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Chemical synthetic process of D-fluorescein and device therefor

A technology of chemical synthesis and fluorescein, which is applied in organic chemistry and other fields, can solve the problems of harsh reaction conditions, difficulty in control, and low total yield of D-fluorescein, and achieve the effect of high luminescence coefficient and efficient synthesis

Inactive Publication Date: 2006-04-05
GUANGDONG INST OF MICROBIOLOGY GUANGDONG DETECTION CENT OF MICROBIOLOGY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The above-mentioned reaction pathway for preparing D-luciferin is complex, requires harsh reaction conditions, high requirements for reaction equipment, and is difficult to control, and the total yield of D-luciferin is not high

Method used

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  • Chemical synthetic process of D-fluorescein and device therefor
  • Chemical synthetic process of D-fluorescein and device therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: About the simple and convenient synthesis device of D-fluorescein

[0030] The reaction device consists of a temperature control device that can be adjusted more accurately in a wide range (0-300°C), a high-temperature oil bath heating system, a vacuum pumping nitrogen gas regulating system, and three ports with a condenser tube 4 and a waste gas absorption device. Flask 2 reaction system composition. The entire reaction device was placed in a fume hood except for the nitrogen supply bottle, vacuum device and temperature control device.

[0031] like figure 1 As shown, the high-temperature oil bath system can be used to hold castor oil (about 2000mL) in a stainless steel pot 6 on an adjustable electric furnace 1 (500W), and finely adjust the temperature through a temperature sensor 3; The opening is used for vacuuming and nitrogen gas, the middle opening is used for sample addition and cooling cycle, and the right opening is used for sampling detection (...

Embodiment 2

[0032] Embodiment 2: about the synthetic method of D-fluorescein

[0033] 1. Demethylation reaction

[0034] Weigh 940mg 2-cyano-6-methoxybenzothiazoe (2-Cyano-6-methoxybenzothiazoe) (99%) and 1000~3060mg pyridine hydrochloride (Pyridine hydrochloride) (98%) and put them into a small test tube, draw Put nitrogen into a temperature-adjustable high-temperature oil-bath reaction bottle after vacuuming, and keep warm at 190-220°C for 1-3 hours, stop heating to terminate the reaction, and extract the target product of demethylation after cooling.

[0035] 2. Extraction of demethylation target product

[0036] Add 200mL-400mL ice water to the above-mentioned reaction tube, and add 100mL-200mL ethyl acetate. The organic layer was washed once with ~400 mL of ice water, combined and dried by a rotary vacuum evaporator to obtain 1480 mg of a yellow-red substance.

[0037] 3. Purification of demethylated products

[0038]Add 80-120 mesh coarse-pore silica gel to an organic pressuriza...

Embodiment 3

[0052] Embodiment 3: about the synthetic method of D-fluorescein

[0053] 1. Methyl reaction (2002, 6 / 17)

[0054] Weigh 949mg of 2-cyano-6-methoxybenzothiazoe (2-Cyano-6-methoxybenzothiazoe) (99%) and 1000mg of pyridine hydrochloride (Pyridine hydrochloride) (98%) into a small test tube, vacuum After nitrogen gas, put it into a temperature-adjustable high-temperature oil-bath reaction flask, keep it at 200°C for 1 hour, stop heating to terminate the reaction, and extract the target product of demethylation after cooling.

[0055] 2. Extraction of methyl target product

[0056] Add 200mL of ice water to the above reaction tube, and add 100mL of ethyl acetate, shake well, extract the organic layer with a separatory funnel, extract the water layer twice with 100mL of ethyl acetate, wash the organic layer once with 200mL of ice water , after combining the organic layers, dried by a rotary vacuum evaporator to obtain 776 mg of a yellow-red substance.

[0057] 3. Purification of...

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Abstract

The invention relates to chemical synthesis for D-fluorescein. Wherein, using hot demethylate reaction to 2- cyano-6-methoxyl benzothiazole and pyridine hydrochloride with high purity to extract reaction production for column chromatography; finally, taking condensation reaction for demethylate production and D-cysteine to obtain objective product. This invention is simple, needs mild condition and easy to control. The product has yield more than 60% and purity more than 50%, and achieves level of Sigma L-9504 but with low price.

Description

[Affiliated technical field] [0001] The invention belongs to the field of chemical synthesis, and relates to a chemical synthesis method and a reaction device of D-fluorescein. [Background technique] [0002] D-luciferin is the substrate of ATP-dependent bioluminescent reaction, and the principle of bioluminescence is that luciferase in Mg 2++ , O 2 In the presence of ATP, D-luciferin is catalyzed to form oxidized luciferin, an enzymatic reaction process in which photons are emitted during the reaction, and the reaction formula is expressed as: [0003] <chemistry num="001"> <chem file="200410051705_cml001.xml" / > < / chemistry> [0004] Because the ATP in the reaction is the energy source of all organisms, under certain conditions, the intensity of the emitted light is proportional to the amount of ATP in the reaction system, so the bioluminescence method can be widely used in the detection of biological materials, such as the quantification of ultra-mic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C07D311/00C07D307/00
Inventor 吴慧清吴清平张菊梅郭伟鹏李程思
Owner GUANGDONG INST OF MICROBIOLOGY GUANGDONG DETECTION CENT OF MICROBIOLOGY
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