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Bacitracin oxidation component, analysis method thereof and fragmentation mode of double-bond sulfated cysteine oxidation component

An analysis method and technology for oxidizing components, applied in chemical instruments and methods, analysis materials, peptides, etc., can solve problems such as the research on the cracking mechanism of mass spectrometry of sulfonated products

Pending Publication Date: 2020-09-18
SHANGHAI INST FOR FOOD & DRUG CONTROL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Bacitracin will be oxidized to sulfonated products in the presence of performic acid or hydrogen peroxide solution (Rapid Commun. Mass Spectrom., 2003, 17:1366-1379; Environ. Sci. Technol., 2016, 50:8586-8595), but the mass spectrometric fragmentation mechanism of the sulfonated product has not been studied in detail

Method used

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  • Bacitracin oxidation component, analysis method thereof and fragmentation mode of double-bond sulfated cysteine oxidation component
  • Bacitracin oxidation component, analysis method thereof and fragmentation mode of double-bond sulfated cysteine oxidation component
  • Bacitracin oxidation component, analysis method thereof and fragmentation mode of double-bond sulfated cysteine oxidation component

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Experimental program
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Embodiment 1

[0067] This embodiment provides a method for analyzing bacitracin oxidation components, comprising the following steps:

[0068] S1, preparation of bacitracin test solution and bacitracin oxidation solution:

[0069] Accurately weigh bacitracin reference substance 40mg, put in 10ml measuring bottle, add mobile phase A and mobile phase B that volume ratio is 77:23 and dissolve to concentration and be 4mg / mL, obtain described bacitracin need testing solution;

[0070] Accurately weigh 40 mg of bacitracin reference substance, add 1 ml of hydrogen peroxide solution with a hydrogen peroxide concentration of 30%, dissolve, leave at room temperature for 5 hours, dilute to a concentration of 4 mg / mL with mobile phase A and mobile phase B at a volume ratio of 77:23, That is, the bacitracin oxidation solution is obtained;

[0071] S2, the bacitracin test solution and the bacitracin oxidation solution obtained in S1 were analyzed by HPLC-ESI-Q / TOF-MS:

[0072] Mass spectrometry conditi...

Embodiment 2

[0080] Structural analysis of enamine / double bond sulfonated bacitracin A and deamination / enamine / double bond sulfonated bacitracin A:

[0081] The structural analysis of bacitracin A can be found in the Chinese invention patent (Zhang Hanzhi et al., a high-performance liquid chromatography method for the analysis of bacitracin components, Chinese invention patent, 201811467424.3). After comparing the secondary mass spectra, it can be found that bacitracin The fragmentation mode can be significantly affected after sulfonation. Since the changed positions are mainly concentrated on the 1-position isoleucine and the 2-position cysteine, the structural analysis of the sulfonated components is mainly concentrated on the end of the linear peptide chain.

[0082] Enamine / double bond sulfonated bacitracin A ( Figure 9 ) and deamination / enamine / double bond sulfonated bacitracin A ( Figure 10 ) compared with the difference in molecular weight of 17, it is speculated that the latter...

Embodiment 3

[0084] Structural Analysis of Double Bond Sulfonated Bacitracin A:

[0085] Double bond sulfonated bacitracin A ( Figure 13 ) is 2 less than the molecular weight of sulfonated bacitracin A. By analyzing its characteristic ions m / z 703.8905, 425.2385, 296.1956, 268.2006, etc., it can be deduced that the α, β-carbon of the 2-position cysteine ​​forms a double bond, and the fragment ion and Ascription between structures see Figure 14 shown. SO 3 For the mechanism of departure see Figure 12 .

[0086] In summary, a new bacitracin oxidation component has been discovered in the present invention, and its structure can be analyzed by UPLC-MS and MS / MS methods, and it is named as enamine / double bond sulfonated bacitracin A and deamination / enamine / double bond sulfonated bacitracin A. Additionally, the present invention reveals a novel fragmentation mode of the double bond sulfonated cysteine ​​oxidation component, i.e. the easy loss of SO with the assistance of the double ...

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Abstract

The invention discloses a bacitracin oxidation component, an analysis method of the bacitracin oxidation component and a fragmentation mode of a double-bond sulfated cysteine oxidation component. By adopting the analysis method provided by the invention, double-bond sulfated bacitracin A, enamine / double-bond sulfated bacitracin A and deamination / enamine / double-bond sulfated bacitracin A are discovered for the first time; and the structures of the double-bond sulfonation bacitracin A, the enamine / double-bond sulfonation bacitracin A and the deamination / enamine / double-bond sulfonation bacitracinA are identified through high-resolution mass spectrometry and secondary mass spectrometry data for the first time. The invention also discloses a fragmentation mode of the double-bond sulfonated cysteine oxidation component, i.e., SO3 is easy to lose under the assistance of double bonds, so that a series of characteristic ions are obtained, and the chemical structure of the oxidation component is judged. The mass spectrometric analysis strategy method can be used in research of analyzing double-bond sulfonation oxidation components of other bacitracin, including but not limited to bacitracinB, C, D, E, F, H, J, M, N, X, Y and the like.

Description

technical field [0001] The invention relates to the field of bacitracin detection, in particular to a bacitracin oxidation component, an analysis method thereof and a fragmentation mode of the double bond sulfonated cysteine ​​oxidation component. Background technique [0002] Bacitracin is a multicomponent antimicrobial peptide produced by Bacillus licheniformis or Bacillus subtilis, which can strongly inhibit Gram-positive bacteria and is mainly used to treat penicillin-resistant staphylococcal infections. At present, more than 30 kinds of bacitracin components have been reported, and the main active component is bacitracin A (for the structural formula see figure 1 ). In the early stage of this study, an ammonium formate-acetonitrile separation system was developed (Chinese Journal of Pharmaceutical Sciences, 2018, 53(23): 2041-2046 and Chinese invention patent: 201811467424.3), which has a better separation effect on the components of bacitracin and can directly for ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/02C07K14/32
CPCG01N30/02C07K14/32G01N2030/047
Inventor 张含智刘浩罗文燕
Owner SHANGHAI INST FOR FOOD & DRUG CONTROL