DCHA (Boc-mini-PEG3) and Fmoc-11-3,6,9-trioxaundecanoic acid (Fmoc-mini-PEG3) were purchased from Peptides International (Kentucky, USA). N,N-Dimethylformamide (DMF) was purchased from Kanto Chemical (Tokyo, Japan). All reagents were used without further purification. Fatty acid free human serum albumin and myristic acid were purchased from Sigma-Aldrich. Tetradecylamine, hexadecylamine and sodium salt of 8-anilino-1-naphthalenesulfonate (ANS•Na) were purchased from Tokyo Chemical Industry (Tokyo, Japan).
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