Fluorescent probe for detecting high-concentration gamma-Glutamyl Transpeptidase and preparation method thereof
A technology of glutamyl transpeptidase and fluorescent probe, which is applied in the field of analytical chemistry, and achieves the effects of low preparation cost, easy promotion, and simple synthesis process
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Embodiment 1
[0055] Synthesis of TAB-3-GSH
[0056]
[0057] (1) Preparation of Compound 2: Under the protection of nitrogen, 10g (32mmol) of Compound 2 was dissolved in 60mL of dry ether, cooled to -78°C, and 20mL of 1.6M n-butyllithium n-hexane was added dropwise. Hexane solution. The reaction was warmed to room temperature and stirred for 20 min. Then, it was cooled to -78°C again, and 1.25 mL (10 mmol) of boron trifluoride ether was added. The reaction continued at room temperature and stirred overnight. The solvent was spin-dried, and further purified by silica gel column chromatography to obtain 4.0 g of white solid with a yield of 71%.
[0058] (2) Preparation of compound 3: Put 595 mg (3.2 mmol) of N-butyl ester piperazine, 560 mg (1 mmol) of compound 2, 864 mg (9 mmol) of sodium tert-butyl alkoxide, and 27 mg (0.12 mmol) of palladium acetate into three mouths In the bottle, pump three times on a double-row tube, under the protection of nitrogen, add 50 mL of toluene, and then add 2...
Embodiment 2
[0063] Synthesis of TAB-3-Cys-Gly
[0064]
[0065] (1) Preparation of Compound 2: Under the protection of nitrogen, 10g (32mmol) of Compound 2 was dissolved in 60mL of dry ether, cooled to -78°C, and 20mL of 1.6M n-butyllithium n-hexane was added dropwise. Hexane solution. The reaction was warmed to room temperature and stirred for 20 min. Then, it was cooled to -78°C again, and 1.25 mL (10 mmol) of boron trifluoride ether was added. The reaction continued at room temperature and stirred overnight. The solvent was spin-dried, and further purified by silica gel column chromatography to obtain 4.0 g of white solid with a yield of 71%.
[0066] (2) Preparation of compound 3: Put 595 mg (3.2 mmol) of N-butyl ester piperazine, 560 mg (1 mmol) of compound 2, 864 mg (9 mmol) of sodium tert-butyl alkoxide, and 27 mg (0.12 mmol) of palladium acetate into three mouths In the bottle, pump three times on a double-row tube, under the protection of nitrogen, add 50 mL of toluene, and then a...
Embodiment 3
[0071] Synthesis of TAB-3-Cys
[0072]
[0073] (1) Preparation of Compound 2: Under the protection of nitrogen, 10g (32mmol) of Compound 2 was dissolved in 60mL of dry ether, cooled to -78°C, and 20mL of 1.6M n-butyllithium n-hexane was added dropwise. Hexane solution. The reaction was warmed to room temperature and stirred for 20 min. Then, it was cooled to -78°C again, and 1.25 mL (10 mmol) of boron trifluoride ether was added. The reaction continued at room temperature and stirred overnight. The solvent was spin-dried, and further purified by silica gel column chromatography to obtain 4.0 g of white solid with a yield of 71%.
[0074] (2) Preparation of compound 3: Put 595 mg (3.2 mmol) of N-butyl ester piperazine, 560 mg (1 mmol) of compound 2, 864 mg (9 mmol) of sodium tert-butyl alkoxide, and 27 mg (0.12 mmol) of palladium acetate into three mouths In the bottle, pump three times on a double-row tube, under the protection of nitrogen, add 50 mL of toluene, and then add 2...
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