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Synthesis of Chlorotrityl Chloride Resin and Cell Assay

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2-Chlorotrityl chloride resin (0.53 mmol·g−1 loading) was purchased from Jiangsu Shenlang Biotech Co., (Jiangsu, China). Fmoc-protected amino acids were purchased from Shanghai GL Biochem Ltd., and Jiangsu Shenlang Biotech Co., (Shanghai and Jiangsu, China). Phenol, DIC, TIPS, DIEA, HoBt, PyBOP, and HCTU were obtained from Adamas-beta (Shanghai, China). DMF, DCM, petroleum ether, ethyl ether, AgNO3, TFA, piperidine and other common reagents were purchased from CHRON Chemical Co., Ltd., (Chengdu, China). HCT116 cells were obtained from Shanghai Cellular Institute of Chinese Academy of Sciences (Shanghai, China). The CCK-8 value-added test kit was purchased from Shanghai Tongren Group (Shanghai, China). RPMI-1640, phosphate buffer solution, 0.25% trypsin, penicillin–streptomycin solution, and fetal bovine serum were purchased from Gibco Thermo Fisher Scientific (United States).
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2

Osteoclast Differentiation Protocol

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Rink Amide MBHA resin (0.3 mmol g−1 loading) was purchased from Tianjin Nankai Hecheng Science & Technology Co. Ltd (Tianjing, China). Fmoc-protected amino acids were purchased from Shanghai GL Biochem Ltd (Shanghai, China). HCTU, phenol, DIC, TIPS were obtained from adamas-beta (Shanghai, China). DMF, DCM were purchased from Wohua Chemical Co. Ltd (Shanghai, China). Ethyl ether, NMP, TFA, piperidine and other common reagent were purchased from Sinopharm Chemical Reagent Co. Ltd (Shanghai, China). The alpha modification of Eagle's medium (α-MEM), penicillin/streptomycin and fetal bovine serum (FBS) were purchased from Gibco-BRL (Gaithersburg, MD, USA). The cell counting kit-8 (CCK-8) was obtained from Dojindo Molecular Technology (Kumamoto, Kyushu, Japan). Recombinant mouse M-CSF and mouse RANKL were obtained from R&D (Minneapolis, MN, USA). The tartrate-resistant acid phosphatase (TRAP) staining kit were purchased from Joytech Bio Inc (Shaoxing, Zhejiang, China). Specific antibodies against phospho-GSK3β, GSK3β and GAPDH were obtained from Abcam (Cambridge, UK). Secondary antibodies were purchased from Cell Signaling Technology (Danvers, MA, USA). RIPA lysis buffer, PMSF and SDS-PAGE loading buffer were purchased from Beyotime (Shanghai, China).
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Chiral Catalysts and Substrate Synthesis

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Phenol, (1R, 2R)-1,2-diphenyl-1,2-ethanediamine, hexamethylenetetramine (HMTA), 1-allylimidazole, 1,4-dibromobutane, azodiisobutyronitrile (AIBN), (3-mercaptopropyl) trimethoxysilane, trifluoroacetic acid (TFA) and K2CO3 were obtained from Adamas-beta (Shanghai, China). Commercial spherical silica (5 µm, 300 m2 g−1) was provided from Suzhou Nanwei Technology Co., Ltd. (Suzhou, China). Other commonly used solvents, such as N, N-dimethylformamide (DMF), chloroform, toluene, acetonitrile, ethanol, and pyridine, were obtained from Tianjin Fengchuan Chemical Reagent Technology Co., Ltd. (Tianjin, China). Racemic 1-(3-methylphenyl) ethanol, 1-(1-naphthyl) ethanol, 1-(4-chlorophenyl) ethanol, mandelic acid, naproxen and ofloxacin were purchased from Adamas-beta (Shanghai, China); 2-phenyl-1-propanol, 3-benzyloxy-1,2-propanediol, hydrobenzoin, 1-phenyl-1-propanol, 1-phenylethylamine, benzoin, and trans-1,2-diphenylethylene oxide were obtained from Aladdin (Shanghai, China). Positional isomers, such as iodoaniline, bromoaniline, chloroaniline, dichlorobenzene, dibromobenzene, toluidine, nitroaniline, and nitrobromobenzene were provided from Adamas-beta (Shanghai, China).
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Evaluation of Aluminum Salts and Organic Compounds

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The chemicals were purchased from commercial suppliers and used as provided. The supplier and purity of the chemicals are indicated in the brackets. d-fructose (Sigma-Aldrich, >99%), d-glucose (AnalaR, >99%), sucrose (Sigma-Aldrich, >99.5%), 5-hydroxymethyl furfural (Sigma-Aldrich, >99%), methanol (Fisher, HPLC assay), dimethyl sulfoxide (DMSO, Ajax Finechem, >99%), aluminium (III) nitrate nonahydrate (Ajax Finechem, >98%), aluminium chloride (Greagent, ≥99%), aluminium sulfate octadecahydrate (Aladdin, 99.95%), aluminium acetate (Macklin, ≥98%), fulvic acid soluble powder (FA, Agtech Natural Resources, >92%), phenol (Adamas, 99%), catechol (Adamas, 99%), pyrogallol (Adamas, 99%), epinephrine (Adamas, 97%), trimesic acid (Adamas, >99%), 2-aminoterephthalic Acid (Adamas, >98%), salicylic acid (Adamas, 99%), DMSO-δ (Sigma-Aldrich), Ar (Supagas, >99.99%).
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