CN104792724A - Rapid and nondestructive identification method of optical isomer with biochemical activity - Google Patents
Rapid and nondestructive identification method of optical isomer with biochemical activity Download PDFInfo
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- CN104792724A CN104792724A CN201510159231.1A CN201510159231A CN104792724A CN 104792724 A CN104792724 A CN 104792724A CN 201510159231 A CN201510159231 A CN 201510159231A CN 104792724 A CN104792724 A CN 104792724A
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Abstract
The invention provides a rapid and nondestructive identification method of an optical isomer with biochemical activity. The method comprises steps as follows: (1) adopting a selective adsorption material to perform selective adsorption treatment on an optical isomer sample; (2) collecting vibration spectrum data of a product obtained after treatment in Step (1); (3) identifying whether the sample is the optical isomer with the biochemical activity or not according to characteristic differences of the vibration spectrum data obtained in Step (2) under specific frequency. With the adoption of the method, rapid, efficient and environment-friendly identification can be performed on the optical isomer with the biochemical activity, no polarized light accessory is required, and the application range of vibration spectrum is extended, so that an important technological means is provided for separation, purification, efficient production, safe usage and the like of the optical isomer with the biochemical activity.
Description
Technical field
The present invention relates to food and drug safety field, specifically, relate to a kind of quick nondestructive discrimination method of biochemical activity optical isomer.
Background technology
Organism optical isomerism belongs to the one of organism rotamerism.Optical isomer is mainly present in organism, especially containing sp
3in the carbon atom organism of hydridization.When sp occurs carbon atom
3during hydridization, its 4 outer-shell electron tracks are the distribution of tetrahedron solid.When above-mentioned carbon atom 4 outer-shell electron tracks are in conjunction with different functional group (A, B, C, D), i.e. asymmetric carbon atom (i.e. C
*), just produce optical isomer (as shown in Figure 1), wherein, fine rule represents sp
3the tetrahedron spatial structure of hydbridized carbon atoms, thick line represents asymmetric carbon atom (C
*) be parallel to two sp of paper
3hybrid orbital, real wedge shape line represents asymmetric carbon atom (C
*) stretch out the sp of paper
3hybrid orbital, empty wedge shape line represents asymmetric carbon atom (C
*) sp of recessed paper
3hybrid orbital.
Optical isomer is generally divided into levo form (L-type) and d-isomer (D type).In the fields such as life science, agronomy, materia medica, medical science and physiology, most levo form has biochemical activity, that is biochemical activity optical isomer, otherwise, most d-isomer is without biochemical activity, that is non-biochemical activity optical isomer, even has certain toxicity.
As can be seen here, the quick nondestructive of biochemical activity optical isomer is differentiated and/or the quick nondestructive whether being mixed into non-biochemical activity optical isomer in biochemical activity optical isomer is differentiated at agricultural product/numerous areas such as food security, medical and health to be extremely important detections.To traditional discrimination method of optical isomer based on chromatography, mainly there are the problems such as length consuming time, contaminated environment, efficiency is low.Vibrational spectrum technology based on the vibration of material molecule, rotational energy level transition to electromagnetic absorption.Common vibrational spectrum technology comprises closely/middle infrared spectrum, Raman spectrum, tera-hertz spectra etc.Vibrational spectrum technology has the features such as spectral data sample rate is fast, analysis efficiency is high, green non-pollution, has a wide range of applications in the field such as life science, medical science and physiology, materia medica, agronomy at present.In vibrational spectrum, common vibrational spectrum can only respond for the absorption of vibrations of functional group due to it; And optical isomer to be functional group locus different, on structure of functional groups and indifference, therefore common vibrational spectrum cannot be differentiated optical isomer.Even if employing polarization spectrum, annex use procedure complexity is loaded down with trivial details, is difficult to operation.Therefore, problem demanding prompt solution is become to the exploitation of efficient, the green discrimination method of biochemical activity optical isomer.
Still be in the starting stage at present to the research of tera-hertz spectra, differentiate and differentiate to there is not yet in principle clearly to report at the quick nondestructive of biochemical activity optical isomer.
Summary of the invention
The present invention is directed to a discriminating difficult problem for biochemical activity optical isomer, provide a kind of based on vibrational spectrum technology, its objective is and quick nondestructive discriminating is carried out to biochemical activity optical isomer.
Specifically, the method for the invention comprises the following steps:
(1) adopt selective absorbent, selective adsorption process is carried out to optical isomer sample;
(2) the vibrational spectrum data of the rear products therefrom of acquisition step (1) process;
(3) according to the feature difference of step (2) gained vibrational spectrum data under characteristic frequency, differentiate whether sample is the biochemical active optical isomer of tool.
The flow process of above-mentioned steps as shown in Figure 2.
Optical isomer sample of the present invention specifically refers to levo form, d-isomer or raceme.In the fields such as life science, agronomy, materia medica, medical science and physiology, most levo form has biochemical activity, that is biochemical activity optical isomer.Such as, left-handed-glutamic acid participates in metabolic process and the biochemical reaction of human body, have biochemical activity, and dextrorotation-glutamic acid does not have biochemical activity.Again such as, left-handed-tartrate has anti-oxidant biochemical activity of Denging, be widely used in food and medicine field, and d-tartaric acid does not have biochemical activity, and even have certain toxicity, racemic tartaric acid does not also have biochemical activity.In the present invention, the biochemical active optical isomer of described tool refers to levo form.
Because tera-hertz spectra has longer wavelength, therefore, than other vibrational spectrum, there is larger advantage in the relative position of this character functional group in research molecule of tera-hertz spectra, that is, tera-hertz spectra not only has response to intramolecular structure of functional groups, and in more large scale, have response to the overall configuration of molecule, this is that the present invention preferably uses tera-hertz spectra to carry out the principle of quick nondestructive discriminating to biochemical activity optical isomer.
The present invention, by selective adsorption and tera-hertz spectra being combined, enhances the difference of different optical isomer to a certain extent, is conducive to the discriminating of tera-hertz spectra to biochemical activity optical isomer.
Step of the present invention (1) specifically comprises the following steps: take optical isomer sample and selective absorbent with mol ratio 1:2 ~ 3, fully to be infiltrated by sample and mix with pure water with selective absorbent, for subsequent use after natural air drying.Described selective absorbent is preferably beta-schardinger dextrin-.
Furthermore, tera-hertz spectra is on data representation, and comprise the many forms such as absorption spectra, spectrum of refractive index, the present invention is preferably spectrum of refractive index.After interacting with selective absorbent, the absorption coefficient of sample can be disturbed to a certain extent, even occurs stronger background interference; Spectrum of refractive index is the spectrogram of material to tera-hertz spectra refractive index at different frequencies, even if when selective absorbent enough and/or excessive to ensure that optical isomer is adsorbed completely, sample can not be interfered to the refraction of terahertz light, and is reinforced owing to there is selective adsorption the difference of the refraction of terahertz light by the biochemical activity optical isomer of selective adsorption wherein.Therefore, preferred index spectrum of the present invention.
The mode of collected specimens tera-hertz spectra comprises attenuated total reflection (Attenuated TotalReflection, ATR), transmission (Transmission) etc.The present invention preferably adopts the tera-hertz spectra of attenuated total reflectance collected specimens, and resolution, the accuracy of which are higher, sample rate is faster, sample preparation is more simple, sample nondestructive detection, sample detection can be realized after recyclable, and operate more convenient.
As a kind of preferred version, the method for the invention comprises the following steps:
(1) take optical isomer sample and beta-schardinger dextrin-with mol ratio 1:2 ~ 3, mix after fully infiltrating with pure water, natural air drying, obtain absorption potpourri, for subsequent use;
(2) Terahertz-time-domain spectroscopy data of described absorption potpourri are gathered; Gather required condition to comprise:
Terahertz light spectral resolution: 0.007 ~ 0.008THz;
Terahertz light spectral frequency: 0.6 ~ 0.9THz;
Tera-hertz spectra sample mode: attenuated total reflection;
Tera-hertz spectra reference: empty light path;
Tera-hertz spectra accumulative frequency: 2000 ~ 2100 times;
(3) by Fourier transform, Terahertz-time-domain spectroscopy data are converted to Terahertz-spectrum of refractive index data; According to the refractive index value in Terahertz-spectrum of refractive index, differentiate whether optical isomer sample is the biochemical active optical isomer of tool.
Terahertz light spectral resolution of the present invention is preferably 0.0076THz.
Tera-hertz spectra accumulative frequency of the present invention is preferably 2048 times.
When practical operation, terahertz light spectral frequency is the single-frequency selected in described frequency range.Terahertz light spectral frequency of the present invention is preferably 0.7 ~ 0.8THz, more preferably 0.7THz.
Adopt method provided by the invention, d-isomer and raceme all can't detect obvious refractive index value, only have levo form to have obvious refractive index value.Therefore, method provided by the invention is without the need to reference substance, and whether the testing sample that identifies that just can be quick, easy by means of only refractive index value is the biochemical active optical isomer of tool, and the biochemical active optical isomer of described tool refers to levo form.
Because the detectability of terahertz light-spectrum of refractive index is generally 0.1, based on this, the criterion of the method for the invention is: if the refractive index of sample is greater than 0.1, then judgement sample is the biochemical active optical isomer of tool, and namely sample is levo form, for improving the accuracy of judgement further, preferred judgment threshold is 0.3, that is: if the refractive index of sample is greater than 0.3, then judgement sample is the biochemical active optical isomer of tool, and namely sample is levo form.Correspondingly, if the refractive index of sample is less than 0.1, then judgement sample does not have biochemical activity, and namely sample is d-isomer or raceme.
Optical isomer sample of the present invention is left-handed-tartrate, d-tartaric acid or racemic-tartrate preferably, and correspondingly, the biochemical active optical isomer of described tool is left-handed-tartrate.
The present invention protects described method further and to prepare the application in food or medicine with biochemical activity optical isomer for raw material.Adopt the method for the invention can judge whether testing sample is the biochemical active optical isomer of tool quickly and accurately, thus with testing sample be raw material prepare food or medicine time, the functional of product and security can be guaranteed.
The present invention proposes a kind of biochemical activity optical isomer quick nondestructive discrimination method based on vibrational spectrum technology, extends the purposes of vibrational spectrum in the discriminating of biochemical activity optical isomer quick nondestructive.The features such as the method has fast, accurate, work efficiency is high, green non-pollution, not only can differentiate to provide powerful guarantee and technical support for the quick nondestructive of biochemical activity optical isomer, and to aspects such as guarantee food and drug safety, raising industrial and agricultural production efficiency, promotion life science, medical science and physiology sound development, there is positive role.
Accompanying drawing explanation
Fig. 1 is optical isomer schematic diagram of the present invention;
Fig. 2 is the schematic flow sheet of the method for the invention;
Fig. 3 is Terahertz described in experimental example 1-refractive index spectrogram;
Fig. 4 is Terahertz described in experimental example 2-refractive index spectrogram.
Embodiment
Below in conjunction with drawings and Examples, the specific embodiment of the present invention is described in further detail.Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.
Each embodiment adopts INSTRUMENT MODEL: TAS7500SP (Japanese ADVANTEST company).
The sample that the embodiment of the present invention relates to be optical activity the unknown left-handed-tartrate, d-tartaric acid or racemic-tartrate.
Embodiment 1
Following steps are adopted to differentiate the tartrate sample A of optical activity the unknown:
(1) take tartrate sample A and beta-schardinger dextrin-, the mol ratio of described tartrate sample A and beta-schardinger dextrin-is 1:2.5; Mix after fully infiltrating with pure water, natural air drying, obtain absorption potpourri, for subsequent use;
(2) Terahertz-time-domain spectroscopy data of described absorption potpourri are gathered; Gather required condition to comprise:
Terahertz light spectral resolution: 0.0076THz;
Terahertz light spectral frequency: 0.7THz;
Tera-hertz spectra sample mode: attenuated total reflection;
Tera-hertz spectra reference: empty light path;
Tera-hertz spectra accumulative frequency: 2048 times;
(3) by Fourier transform, Terahertz-time-domain spectroscopy data are converted to Terahertz-spectrum of refractive index data; According to the refractive index in Terahertz-spectrum of refractive index, differentiate whether tartrate sample A is the biochemical active L-TARTARIC ACID of tool (left-handed-tartrate).
After testing, the refractive index of sample is 0.7, and judgement sample is the biochemical active L-TARTARIC ACID of tool.
Embodiment 2
Compared with embodiment 1, difference is only, the mol ratio of tartrate sample A and beta-schardinger dextrin-is 1:2, and terahertz light spectral frequency is 0.8THz, and tera-hertz spectra accumulative frequency is 2000 times.
After testing, the refractive index of sample is 0.6, and judgement sample is the biochemical active L-TARTARIC ACID of tool.
Embodiment 3
Compared with embodiment 1, difference is only, the mol ratio of tartrate sample A and beta-schardinger dextrin-is 1:3, and terahertz light spectral resolution is 0.008THz, and terahertz light spectral frequency is 0.6THz, and tera-hertz spectra accumulative frequency is 2100 times.
After testing, the refractive index of sample is 0.7, and judgement sample is the biochemical active L-TARTARIC ACID of tool.
Embodiment 4
Compared with embodiment 1, difference is only, terahertz light spectral resolution is 0.007THz, and terahertz light spectral frequency is 0.9THz.
After testing, the refractive index of sample is 0.4, and judgement sample is the biochemical active L-TARTARIC ACID of tool.
Embodiment 5
Compared with embodiment 1, difference is only, testing sample is the tartrate sample B of optical activity the unknown.
After testing, the refractive index of sample is less than 0.1, and judgement sample does not have biochemical activity.
Embodiment 6
Compared with embodiment 1, difference is only, testing sample is the tartrate sample C of optical activity the unknown.
After testing, the refractive index of sample is less than 0.1, and judgement sample does not have biochemical activity.
Experimental example 1
Respectively with known L-TTA, D-TTA, the DL-TTA of optical activity for testing sample, process without β-CD, in the frequency range of 0-1THz, gather Terahertz-spectrum of refractive index (other parameter is with embodiment 1).Wherein, β-CD i.e. beta-schardinger dextrin-, L-TTA and L-TARTARIC ACID (levotartaric acid, biochemical activity tartrate), D-TTA and D-tartrate (dextrotartaric acid, non-biochemical activity tartrate), DL-TTA and DL-tartrate (racemic tartaric acid, non-biochemical activity tartrate).
Being horizontal ordinate with frequency, take refractive index as ordinate, the spectrum of refractive index of L-TTA, D-TTA, DL-TTA is plotted in same figure upper (as shown in Figure 3).As seen from the figure, three kinds of materials all have refraction in the frequency range of 0-1THz, spectrogram close to and without evident regularity, therefore, do not carry out selective adsorption process and accurately cannot identify the biochemical active L-TTA of tool.
Experimental example 2
Respectively with β-CD and known L-TTA, D-TTA, the DL-TTA of optical activity for testing sample, in the frequency range of 0-1THz, gather Terahertz-spectrum of refractive index (other parameter is with embodiment 1).Wherein, β-CD i.e. beta-schardinger dextrin-, L-TTA and L-TARTARIC ACID (levotartaric acid, biochemical activity tartrate), D-TTA and D-tartrate (dextrotartaric acid, non-biochemical activity tartrate), DL-TTA and DL-tartrate (racemic tartaric acid, non-biochemical activity tartrate).
Being horizontal ordinate with frequency, take refractive index as ordinate, the spectrum of refractive index of β-CD, β-CD_L-TTA, β-CD_D-TTA, β-CD_DL-TTA is plotted in same figure upper (as shown in Figure 4).As seen from the figure, in the frequency range of 0.6 ~ 0.9THz, after beta-schardinger dextrin-process left-handed-refractive index value is significantly greater than other sample with tartrate (β-CD_L-TTA), and the refractive index of β-CD, β-CD_D-TTA and β-CD_DL-TTA is all lower than 0.1.
Preferred tera-hertz spectra characteristic frequency 0.7THz further, β-CD_L-TTA refractive index is 0.7, and β-CD_D-TTA, β-CD_DL-TTA, β-CD are when characteristic frequency 0.7THz, refractive index is all less than 0.1, that is under this characteristic frequency, β-CD_L-TTA is obviously greater than β-CD_D-TTA, β-CD_DL-TTA, β-CD to 3 of the refractive index of terahertz light times to the refractive index of terahertz light, accordingly, quick nondestructive discriminating can be carried out to biochemical activity tartrate (L-TARTARIC ACID).
Although above the present invention is described in detail with a general description of the specific embodiments, on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (10)
1. a quick nondestructive discrimination method for biochemical activity optical isomer, is characterized in that, comprise the following steps:
(1) adopt selective absorbent, selective adsorption process is carried out to optical isomer sample;
(2) the vibrational spectrum data of the rear products therefrom of acquisition step (1) process;
(3) according to the feature difference of step (2) gained vibrational spectrum data under characteristic frequency, differentiate whether sample is the biochemical active optical isomer of tool.
2. method according to claim 1, is characterized in that, described optical isomer sample is levo form, d-isomer or raceme, and the biochemical active optical isomer of described tool is levo form.
3. method according to claim 1 and 2, is characterized in that, described vibrational spectrum is tera-hertz spectra.
4. the method according to claims 1 to 3 any one, is characterized in that, described selective absorbent is beta-schardinger dextrin-.
5. the method according to Claims 1 to 4 any one, is characterized in that, said method comprising the steps of:
(1) adopt beta-schardinger dextrin-, selective adsorption process is carried out to optical isomer sample;
(2) Terahertz-time-domain spectroscopy data of the rear products therefrom of acquisition step (1) process; During collection, required condition comprises:
Terahertz light spectral resolution: 0.007 ~ 0.008THz;
Terahertz light spectral frequency: 0.6 ~ 0.9THz;
Tera-hertz spectra sample mode: attenuated total reflection;
Tera-hertz spectra reference: empty light path;
Tera-hertz spectra accumulative frequency: 2000 ~ 2100 times;
(3) by Fourier transform, Terahertz-time-domain spectroscopy data are converted to Terahertz-spectrum of refractive index data; According to the refractive index value in Terahertz-spectrum of refractive index, differentiate whether optical isomer sample is the biochemical active optical isomer of tool.
6. method according to claim 5, is characterized in that, the frequency of described tera-hertz spectra is: 0.7 ~ 0.8THz.
7. the method according to claim 1 ~ 6 any one, is characterized in that, described optical isomer sample is left-handed-tartrate, d-tartaric acid or racemic-tartrate; The biochemical active optical isomer of described tool is left-handed-tartrate.
8. method according to claim 7, is characterized in that, said method comprising the steps of:
(1) take tartrate sample and beta-schardinger dextrin-with mol ratio 1:2 ~ 3, mix after fully infiltrating with pure water, natural air drying, obtain absorption potpourri, for subsequent use;
(2) Terahertz-time-domain spectroscopy data of described absorption potpourri are gathered; Gather required condition to comprise:
Terahertz light spectral resolution: 0.007 ~ 0.008THz;
Terahertz light spectral frequency: 0.7 ~ 0.8THz;
Tera-hertz spectra sample mode: attenuated total reflection;
Tera-hertz spectra reference: empty light path;
Tera-hertz spectra accumulative frequency: 2000 ~ 2100 times;
(3) by Fourier transform, Terahertz-time-domain spectroscopy data are converted to Terahertz-spectrum of refractive index data; According to the refractive index value in Terahertz-spectrum of refractive index, differentiate tartrate sample be whether tool biochemical active left-handed-tartrate.
9. method according to claim 8, is characterized in that, if the refractive index value in Terahertz-spectrum of refractive index is greater than 0.1, then judgement sample be tool biochemical active left-handed-tartrate.
10. method described in claim 1 ~ 9 any one to prepare the application in food or medicine for raw material with biochemical activity optical isomer.
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