[
    {
        "id": 1,
        "chunk": "# Supplemental Information",
        "category": " References"
    },
    {
        "id": 2,
        "chunk": "# Mechanism and effects of polyphenol derivatives for modifying collagen  \n\nLeping Wu1, Hui Shao1, Zehui Fang1, Yuancong Zha $O^{2}$ , Ying Cao1, Quanli Li1\\*  \n\n1 Key Lab. of Oral Diseases Research of Anhui Province, College ＆ Hospital of Stomatology, Anhui Medical University, Hefei, 230032, China  \n\n2 Key Lab. of Advanced Technology for Materials of Education Ministry, School of Materials Science and Engineering, Southwest Jiaotong University, Chengdu, 610031, China  \n\nCorresponding Author’s email address: ql-li $@$ 126.com",
        "category": " Introduction"
    },
    {
        "id": 3,
        "chunk": "# Synthesis of N-2-(3,4-dihydroxyphenethyl) acrylamide (dopamine acrylamide) (DAA)  \n\nThe N-2-(3,4-dihydroxyphenethyl) acrylamide (DAA) was synthesized according to the reported method (Patil N, Falentin-Daudré C, Jérôme C, Detrembleur C. Mussel-inspired protein-repelling ambivalent block copolymers: controlled synthesis and characterization. Polym. Chem., 2015, 6, 2919–2933) (Scheme 1). $\\mathrm{Na_{2}B_{4}O_{7}{\\cdot}10H_{2}O\\left(6.0g\\right)}$ and $\\mathrm{Na}_{2}\\mathrm{CO}_{3}\\left(3.0\\mathrm{g}\\right)$ were added in a three-neck round-bottom flask containing $250.0\\mathrm{mL}$ of deionized water. This basic aqueous solution was stirring and degassed by argon bubbling with high pure argon $(99.999\\%)$ for 2h, and then dopamine hydrochloride $(1.5~\\mathrm{g})$ was added under argon atmosphere. After the solution was stirring for another 30 minutes, the acryloyl chloride $(3.0~\\mathrm{mL})$ ) was drop-wise added in flask at $0~^{\\circ}\\mathrm{C}$ , $\\ensuremath{4.5\\mathrm{~g~}}$ of ${\\bf N a}_{2}{\\bf C O}_{3}$ was added subsequently to keep the pH above 9 during the reaction. After the reaction was carried out with stirring for 12h at room temperature, the solution was adjusted to $\\mathsf{p H}1-2$ with HCl solution $\\mathrm{\\hbar(6mol/L)}$ . The solution was extracted with ethyl acetate. The organic layer washed with diluted HCl solution $\\mathrm{(0.1~mol/L)}$ and dried over $\\mathrm{Mg}\\mathrm{SO}_{4}$ . The solvent was removed in vacuum to yield crude product, and the pure product was further purified by flash silica gel column chromatography eluting with ethyl acetate and petroleum ether (white solid, $80\\%$ yield).  \n\n![](images/6f5e2cabdc578380b3616fd14a60a9257c99434fb7d3cf8053c4fafbd968eb57.jpg)  \nScheme S1. Synthesis of N-2-(3,4-dihydroxyphenethyl) acrylamide (DAA) monomer.  \n\n$^{1}\\mathrm{H}$ -NMR spectra of DAA was measured on a Bruker AV II-400 spectrometer (400 MHz), and tetramethylsilane (TMS) was used as an internal standard in DMSO- $d_{6}$ (Fig. 1). $\\mathrm{^{1}H}$ -NMR ( $\\delta\\mathsf{p p m}_{,}^{\\cdot}$ : 8.12 (t, 1H, -NH-C=O), 6.40-6.65 (m, 3H, Ph), 6.19 (dd, 1H, - ${\\mathrm{CH}}{=}\\mathrm{CH}_{2}\\backslash$ ), 6.08 (dd, 1H, $\\mathrm{CH}_{2}{=}\\mathrm{CH}{-}$ ) 5.57 (dd, 1H, $\\mathrm{CH}_{2}{=}\\mathrm{CH}{-}$ ), 3.27 (q, 2H, - ${\\mathrm{-CH}}_{2}{\\mathrm{-CH}}_{2}$ NH-), 2.55 (t, 2H, ${\\mathrm{-C}}{\\underline{{\\mathrm{H}}}}_{2}$ - $\\mathrm{CH}_{2}$ -NH-).  \n\n![](images/79478d262c81d45e63483331894fab03ff291eb24d255b1d5773484a19d3a002.jpg)  \nFigure S1. $^{1}\\mathrm{H}\\cdot$ -NMR spectral analysis of DAA  \n\nThe high resolution mass spectrometer analysis (HRMS) of DAA was recorded on Mass spectrometer ICS90. HRMS $(\\mathrm{ESI^{+}})$ : calcd for $\\mathrm{C}_{11}\\mathrm{H}_{13}\\mathrm{N}0_{3}(\\mathrm{N}$ M): 207.0895, Found: 208.0953 $(\\mathsf{M}{+}\\mathsf{H})^{+}$ , 230.0778(M+Na)+.  \n\n![](images/f83052a25d82957edd45945c378c638e80c4c5000b3ea92f4d9034f5b7e63f0f.jpg)  \nFigure S2. High resolution mass spectrometer analysis of DAA",
        "category": " Materials and methods"
    }
]