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N-azido acetyl-D-mannosamine derivative, preparation method thereof, and application of N-azido acetyl-D-mannosamine derivative in esterase detection

A technology of azidoacetyl and mannosamine, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., to achieve high specificity

Active Publication Date: 2020-05-15
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Esterase probes have important applications in evaluating the therapeutic efficacy of various drugs with ester bonds, but many fluorescent probes for esterase detection are far from satisfactory. Therefore, using bioorthogonal click The detection method of esterase in reaction and sugar metabolism process provides a new way to study the function of esterase

Method used

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  • N-azido acetyl-D-mannosamine derivative, preparation method thereof, and application of N-azido acetyl-D-mannosamine derivative in esterase detection
  • N-azido acetyl-D-mannosamine derivative, preparation method thereof, and application of N-azido acetyl-D-mannosamine derivative in esterase detection
  • N-azido acetyl-D-mannosamine derivative, preparation method thereof, and application of N-azido acetyl-D-mannosamine derivative in esterase detection

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Experimental program
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Effect test

preparation example 1

[0059] Preparation of compound (III-1)

[0060]

[0061] Under ice-water bath, compound (IV-1) (0.75g, 1.5mM) was dissolved in anhydrous tetrahydrofuran, and then a tetrahydrofuran solution of 1M tetrabutylammonium fluoride (1.5eq., 2.25mM) was added, and then in The reaction was stirred at room temperature for 3 hours. After the reaction was completed, the reaction was quenched with 10 mL of a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate (50 mL×3), the organic layer was collected, dried over anhydrous sodium sulfate, filtered, and the solvent was removed. The crude product was purified by silica gel column chromatography, and the eluent was petroleum ether / ethyl acetate (v / v=1:2~1:3) to obtain a white solid (541 mg, 93%).

Embodiment 1

[0063] Preparation of compound (1)

[0064]

[0065] Under the protection of an ice-water bath and argon, the compound of formula (III-1) (388 mg, 1 mM) was dissolved in 15 mL of a dry mixed solution of tetrahydrofuran / dichloromethane (THF / DCM, 1:1 v / v), and then added Triethylamine (0.809g, 8mM) and N,N-diisopropylethylamine (1.034g, 8mM) were reacted for 10 minutes, and dissolved in 10mL of dry THF / DCM (1:1v / v) was added dropwise 2-(furan-2-yl)ethyl chloroformate (696 mg, 4 mM) in solution. Continue to react at 0°C for 1 hour, remove the ice-water bath, return to room temperature, and react for 3 hours. After the reaction was complete, the solvent was removed, and the crude product was purified by silica gel column chromatography with petroleum ether / ethyl acetate (v / v=1:1) as the eluent to obtain a white solid (189 mg, 36%). 1 H NMR (400MHz, CD 3 OD): δ7.511(d,1H),6.362(m,1H),6.125(d,1H),5.983(s,1H),5.328-5.098(m,4H),4.733(s,1H),4.359 -4.280(m,1H),4.150-4.070(m,2H),3...

Embodiment 2

[0067] Preparation of compound (2)

[0068]

[0069] Under the protection of an ice-water bath and argon, the compound of formula (III-1) (388 mg, 1 mM) was dissolved in 15 mL of a dry mixed solution of tetrahydrofuran / dichloromethane (THF / DCM, 1:1 v / v), and then added Triethylamine (0.809g, 8mM) and N,N-diisopropylethylamine (1.034g, 8mM) were reacted for 10 minutes, and dissolved in 10mL of dry THF / DCM (1:1v / v) was added dropwise solution of benzyl chloroformate (680 mg, 4 mM). Continue to react at 0°C for 1 hour, remove the ice-water bath, return to room temperature, and react for 3 hours. After the reaction was complete, the solvent was removed, and the crude product was purified by silica gel column chromatography with petroleum ether / ethyl acetate (v / v=1:1) as the eluent to obtain a white solid (198 mg, 38%). 1 H NMR (400MHz, CD 3 OD):δ7.32-7.35(d,5H),5.997(s,1H),5.330-5.090(m,4H),4.725(s,1H),4.356-4.281(m,1H),4.150-4.073( m,2H), 3.936(s,2H), 2.173-1.910(m,9H).ESI...

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Abstract

The invention relates to an N-azido acetyl-D-mannosamine derivative, a preparation method thereof, and application of the N-azido acetyl-D-mannosamine derivative in esterase detection, and mainly relates to the N-azido acetyl-D-mannosamine derivative disclosed in a following formula (I), the preparation method for the N-azido acetyl-D-mannosamine derivative, and the application of the N-azido acetyl-D-mannosamine derivative in the esterase detection. R1 is selected from H, F, Cl, Br, I, -OH, -NH2, -NO2, -N3, C1-6 alkyl, C1-6 alkoxy, -CO-C1-6 alkyl, -CO-NH-C1-6 alkyl, -COOC1-6 alkyl, aryl, aryl-oxygen radicals, heteroaryl, heteroaryl-oxygen radicals, heterocyclic radicals and heterocyclic radical-oxygen radicals, wherein the aryl, the aryl-oxygen radicals, the heteroaryl, the heteroaryl-oxygen radicals, the heterocyclic radicals and the heterocyclic radical-oxygen radicals are optionally substituted by any following radicals: F, Cl, Br, I, -OH, -NH2, -NO2, -N3, C1-6 alkyl and C1-6 alkoxy; R2 and R3 are the same or different and are mutually independently selected from O, S, NH and NMe; n1 and n2 are the same or different and are mutually independently selected from integers from 1 to 4; and a brake line shows a key a or a key e.

Description

technical field [0001] The invention relates to N-azidoacetyl-D-mannosamine derivatives and their preparation methods and applications, in particular to the application of N-azidoacetyl-D-mannosamine derivatives in detecting esterases. Background technique [0002] In eukaryotic cells, polysaccharides participate in the construction of cell membranes and play an important role in cell information exchange and interaction. However, polysaccharides in cells have different molecular structures, and there are certain difficulties in their labeling and functional research. Some non-natural sugars chemically modified can express polysaccharides on the cell membrane through the carbohydrate metabolism process of cells, thus providing a new method for the study of polysaccharide functions. Bioorthogonal click reaction without catalyst catalysis is becoming a safe and effective method for cell detection and labeling due to its advantages of high specificity, fast reaction speed, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26C07H1/00G01N21/64G01N33/58
CPCC07H1/00C07H15/26G01N21/6428G01N21/6458G01N33/582
Inventor 杨国强鲁凤仙胡睿王双青郭旭东
Owner INST OF CHEM CHINESE ACAD OF SCI
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