CN108265094A - A kind of preparation method of α -2,3 deaminations sialic acid lactulose - Google Patents
A kind of preparation method of α -2,3 deaminations sialic acid lactulose Download PDFInfo
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- CN108265094A CN108265094A CN201710024368.5A CN201710024368A CN108265094A CN 108265094 A CN108265094 A CN 108265094A CN 201710024368 A CN201710024368 A CN 201710024368A CN 108265094 A CN108265094 A CN 108265094A
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- C12P19/00—Preparation of compounds containing saccharide radicals
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Abstract
The invention discloses a kind of preparation methods of 2,3 deamination sialic acid lactuloses of α, it is characterised in that：40~80 parts by weight of mannose, 100~200 parts by weight of Sodium Pyruvate, 50~100 parts by weight of lactulose, 125~260 parts by weight of sodium triphosphate (CTP), it is dissolved in 4000~8000 parts by weight ultra-pure waters, with the NaOH tune pH8.5 of 4 mol/Ls, the Tris HCl of the pH8.5 of 400~1000 parts by weight, 1 mol/L are added in；Add in the MgCl of 40~100 parts by weight, 2 mol/L2；Add in 5~8 parts by weight acetylneuraminate aldolases, the CMP sialyltransferases of 6~10 parts by weight；2, the 3 sialic acid glycosides transferases of α of 6~10 parts by weight.Then it is reacted 24 hours in 37 DEG C of gas bath oscillators.After the reaction was complete after lactulose, 95% ethyl alcohol of same volume is added into reaction solution, is put into 4 DEG C of refrigerators and stands 30min, 30min is then centrifuged under 7000 revs/min, supernatant is concentrated using rotary evaporation.Using biogum column purification, rotary evaporation concentration, and it is sterling to be freeze-dried.
Description
Technical field
The invention belongs to functional oligosaccharide preparing technical fields, and in particular to a kind of α -2,3 deamination sialic acid lactuloses
Preparation method.
Background technology
Sialic acid (Sialic acid) is the general name of a kind of nine carbon monosaccharide compounds acyl derivatives with carboxyl, extensively
It is present in a variety of organisms such as bacterium, fish, mammal, usually in zooblast surface glycoprotein matter and the sugar chain of glycolipid
End participates in and adjusts many important vital movements, such as cell recognition, biofilm flow and endocytosis, is high
The important molecule that grade animals and certain micro-organisms have.Existing known nearly more than 50 kinds of sialic acid member, wherein, N- acetyl group nerve
Propylhomoserin (Neu5Ac), N- glycoloylneuraminic acids (Neu5Gc) and deamination neuraminic acid (KDN) are three kinds of cores of sialic acid
Monomer, remaining sialic acid is by these three monomer deriveds.
Deamination sialic acid (KDN) is one of three kinds of core members in sialic acid family, can be by mannose as precursor
Synthesis obtains.Deamination sialic acid is largely present in low vertebrate and bacterium, and expression quantity in mammals
It is very low.Studies have reported that deamination sialic acid is highly expressed in human tumor, and is proportionate with malignancy,
Therefore, KDN may be the tumor marker Data Bank of certain tumours.
Recent studies indicate that sialic acid and its derivative inhibit sialidase and resisiting influenza virus, anti-adenovirus,
Anti- parainfluenza virus, anti respiratory syncytial virus, anti-rotavirus etc. play an important roll.Recently it is proposed that " saliva
The concept of liquid acid group " refers to the sialic acid type expressed for specific kind, organ, tissue, cell or subcellular and link
Summation.Using sialic acid as guide synthesize and screen bioactive substance in terms of research it is more active, especially anti-senile dementia,
The research of Anti-tumor metastasis, anti-inflammatory, antiviral etc. has been achieved for greater advance, it was found that some toxic side effects are small, effect
The unique compound of mechanism.It is many to endanger the human health disease such as pathogenesis such as meningitis, influenza, periodontal disease and cause of disease
The sialidase or sialic acid glycosyl transferase of body secretion have substantial connection, will likely be into the research of sialic acid biological activity
For glycobiology research hotspot, sialyloligosaccharide is also constantly presented in completely new posture in the visual field of people.At present, sialic acid
It is mainly used for treating neurogenic disease and senile dementia on the market.And the anti-recognition reaction of sialic acid is that it participates in cell
A kind of mode of identification, there is certain physiology and pathology sense.If sialic acid has the effect for the treatment of cancer to a certain degree, can incite somebody to action
Cancer cell is extracted from human body, and the sialic acid of cell surface is removed with specific enzyme, is being refilled in vivo, is being made one internal
Original cancer cell disintegrates or disappears.But sialic acid market domestic at present relies primarily on import, domestic appearance not yet is big
The manufacturer of scale.So the investigative technique of sialic acid and its oligosaccharides is particularly important in China.
There is large-scale manufacturer or even connects normally to give birth to not yet in domestic deamination sialyloligosaccharide at present
The producer of production is also considerably less.Due to starting late, the core technology of production oxyacetic acid sialyloligosaccharide is not grasped, and domestic
Product of the sialic acid of production also with import in quality and price has a certain distance.The present invention using have lactulose as parent into
Row α -2,3 deamination sialic acids are glycosylation, and obtained novel alpha -2,3 deamination sialic acid lactulose is that very promising activity is few
Sugar has very important science and people's livelihood meaning to their functional study.Exactly according to the demand in market, by continuous
Experiment and exploration, we have invented a kind of α -2, the sialylated lactulose preparation method of 3 deaminations.
Invention content
It is chemically relatively difficult to lactulose progress deamination sialic acid glycosylation the present invention seeks to overcome
Problem.This is because the more general glycosylation reaction of sialic acid glycosylation reaction condition is harsh, stereoselectivity is usually poor, end group
The spatial configuration of carbon is more difficult to control, and sialic acid glycosylation reaction yield is poor, it is difficult to prepare.Using the enzyme process of latest developments to newborn fruit
Sugar progress hydroxyl acetylsalicylic acid is glycosylation modified, using efficient enzymatic clarification technology of preparing, can be successfully prepared out one kind
α -2,3 hydroxyl acetylsalicylic acid lactuloses.
The technical scheme is that：
A kind of α -2,3 deamination sialic acid lactulose preparation methods, it is characterised in that：40~80 parts by weight of mannose, third
100~200 parts by weight of ketone acid sodium, 50~100 parts by weight of lactulose, 125~260 parts by weight of sodium triphosphate (CTP) are dissolved in
In 4000~8000 parts by weight ultra-pure waters, with the NaOH tune pH8.5 of 4 mol/Ls, 400~1000 parts by weight, 1 mol/L is added in
PH8.5 Tris-HCl；Add in the MgCl of 40~100 parts by weight, 2 mol/L2；Add in the contracting of 5~8 parts by weight sialic acid aldehyde
Enzyme, the cmp sialic acid transferase of 6~10 parts by weight；α -2 of 6~10 parts by weight, 3 sialic acid glycosides transferases.It then will mixing
Object is put into 37 DEG C of gas bath oscillators, is reacted 24 hours.The extent of reaction is detected using silica gel thin-layer chromatography (TLC), TLC expansion is molten
Agent uses normal propyl alcohol: methanol: water=4: 2: 1.After the reaction was complete after lactulose, 95% ethyl alcohol of same volume is added into reaction solution,
It is uniformly mixed, is put into 4 DEG C of refrigerators and stands 30min, 30min is then centrifuged under 7000 revs/min, supernatant uses rotary evaporation
Concentration.Concentrate uses biogum (Bio-gel P-2) column chromatography.Solution after purification is collected, rotary evaporation concentrates, and
Freeze-drying is sterling.Gained sterling identifies its molecular weight and structure using mass spectrum and nuclear magnetic resonance, passes through Mass Spectrometric Identification
Molecular weight (see attached drawing 1), abscissa (m/z) is mass-to-charge ratio in attached drawing 1, and ordinate (relative abundance) is relatively rich
Degree, it is 592 that can identify the sterling molecular weight that the present invention prepares, with a kind of α -2,3 deamination sialic acid lactulose molecules
It is identical (since mass spectroscopy uses negative ion mode, so the data that molecular weight is shown on mass spectrogram are 591) explanation to measure 592
The sterling that the present invention prepares is a kind of deamination sialic acid lactulose；Molecular structure (see attached drawing 2) is identified by nuclear magnetic resonance,
Abscissa f1 (ppm) is chemical shift in attached drawing 2, and ordinate is the intensity of absorption peak, can identify what the present invention prepared
Sterling molecular structure is a kind of α -2, and 3 deamination sialic acid lactuloses illustrate a kind of α -2 of the invention, 3 deamination saliva yogurts
Fructose is successfully prepared.A kind of α -2, the structure of 3 deamination sialic acid lactuloses are as follows：See attached drawing 4.
Description of the drawings
A kind of αs -2 of the Fig. 1 for the present invention, 3 deamination sialic acid lactulose mass spectrograms.
A kind of αs -2 of the Fig. 2 for the present invention, 3 deamination sialic acid lactulose nuclear magnetic resonance1H spectrograms.1H-NMR is composed
(600MHz, D2O)1H NMR (600MHz, D2O) δ 4.54 (d, J=7.8Hz, 0.6H), 4.44 (d, J=8.4Hz, 0.4H),
4.20-3.43 (m, 21H), 2.62 (dd, J=12.0and 4.8Hz, 1H), 1.66 (t, J=12.0Hz, 1H).
A kind of αs -2 of the Fig. 3 for the present invention, 3 deamination sialic acid lactulose nuclear magnetic resonance13C spectrograms.13C-NMR is composed
(150MHz, D2O) 13C NMR (151MHz, D2O) δ 173.96,100.32,99.74,98.03,77.23,75.60,75.14,
73.86,72.06,70.21,69.71,69.18,67.67,67.42,66.55,66.03,63.88,62.91,62.59,
61.09。
A kind of α -2 of Fig. 4, the structure chart of 3 deamination sialic acid lactuloses.
Specific embodiment
Embodiment 1
A kind of α -2,3 deamination sialic acid lactulose preparation methods, it is characterised in that：40 parts by weight of mannose, pyruvic acid
100 parts by weight of sodium, 50 parts by weight of lactulose, 150 parts by weight of sodium triphosphate (CTP) are dissolved in 4000 parts by weight ultra-pure waters,
With the NaOH tune pH8.5 of 4 mol/Ls, the Tris-HCl of the pH8.5 of 400 parts by weight, 1 mol/L is added in；Add in 40 parts by weight 2
The MgCl of mol/L2；Add in 5 parts by weight acetylneuraminate aldolases, the cmp sialic acid transferase of 6 parts by weight；The α of 6 parts by weight-
2,3 sialic acid glycosides transferases.Then mixture is put into 37 DEG C of gas bath oscillators, reacted 24 hours.Using silica gel thin-layer layer
(TLC) detection extent of reaction is analysed, TLC developing solvents use normal propyl alcohol: methanol: water=4: 2: 1.After after lactulose, the reaction was complete,
Add 95% ethyl alcohol of same volume into reaction solution, be uniformly mixed, be put into 4 DEG C of refrigerators and stand 30min, then at 7000 revs/min
Lower centrifugation 30min, supernatant are concentrated using rotary evaporation.Concentrate uses biogum (Bio-gel P-2) column chromatography.It receives
The solution of collection after purification, rotary evaporation concentration, and it is sterling to be freeze-dried.A kind of α -2 finally obtained, 3 hydroxyl acetyl salivas
Yogurt fructose sterling is using mass spectrum and nuclear-magnetism identification structure.
Embodiment 2
A kind of α -2,3 deamination sialic acid lactulose preparation methods, it is characterised in that：80 parts by weight, 200 weight of Sodium Pyruvate
Part, 100 parts by weight of lactulose are measured, 260 parts by weight of sodium triphosphate (CTP) are dissolved in 8000 parts by weight ultra-pure waters, are rubbed with 4
You/liter NaOH tune pH8.5, add in 1000 parts by weight, 1 mol/L pH8.5 Tris-HCl；100 parts by weight 2 are added in rub
You/liter MgCl2；Add in 8 parts by weight acetylneuraminate aldolases, the cmp sialic acid transferase of 10 parts by weight；The α of 10 parts by weight-
2,3 sialic acid glycosides transferases.Then mixture is put into 37 DEG C of gas bath oscillators, reacted 24 hours.Using silica gel thin-layer layer
(TLC) detection extent of reaction is analysed, TLC developing solvents use normal propyl alcohol: methanol: water=4: 2: 1.After after lactulose, the reaction was complete,
Add 95% ethyl alcohol of same volume into reaction solution, be uniformly mixed, be put into 4 DEG C of refrigerators and stand 30min, then at 7000 revs/min
Lower centrifugation 30min, supernatant are concentrated using rotary evaporation.Concentrate uses biogum (Bio-gel P-2) column chromatography.It receives
The solution of collection after purification, rotary evaporation concentration, and it is sterling to be freeze-dried.A kind of α -2 finally obtained, 3 hydroxyl acetyl salivas
Yogurt fructose sterling is using mass spectrum and nuclear-magnetism identification structure.
Embodiment 3
A kind of α -2,3 deamination sialic acid lactulose preparation methods, it is characterised in that：50 parts by weight of mannose, pyruvic acid
120 parts by weight of sodium, 65 parts by weight of lactulose, 160 parts by weight of sodium triphosphate (CTP) are dissolved in 6000 parts by weight ultra-pure waters,
With the NaOH tune pH8.5 of 4 mol/Ls, the Tris-HCl of the pH8.5 of 600 parts by weight, 1 mol/L is added in；Add in 60 parts by weight 2
The MgCl of mol/L2；Add in 6 parts by weight acetylneuraminate aldolases, the cmp sialic acid transferase of 7 parts by weight；The α of 7 parts by weight-
2,3 sialic acid glycosides transferases.Then mixture is put into 37 DEG C of gas bath oscillators, reacted 24 hours.Using silica gel thin-layer layer
(TLC) detection extent of reaction is analysed, TLC developing solvents use normal propyl alcohol: methanol: water=4: 2: 1.After after lactulose, the reaction was complete,
Add 95% ethyl alcohol of same volume into reaction solution, be uniformly mixed, be put into 4 DEG C of refrigerators and stand 30min, then at 7000 revs/min
Lower centrifugation 30min, supernatant are concentrated using rotary evaporation.Concentrate uses biogum (Bio-gel P-2) column chromatography.It receives
The solution of collection after purification, rotary evaporation concentration, and it is sterling to be freeze-dried.A kind of α -2 finally obtained, 3 hydroxyl acetyl salivas
Lactulose sterling is acidified using mass spectrum and nuclear-magnetism identification structure.
Embodiment 4
56 parts by weight of mannose, 140 parts by weight of Sodium Pyruvate, 72 parts by weight of lactulose, sodium triphosphate (CTP) 200
Parts by weight are dissolved in 7000 parts by weight ultra-pure waters, with the NaOH tune pH8.5 of 4 mol/Ls, add in 700 parts by weight, 1 mol/L
The Tris-HCl of pH8.5；Add in the MgCl of 80 parts by weight, 2 mol/L2；Add in 7 parts by weight acetylneuraminate aldolases, 7.5 parts by weight
Cmp sialic acid transferase；α -2 of 8 parts by weight, 3 sialic acid glycosides transferases.Then mixture is put into 37 DEG C of gas bath oscillations
In device, react 24 hours.The extent of reaction is detected using silica gel thin-layer chromatography (TLC), TLC developing solvents use normal propyl alcohol: methanol:
Water=4: 2: 1.After the reaction was complete after lactulose, 95% ethyl alcohol of same volume is added into reaction solution, is uniformly mixed, is put into 4 DEG C of ice
30min is stood in case, 30min is then centrifuged under 7000 revs/min, supernatant is concentrated using rotary evaporation.Concentrate is using life
Object glue (Bio-gel P-2) column chromatography.Solution after purification, rotary evaporation concentration are collected, and it is sterling to be freeze-dried.
A kind of α -2 finally obtained, 3 hydroxyl acetylsalicylic acid lactulose sterlings are using mass spectrum and nuclear-magnetism identification structure.
Claims (1)
1. a kind of α -2,3 deamination sialic acid lactulose preparation methods, it is characterised in that：40~80 parts by weight of mannose, acetone
Sour 100~200 parts by weight of sodium, 50~100 parts by weight of lactulose, 125~260 parts by weight of sodium triphosphate (CTP) are dissolved in
In 4000~8000 parts by weight ultra-pure waters, with the NaOH tune pH8.5 of 4 mol/Ls, 400~1000 parts by weight, 1 mol/L is added in
PH8.5 Tris-HCl；Add in the MgCl of 40~100 parts by weight, 2 mol/L2；Add in the contracting of 5~8 parts by weight sialic acid aldehyde
Enzyme, the cmp sialic acid transferase of 6~10 parts by weight；α -2 of 6~10 parts by weight, 3 sialic acid glycosides transferases.It then will mixing
Object is put into 37 DEG C of gas bath oscillators, is reacted 24 hours.The extent of reaction is detected using silica gel thin-layer chromatography (TLC), TLC expansion is molten
Agent uses normal propyl alcohol: methanol: water=4: 2: 1.After the reaction was complete after lactulose, 95% ethyl alcohol of same volume is added into reaction solution,
It is uniformly mixed, is put into 4 DEG C of refrigerators and stands 30min, 30min is then centrifuged under 7000 revs/min, supernatant uses rotary evaporation
Concentration.Concentrate uses biogum (Bio-gel P-2) column chromatography.Solution after purification is collected, rotary evaporation concentrates, and
Freeze-drying is sterling, using the molecular weight and structure of mass spectrum profit nuclear magnetic resonance identification sterling.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1156480A (en) * | 1994-06-28 | 1997-08-06 | 生化学工业株式会社 | Novel deaminoneuraminidase and process for producing same |
| CN101809143A (en) * | 2006-09-26 | 2010-08-18 | 锡拉丘兹大学 | Metabolically engineered escherichia coli for enchanced production of sialic acid |
| CN103820513A (en) * | 2014-02-27 | 2014-05-28 | 中国科学院微生物研究所 | Method for synthesizing sialylated oligosaccharide and analogue thereof |
| WO2015124930A1 (en) * | 2014-02-19 | 2015-08-27 | The University Court Of The University Of Edinburgh | Compositions and methods |
| CN105949250A (en) * | 2016-04-26 | 2016-09-21 | 河南科技学院 | Preparation method of alpha-2,3-sialyllactulose |
-
2017
- 2017-01-04 CN CN201710024368.5A patent/CN108265094B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1156480A (en) * | 1994-06-28 | 1997-08-06 | 生化学工业株式会社 | Novel deaminoneuraminidase and process for producing same |
| CN101809143A (en) * | 2006-09-26 | 2010-08-18 | 锡拉丘兹大学 | Metabolically engineered escherichia coli for enchanced production of sialic acid |
| WO2015124930A1 (en) * | 2014-02-19 | 2015-08-27 | The University Court Of The University Of Edinburgh | Compositions and methods |
| CN103820513A (en) * | 2014-02-27 | 2014-05-28 | 中国科学院微生物研究所 | Method for synthesizing sialylated oligosaccharide and analogue thereof |
| CN105949250A (en) * | 2016-04-26 | 2016-09-21 | 河南科技学院 | Preparation method of alpha-2,3-sialyllactulose |
Non-Patent Citations (2)
| Title |
|---|
| ILIA V. BASKAKOV: "Multifaceted Role of Sialylation in Prion Diseases", 《FRONTIERS IN NEUROSCIENCE》 * |
| 王汝一等: "唾液酸衍生物的合成进展", 《有机化学》 * |
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