CN110295210A - A method of preparing fine jade trisaccharide - Google Patents
A method of preparing fine jade trisaccharide Download PDFInfo
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- CN110295210A CN110295210A CN201910657361.6A CN201910657361A CN110295210A CN 110295210 A CN110295210 A CN 110295210A CN 201910657361 A CN201910657361 A CN 201910657361A CN 110295210 A CN110295210 A CN 110295210A
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
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Abstract
The present invention provides a kind of method of fine jade trisaccharide prepared, is after being digested the pickling agent of agarose using β-agarase, then carries out purifying preparation；Agarase therein is the enzyme that can be digested agarose as new fine jade tetrose；The present invention realizes method that is special and efficiently preparing odd number fine jade trisaccharide by combining acid hydrolyzation and enzyme process.Compared with acid hydrolyzation prepares the method for odd number fine jade oligosaccharides, yield of the present invention is obviously improved, and can be realized specific preparation；Compared with enzymatic isolation method prepares odd number fine jade oligosaccharides, it is capable of handling the substrate of high concentration, so that the method for the present invention be made to have higher efficiency compared to existing method.
Description
Technical field
The invention belongs to oligosaccharides preparation technical fields, and in particular to a method of prepare fine jade trisaccharide.
Background technique
Agaropectin oligose is derived from agar polysaccharide and (is mainly isolated from certain red algaes, such as agar, Porphyra yezoensis, wart
Shape fragrant plant mentioned in ancient texts) one kind native oligosaccharides, there are a variety of physiological activity.Agaropectin oligose is by by (1 → 3)-O- β-D- galactose residue
The linear chain molecule that (1 → 4)-O-3,6- inner ether-α-L- galactose residue alternately forms.It is non-according to agaropectin oligose
The difference of reducing end, it is the new fine jade oligosaccharides of 3,6- inner ether-L- galactolipin and non-reduced that agaropectin oligose can be divided into non-reducing end
End is the fine jade oligosaccharides of D- galactolipin.Fine jade oligosaccharides has certain physiological activity, and the researchs such as Jin discovery fine jade oligosaccharides can inhibit alcohol
Toxicity provides certain protective effect for liver.Performance in terms of the result of study of Ye etc. shows fine jade pentasaccharides for anti-neurotrosis
Preferable physiological activity out.
The method for preparing agaropectin oligose at present mainly has chemical method and two kinds of enzyme process, mainly prepares odd number by chemical method
Fine jade oligosaccharides, enzyme process is then usually to prepare the new fine jade oligosaccharides of even number and even number fine jade oligosaccharides, if it is desired to odd number fine jade oligosaccharides is prepared, it can only
By combining β-agarase and Xin Qiong disaccharide-hydrolysing enzymes two-step method to prepare.It is few that odd number fine jade is wherein prepared by chemical method, that is, acid hydrolyzation
Sugar has many advantages, such as to be swift in response, it is larger handle concentration of substrate, but product is more miscellaneous after acidolysis, separates more difficulty.Enzyme
Solution has many advantages, such as that reaction is mild, product is single, is easily isolated compared to acid hydrolyzation, but its can substrate specificity concentration compared with
It is low.Therefore, the specific technology of preparing for developing specific aggregation degree odd number fine jade oligosaccharides is of great significance.
Summary of the invention
Present invention aims to overcome that prepare fine jade product oligosaccharides complicated for traditional acid hydrolyzation, it is difficult to which separation and enzymatic isolation method are logical
Fine jade trisaccharide can not be prepared by crossing single agarase, and the present invention pre-processes agarose by acidolysis, is new fine jade four using primary product
β-agarase of sugar prepares fine jade trisaccharide to digest agarose pickling agent；To make up the deficiencies in the prior art.
The present invention provides a kind of method of fine jade trisaccharide prepared, is to carry out the pickling agent of agarose using β-agarase
After enzymatic hydrolysis, then carry out purifying preparation；Agarase therein is the enzyme that can be digested agarose as new fine jade tetrose；
Wherein agarase is β-agarase AgWH50B, and amino acid sequence is SEQ ID NO:1:
MTFTKSKIATVLSLSLLGIYGCASTTPQNEQAAAGEQVVEDMGGALPDFESDKFFSKLKAEHAKASAV
TDTGVTAGSQALKIDFDSVNEANKFKFWPNVKLHPDTGNWNWNAKGSLTLDVTNPTDSTANIILKIADNVGVMGAG
DNQLNYALSVPAGETVPVEMIFNGSKRKLDGYWGGEKINLRKLVEFQIFVQGPIDQQSVIVDNFALVDATGDFVEA
SGAEEVVTGPVPTVLAITDFEKGQDSFISAERSVATTISPVKTDDGAAIDVLFSASNSYPNITFRPDVPWDWSGQG
DFNVAFDMVNKSDEPLQLFVRVDDDEHEAFGGTANGVQNSWSGYVTIAPNDEGTYYLSLMPAGDQMVSGMRGEPPK
KSYKAQAISYGWGDNNLDLSNIYSMQLYLQNPTADQKLQISSVRLIPNLESDTSRYEGLLDEFGQYTGQDWAQKVK
SLEDLQAAGAAELDSLEHPTQLPDRSKFGGWADGPKLEATGFFRAEKVDGKWALVDPEGYLFFVTGLDNIRMDDTV
TITGVDFSNKETREGREVASELRNSMFTWLPEYDDVLAESYDYADWIHTGALKKGEVFSFYSANLQRKYQTSREEA
LKIWKDVTLNRMQDWGFTTLGNWADPKFYDNQQIAYAANGWIFGDHARISTGNDYWGPIHDPFDPEFAVSTRKMAE
KVASEVSKDDPWLMGIFVDNEISWGNTKNEANHYGLVVNALSYDIKESPAKAAFTKHLQDKYSSIDALNQSWGTKV
TSWADFEVSFDHRSRLSSSMKKDYSEMLQMLSEKYFSTVQAELKKVLPNHMYLGARFADWGVTPEIARGAAPYVDV
MSYNLYAEDLNSKGDWSLLPELDKPSIIGEFHFGATDTGLFHGGIVSASNQADRAKKYTHYMQSIVDNPYFVGAHW
FQYLDSPTTGRAWDGENYNVGFVSITDTPYQELIDAAKQFNRDLYNLRYKK；
The pickling agent of the agarose is, it is preferable to use citric acid treatment agarose prepares；
Wherein a kind of specific concentration of citric acid is the monohydrate potassium of 2.5% (w/v).
The acid processing of the agarose is to handle agarose with 2.5% monohydrate potassium, reacts in 90 DEG C, cold
But to after room temperature, the pH of reaction solution is adjusted to 7.0.
The purifying, a kind of mode are purified using column gel chromatography chromatography.
The present invention realizes method that is special and efficiently preparing odd number fine jade trisaccharide by combining acid hydrolyzation and enzyme process.With
The method that acid hydrolyzation prepares odd number fine jade oligosaccharides is compared, and yield of the present invention is obviously improved, and can be realized specific preparation；With enzymatic isolation method
Preparation (in conjunction with β-agarase and Xin Qiong disaccharide-hydrolysing enzymes) odd number fine jade oligosaccharides is compared, and the substrate of high concentration is capable of handling, to make
The method of the present invention has higher efficiency compared to existing method.
Detailed description of the invention
Fig. 1: fine jade trisaccharide (a) Ji Xinqiong tetrose (b) structure chart prepared by the present invention
Fig. 2: β of the invention-agarase AgWH50B hydrolyzes the TLC figure of nine sugar of seven sugar of fine jade and fine jade, A3: fine jade trisaccharide, A7: fine jade
Seven sugar, A9: nine sugar of fine jade
The enzyme concentration that Fig. 3: β of the invention-agarase AgWH50B hydrolyzes acidolysis agar liquid glucose optimizes figure
Fig. 4: β of the invention-agarase AgWH50B (b) hydrolyzes acidolysis agar liquid glucose sugar under the conditions of most suitable enzyme concentration and produces
Measure the liquid phase analysis result (a) changed over time
Fig. 5: AgWH50B combination acidolysis of the invention prepares fine jade trisaccharide liquid phase result figure (b)
Fig. 6: AgWH50B combination acidolysis of the invention prepares fine jade trisaccharide mass spectrometry results figure.
Specific embodiment
The agarose is by D- beta galactose and 3, and 6- inner ether-L- α-galactolipin repeats disaccharide unit and constitutes, by β-
1,4 glycosidic bonds and α -1,3 glycosidic bond are alternately formed by connecting.
Fine jade trisaccharide refers to that non-reducing end is the agaropectin oligose that the D- beta galactose degree of polymerization is 3, shown in structure such as Fig. 1 (a),
When the present invention prepares β used in fine jade trisaccharide-agarase AgWH50B and directly acts on agarose, primary product is
New fine jade tetrose shown in structure such as Fig. 1 (b), when preparing new fine jade tetrose as substrate using 0.3% (w/v) low melting-point agarose, produces
Rate is 30% or so, further acts on new fine jade tetrose with new fine jade disaccharide-hydrolysing enzymes and fine jade trisaccharide, purified fine jade trisaccharide is prepared
Yield is 25% or so.
The present invention is with fine jade trisaccharide is prepared in conjunction with acidolysis, and with seven sugar of fine jade and nine sugar of fine jade for substrate, acid hydrolysis solution is through β-agar-agar
After enzyme AgWH50B effect, as shown in Fig. 2, its primary product is fine jade trisaccharide.
Method of the invention is described further below by specific example.
The preparation of 1 agarose acid hydrolysis solution of embodiment
Using the reaction system of 200mL, substrate is the agarose of 15% (w/v), and solvent is that 2.5% (w/v) one is hydrated lemon
The pH of reaction solution after being cooled to room temperature, is adjusted to 7.0 using 20% sodium hydroxide in 90 DEG C of reaction 50min by lemon aqueous acid
Agarose acid hydrolysis solution is made.
By gained acid hydrolysis solution, ten times are diluted, crosses 0.22 μm of water phase filter membrane, carries out liquid phase detection, as shown in Fig. 4 (a), gained
The degree of polymerization of agaropectin oligose is in 4 or more.
The optimization of 2 AgWH50B enzyme concentration of embodiment
Using the optimizing reaction system of 10ml, substrate is acidolysis neutrality liquid glucose obtained in embodiment 1；Prepare three sugar of fine jade
Not Cai Yong 0.244,0.488,0.975,1.950 and 2.925U/mL AgWH50B enzyme concentration, reaction boil for 24 hours ten minutes, from
The heart takes supernatant, dilutes ten times, crosses 0.22 μm of water phase filter membrane, is detected to liquid phase；Determine that 1.950U/mL enzyme concentration effect is best
(Fig. 3).
The preparation and purifying of 3 fine jade trisaccharide of embodiment
Using the preparation system of 100mL, substrate is acidolysis neutrality liquid glucose obtained in embodiment 1, using excellent in embodiment 2
Change obtained most suitable enzyme concentration, i.e. 1.950U/mL AgWH50B reacts for 24 hours in 37 DEG C of shaking baths.With the reaction time
It carries out, centrifuging and taking supernatant after 10min is boiled in sampling, dilutes ten times, crosses 0.22 μm of water phase filter membrane, is detected to liquid phase, draws
The time graph of Fig. 4 (b).
After reaction for 24 hours, boil centrifuging and taking supernatant after 10min, carry out P2 column gel chromatography chromatography, obtain by
The high-purity fine jade trisaccharide of AgWH50B preparation, after freeze-drying, weighing.High performance liquid chromatography detection and mass spectrum inspection are carried out after redissolving
It surveys.
As a result as shown in figure 5, purifying obtained fine jade trisaccharide without other miscellaneous sugars, purity is high.Mass spectral results are as shown in fig. 6, institute
Obtaining product is fine jade trisaccharide.Using 1.5g agarose as substrate, 0.727g fine jade trisaccharide conversion ratio is prepared is respectively the calculation shows that
48.45%.
Sequence table
<110>Chinese Marine University
<120>a kind of method for preparing fine jade trisaccharide
<160> 1
<170> SIPOSequenceListing 1.0
<210> 1
<211> 955
<212> PRT
<213>artificial sequence (Artificial Sequence)
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Met Thr Phe Thr Lys Ser Lys Ile Ala Thr Val Leu Ser Leu Ser Leu
1 5 10 15
Leu Gly Ile Tyr Gly Cys Ala Ser Thr Thr Pro Gln Asn Glu Gln Ala
20 25 30
Ala Ala Gly Glu Gln Val Val Glu Asp Met Gly Gly Ala Leu Pro Asp
35 40 45
Phe Glu Ser Asp Lys Phe Phe Ser Lys Leu Lys Ala Glu His Ala Lys
50 55 60
Ala Ser Ala Val Thr Asp Thr Gly Val Thr Ala Gly Ser Gln Ala Leu
65 70 75 80
Lys Ile Asp Phe Asp Ser Val Asn Glu Ala Asn Lys Phe Lys Phe Trp
85 90 95
Pro Asn Val Lys Leu His Pro Asp Thr Gly Asn Trp Asn Trp Asn Ala
100 105 110
Lys Gly Ser Leu Thr Leu Asp Val Thr Asn Pro Thr Asp Ser Thr Ala
115 120 125
Asn Ile Ile Leu Lys Ile Ala Asp Asn Val Gly Val Met Gly Ala Gly
130 135 140
Asp Asn Gln Leu Asn Tyr Ala Leu Ser Val Pro Ala Gly Glu Thr Val
145 150 155 160
Pro Val Glu Met Ile Phe Asn Gly Ser Lys Arg Lys Leu Asp Gly Tyr
165 170 175
Trp Gly Gly Glu Lys Ile Asn Leu Arg Lys Leu Val Glu Phe Gln Ile
180 185 190
Phe Val Gln Gly Pro Ile Asp Gln Gln Ser Val Ile Val Asp Asn Phe
195 200 205
Ala Leu Val Asp Ala Thr Gly Asp Phe Val Glu Ala Ser Gly Ala Glu
210 215 220
Glu Val Val Thr Gly Pro Val Pro Thr Val Leu Ala Ile Thr Asp Phe
225 230 235 240
Glu Lys Gly Gln Asp Ser Phe Ile Ser Ala Glu Arg Ser Val Ala Thr
245 250 255
Thr Ile Ser Pro Val Lys Thr Asp Asp Gly Ala Ala Ile Asp Val Leu
260 265 270
Phe Ser Ala Ser Asn Ser Tyr Pro Asn Ile Thr Phe Arg Pro Asp Val
275 280 285
Pro Trp Asp Trp Ser Gly Gln Gly Asp Phe Asn Val Ala Phe Asp Met
290 295 300
Val Asn Lys Ser Asp Glu Pro Leu Gln Leu Phe Val Arg Val Asp Asp
305 310 315 320
Asp Glu His Glu Ala Phe Gly Gly Thr Ala Asn Gly Val Gln Asn Ser
325 330 335
Trp Ser Gly Tyr Val Thr Ile Ala Pro Asn Asp Glu Gly Thr Tyr Tyr
340 345 350
Leu Ser Leu Met Pro Ala Gly Asp Gln Met Val Ser Gly Met Arg Gly
355 360 365
Glu Pro Pro Lys Lys Ser Tyr Lys Ala Gln Ala Ile Ser Tyr Gly Trp
370 375 380
Gly Asp Asn Asn Leu Asp Leu Ser Asn Ile Tyr Ser Met Gln Leu Tyr
385 390 395 400
Leu Gln Asn Pro Thr Ala Asp Gln Lys Leu Gln Ile Ser Ser Val Arg
405 410 415
Leu Ile Pro Asn Leu Glu Ser Asp Thr Ser Arg Tyr Glu Gly Leu Leu
420 425 430
Asp Glu Phe Gly Gln Tyr Thr Gly Gln Asp Trp Ala Gln Lys Val Lys
435 440 445
Ser Leu Glu Asp Leu Gln Ala Ala Gly Ala Ala Glu Leu Asp Ser Leu
450 455 460
Glu His Pro Thr Gln Leu Pro Asp Arg Ser Lys Phe Gly Gly Trp Ala
465 470 475 480
Asp Gly Pro Lys Leu Glu Ala Thr Gly Phe Phe Arg Ala Glu Lys Val
485 490 495
Asp Gly Lys Trp Ala Leu Val Asp Pro Glu Gly Tyr Leu Phe Phe Val
500 505 510
Thr Gly Leu Asp Asn Ile Arg Met Asp Asp Thr Val Thr Ile Thr Gly
515 520 525
Val Asp Phe Ser Asn Lys Glu Thr Arg Glu Gly Arg Glu Val Ala Ser
530 535 540
Glu Leu Arg Asn Ser Met Phe Thr Trp Leu Pro Glu Tyr Asp Asp Val
545 550 555 560
Leu Ala Glu Ser Tyr Asp Tyr Ala Asp Trp Ile His Thr Gly Ala Leu
565 570 575
Lys Lys Gly Glu Val Phe Ser Phe Tyr Ser Ala Asn Leu Gln Arg Lys
580 585 590
Tyr Gln Thr Ser Arg Glu Glu Ala Leu Lys Ile Trp Lys Asp Val Thr
595 600 605
Leu Asn Arg Met Gln Asp Trp Gly Phe Thr Thr Leu Gly Asn Trp Ala
610 615 620
Asp Pro Lys Phe Tyr Asp Asn Gln Gln Ile Ala Tyr Ala Ala Asn Gly
625 630 635 640
Trp Ile Phe Gly Asp His Ala Arg Ile Ser Thr Gly Asn Asp Tyr Trp
645 650 655
Gly Pro Ile His Asp Pro Phe Asp Pro Glu Phe Ala Val Ser Thr Arg
660 665 670
Lys Met Ala Glu Lys Val Ala Ser Glu Val Ser Lys Asp Asp Pro Trp
675 680 685
Leu Met Gly Ile Phe Val Asp Asn Glu Ile Ser Trp Gly Asn Thr Lys
690 695 700
Asn Glu Ala Asn His Tyr Gly Leu Val Val Asn Ala Leu Ser Tyr Asp
705 710 715 720
Ile Lys Glu Ser Pro Ala Lys Ala Ala Phe Thr Lys His Leu Gln Asp
725 730 735
Lys Tyr Ser Ser Ile Asp Ala Leu Asn Gln Ser Trp Gly Thr Lys Val
740 745 750
Thr Ser Trp Ala Asp Phe Glu Val Ser Phe Asp His Arg Ser Arg Leu
755 760 765
Ser Ser Ser Met Lys Lys Asp Tyr Ser Glu Met Leu Gln Met Leu Ser
770 775 780
Glu Lys Tyr Phe Ser Thr Val Gln Ala Glu Leu Lys Lys Val Leu Pro
785 790 795 800
Asn His Met Tyr Leu Gly Ala Arg Phe Ala Asp Trp Gly Val Thr Pro
805 810 815
Glu Ile Ala Arg Gly Ala Ala Pro Tyr Val Asp Val Met Ser Tyr Asn
820 825 830
Leu Tyr Ala Glu Asp Leu Asn Ser Lys Gly Asp Trp Ser Leu Leu Pro
835 840 845
Glu Leu Asp Lys Pro Ser Ile Ile Gly Glu Phe His Phe Gly Ala Thr
850 855 860
Asp Thr Gly Leu Phe His Gly Gly Ile Val Ser Ala Ser Asn Gln Ala
865 870 875 880
Asp Arg Ala Lys Lys Tyr Thr His Tyr Met Gln Ser Ile Val Asp Asn
885 890 895
Pro Tyr Phe Val Gly Ala His Trp Phe Gln Tyr Leu Asp Ser Pro Thr
900 905 910
Thr Gly Arg Ala Trp Asp Gly Glu Asn Tyr Asn Val Gly Phe Val Ser
915 920 925
Ile Thr Asp Thr Pro Tyr Gln Glu Leu Ile Asp Ala Ala Lys Gln Phe
930 935 940
Asn Arg Asp Leu Tyr Asn Leu Arg Tyr Lys Lys
945 950 955
Claims (6)
1. a kind of method of the fine jade trisaccharide prepared, which is characterized in that the method is that the pickling agent of agarose is used β-
Agarase is digested, then carries out purifying preparation；Agarase therein is the enzyme that can be digested agarose as new fine jade tetrose.
2. the method as described in claim 1, which is characterized in that the amino acid sequence of the agarase is SEQ ID NO:1.
3. the method as described in claim 1, which is characterized in that the pickling agent is using citric acid treatment agarose
It prepares.
4. method as claimed in claim 3, which is characterized in that the citric acid is the citrate hydrate that concentration is 2.5%
Acid.
5. method as claimed in claim 4, which is characterized in that the pickling agent is the monohydrate potassium with 2.5%
Agarose is handled, is reacted in 90 DEG C, after being cooled to room temperature, the pH of reaction solution is adjusted to 7.0 preparations.
6. the method as described in claim 1, which is characterized in that the purifying is pure using the progress of column gel chromatography chromatography
Change.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07322886A (en) * | 1994-06-01 | 1995-12-12 | Japan Tobacco Inc | Production of oligosaccharide and monosaccharide |
| CN1513860A (en) * | 2003-08-04 | 2004-07-21 | 中国海洋大学 | Odd number agar oligosaccharide monomer and its preparation method |
| CN103881995A (en) * | 2014-04-14 | 2014-06-25 | 中国海洋大学 | Beta-agarase capable of degrading agarose to produce neoagarotetraose |
| CN108410632A (en) * | 2018-05-18 | 2018-08-17 | 中国海洋大学 | A kind of preparation method with healthcare function ocean agar oligosaccharide yellow rice wine |
-
2019
- 2019-07-19 CN CN201910657361.6A patent/CN110295210A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07322886A (en) * | 1994-06-01 | 1995-12-12 | Japan Tobacco Inc | Production of oligosaccharide and monosaccharide |
| CN1513860A (en) * | 2003-08-04 | 2004-07-21 | 中国海洋大学 | Odd number agar oligosaccharide monomer and its preparation method |
| CN103881995A (en) * | 2014-04-14 | 2014-06-25 | 中国海洋大学 | Beta-agarase capable of degrading agarose to produce neoagarotetraose |
| CN108410632A (en) * | 2018-05-18 | 2018-08-17 | 中国海洋大学 | A kind of preparation method with healthcare function ocean agar oligosaccharide yellow rice wine |
Non-Patent Citations (1)
| Title |
|---|
| 江承程 等: "酸解酶解相结合制备新琼四糖", 《中国食品科学技术学会第十五届年会论文摘要集》 * |
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Application publication date: 20191001 |