CN113583062A - Derivatization method of lincomycin, lincomycin derivative and application of derivatization method - Google Patents

Derivatization method of lincomycin, lincomycin derivative and application of derivatization method Download PDF

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CN113583062A
CN113583062A CN202110843425.9A CN202110843425A CN113583062A CN 113583062 A CN113583062 A CN 113583062A CN 202110843425 A CN202110843425 A CN 202110843425A CN 113583062 A CN113583062 A CN 113583062A
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lincomycin
derivatization
derivative
reaction
derivatizing
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方炳虎
侯丽敏
陈良柱
史仁彬
李仲林
刘可欣
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Guangdong Wens Dahuanong Biotechnology Co ltd
South China Agricultural University
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Abstract

The invention discloses a derivatization method of lincomycin, a lincomycin derivative and application of the derivatization method; the derivatization method comprises the steps of adding a reaction solvent without active hydrogen and a derivatization reagent into lincomycin for reaction; the structural general formula of the lincomycin derivative is C50H62N6O18S5(ii) a The application of the lincomycin derivatization method is that the lincomycin derivative is obtained by the lincomycin derivatization method, and then the lincomycin derivative is used for determining the lincomycin content; the derivatization method is used for processing the lincomycin, so that the sensitivity of detecting the lincomycin content in a liquid phase can be improved.

Description

Derivatization method of lincomycin, lincomycin derivative and application of derivatization method
Technical Field
The invention relates to a derivatization method of lincomycin, a lincomycin derivative and application of the derivatization method, and belongs to the technical field of compounds.
Background
Lincomycin is an antibiotic extracted from lincomycin streptococcus fermentation broth, and lincomycin in a determination sample disclosed by the prior art mainly comprises a high performance liquid chromatography, a high performance liquid chromatography-mass spectrometry combined method, a gas chromatography-mass spectrometry determination method and the like. In the determination method, instruments required by the high performance liquid chromatography-mass spectrometry combined method and the gas chromatography-mass spectrometry combined method are expensive and are not easy to popularize. When the high performance liquid chromatograph detects lincomycin, the ultraviolet absorption of the lincomycin is weak, the detection limit and the quantification limit are both higher when the lincomycin is loaded on the computer, and the sensitivity is lower.
Therefore, in the field of analytical chemistry, it is necessary to further study the improvement of lincomycin detection efficiency, sensitivity, and the like.
Disclosure of Invention
In order to overcome the defects of the prior art, the first object of the invention is to provide a lincomycin derivatization method, by which the lincomycin can be treated, so that the sensitivity of detecting the lincomycin content in a liquid phase can be improved.
The second purpose of the invention is to provide a lincomycin derivative.
The third purpose of the invention is to provide the application of the lincomycin derivatization method, which is used for measuring the lincomycin content and greatly improves the sensitivity and efficiency of the measurement.
The first purpose of the invention can be achieved by adopting the following technical scheme: a derivatization method of lincomycin is characterized in that a reaction solvent without active hydrogen and a derivatization reagent are added into lincomycin for reaction.
Further, the reaction solvent containing no active hydrogen is at least one of acetonitrile, tetrahydrofuran, diethyl ether and toluene.
Further, the derivatization reagent is p-toluenesulfonyl isocyanate.
Further, the derivatizing agent was diluted with acetonitrile as a solvent prior to use.
Further, the reaction condition is under the protection of nitrogen, the temperature is 10-30 ℃, and the oscillation is carried out for 20-60 min.
Further, a terminator was added after the reaction to terminate the reaction.
Further, the terminating agent is at least one of water, hydrochloric acid, methanol and ethanol.
Furthermore, the molar ratio of the lincomycin to the derivatization reagent is 1 (1-10).
The second purpose of the invention can be achieved by adopting the following technical scheme: a lincomycin derivative is obtained by a lincomycin derivatization method; the structural general formula of the lincomycin derivative is C50H62N6O18S5The chemical formula is shown as formula I:
Figure BDA0003179893990000021
the derivatization method of lincomycin is to add a reaction solvent without active hydrogen and a derivatization reagent into lincomycin for reaction.
The third purpose of the invention can be achieved by adopting the following technical scheme: the application of the lincomycin derivatization method comprises the steps of obtaining a lincomycin derivative by the lincomycin derivatization method, and then using the lincomycin derivative for determining the lincomycin content; the derivatization method of lincomycin is to add a reaction solvent without active hydrogen and a derivatization reagent into lincomycin for reaction.
Further, the method for determining the lincomycin content is chromatography.
Further, the chromatography includes high performance liquid chromatography, high performance liquid chromatography-mass spectrometry or thin layer chromatography.
Compared with the prior art, the invention has the beneficial effects that:
1. the derivatization method of lincomycin provided by the invention is used for processing lincomycin, so that the sensitivity of detecting the lincomycin content in a liquid phase can be improved;
2. the derivatization method of lincomycin can be used for measuring the lincomycin content, has the characteristics of rapidness, accuracy, simplicity, convenience, easy popularization and low cost, and also has the advantages of mild reaction conditions, few byproducts, no influence of excessive derivatization reagent on the detection of a sample and the like.
Drawings
FIG. 1 is an infrared spectrum of a lincomycin derivative;
FIG. 2 is a high performance liquid chromatogram of a lincomycin standard solution;
FIG. 3 is a high performance liquid chromatogram of a derivatized lincomycin;
FIG. 4 is a high performance liquid chromatogram of lincomycin-containing beef directly measured without derivatization treatment;
FIG. 5 is a high performance liquid chromatogram of lincomycin-containing beef after derivatization treatment;
FIG. 6 is a high performance liquid chromatogram of lincomycin-containing chicken after derivatization treatment.
Detailed Description
The invention will be further described with reference to the accompanying drawings and the detailed description below:
a derivatization method of lincomycin comprises the following steps:
pretreating lincomycin, such as removing water or drying methanol under nitrogen;
diluting p-toluenesulfonyl isocyanate with acetonitrile to obtain a p-toluenesulfonyl isocyanate acetonitrile solution;
adding a reaction solvent without active hydrogen and a tosyl isocyanate acetonitrile solution into lincomycin, wherein the molar ratio of the lincomycin to a derivatization reagent is 1 (1-10), reacting at the temperature of 10-30 ℃ under the protection of nitrogen and under the condition of shaking for 20-60min, adding a terminator for termination, carrying out reduced pressure rotary evaporation to obtain an oily substance, and carrying out vacuum drying.
Wherein the reaction solvent without active hydrogen is at least one of acetonitrile, tetrahydrofuran, diethyl ether and toluene.
Wherein the terminating agent is at least one of water, hydrochloric acid, methanol and ethanol.
The lincomycin derivative is obtained by a lincomycin derivatization method, and the structural general formula is C50H62N6O18S5The chemical formula is shown as formula I:
Figure BDA0003179893990000041
the method for measuring the lincomycin content comprises the following steps:
adding a reactive solvent without active hydrogen and a derivatization reagent into lincomycin for reaction to obtain a lincomycin derivative, and then determining by high performance liquid chromatography, high performance liquid chromatography-mass spectrometry or thin layer chromatography to obtain the lincomycin content in the sample.
The lincomycin contains weak ultraviolet absorption, if the high-sensitivity determination is carried out by adopting a common high performance liquid chromatography, an ultraviolet absorption group needs to be introduced, if the lincomycin is subjected to derivatization treatment firstly, a derivatization reagent is added, particularly, p-toluenesulfonyl isocyanate is a hydroxyl derivatization reagent, the lincomycin is a compound with strong nucleophilicity, and can quickly react with a compound with hydroxyl, so that the lincomycin generates the strong ultraviolet absorption group with a benzene ring, the sensitivity of the lincomycin in the high performance liquid chromatography detection is improved, and the lincomycin has a good application prospect.
Example 1:
preparation of lincomycin derivatives:
adding 10mL of anhydrous acetonitrile and a p-toluenesulfonyl isocyanate acetonitrile solution (4mL of p-toluenesulfonyl isocyanate is diluted by adding 10mL of acetonitrile to obtain the solution with the concentration of 2.5mmol/mL), reacting at 25 ℃ and shaking for 50min under the protection of nitrogen, adding 1mL of water to terminate, swirling for 1min, carrying out reduced pressure rotary evaporation to obtain an oily substance, and carrying out vacuum drying in a vacuum drying oven at 30-35 ℃ for 12h to obtain 1.5g of a white or light yellow solid, namely a lincomycin derivative, with the purity of 96.3%.
1HNMR(600MHz,Chloroform-d)δ9.61(s,1H),8.72(d,1H),7.70-7.76(m,5H),7.59-7.64(m,3H),7.36-7.45(m,6H),7.29(d,J＝3.6Hz,2H),5.50(d,J＝5.1Hz,1H),5.04(d,J＝12.3Hz,1H),4.72-4.81(m,2H),4.51-4.53(m,1H),4.11(d,1H),3.98-4.06(m,2H),3.45-3.59(m,3H),2.81(s,3H),2.40(s,3H),2.37(s,3H),2.35(s,3H),2.32(s,3H),2.08-2.15(m,2H),1.99(s,3H),1.35-1.39(m,2H),1.24-1.29(m,2H),1.16-1.19(t,3H),0.98-1.02(d,J＝4.8Hz,3H),0.86-0.89(t,3H)；13CNMR(101MHz,DMSO-d)δ171.60(C＝O),168.10(C＝O),150.60(C＝O),150.32(C＝O),150.31(C＝O),144.78,144.69,136.65,136.29,136.19,129.72,129.33,129.19,127.74,127.70,127.51,127.11,84.65,71.26,69.71,69.00,68.54,67.25,61.32,60.14,49.07,41.07,37.11,35.29,34.09,20.82,20.19,20.17,19.47,13.07,13.03,12.45,12.23。
The infrared spectrum of the derivative is shown in figure 1.
Example 2:
content determination (HPLC) in lincomycin standard solution:
instruments and conditions:
an Agilent 1260 type high performance liquid chromatography system in America, which comprises a quaternary gradient system, a column temperature control box, an ultraviolet visible variable wavelength detector, an online vacuum degasser and an automatic sampling system; a chromatographic column: agile nt C18(150 × 4.6mm,3.5 μm), ZORBAX; water phase: 0.1 vt% triethylamine water. Organic phase: and (3) acetonitrile. Isocratic elution, wherein the ratio of the water phase to the organic phase is 90: 10; flow rate: 1.0 mL/min; column temperature: 25 ℃; detection wavelength: 210 nm; sample introduction amount: 20 μ L.
The experimental steps are as follows:
the lincomycin standard solution is diluted to 100 mu g/mL by a mobile phase, passes through a 0.22 mu m organic filter membrane, is injected with 20 mu L of sample for high performance liquid chromatography determination, and a High Performance Liquid Chromatography (HPLC) chart is shown in figure 2, and the data are as follows. Signal: VWD1A, wavelet-210 nm
Figure BDA0003179893990000061
Adding a 28.5 vt% p-toluenesulfonyl isocyanate acetonitrile solution and acetonitrile into lincomycin standard solution, respectively 100 mu L, vortexing for 30s, standing at room temperature for 30min, after the materials react sufficiently, adding 100 mu L methanol to stop the reaction, vortexing and mixing uniformly, fixing the volume to 1mL by using a mobile phase, passing through a 0.22 mu m organic filter membrane, injecting 20 mu L of the solution for high performance liquid chromatography determination, wherein a High Performance Liquid Chromatography (HPLC) diagram is shown in figure 3, and the data are as follows.
Signal: VWD1A, wavelet-227 nm
Figure BDA0003179893990000062
Figure BDA0003179893990000071
The detection sensitivity on a high performance liquid chromatograph after the derivatization of the lincomycin is up to 17 times higher than that before the derivatization.
Example 3:
determination of lincomycin content in beef (HPLC):
instruments and conditions:
an Agilent 1260 type high performance liquid chromatography system in America, which comprises a quaternary gradient system, a column temperature control box, an ultraviolet visible variable wavelength detector, an online vacuum degasser and an automatic sampling system; a chromatographic column: agile nt C18(150 × 4.6mm,3.5 μm), ZORBAX; water phase: 0.385g of ammonium acetate was weighed out and dissolved in 1L of purified water plus 0.1 vt% formic acid. Organic phase: and (3) acetonitrile. Isocratic elution, organic phase 40:60 (after mixing well, adding 100mL water, mixing well again); flow rate: 1.0 mL/min; column temperature: 25 ℃; detection wavelength: 227 nm; sample introduction amount: 20 μ L.
The experimental steps are as follows:
accurately weighing 5g of beef and placing the beef in a 50mL centrifuge tube, adding lincomycin standard solution, standing for 10min, adding 10mL of acetonitrile, vortexing for 30s, performing ultrasound for 10min, performing medium-speed oscillation for 15min, centrifuging at 6500rpm/min for 5min, and taking supernatant and placing the supernatant in another 50mL centrifuge tube; the tissue residue was re-extracted once with 10mL acetonitrile, the supernatants from the two extractions were combined and the nitrogen was allowed to evaporate to about 1 mL. Adding 5mL of water for redissolving, then adding 5mL of saturated acetonitrile n-hexane for degreasing, centrifuging at 6500rpm/min for 5min, discarding the n-hexane layer, and waiting for purification.
Purifying:
and activating the C18 solid-phase extraction column by using 3mL of methanol, 3mL of water and 3mL of sodium dodecyl sulfate buffer solution in sequence, enabling the sample re-solution to pass through the column, keeping the flow rate at 20 drops/min, leaching the sample solution by using 3mL of water after the sample solution completely flows out, and discarding all effluent liquid. After 5min of vacuum suction, the mixture was eluted with 3mL of methanol in a 10mL glass tube with a stopper. Volatilizing at 40 ℃ under nitrogen, adding 100 mu L of 28.5 vt% of p-toluenesulfonyl isocyanate acetonitrile solution and acetonitrile respectively, whirling for 30s, standing at room temperature for 30min, after the reaction is completed, adding 100 mu L of methanol to stop the reaction, whirling and mixing uniformly, fixing the volume to 1mL by using a mobile phase, passing through a 0.22 mu m organic filter membrane, and injecting 20 mu L of sample for high performance liquid chromatography determination.
FIG. 4 is a High Performance Liquid Chromatography (HPLC) chart of lincomycin-containing beef directly measured without derivatization treatment; FIG. 5 is a High Performance Liquid Chromatography (HPLC) chart of lincomycin-containing beef after derivatization treatment.
Example 4:
determination of lincomycin content (HPLC) in chicken:
instruments and conditions:
an Agilent 1260 type high performance liquid chromatography system in America, which comprises a quaternary gradient system, a column temperature control box, an ultraviolet visible variable wavelength detector, an online vacuum degasser and an automatic sampling system; a chromatographic column: agile nt C18(150 × 4.6mm,3.5 μm), ZORBAX; water phase: 0.385g of ammonium acetate was weighed out and dissolved in 1L of purified water plus 0.1 vt% formic acid. Organic phase: and (3) acetonitrile. Isocratic elution, organic phase 40:60 (after mixing well, adding 100mL water, mixing well again); flow rate: 1.0 mL/min; column temperature: 25 ℃; detection wavelength: 227 nm; sample introduction amount: 20 μ L.
The experimental steps are as follows:
accurately weighing 5g of chicken, placing the chicken in a 50mL centrifuge tube, adding lincomycin standard solution, standing for 10min, adding 7.5mL of acetonitrile, vortexing for 30s, performing ultrasound for 10min, oscillating at medium speed for 15min, centrifuging at 6500rpm/min for 5min, and taking supernatant to place in another 50mL centrifuge tube; the tissue residue was re-extracted once with 7.5mL acetonitrile, centrifuged at 8000rpm/min for 10min, the supernatants from the two extractions were combined and nitrogen was allowed to evaporate to about 1 mL. Adding 5mL of water for redissolving, then adding 5mL of saturated acetonitrile n-hexane for degreasing, centrifuging at 8000rpm/min for 5min, discarding the n-hexane layer, and waiting for purification.
Purifying:
and activating the C18 solid-phase extraction column by using 3mL of methanol, 3mL of water and 3mL of sodium dodecyl sulfate buffer solution in sequence, enabling the sample re-solution to pass through the column, keeping the flow rate at 20 drops/min, leaching the sample solution by using 3mL of water after the sample solution completely flows out, and discarding all effluent liquid. After 5min of vacuum suction, the mixture was eluted with 3mL of methanol in a 10mL glass tube with a stopper. Volatilizing at 40 ℃ under nitrogen, adding 100 mu L of 28.5 vt% of p-toluenesulfonyl isocyanate acetonitrile solution and acetonitrile respectively, whirling for 30s, standing at room temperature for 30min, after the reaction is completed, adding 100 mu L of methanol to stop the reaction, whirling and mixing uniformly, fixing the volume to 1mL by using a mobile phase, passing through a 0.22 mu m organic filter membrane, and injecting 20 mu L of sample for high performance liquid chromatography determination.
FIG. 6 is a High Performance Liquid Chromatography (HPLC) chart of lincomycin-containing chicken after derivatization treatment.
Various other changes and modifications to the above-described embodiments and concepts will become apparent to those skilled in the art from the above description, and all such changes and modifications are intended to be included within the scope of the present invention as defined in the appended claims.

Claims (10)

1. A derivatization method of lincomycin is characterized in that a reaction solvent without active hydrogen and a derivatization reagent are added into lincomycin for reaction.
2. The method for derivatizing lincomycin as claimed in claim 1, wherein the reaction solvent containing no active hydrogen is at least one of acetonitrile, tetrahydrofuran, diethyl ether and toluene.
3. The method for derivatizing lincomycin as claimed in claim 1, wherein the derivatizing agent is p-toluenesulfonyl isocyanate.
4. The derivatization method of lincomycin according to claim 1, wherein the reaction conditions are nitrogen protection, temperature 10-30 ℃, and shaking for 20-60 min.
5. The method for derivatizing lincomycin as claimed in claim 1, wherein a terminator is added after the reaction to terminate the reaction.
6. The method for derivatizing lincomycin as claimed in claim 5, wherein the terminating agent is at least one of water, hydrochloric acid, methanol and ethanol.
7. The method for derivatizing lincomycin according to claim 1, wherein the molar ratio of the lincomycin to the derivatizing agent is 1 (1-10).
8. Lincomycin derivative, and lincomycin derivative is prepared by a lincomycin derivatization methodObtaining; characterized in that the structural general formula of the lincomycin derivative is C50H62N6O18S5The chemical formula is shown as formula I:
Figure FDA0003179893980000021
the derivatization method of the lincomycin comprises the step of adding a reaction solvent without active hydrogen and a derivatization reagent into the lincomycin for reaction.
9. The application of the lincomycin derivatization method is characterized in that the lincomycin derivative is obtained by the lincomycin derivatization method, and then the lincomycin derivative is used for determining the lincomycin content; the derivatization method of the lincomycin comprises the step of adding a reaction solvent without active hydrogen and a derivatization reagent into the lincomycin for reaction.
10. Use of the method for derivatizing lincomycin according to claim 9, wherein the method for determining the lincomycin content is chromatography.
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CN103424481A (en) * 2013-05-06 2013-12-04 华中农业大学 Residue analysis method of lincomycin, clindamycin and spectinomycin
CN107957463A (en) * 2017-12-29 2018-04-24 宁夏希望田野生物农业科技有限公司 The detection method of lincomycin residual quantity in a kind of soil

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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