CN113801103B - Patern co-Buchi optimized reaction method - Google Patents
Patern co-Buchi optimized reaction method Download PDFInfo
- Publication number
- CN113801103B CN113801103B CN202110983623.5A CN202110983623A CN113801103B CN 113801103 B CN113801103 B CN 113801103B CN 202110983623 A CN202110983623 A CN 202110983623A CN 113801103 B CN113801103 B CN 113801103B
- Authority
- CN
- China
- Prior art keywords
- reaction
- reagent
- patern
- buchi
- parallel light
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
- G01N2030/067—Preparation by reaction, e.g. derivatising the sample
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a Patern co-Buchi optimized reaction method, which relates to the Patern co-Buchi reaction field, wherein the reaction condition is that 20 parts of PB reagent is added into 2 parts of reaction reagent, the mixture is dissolved in 20 parts of mixed solvent of acetonitrile and water mixed in a ratio of 14:6, an irradiation lamp of a parallel light reactor is 254nm, and the mixed solvent is irradiated for 30min with irradiation power of 25%, 50%, 75% or 100%, 3-formaldehyde pyridine is adopted as the reaction reagent, and PB reaction is carried out in a parallel light reaction instrument; the reaction is rapid and the reaction binding factor is the largest; the invention effectively widens the application of PB reaction in the fields of lipid isomer identification and quantitative research in lipidomics, and greatly improves PB reaction efficiency.
Description
Technical Field
The invention relates to the field of Patern co-Buchi reaction, in particular to a Patern co-Buchi optimized reaction method.
Background
Lipids are important components constituting cell membranes, mainly responsible for storing energy, controlling complex signaling pathways in cell biology; modern research has shown that lipids play an important role in the pathogenesis of non-alcoholic fatty liver disease (NAFLD), neurological diseases, and cancer; lipids include saturated lipids and unsaturated lipids, which have multiple isomers due to the difference in the positions of the carbon-carbon double bonds (c=c) in the unsaturated lipids and have different physiological meanings; thus, the accurate knowledge of the lipid is important; researchers have successfully used a photochemical reaction with ultraviolet radiation, i.e., the Patern co-Buchi (PB) reaction, in combination with tandem mass spectrometry (MS/MS) to identify and quantify unsaturated lipids in complex mixtures; however, there is still a great challenge, firstly the addition rate of PB reaction is low, and PB reagent is less selected; the PB reaction is a classical [2+2] photochemical reaction of a carbonyl compound with an olefin to form a compound comprising an oxetane, which can be used to synthesize some oxetanes that are difficult to obtain by heating or other chemical methods; the PB reaction mechanism and thermal instability react carbonyl-containing aldehydes or ketones with c=c bonds in olefins under UV excitation, and due to the relative positions of the carbonyl groups and the c=c bonds, two oxetane isomers are formed, so how to increase the addition rate of PB reactions is a technical problem to be solved urgently by those skilled in the art.
Disclosure of Invention
The invention aims to solve the technical problems of overcoming the defects in the prior art and providing a Patern co-Buchi optimized reaction method.
The invention is realized by the following technical scheme: a Patern co-Buchi optimized reaction method comprises adding 20 parts PB reagent into 2 parts of reactant, dissolving in 20 parts of mixed solvent of acetonitrile and water mixed at a ratio of 14:6, irradiating the mixed solvent with irradiation power of 25%, 50%, 75% or 100% for 30min at 254nm as an irradiation lamp of a parallel light reactor.
According to the above technical scheme, preferably, the reactant is one or more of benzaldehyde, formaldehyde, acetaldehyde, 2-pyridylaldehyde, 3-formylpyridine, 4-pyridylaldehyde, acetone, 3-acetylpyridine and 3-acetylpyrrole.
According to the above technical scheme, preferably, the PB reagent is 3-formaldehyde pyridine.
According to the above technical scheme, preferably, the irradiation lamp of the parallel light reactor is 254nm, and the reaction solvent is irradiated for 30min at 100% irradiation power.
According to the above technical scheme, preferably, the parameters of the parallel light reactor are set to be 50 percent of stirring, 90 percent of rotation and 100 percent of rotation speed.
The beneficial effects of the invention are as follows: the invention adopts a parallel light reaction instrument to carry out PB reaction and adopts a mass spectrum MRM mode to carry out detection; screening the PB reactant to obtain an optimal PB reactant 3-formaldehyde pyridine, wherein the reaction is rapid and the reaction binding factor is the largest; the PB reaction and the mass spectrum detection are separated and are not interfered with each other, so that the PB reaction is as complete as possible, and the mass spectrum detection can also reach the optimal condition; in conclusion, PB reaction combined with MS/MS can be used as a powerful tool for screening unsaturated lipids in lipid biology; the invention adopts the optimal PB reagent, combines a parallel light reaction device with a mass spectrum MRM model, can widen the application of PB reaction in the fields of lipid isomer identification and quantitative research in lipidomics, and greatly improves PB reaction efficiency.
Drawings
FIG. 1 shows histograms representing additive factor X generated by different PB agents;
FIG. 2 shows Total Ion Chromatogram (TIC) of 2mM oleic acid added to 20mM 3-formylpyridine, dissolved in 20mL of a mixed solvent of isopropanol and water (14:6), and irradiated under 254nm UV for 10min,30min,60 min;
FIG. 3 shows Total Ion Chromatogram (TIC) of 2mM oleic acid added to 20mM acetone, dissolved in 20mL of a mixed solvent of isopropanol and water (14:6), and irradiated with 254nm UV for 10min,30min,60 min;
FIG. 4 shows a histogram of addition factor X generated from 3-acetylpyridine and 3-formylpyridine as PB reagent;
FIG. 5 shows a histogram indicating the effect of different solvents on PB reaction with increasing irradiation time;
FIG. 6 shows a histogram indicating the effect of different solvents on PB reaction;
the histogram shown in fig. 7 represents the effect of different illumination intensities on PB response.
Detailed Description
The following description of the embodiments of the invention will be made apparent and complete in conjunction with the accompanying drawings, in which it is evident that the embodiments described are some, but not all embodiments of the invention. All other embodiments, based on the embodiments of the invention, which would be apparent to one of ordinary skill in the art without making any inventive effort are intended to be within the scope of the invention.
As shown in the figure, the invention provides a Patern-Buchi optimized reaction method, which comprises the steps of adding 20 parts of PB reagent into 2 parts of reaction reagent according to the volume part ratio, dissolving the PB reagent in 20 parts of mixed solvent of acetonitrile and water mixed in a ratio of 14:6, and irradiating the mixed solvent for 30min at 25%, 50%, 75% or 100% of irradiation power by using an irradiation lamp of a parallel light reactor at 254 nm.
According to the above embodiment, the reactant is preferably a mixture of one or more of benzaldehyde, formaldehyde, acetaldehyde, 2-pyridinecarboxaldehyde, 3-carboxaldehyde pyridine, 4-pyridinecarboxaldehyde, acetone, 3-acetylpyridine, 3-acetylpyrrole.
According to the above embodiment, preferably, the PB reagent is 3-formylpyridine.
According to the above embodiment, it is preferable that the irradiation lamp of the parallel light reactor is 254nm, and the reaction solvent is irradiated at 100% irradiation power for 30min.
According to the above embodiment, preferably, the parameters of the parallel light reactor are set to 50% stirring, 90% rotation and 100% rotation speed.
UHPLC-MS instrument conditions UHPLC analysis adopts the Shimadzu LC-30AD system (Kyoto Shimadzu, japan); separation was performed using an ACQUITY UPLC C18 column (Waters, 1.7 μm, 2.1X100 mm 2); the mobile phase is water, methanol, acetonitrile (3:1:1, v/v/v) (A) and acetonitrile (B); both A and B contain 5mmol/L ammonium acetate; the flow rate is 0.3mL/min, and the sample injection amount is 2 mu L; gradient elution is carried out for 0 to 0.5min, and the concentration of B is 20 percent; 0.5 to 1.5min,20 to 40 percent of B; 1.5-3 min, 40-60% B;3-13 minutes, 60-100% B;13-14 minutes, 100% B; 14-17 minutes, 20%; mass spectrometry was performed on a triple quadrupole ion trap mass spectrometer (QTRAP 6500+) (AB SCIEX, framingham, MA, USA) equipped with an ESI source; the chromatogram is obtained in a predetermined Multiple Reaction Monitoring (MRM) with a certain time window; in either positive or negative ion mode; MS parameter settings are as follows: gas temperature,400 ℃; ion spray voltage,5500V; GS1and GS2, both 50psi; CUR,35psi.
The MRM acquisition mode is to infer parent ions and child ions obtained by collision induction according to PB binding experiments; taking 3-formaldehyde pyridine as an example, the mass-core ratio of 3-formaldehyde pyridine to oleic acid is 107.04 and 282.26 respectively. In the positive ion mode, oleic acid is combined with K ions, and the ratio of mass to atomic nucleus is 321.22; the oleic acid and 3-formaldehyde pyridine react with each other under the condition of light radiation to generate two PB reaction binders which are isomers, and the PB reaction binder has a molecular mass of 389.29 in a positive ion mode; from an understanding of the PB reaction and an observation of its reaction binders, we can infer that two PB reaction binders will produce two daughter ions with molecular masses 218.19 and 248.16 under collision induction by mass spectrometry, and that they can be targeted qualitatively and quantitatively by MRM mode.
Parallel light reflector conditions A parallel light reactor (PL-DY 1600) for PB reaction was manufactured by Cisco technologies Co., ltd. Beijing plar Lin Sai; the parameters were set to 50 agitations, 90 revolutions, 100% rotational speed. The irradiation lamp was 254nm, and the irradiation power was 25%, 50%, 70% or 100%, respectively.
MS data processing: all raw data were analyzed using analysis 1.6.2 software; peak area derivation using Sciex OS1.4 software (AB Sciex, framingham, MA, USA); statistical analysis was performed using Prism 8.0 (Graph Pad Prism); taking an addition factor X as an evaluation index; the calculation formula is x= (I (PB on -PB off ))/I(reference(OA))。
PB reagent selection
A suitable PB reagent should firstly be able to react rapidly with the unsaturated lipid PB and secondly its PB adduct should be easily detectable with a higher addition factor in order to better localize the double bond position of the unsaturated lipid. Considering the first element, the test examined the more chemically active benzaldehyde, formaldehyde, acetaldehyde, acetone, 2-acetylpyridine, 3-acetylpyrrole, 2-formylpyridine, 3-formylpyridine, 4-pyridinecarboxaldehyde. The test result shows that the acetone, benzaldehyde, formaldehyde and acetaldehyde have better response to the diagnosis ions in the negative ion mode; the diagnosis ions obtained by PB reagent such as 3-acetylpyrrole and 3-formaldehyde pyridine with N on benzene ring have better response in positive ion mode, and the PB reaction and the diagnosis ions are shown as follows by taking acetone and 3-formaldehyde pyridine as examples, and oleic acid is used as a standard unsaturated lipid reagent in the test; oleic acid has an m/z of 282.26Da, in negative ion mode, an m/z of 281.25Da, in positive ion mode, an m/z of 321.22Da, and acetone has an m/z of 58.04Da, and 3-formaldehyde pyridine has an m/z of 107.04Da. PB reaction adduct of oleic acid and acetone gives two isomers (T-1, T-2) with m/z of 339.29Da under the negative ion mode, and gives two diagnostic ions with m/z of 197.15Da (T-1) and 171.10Da (T-2) respectively under the action of collision energy. PB reaction adduct of oleic acid and 3-formaldehyde pyridine gives two isomers (F-1, F-2) with m/z of 390.30Da in positive ion mode, and gives two diagnostic ions with m/z of 218.19Da (F-1) and 248.16Da (F-2) respectively under the action of collision energy. The double bond position of the unsaturated lipid can be calculated according to the diagnostic ion, wherein two peaks appear in the diagnostic ion f-1m/z218.19 Da, which is estimated to be the front of the retention time, namely the diagnostic ion f-2 loses carboxyl under the action of collision energy, so as to form m/z218.19 Da. All selected PB reagents were examined, and the addition factor of 3-formylpyridine was first obtained according to the addition factor, and the experiment examined that under the same conditions, as the UV irradiation time was increased, the mass spectrum response of PB reaction conjugate was significantly enhanced when PB reagent was 3-formylpyridine, but no significant change was observed when PB reagent was acetone. Meanwhile, the PB addition factor of the 3-formaldehyde pyridine is obviously better than that of the 3-acetyl pyridine in 10 seconds by comparing the 3-formaldehyde pyridine with the 3-acetyl pyridine with higher PB addition rate, and the PB reaction of the 3-formaldehyde pyridine is proved to be very rapid, so that the method can be applied to offline PB reaction, and can be better used with online liquid phase mass spectrum. Thus, the selection of 3-formylpyridine as PB reagent was started to optimize its reaction conditions, and its reaction rate was further examined.
Optimizing PB solvent conditions: respectively taking isopropanol and acetonitrile as solvents for PB reaction to examine the influence of the solvents on PB reaction; meanwhile, the influence of the solvent on PB reaction when the PB reagent is acetone can be examined.
The structure of the 3-formaldehyde pyridine can be known that N element is combined on a benzene ring, and the fatty acid is known to have carboxyl groups, if the hydroxyl group in the solvent possibly has an inhibition effect on PB reaction of PB reagent and unsaturated lipid, so that the solvent isopropanol and acetonitrile are examined, and the PB reagent and PB reaction change of oleic acid in the two solvents is observed; we compared the response of the PB reagent in AC and 3-formylpyridine, when the PB reagent is AC, the response of the PB reaction conjugate is not obviously changed no matter the solvent is acetonitrile or isopropanol, but when the PB reagent is 3-formylpyridine, the response of the PB reaction conjugate is obviously higher than that when the solvent is isopropanol, when the solvent is acetonitrile, the response of oleic acid is gradually reduced along with the increase of time, and when the solvent is isopropanol, the response is not obviously changed, so that the PB reaction is more strongly reacted in a system with the solvent being acetonitrile; therefore, acetonitrile is preferably selected as the PB reaction solvent.
Optimizing ultraviolet irradiation power: examining 25%, 50%, 75% and 100% illumination power in a parallel light reaction instrument; in order to examine the influence of different irradiation intensities on PB reaction, four irradiation powers in a parallel light reaction instrument are examined, wherein the PB reaction addition factor X reaches the highest when the irradiation powers of the four parallel light reaction instruments are respectively 25%, 50%, 75% and 100% and the irradiation power of 254nm ultraviolet is 100%; the final selection of irradiation power for this study was 100%.
Optimizing PB reaction conditions: and (3) a response surface experiment is designed by using software, the ratio of a lipid sample to a PB reagent in the PB reaction and the ratio of a reaction solvent to water are examined, the influence of ultraviolet irradiation time on the PB reaction is optimized, and the PB reaction condition is optimized, and the detection limit and the quantitative limit of the PB reaction are obtained.
In order to further improve the PB addition reaction factor, a response surface test is designed by using design software according to the screened PB reagent and reaction solvent, the reaction proportion (A) of a lipid sample and the PB reagent in PB addition reaction is examined, the ratio (B) of the reaction solvent is examined, the influence of 254nm ultraviolet irradiation time (C) on the PB reaction addition factor is shown as a result, and a test fitting equation has significance; the PB reagent proportion and the reaction solvent proportion obtained from the test result are larger, the ultraviolet irradiation time of 254nm is longer, and the PB reaction addition factor is larger; the optimal PB reaction condition obtained by the response surface optimization result is as follows: 1mM oleic acid and 10mM 3-formylpyridine were dissolved in 18 mM LACN and 2mL water, 254nm100% irradiation power, and irradiation time was 120 minutes. And verifying for three times according to the optimized condition; the result shows that the PB addition factor X reaches 4, so that the mass spectrum response of the PB reaction conjugate is greatly improved; based on the optimized conditions, a detection limit (S/n=3) of 10pM and a quantification limit (S/n=10) of 100pM were obtained.
Accurate positioning of unsaturated lipid double bond position by 3-formaldehyde pyridine
First, in the positive ion mode, since 3-formylpyridine contains N, the m/z value of the diagnostic ion is even, and thus the PB reaction conjugate is easily recognized.
Second, PB reaction produces two isomers, the molecules of which are (C a H b O c +3-formylpyridine +h), by collision-induced dissociation, two diagnostic ions F1 and F2 (containing carboxyl groups), f1=14n1+92, f2=14n2+92+30, and n1+n2=a, (n 1 is an unsaturated double bond site lipid).
Taking oleic acid (n=9) as an example, taking 3-formaldehyde pyridine as a PB reagent, wherein 3-formaldehyde pyridine contains carbonyl aldehyde, reacting with C=C bond in olefin under UV excitation, splitting double bond of oleic acid and combining with 3-formaldehyde pyridine to generate PB reaction conjugate, obtaining two isomers with m/z value of 390.3da under positive ion mode, and breaking PB reaction conjugate at double bond combining position by collision induction to obtain diagnostic ion fragments F1 and F2; f1 As calculated, n1=9, calculated as 218.19 =14n1+92, f2= 248.16 =14n2+92+30, the double bond position of oleic acid is at position 9.
Lipids are important substances in various organs and tissues of the human body, play an important role in various vital activities of the human body, including a large amount of unsaturated lipids; unsaturated lipids have a large number of isomers due to the difference in the double bond positions; the structure determining function, it is important to accurately identify the double bond position of unsaturated lipid; the invention adopts a parallel light reaction instrument to carry out PB reaction and adopts a mass spectrum MRM mode to carry out detection; screening the PB reactant to obtain an optimal PB reactant 3-formaldehyde pyridine, wherein the reaction is rapid and the reaction binding factor is the largest; the PB reaction and the mass spectrum detection are separated and are not interfered with each other, so that the PB reaction is as complete as possible, and the mass spectrum detection can also reach the optimal condition; in conclusion, PB reaction combined with MS/MS can be used as a powerful tool for screening unsaturated lipids in lipid biology; the invention adopts the optimal PB reagent, combines a parallel light reaction device with a mass spectrum MRM model, can widen the application of PB reaction in the fields of lipid isomer identification and quantitative research in lipidomics, and greatly improves PB reaction efficiency.
In the description of the present invention, it should be noted that the directions or positional relationships indicated by the terms "center", "upper", "lower", "left", "right", "vertical", "horizontal", "inner", "outer", etc. are based on the directions or positional relationships shown in the drawings, are merely for convenience of describing the invention and simplifying the description, and do not indicate or imply that the apparatus or elements referred to must have a specific orientation, be constructed and operated in a specific orientation, and thus should not be construed as limiting the invention. Furthermore, the terms "first," "second," and "third" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance.
In the description of the invention, it should be noted that, unless explicitly stated and limited otherwise, the terms "mounted," "connected," and "connected" are to be construed broadly, and may be, for example, fixedly connected, detachably connected, or integrally connected; can be mechanically or electrically connected; can be directly connected or indirectly connected through an intermediate medium, and can be communication between two elements. The specific meaning of the terms in the invention will be understood by those of ordinary skill in the art in a specific context.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the invention, but not for limiting the same; although the invention has been described in detail with reference to the foregoing embodiments, it will be appreciated by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the invention.
Claims (2)
1. A method for the optimized Patern co-Buchi reaction, characterized in that it comprises the following steps:
1mM oleic acid and 10mM 3-formylpyridine were dissolved in 18 mM LACN and 2mL water as solvents to obtain a mixed solution;
and (3) irradiating the mixed solution by using an irradiation lamp of a parallel light reactor with the wavelength of 254nm at 100% of irradiation power for 120 minutes.
2. A Patern co-B chi optimized reaction method according to claim 1, characterized in that the parameters of the parallel light reactor are set to 50 stirring, 90 rotation and 100 rotation speed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110983623.5A CN113801103B (en) | 2021-08-25 | 2021-08-25 | Patern co-Buchi optimized reaction method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110983623.5A CN113801103B (en) | 2021-08-25 | 2021-08-25 | Patern co-Buchi optimized reaction method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113801103A CN113801103A (en) | 2021-12-17 |
| CN113801103B true CN113801103B (en) | 2023-06-23 |
Family
ID=78894155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110983623.5A Active CN113801103B (en) | 2021-08-25 | 2021-08-25 | Patern co-Buchi optimized reaction method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113801103B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109884212A (en) * | 2019-03-27 | 2019-06-14 | 清华大学深圳研究生院 | Unsaturated fatty acid quantitative approach based on chemical derivatization and HPLC-MS |
| CN111060584A (en) * | 2019-12-31 | 2020-04-24 | 武汉大学 | Method for identifying position of double bonds of carbon-carbon double bond isomer |
-
2021
- 2021-08-25 CN CN202110983623.5A patent/CN113801103B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109884212A (en) * | 2019-03-27 | 2019-06-14 | 清华大学深圳研究生院 | Unsaturated fatty acid quantitative approach based on chemical derivatization and HPLC-MS |
| CN111060584A (en) * | 2019-12-31 | 2020-04-24 | 武汉大学 | Method for identifying position of double bonds of carbon-carbon double bond isomer |
Non-Patent Citations (1)
| Title |
|---|
| Paternò － Büchi( PB) 反应与串联质谱结合实现不饱和脂质精确结构解析;马潇潇 等;《分析测试学报》;20200131;第39卷(第1期);第19-27页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113801103A (en) | 2021-12-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Heiles | Advanced tandem mass spectrometry in metabolomics and lipidomics—methods and applications | |
| US7718958B2 (en) | Mass spectroscopic reaction-monitoring method | |
| Chen et al. | cis-Diol functional group recognition by reactive desorption electrospray ionization (DESI) | |
| Osburn et al. | Ion–molecule reactions: analytical and structural tool | |
| Qian et al. | Identification of all classes of spin-trapped carbon-centered radicals in soybean lipoxygenase-dependent lipid peroxidations of ω-6 polyunsaturated fatty acids via LC/ESR, LC/MS, and tandem MS | |
| Vu et al. | Ozone‐induced dissociation on a traveling wave high‐resolution mass spectrometer for determination of double‐bond position in lipids | |
| Chen et al. | N-(1-naphthyl) ethylenediamine dinitrate: a new matrix for negative ion MALDI-TOF MS analysis of small molecules | |
| JP2019082481A (en) | Method for detecting reverse triiodothyronine through mass analysis | |
| Gorman et al. | The quenching of aromatic ketone triplets by oxygen: competing singlet oxygen and biradical formation? | |
| Tang et al. | De novo glycan sequencing by electronic excitation dissociation and fixed-charge derivatization | |
| Wan et al. | Nonuniform electric field-enhanced in-source declustering in high-pressure photoionization/photoionization-induced chemical ionization mass spectrometry for operando catalytic reaction monitoring | |
| CN113801103B (en) | Patern co-Buchi optimized reaction method | |
| Hu et al. | Metabolite identification of ursolic acid in mouse plasma and urine after oral administration by ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry | |
| JP2001526398A (en) | Method and apparatus for determining reaction rates in liquids by mass spectrometry | |
| Radisavljević et al. | Colloidal TiO2 nanoparticles as substrates for M (S) ALDI mass spectrometry of transition metal complexes | |
| Damnjanović et al. | Laser desorption and ionization time-of-flight versus matrix-assisted laser desorption and ionization time-of-flight mass spectrometry of Pt (II) and Ru (III) metal complexes | |
| Olivo et al. | Following a chemical reaction on the millisecond time scale by simultaneous X-ray and UV/Vis spectroscopy | |
| Chu et al. | Catalyst-free oxidation reactions in a microwave plasma torch-based ion/molecular reactor: an approach for predicting the atmospheric oxidation of pollutants | |
| Palanisamy et al. | In situ derivatization of Au nanoclusters via aurophilic interactions of a triphenylphosphine gold (i) salt with neurotransmitters and their rapid MALDI-TOF-MS detection in mice brain tissue extracts | |
| Domingues et al. | Detection and characterization of hydroxyl radical adducts by mass spectrometry | |
| Li et al. | Site-specific photochemical reaction for improved C= C location analysis of unsaturated lipids by ultraviolet photodissociation | |
| Murashima et al. | Quantification of monosaccharide enantiomers using optical properties of hydrogen-bonded tryptophan | |
| Hadavi et al. | Ion mobility spectrometry-tandem mass spectrometry strategies for the on-line monitoring of a continuous microflow reaction | |
| JP4838639B2 (en) | Substrate for mass spectrometry and mass spectrometer | |
| Aubriet et al. | Studies of the chromium oxygenated cluster ions produced during the laser ablation of chromium oxides by laser ablation/ionization Fourier transform ion cyclotron resonance mass spectrometry |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |