CN106279308B - The method for detaching muramic acid using the bacteria residue of production glutamic acid - Google Patents
The method for detaching muramic acid using the bacteria residue of production glutamic acid Download PDFInfo
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- CN106279308B CN106279308B CN201610565555.XA CN201610565555A CN106279308B CN 106279308 B CN106279308 B CN 106279308B CN 201610565555 A CN201610565555 A CN 201610565555A CN 106279308 B CN106279308 B CN 106279308B
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- bacteria residue
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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- 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
- G01N30/90—Plate chromatography, e.g. thin layer or paper chromatography
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Abstract
The invention discloses a kind of methods that the bacteria residue using production glutamic acid removes muramic acid, and steps are as follows：(1) glutamic acid wet bacteria slag is taken, water is added into bacteria residue and carries out ultrasonic extraction, filtering obtains filtrate；(2) filtrate concentrates, and the ethanol solution of 8-12 times of volume (ml/ml), stirring extraction are added into the filtrate after concentration, and filtering obtains white powder；(3) add water mixing into white powder, add hydrochloric acid solution and hydrolyzed 3-5 hours under the conditions of 15-30 DEG C；(4) ether, liquid separation are added into hydrolyzate, solution is divided into three layers, and separation takes upper layer and middle level liquid, is concentrated to dryness to get muramic acid powder.Method using the present invention prepares muramic acid, and the type of required reagent is few, and quantity is small, reduces manufacturing cost, reduces the pollution to environment；And without decoloration, column chromatography for separation, simplify preparation process；The recovery rate of muramic acid is high.
Description
Technical field
The present invention relates to a kind of methods that the bacteria residue using production glutamic acid detaches muramic acid, belong to food and chemical field.
Background technology
Muramic acid is the important component of bacteria cell wall mucopeptide structure, is the biological marker of prokaryotic micro-organisms cell
Close object.The most common use of muramic acid is as the marker for speculating microorganism total amount in varying environment；In addition, muramic acid is solidifying
There is very big research application prospect in collection element, potential bacterial lipase inhibitor and antitumor action.
Currently, muramic acid in the market is expensive, the market demand potential is big.Preparation for muramic acid can pass through
Prepared by chemically synthesized method, but chemically synthesized expensive, be easy to cause the pollution of environment.It is new it is therefore desirable to develop
The stripping means of muramic acid.
Glutamic acid bacteria residue is the principal by product of monosodium glutamate industry, and the glutamic acid bacteria residue that China produces every year is right up to million tons
In the recycling of glutamic acid bacteria residue, it is used as feed and Fertilizer application, generated utility value relatively low at present more.
Jiang Xinying etc. prepares muramic acid to the bacteria residue using production glutamic acid and is studied, in the preparation and inspection of muramic acid
It is achieved compared with much progress in survey method, but the step of it extracts muramic acid includes：Washing, stirring cracking, grease removal, acidolysis, extraction,
Decoloration, concentration extraction, HPTLC detections, column chromatography for separation and purity detecting, entire extraction process step is more, and consuming largely has
Machine reagent, such as chloroform, trichloroacetic acid, not only increase the economic cost of extraction, also pollute the environment if discharging these reagents.
Jiang Xinying etc. further improves the extraction process of muramic acid, and improved extraction process includes being suitble to factory extensive
Two kinds of extraction processes of production of extraction and suitable small lot muramic acid.Wherein, it is suitble to the technological process extracted on a large scale of factory to be：
Acidolysis, decoloration, methanol/ethanol extraction, HPTLC detections, column chromatography for separation and purity detecting；But the technological process is will to produce paddy
The bacteria residue of propylhomoserin directly carries out acidolysis, if carrying out industrial production, the amount of the acid solution of required addition is too big, and production cost is still higher.
It is suitble to the technological process of small lot muramic acid extraction to be：Ultrasonic treatment, centrifugation, acidolysis, decoloration, methanol/ethanol extraction,
HPTLC detections, column chromatography for separation and purity detecting；But the technique is directly split the bacteria residue for producing glutamic acid using supercritical ultrasonics technology
Solution, will produce the impurity such as lipid, need to be purified by operations such as decoloration, column chromatography for separation, preparation process is still comparatively laborious.
Invention content
For the above-mentioned prior art, the object of the present invention is to provide a kind of bacteria residues using production glutamic acid to prepare muramic acid
Method.
To achieve the above object, the present invention uses following technical proposals：
A method of muramic acid being detached using the bacteria residue of production glutamic acid, steps are as follows：
(1) glutamic acid wet bacteria slag is taken, water is added into bacteria residue and carries out ultrasonic extraction, filtering obtains filtrate；
(2) filtrate concentrates, and the ethanol solution of 8-12 times of volume (ml/ml) is added into the filtrate after concentration, and stirring is extracted,
Filtering, obtains white powder；
(3) add water mixing into white powder, add hydrochloric acid solution and hydrolyzed 3-5 hours under the conditions of 15-30 DEG C；
(4) ether, liquid separation are added into hydrolyzate, solution is divided into three layers, and separation takes upper layer and middle level liquid, is concentrated into
It does to get muramic acid powder.
In step (1), the water content of the glutamic acid wet bacteria slag is 40-60% (mass percent).
In step (1), the condition of ultrasonic extraction is：20kHz, 700~900W of ultrasonic power, 2 seconds gaps of ultrasound 2 seconds, surpass
Sound 4-6 times, each 0.5-1h.The purpose of ultrasonic extraction is to carry out broken wall treatment；Power, extraction time and the ultrasound of ultrasonic extraction
Time be influence broken wall treatment effect principal element, the present invention by the optimization to ultrasonic technique condition, make its ensure compared with
Under the premise of good shell-broken effect, and reduce energy consumption.
In step (1), the addition of water is the 8-12 times of volume (g/ml) of glutamic acid bacteria residue dry weight (i.e. in every gram of dry bacteria residue
Water 8-12ml is added).
In step (2), the 45-55% of glutamic acid bacteria residue dry weight, preferably 50% are concentrated the filtrate to.
In step (2), the percentage by volume of the ethanol solution is 90-100%.The mesh that it is extracted using ethanol solution
Be grease removal.
In step (2), the time for stirring extraction is 0.5-1 hours.
In step (3), white powder adds the quality after water mixing to be the 45-55% of glutamic acid bacteria residue dry weight, preferably
50%.
In step (3), the volume fraction of hydrochloric acid solution is that 50% (v/v, i.e. concentrated hydrochloric acid press 1 with water：1 proportioning).
In step (4), the addition of ether and the volume ratio of hydrolyzate are 1：1.Present invention firstly discovers that utilizing ether pair
Hydrolyzate after sour water solution carries out liquid separation processing, can separate object muramic acid and other substances, greatly simplifies
The purification procedures of muramic acid.
The muramic acid prepared to the present invention using the method for thin-layer chromatography Scanning Detction is detected, by the muramic acid of preparation
0.3 milligram of crystallization, which is dissolved in 1 ml methanol solution, is used as sample liquid.The titer for preparing muramic acid is respectively 0.1,0.2,
0.3,0.4,0.5,0.6 mg/ml.Sample liquid (1 μ l/ points) and titer (1 μ l/ points) point is efficient in same GF254
On thin layer silica gel plate (10cm*10cm), solvent is methanol-acetone-acetic acid-water-isopropanol (5：3：1：1：1, volume/volume)
Mixed liquor.It is started to spread out after being saturated 25 minutes at room temperature, 8 centimetres of Zhan Cheng, silica gel plate taking-up is dried.It is with mass concentration
1% ethanol solution of ninhydrin sprays plate dyeing, and plate is placed on 110 degree and bakes 5 minutes.Sample liquid point and standard items liquid point dye red,
Rf values are 0.84, are scanned in 492nm with CAMAG3 thin-layer chromatogram scanners.With the WINCATS1.4.1 software statistics peak areas of the instrument
Integrated value, according to the regression equation calculation of titer quality.Detect and calculate muramic acid content.
Beneficial effects of the present invention：
(1) method using the present invention prepares muramic acid, and the type of required reagent is few, and quantity is small, reduces and is prepared into
This, reduces the pollution to environment；And without decoloration, column chromatography for separation, simplify preparation process；Muramic acid carries
Take rate high, it is 1.2% or more of the dry bacteria residue quality of glutamic acid to use the muramic acid that the method for the present invention is extracted, and preparation
The purity of muramic acid is high.
(2) method for preparing muramic acid using the bacteria residue of production glutamic acid of the invention, first to the bacteria residue of glutamic acid into
Row ultrasonication is handled, and first concentrates filtrate after broken wall treatment, is added ethanol solution and is carried out grease removal processing, is filtered after grease removal
Acid adding carries out acidolysis to the white powder arrived again, the dosage of acid hemolysis process acid solution is greatly reduced, using ether to hydrolysis after acidolysis
Liquid carries out liquid separation processing, can separate object muramic acid and other substances, greatly simplify the separation of muramic acid
Purification step.Above-mentioned each processing step is an organic whole, conditional, is effectively simplified the bacteria residue from production glutamic acid
It is middle to prepare the technological process of muramic acid, and improve the recovery rate of muramic acid.
Specific implementation mode
With reference to embodiment, the present invention is further illustrated, it should explanation, following embodiments merely to
It explains the present invention, its content is not defined.
Embodiment 1：Muramic acid is detached using the bacteria residue of production glutamic acid
It is as follows：
(1) the wet bacteria slag 120g of production glutamic acid (bacteria residue dry weight is 48g).The total volume is set to be after adding water to be dispersed with stirring
500ml.It filters to get filtrate in 20kHz, 700w, ultrasonic 2 seconds gaps ultrasound 0.5h under the conditions of 2 seconds.Filter residue adds water repetition or more
Process 4 times, ultrasound filtration 5 times, merges 5 filtrates and is total to about 1000ml altogether.
(2) combined filter vacuum is concentrated into 20ml, 95% ethyl alcohol 200ml stirrings is added to extract 0.5h, it is static, it isolates
Supernatant.Remainder adds 95% ethyl alcohol of 200ml stirring extraction 0.5h again, filters to obtain 5g white dry powder.
(3) add water into 5g white dry powder, mixing makes total volume be 20ml, then (the volumes point of 20ml 50% are added thereto
Number, v/v) HCl, ordinary-temp hydrolysis 4h under magnetic agitation.
(4) 40ml ether is added into hydrolyzate.It pours into separatory funnel, shakes up, standing is divided into three layers, and upper layer is transparent micro-
Huang, middle level are white slimy, lower layer's brownish red.Identified upper layer and middle level are muramic acid, and upper layer and middle level liquid are taken out in separation,
Through rotary evaporation in vacuo to doing, white muramic acid powder 0.62g is obtained.
Muramic acid manufactured in the present embodiment is detected using the method for thin-layer chromatography Scanning Detction, by the cell wall of preparation
0.3 milligram of acid crystal, which is dissolved in 1 ml methanol solution, is used as sample liquid.The titer for preparing muramic acid is respectively 0.1,0.2,
0.3,0.4,0.5,0.6 mg/ml.Sample liquid (1 μ l/ points) and titer (1 μ l/ points) point is efficient in same GF254
On thin layer silica gel plate (10cm*10cm), solvent is methanol-acetone-acetic acid-water-isopropanol (5：3：1：1：1, volume/volume)
Mixed liquor.It is started to spread out after being saturated 25 minutes at room temperature, 8 centimetres of Zhan Cheng, silica gel plate taking-up is dried.It is with mass concentration
1% ethanol solution of ninhydrin sprays plate dyeing, and plate is placed on 110 degree and bakes 5 minutes.Sample liquid point and standard items liquid point dye red,
Rf values are 0.84, illustrate that white powder manufactured in the present embodiment is muramic acid.
It is scanned in 492nm with CAMAG3 thin-layer chromatogram scanners.It is accumulated with the WINCATS1.4.1 software statistics peak areas of the instrument
Score value, according to the regression equation calculation of titer quality.Detect and calculate muramic acid content.It is computed, prepared by the present embodiment
The purity of muramic acid be 98.2%, gained muramic acid is dry bacteria residue heavy 1.27%.
Embodiment 2：Muramic acid is detached using the bacteria residue of production glutamic acid
It is as follows：
(1) the wet bacteria slag 150g (bacteria residue dry weight be 60g) for taking production glutamic acid, makes the total volume be after adding water to be dispersed with stirring
600ml, ultrasound 0.5h under the conditions of 20kHz, 900w, 2 seconds gaps of ultrasound 2 seconds, filters to get filtrate.Filter residue adds water repetition or more
Process 4 times, total ultrasound filtration 5 times, the total 1200ml of merging filtrate.
(2) combined filter vacuum is concentrated into 30ml, absolute ethyl alcohol 300ml, stirring extraction 0.5h is added to stand, pour out
Supernatant, remainder add 300ml ethyl alcohol stirring extraction 0.5h, filter to obtain 5.5g white dry powder again.
(3) add water into white dry powder, mixing makes total volume be 30ml, then (the volumes point of 30ml 50% are added thereto
Number, v/v) HCl, ordinary-temp hydrolysis 4h under magnetic agitation.
(4) 60ml ether is added into hydrolyzate, pours into separatory funnel, shakes up, stands and divides three layers, upper layer is taken out in separation
With middle level liquid.Through rotary evaporation in vacuo to doing, white muramic acid powder 0.74g is obtained.
Muramic acid manufactured in the present embodiment is detected using the method for thin-layer chromatography Scanning Detction, the results showed that this reality
The purity for applying the muramic acid of example preparation is 97.4%, and gained muramic acid is the 1.20% of dry bacteria residue weight.
Embodiment 3：Muramic acid is detached using the bacteria residue of production glutamic acid
It is 800w by power adjustment used in ultrasound, remaining operation obtains white muramic acid powder 0.65g with embodiment 1.
Muramic acid manufactured in the present embodiment is detected using the method for thin-layer chromatography Scanning Detction, the results showed that this reality
The purity for applying the muramic acid of example preparation is 97.8%, and gained muramic acid is the 1.32% of dry bacteria residue weight.
Comparative example 1：
It is 450w by power adjustment used in ultrasound, with embodiment 1, the muramic acid powder being prepared is weighed for remaining operation.
Gained muramic acid is 0.53g.
Muramic acid manufactured in the present embodiment is detected using the method for thin-layer chromatography Scanning Detction, the results showed that this reality
The purity for applying the muramic acid of example preparation is 96.8%, and gained muramic acid is the 1.07% of dry bacteria residue weight.
Comparative example 2：
Ether in 1 step of embodiment (4) is replaced with into dichloromethane, remaining operation is examined with embodiment 1 through thin-layer chromatography
It surveys, not isolated muramic acid.
Comparative example 3：
Ether in 1 step of embodiment (4) is replaced with into toluene, remaining operation is detected with embodiment 1 through thin-layer chromatography,
Not isolated muramic acid.
Comparative example 4：
The extraction that muramic acid is carried out using the method for embodiment 2 in patent CN103954726A, takes fresh glutamic acid rodlike
120 grams of bacillus bacteria residue (water content 60%, 48 grams of bacteria residue dry weight) carries out the extraction and inspection of muramic acid as described in Example 2
It surveys (amount of reaction reagent doubles by corresponding mass ratio), after testing and calculates, the muramic acid extracted is paddy ammonia
The 1.09% of sour corynebacteria bacteria residue dry weight.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, it is other it is any without departing from the spirit and principles of the present invention made by changes, modifications, substitutions, combinations, simplifications,
Equivalent substitute mode is should be, is included within the scope of the present invention.
Claims (12)
1. a kind of method of bacteria residue separation muramic acid using production glutamic acid, which is characterized in that steps are as follows：
(1) glutamic acid wet bacteria slag is taken, water is added into bacteria residue and carries out ultrasonic extraction, filtering obtains filtrate；
(2) filtrate concentrates, and the ethanol solution of 8-12 times of volume, stirring extraction are added into the filtrate after concentration, and filtering obtains white
Powder；
(3) add water mixing into white powder, add hydrochloric acid solution and hydrolyzed 3-5 hours under the conditions of 15-30 DEG C；
(4) ether, liquid separation are added into hydrolyzate, solution is divided into three layers, and separation takes upper layer and middle level liquid, is concentrated to dryness, i.e.,
Obtain muramic acid powder.
2. the method as described in claim 1, which is characterized in that in step (1), the water content of the glutamic acid wet bacteria slag is
40-60%.
3. the method as described in claim 1, which is characterized in that in step (1), the condition of ultrasonic extraction is：20kHz, ultrasound
2 seconds 700~900W of power, ultrasound gaps 2 seconds, 4-6 times ultrasonic, each 0.5-1h.
4. the method as described in claim 1, which is characterized in that in step (1), the addition of water is glutamic acid bacteria residue dry weight
8-12 times of volume.
5. the method as described in claim 1, which is characterized in that in step (2), concentrate the filtrate to glutamic acid bacteria residue dry weight
45-55%.
6. method as claimed in claim 5, which is characterized in that in the step (2), it is dry to concentrate the filtrate to glutamic acid bacteria residue
The 50% of weight.
7. the method as described in claim 1, which is characterized in that in step (2), the percentage by volume of the ethanol solution is
90-100%.
8. the method as described in claim 1, which is characterized in that in step (2), the time for stirring extraction is 0.5-1 hours.
9. the method as described in claim 1, which is characterized in that in step (3), white powder adds the quality after water mixing to be paddy
The 45-55% of propylhomoserin bacteria residue dry weight,
10. method as claimed in claim 9, which is characterized in that in the step (3), white powder adds the matter after water mixing
Amount is the 50% of glutamic acid bacteria residue dry weight.
11. method described in claim 1, which is characterized in that in step (3), the volume fraction of hydrochloric acid solution is 50%.
12. method described in claim 1, which is characterized in that in step (4), the addition of ether and the volume ratio of hydrolyzate
It is 1：1.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103954726A (en) * | 2014-05-06 | 2014-07-30 | 山东师范大学 | Method for extracting muramic acid from corynebacterium glutamicum dregs and detection method |
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| JPS5215894A (en) * | 1975-07-29 | 1977-02-05 | Yuichi Yamamura | Process for preparing a substance possessing biological actions |
| GB0419722D0 (en) * | 2004-09-06 | 2004-10-06 | Scottish Ass For Marine Scienc | Production and use of surface active agents |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103954726A (en) * | 2014-05-06 | 2014-07-30 | 山东师范大学 | Method for extracting muramic acid from corynebacterium glutamicum dregs and detection method |
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