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A kind of brassinosterol derivatization reagent and its preparation method and application

A technology of brassinosterol and derivatization reagents, applied in the field of organic chemistry and analytical chemistry, can solve the problems of easy decomposition, unstable derivatized products, poor sensitivity, etc., and achieve the effect of not easy to decompose, stable decomposition, and improve sensitivity

Active Publication Date: 2020-07-24
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most reagents are less sensitive to brassinosteroids without methyl or ethyl functional groups at the C24 position
Moreover, in the aqueous phase, the derivatized product is unstable and easy to decompose

Method used

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  • A kind of brassinosterol derivatization reagent and its preparation method and application
  • A kind of brassinosterol derivatization reagent and its preparation method and application
  • A kind of brassinosterol derivatization reagent and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of 2-methyl-4-phenylaminomethylbenzeneboronic acid

[0023] Add 4-formyl-2-methylbenzeneboronic acid (0.92mmol), aniline (0.92mmol), acetic acid (0.01mmol) and methanol (25mL) into the reaction flask, stir the reaction at room temperature for 0.5 hours, and then add cyano Sodium borohydride (0.92mmol) reduced the carbon-nitrogen double bond, continued the reaction for 10 hours, then ended the reaction, evaporated the methanol solvent, added 30mL saturated saline and 30mL ethyl acetate to dissolve the solid, collected the organic layer, added anhydrous sodium sulfate to dry, The product was purified by silica gel column chromatography to obtain 2-methyl-4-phenylaminomethylbenzeneboronic acid in a yield of 44.0%. Product Characterization Data 1 H NMR (400MHz, DMSO-d 6 )δ7.94(s, 2H), 7.36(d, J=7.4Hz, 1H), 7.10(d, J=8.1Hz, 2H), 7.01(t, J=9.0Hz, 2H), 6.53(dd, J=8.6,1.0Hz,2H),6.47(m,1H),6.22(m,1H),4.19(d,J=6.1Hz,2H),2.37(s,3H).m / z(M+H ) + = 24...

Embodiment 2

[0024] Embodiment 2: compare with reported derivatization reagent sensitivity

[0025] The post-derivatization sensitivity of the reported brassinosterol derivatization reagent 4-phenylaminomethylphenylboronic acid was compared. Mix 100μL brassinosterol mixed standard solution (including: CS, 10ng / mL; 28-norBL, 10ng / mL; 28-norCS, 10ng / mL; 28-homoBL, 10ng / mL; BL, 10ng / mL) with 100μL 4-Phenylaminomethylphenylboronic acid (4mM) and 2-methyl-4-phenylaminomethylphenylboronic acid (4mM) were reacted at room temperature for 10 minutes, and then 5 μL of the reaction solution was injected into the ultra-high liquid chromatography- Electrospray-triple quadrupole tandem mass spectrometry was used for analysis.

[0026] Such as figure 1 Shown; The mass spectrum response of the brassinosterol compound (28-norBL; 28-norCS) without methyl or ethyl functional group at the C24 position is good after derivatization with 2-methyl-4-phenylaminomethylbenzeneboronic acid Based on the reported de...

Embodiment 3

[0027] Embodiment 3: Derivative Stability Investigation

[0028] The post-derivatization stability of the reported brassinosterol derivatization reagent 4-phenylaminomethylphenylboronic acid was compared. Mix 100μL brassinosterol mixed standard solution (including: CS, 10ng / mL; 28-norBL, 10ng / mL; 28-norCS, 10ng / mL; 28-homoBL, 10ng / mL; BL, 10ng / mL) with 100μL 4-Phenylaminomethylphenylboronic acid (4mM) and 2-methyl-4-phenylaminomethylphenylboronic acid (4mM) were reacted for 10 minutes, and then 5 μL of the reaction solution was injected into ultra-high liquid chromatography-electrospray- Triple quadrupole tandem mass spectrometry was used for analysis. The separation chromatographic column used was Waters C18 column (2.1×100mm, 1.8 μm), and the mobile phase was A: water phase, B: acetonitrile. Derivatives were separated using high organic and high aqueous gradients, respectively. High organic gradient: 0-5 minutes: 70% vol B, 5-10 minutes: 90% vol B, 10-12 minutes: 70% vol ...

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Abstract

The invention discloses a brassinosteroid derivatization reagent 2-methyl-4-phenyl aminomethyl phenylboric acid, a synthetic method and application. A Schiff base reaction is conducted on 4-formyl group-2-tolylboronic acid and aniline under acidic condition, and then under the reduction of cyano sodium borohydride, the brassinosteroid derivatization reagent 2-methyl-4-phenyl aminomethyl phenylboric acid is obtained. A synthetic reagent can react with brassinosteroid, after derivation of the brassinosteroid, the sensitivity is greatly improved by mass spectrometry, and derivatives also remain stable in water systems.

Description

technical field [0001] The invention relates to a synthesis method of a brassinosterol derivatization reagent 2-methyl-4-phenylaminomethylbenzeneboronic acid, belonging to the fields of organic chemistry and analytical chemistry. Background technique [0002] Brassinosteroids are a class of phytohormones with very low content in plants, which participate in the regulation of various processes of plant growth and development. The establishment of analytical and detection methods for endogenous brassinosterol compounds is very important for studying the physiological functions of brassinosterol. Due to its high sensitivity, mass spectrometry is widely used in the detection of trace plant hormones. The brassinosterol compound has a very low response on the ESI mass spectrum because it does not have an ionizable group. Therefore, easily ionized phenylboronic acid reagents are often used to react with brassinosterol compounds, thereby improving the response of brassinosterol co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02G01N30/02G01N30/06
CPCC07F5/025G01N30/02G01N30/06G01N2030/027G01N2030/067
Inventor 冯钰锜余磊
Owner WUHAN UNIV
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