Perfluoroheptanoic acid (27.5 μmol, 100 mg) was dissolved in dimethyl sulfoxide (DMSO, Sangon Biotech) and then mixed with EDC (78 mg, 1.5 equiv) and NHS (47.43 mg, 1.5 equiv) under stirring in the dark at room temperature for 0.5 h to obtain activated perfluoroheptanoic acid. Then, CS (200 mg) was dissolved in 1% acetic acid solution, mixed dropwise with activated perfluoroheptanoic acid, and stirred in the dark for 12 h to synthesize FCS. The obtained FCS was purified by dialyzing in double-distilled water using a dialysis bag (MWCO 3500 Da, Technologies Co.) for 48 h. Then, the samples were lyophilized, and the degree of substitution of conjugated fluoroalkyl substituents on each CS was characterized by ninhydrin colorimetry following the well-evidenced procedure and analyzed using the microplate reader (Variskan, THERMO). The 19 F NMR (Bruker AV III 600 spectrometers) of FCS (5.0 mg) dissolved in 600 μL of D2O containing 1.0 mg of CF3COOH was also applied for the calculation of conjugated fluoroalkyl substituents.
Av 3 600 spectrometers
Manufactured by Bruker
The AV III 600 spectrometers are high-performance nuclear magnetic resonance (NMR) instruments designed for advanced research and analytical applications. These spectrometers feature a 600 MHz superconducting magnet and state-of-the-art electronics, providing high-resolution and sensitivity for the acquisition of NMR data.
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Synthesizing Fluorinated Chitosan Conjugates
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Analytical Methods for Organic Compounds
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General Experimental Procedures Optical rotations were measured on a Perkin-Elmer 241 polarimeter (Waltham, MA, U.S.A.), and UV data were recorded on Beckman Coulter DU 800 spectrometer (Tokyo, Japan). IR data were recorded using a Shimadzu FTIR-8400S spectrophotometer (Tokyo, Japan). NMR experiments were performed on Bruker AV III 600 spectrometers operating at 600 MHz for 1 H and 150 MHz for 13 C, respectively. Chemical shifts are expressed in δ (ppm) referenced to solvent peaks at δ H 3.31 and δ C 49.2 for CD 3 OD, and coupling constants are in Hz. HR-ESI-MS spectra were obtained from a Thermo Scientific LTQ-Obitrap XL instrument (Thermo Scientific, Bremen, Germany). Silica gel (200-300 mesh, Qingdao Marine Chemistry Co., Ltd.) and Sephadex LH-20 (GE Healthcare, U.S.A.) were used for column chromatography. HPLC chromatography was performed on LC-6AD equipped with a UV detector of SPD-10A (Shimadzu, Kyoto, Japan), and a column of ZORAX SB-phenyl (250×10 mm, 5 µm, Agilent Technologies Co., Ltd., U.S.A.).
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