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Phenylglyoxal compound and hydrate, preparation method and application thereof

A technology of phenylglyoxal and compounds, which is applied in the fields of new probe materials, organic synthesis and fluorescence detection, and can solve the problems of high price, lack of chemical probes, complicated operation, etc.

Active Publication Date: 2020-04-28
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] (1) Antibody-based detection methods are expensive;
[0005] (2) The background of most fluorescence methods is too high and the operation is complicated;
[0006] (3) There is a lack of chemical probes that can perform multiple functions, such as simultaneous detection and capture of protein citrullination, to meet various biochemical research needs
[0011] Among them, BPG and Biotin-PG compounds have no fluorescence and can only be used to capture citrullinated peptides or proteins; Rh-PG compounds have fluorescence, but there is no difference in fluorescence before and after the reaction with citrulline, and SDS-PAGE is required for separation. And it cannot be used to capture citrullinated peptides or proteins; 4MEBz-FluME compound has fluorescence, and there is a difference in fluorescence before and after the reaction with citrulline, but the fluorescence background is high, and it cannot be used to capture citrullinated peptides or proteins

Method used

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  • Phenylglyoxal compound and hydrate, preparation method and application thereof
  • Phenylglyoxal compound and hydrate, preparation method and application thereof
  • Phenylglyoxal compound and hydrate, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the synthesis of compound fluorescent probe A

[0068]

[0069] 278mg SeO 2 (2.5 mmol) dissolved in 5 mL 1,4-dioxane and 750 μL water, heated to 55 °C until SeO 2 After completely dissolving, add 500mg 6-methoxy-2-acetylnaphthalene (2.5mmol) overnight, filter, and concentrate the filtrate in vacuo to obtain crude product, which is separated by silica gel column chromatography (eluent is petroleum ether and acetic acid A mixture of ethyl esters, wherein the volume ratio of the two is petroleum ether: ethyl acetate = 10:1), to obtain 370 mg of fluorescent probe A (yellow solid, yield 70%). NMR of fluorescent probe A: 1 H NMR (400MHz, CDCl 3 )δ9.75(s,0.5H),8.81(s,0.5H),8.63(s,0.5H),8.11(t,J=8.4Hz,1H),7.90(d,J=8.8Hz,1H) ,7.82(d,J=8.8Hz,1H),7.24(dd,J=2.4,8.8Hz,1H),7.17(t,J=2.5Hz,1H),6.09(s,0.5H),3.97(s ,3H); 13 C NMR (101MHz, d 6 -DMSO)δ196.33,193.78,190.55,188.11,160.58,160.14,159.94,138.05,137.63,137.45,133.51,132.19,131.92,131.80,129.32,128.98,127....

Embodiment 2

[0070] Embodiment 2: the synthesis of compound fluorescent probe B

[0071]

[0072] (1) Synthesis of Compound 1

[0073] 1.0g 4-bromoacetophenone (5.02mmol), 65mg triphenylphosphine (PPh 3 , 0.25mmol), 9mg palladium chloride (0.05mmol), 9.1mg copper acetate (0.05mmol) dissolved in 25mL triethylamine (Et 3 N), add 1078μL trimethylsilyne (TMSA, 7.63mmol), and reflux at 100°C for 1.5h. ratio of 1:1 mixture) extracted twice, the organic phase was washed with saturated brine, then dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain the crude product and separated by a normal phase silica gel column (eluent was petroleum ether and A mixture of ethyl acetate, wherein the volume ratio of the two is petroleum ether:ethyl acetate=30:1), to obtain 1.087g of compound 1 (yellow oil, yield 100%). NMR of compound 1: 1 H NMR (400MHz, CDCl 3 ) δ 7.90 (d, J = 8.4Hz, 2H), 7.55 (d, J = 8.4Hz, 2H), 2.60 (s, 3H), 0.26 (s, 9H).

[0074] (2) Synthesis of Compound 2

[0...

Embodiment 3

[0080] Embodiment 3: the synthesis of compound fluorescent probe C

[0081]

[0082] (1) Synthesis of compound 4

[0083] Dissolve 2.0g of 6-bromo-2-naphthol (8.97mmol), 1240mg of potassium carbonate (8.97mmol) and 3863μL of 1,2-dibromoethane (44.83mmol) in 30mL of acetonitrile (MeCN), and heat to reflux at 95°C For 8 hours, after the reaction solution was cooled, it was extracted twice with a mixed solution of dichloromethane and water (such as a mixed solution with a volume ratio of dichloromethane and water of 1:1), and the organic phase was washed with saturated brine, and then Dry over sodium sulfate, filter, and spin dry to obtain the crude product and elute with a normal phase silica gel column (the eluent is a mixed solution of petroleum ether and ethyl acetate, wherein the volume ratio of the two is petroleum ether:ethyl acetate=10: 1) to obtain 1.46 g of compound 4 (yellow solid, yield 50%). NMR of Compound 4: 1 H NMR (400MHz, CDCl 3 )δ7.92(s,1H),7.67(d,J=8.8H...

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Abstract

The invention provides a phenylglyoxal compound and a hydrate, a preparation method and application thereof, and belongs to the technical field of probe new materials, organic synthesis and fluorescence detection. The phenylglyoxal compound is shown as a formula (I), R1 is OCH3 or O-CH2-CH2-N3, and R2 does not exist or is the phenylglyoxal compound and a hydrate thereof, and the preparation methodof the phenylglyoxal compound is simple; the phenylglyoxal compound is used as the probe, the fluorescence background is low and operation is simple and convenient, and the phenylglyoxal compound canbe used for detecting the content of citrulline and can also be used for detecting the citrulline level of peptide or protein and capturing citrulline peptide or protein.

Description

technical field [0001] The invention belongs to the technical field of new probe materials, organic synthesis and fluorescence detection, and relates to a phenylglyoxal compound and a hydrate thereof, a preparation method and an application. Background technique [0002] Post-translational modifications (PTMs) of proteins are critical to the state of the cell. Among the amino acid residues, arginine has become a major player in the post-translational modification of proteins. The arginine residue has a unique guanidino side group, which has a very strong hydrogen bonding ability. The currently known post-translational modifications of arginine mainly include: methylation, citrullination, ADP-ribosylation and phosphorylation. Protein citrullination is the conversion of positively charged guanidine-containing arginine residues into neutral ureido-containing citrulline residues catalyzed by peptidylarginine deiminase (PAD) the process of. Recent studies have shown that dysr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/86C07C45/68C07C49/835C07C49/83C07C247/10C09K11/06G01N21/64
CPCC07C49/86C07C49/835C07C49/83C07C247/10C09K11/06G01N21/6428G01N21/6486C09K2211/1007C09K2211/1011G01N2021/6432
Inventor 张静陈汇鸿
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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