Glycosyl anthraquinone compounds and their graphene sensor construction
A compound and anthraquinone technology is applied in the field of the construction of anthraquinone compounds and graphene electrochemical biosensors, which can solve the problems of complicated synthesis and immobilization modification, changes in biological functional properties, and expensive detection instruments and equipment.
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Embodiment 1
[0029] The preparation of compound (abbreviated as compound IA, hereinafter the same) shown in formula IA:
[0030]
[0031] (1) Preparation of compound VII:
[0032]
[0033] Compound VI (253 mg, 0.68 mmol) and Compound V (94.2 mg, 0.34 mmol) were dissolved in 10 mL CH 2 Cl 2 Add water (10mL), CuSO 4 ·5H 2 O (4 equiv) and L-ascorbate sodium salt (6 equiv), stirred overnight at room temperature. TLC showed that the initial substance basically disappeared, and the upper layer of the reaction solution was green, and the lower layer was brownish yellow, and the mixed solution was washed with CH 2 Cl 2 Diluted, washed with water, anhydrous MgSO 4 Drying, filtration, concentration, the residue was separated and purified by silica gel column chromatography (ethyl acetate:petroleum ether=3:1, V / V) to obtain pale yellow needle crystals (compound VII, 193mg, 52%), R f =0.27 (ethyl acetate:petroleum ether=3:1, V / V).
[0034] 1 HNMR (400MHz, CDCl 3 )δ=8.20(s, 2H), 7.90(d,...
Embodiment 2
[0044] Preparation of compound IB:
[0045]
[0046] (1) Preparation of compound VIII:
[0047]
[0048] Compound VI (224 mg, 0.6 mmol) and Compound IV (100 mg, 0.4 mmol) were dissolved in 10 mL CH 2 Cl 2 , followed by adding water (10mL), CuSO 4 ·5H 2 O (4 equiv) and L-ascorbate sodium salt (6 equiv), stirred overnight at room temperature. TLC showed that the initial substance basically disappeared, and the upper layer of the reaction solution was green, and the lower layer was brownish yellow, and the mixed solution was washed with CH 2 Cl 2 Diluted, washed with water, anhydrous MgSO 4 After drying, filtering, and concentration, the residue was separated and purified by silica gel column chromatography (ethyl acetate:petroleum ether=4:1, V / V) to obtain light yellow needle crystals (compound VIII, 218mg, 88%). R f =0.23 (ethyl acetate:petroleum ether=1:2, V / V).
[0049] 1 HNMR (400MHz, CDCl 3 ): δ=8.31-8.26(m, 2H), 8.25(s, 1H), 8.03(d, J=7.6Hz, 1H), 7.84-7.75...
Embodiment 3
[0059] Electrode self-assembly preparation and characterization
[0060] (1) Activate the screen-printed electrode (SPE) in 0.1M PBS solution with a voltage of 2.0V and an activation time of 200s. The electrodes were allowed to dry at room temperature and stored in the refrigerator until use. 4 mL of an aqueous solution (1 mg / ml) of compound IA or IB was mixed with oxidized graphene (GO, which was prepared using a two-step oxidation method, specifically see Kovtyukhova, N.I., etal. Chem. Mater. 1999, 11, 771-778) Aqueous solution (0.1 mg / L) was mixed and stirred at room temperature for 4 hours. After forming a homogeneous system, 0.2 μL of the mixture of GO and compound IA or IB was dropped on the working electrode of SPE (composed of graphite), and dried at room temperature.
[0061] (2) by figure 1 It can be seen that the thickness of the prepared GO was observed to be 1 to 1.2 nm by atomic force microscopy (Figure a), which was consistent with the literature report (Song...
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