CN105418711A - Application of alpha-L-rhamnosidase to preparing hydroxycarbamide and glycoside derivatives - Google Patents
Application of alpha-L-rhamnosidase to preparing hydroxycarbamide and glycoside derivatives Download PDFInfo
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Abstract
The invention relates to application of alpha-L-rhamnosidase to preparing hydroxycarbamide and glycoside derivatives. The hydroxycarbamide and glycoside derivatives are hydroxyurea and rhamnoside, and a molecular formula of the hydroxycarbamide and glycoside derivatives is C7H14N2O6. Amino acid sequences of the alpha-L-rhamnosidase are shown as SEQ ID NO.1. The application has the advantages that hydroxycarbamide is used as a raw material, rhamnose is used as a glycosyl donor, and the hydroxycarbamide and rhamnoside can be synthesized from the alpha-L-rhamnosidase of a microbial source by means of one-step transglycosylation reaction; a method has simple steps, is low in cost and mild in condition and is environmental friendly, and the alpha-L-rhamnosidase has a potential application prospect; products of the alpha-L-rhamnosidase contain rhamanopyranosyl as compared with the hydroxycarbamide which is the raw material, accordingly, the stability and the targeting can be improved, and the products have broad application prospects for being used as tumor targeted medicines.
Description
Technical field
The present invention relates to a kind of alpha-L-Rhamnosidase and preparing the application in hydroxyurea glycosides derivatives, particularly a kind of method utilizing alpha-L-Rhamnosidase protoenzyme synthesis of hydroxy urea rhamnoside, belongs to sugar engineering technical field.
Technical background
Hydroxyurea (Hydroxyurea) is a kind of ribonucleoside diphosphate reductase inhibitor, as the specificity antineoplastic medicine of cell cycle S phase, is mainly used in treatment chronic myelocytic leukemia, melanoma, incidence cancer, ovarian cancer etc.In recent years, find that it has certain curative effect to Lian shape Xi born of the same parents property Pin Xue ﹑ β Mediterranean Pin Xue ﹑ psoriatic, acquired immune deficiency syndrome (AIDS) etc.Hydroxyurea determined curative effect, of many uses, but due to shortcomings such as its polarity are large and the transformation period is short, strongly limit clinical efficacy.Molecular modification is carried out to hydroxyurea, its bioavailability can be improved, reduce toxic side effect.Antagonism anti-tumor medicine carries out rhamanopyranosyl modification, can increase the tumor-targeting of medicine, heighten the effect of a treatment.
Glucosides enzyme process carries out glycosylation to substrate, and step is simple, with low cost, mild condition, environmental friendliness.But the current molecular modification to hydroxyurea is based on chemosynthesis, as Chinese patent literature CN1061775A (application number 91111219.7) discloses a kind of method adopting chemical process to synthesize hydroximic acid and N-hydroxyl urea derivant; There is no the report that glucosides enzyme process is modified hydroxyurea.
At present, to glycosylation modified N-(β-D-glucopyra glycosyloxy glycosides) urea one example only having glucose to be modified by chemical process of hydroxyurea, there is no the report that rhamanopyranosylization modifies hydroxyurea.
Summary of the invention
The present invention is directed to the deficiencies in the prior art, provide a kind of alpha-L-Rhamnosidase preparing the application in hydroxyurea rhamnoside derivative.
A kind of hydroxyurea glycosides derivatives, name is called: hydroxyurea rhamnoside (1-Hydroxyureal-α-L-rhamnopyranoside), and chemical structural formula is as follows:
Alpha-L-Rhamnosidase is preparing the application in hydroxyurea glycosides derivatives, and described alpha-L-Rhamnosidase aminoacid sequence is as shown in SEQIDNO.1.
Enzyme process prepares a method for hydroxyurea rhamnoside, comprises the steps:
(1) preparing rhamnosyl concentration with sodium phosphate buffer is 0.3M ~ 0.5M, and hydroxyurea concentration is 0.3M ~ 0.5M, and the alpha-L-Rhamnosidase addition of aminoacid sequence as shown in SEQIDNO.1 is the reaction system of 5 μ g ~ 10 μ g/mL;
(2) obtained for step (1) reaction system is reacted 24 ~ 48 hours in 45 ~ 60 DEG C of water-baths, boil termination reaction, centrifugal, get supernatant liquor;
(3) by the supernatant liquor that step (2) is obtained, after separation, drying, obtained hydroxyurea rhamnoside.
In described step (1), the alpha-L-Rhamnosidase of aminoacid sequence as shown in SEQIDNO.1 selects GenBank accession number to be JN704640.1.Above-mentioned alpha-L-Rhamnosidase has hydroxyurea and significantly turns glycosyl activity.
Preferred according to the present invention, the damping fluid in described step (1) is the sodium phosphate buffer of concentration 10 ~ 100mM, pH6 ~ 8; Preferred further according to the present invention, the damping fluid in described step (1) is the sodium phosphate buffer of 50mM, pH6.5.
Preferred according to the present invention, centrifugal in described step (2) be 10000 ~ 12000 revs/min centrifugal 30 minutes.
Preferred according to the present invention, the reaction conditions in described step (2) is 55 DEG C of water-baths 30 hours.
Preferred according to the present invention, the termination reaction condition of boiling in described step (2) is 100 DEG C and boils 5 minutes.
Preferred according to the present invention, the separation in described step (3) adopts thin-layer chromatography to be separated.Preferred further, described separation adopts preparative thin layer chromatography board to be separated.Preparative thin layer chromatography board can adopt model as the thin layer chromatography board of Silicagel60F254 (Merck, Germany).
Preferred according to the present invention, the drying in described step (3) is lyophilize.
Preferred according to the present invention, thin-layer chromatography when also comprising separation in described step (3) detects, and merges the step of the identical product of migration distance.
The step that above-mentioned thin-layer chromatography detects is as follows:
Launch in developing agent after thin layer chromatography board point sample, after spray painting developer, within 5 minutes, make sugared spot development in 120 DEG C of bakings;
Above-mentioned developing agent is by propyl carbinol, dehydrated alcohol and water 10:3:2 mixed preparing by volume; Developer to be volume percent be 20% sulfuric acid and concentration be the solution of 3, the 5-orcins of 0.5wt%.
The application of above-mentioned hydroxyl urine rhamnoside in preparation control tumour medicine.
Useful fruit
1, the alpha-L-Rhamnosidase of Late Cambrian aminoacid sequence of the present invention as shown in SEQIDNO.1 has hydroxyurea and significantly turns glycosyl activity, and successfully synthesizes hydroxyurea rhamnoside;
2, the present invention take hydroxyurea as raw material, with cheap rhamnosyl substrate for rhamanopyranosyl donor, adopt alpha-L-rhamnoside protoenzyme synthesis of hydroxy urea rhamnoside, product is compared with its raw material hydroxyl urea, containing rhamanopyranosyl, add tumour cell targeting, contribute to the anti-tumor activity improving material medicine, reduce its toxic side effect.
Accompanying drawing explanation
Fig. 1 is the mass spectrum of the hydroxyurea rhamnoside that embodiment 1 obtains;
Fig. 2 is the hydrogen spectrum of hydroxyurea rhamnoside;
Fig. 3 is the carbon spectrum of hydroxyurea rhamnoside
Fig. 4 is that the hydrogen hydrogen of hydroxyurea rhamnoside is correlated with nuclear magnetic spectrum;
Fig. 5 is the hydrocarbon directly related nuclear magnetic spectrum of hydroxyurea rhamnoside;
Fig. 6 is the hydrocarbon long-range relevant nuclear magnetic spectrum of hydroxyurea rhamnoside;
Fig. 7 is the hydrogen hydrogen spatial correlation nuclear magnetic spectrum of hydroxyurea rhamnoside.
Embodiment
Below in conjunction with embodiment, the present invention will be further described, but institute of the present invention protection domain is not limited thereto.
PPIC9K plasmid is purchased from Invitrogen company;
PichiapastorisGS115 is purchased from Invitrogen company.
Embodiment 1
Novel hydroxyl urea rhamnoside derivative, its preparation process is as follows:
1. the preparation of alpha-L-Rhamnosidase
Synthetic GenBank accession number is that (proteins encoded GenBank accession number is AFA41506.1 for the alpha-L-Rhamnosidase sequence of JN704640, nucleotide sequence is as SEQIDNO.2), be connected on pPIC9K plasmid, transform PichiapastorisGS115.Alpha-L-Rhamnosidase prepared by the Pichia anomala expression operational manual specification sheets provided according to Invitrogen company, and Coomassie Brilliant Blue measures protein content, and after testing, aminoacid sequence is as shown in SEQIDNO.1.
2. alpha-L-Rhamnosidase catalyzes and synthesizes hydroxyurea rhamnoside
With pH6.5,50mM potassiumphosphate sodium buffer reaction system 1mL, rhamnosyl final concentration is 0.4M, and hydroxyurea final concentration is 0.4M, and the addition of alpha-L-Rhamnosidase is 8 μ g/mL.55 DEG C of reactions after 30 hours, 100 DEG C are boiled 5 minutes, termination reaction.
3. the purifying of hydroxyurea rhamnoside
By centrifugal 30 minutes of the reaction solution 12000 revs/min after boiling, Aspirate supernatant, at Preparative TLC chromatoplate (PLCSilicagel60F254, Merck) point sample exhibition layer.After exhibition layer terminates, chromatoplate gets the wide bar shaped platelet colour developing of 1cm every 10cm, judge the position of target carbohydrate on chromatoplate, then the non-color development area of scraping chromatoplate is containing the silica gel powder of target glucosides, it is dissolved in the water again, centrifuging and taking supernatant, after lyophilize, gained powder is hydroxyurea rhamnoside.
The step that above-mentioned thin-layer chromatography detects is as follows:
Thin layer chromatography board point sample, launches in developing agent, after spray painting developer, within 5 minutes, makes sugared spot development in 120 DEG C of bakings.
Above-mentioned developing agent is by propyl carbinol, dehydrated alcohol and water 10:3:2 mixed preparing by volume; Developer to be volume percent be 20% sulfuric acid and concentration be the solution of 3, the 5-orcins of 0.5wt%.
4. the Structural Identification of hydroxyurea rhamnoside
To get above-mentioned hydroxyurea rhamnoside dilute with water be mass percent be 1% solution, carry out mass spectroscopy, the characteristic molecular quasi-molecular ions (m/z) of target product is [M+Na]
+245.08 (as shown in Figure 1), judge that molecular weight of product is 222, structure is hydroxyurea rhamnoside.Above-mentioned mass spectroscopy instrument is Shimadzu LCMS-IT-TOF mass spectrograph (Japan).
Embodiment 2
Enzyme process prepares a method for hydroxyurea rhamnoside, comprises the steps:
(1) preparing rhamnosyl concentration with sodium phosphate buffer is 0.3M, and hydroxyurea concentration is 0.3M, and the alpha-L-Rhamnosidase addition of aminoacid sequence as shown in SEQIDNO.1 is the reaction system of 5 μ g/mL;
Damping fluid in described step (1) is the sodium phosphate buffer of concentration 10mM, pH6;
(2) obtained for step (1) reaction system reacted 24 hours in 45 DEG C of water-baths, 100 DEG C are boiled 5 minutes termination reactions, and 10000 revs/min centrifugal 30 minutes, gets supernatant liquor;
(3) by supernatant liquor obtained for step (2), be separated by the Bio-gelP2 chromatographic column of specification 15mm × 100cm, take water as moving phase, flow velocity 0.3mL/ minute, collect elution samples, thin-layer chromatography detects, and merges the product that migration distance is identical, make powder after lyophilize, be hydroxyurea rhamnoside.
The step that above-mentioned thin-layer chromatography detects is as follows:
Launch in developing agent after thin layer chromatography board point sample, after spray painting developer, within 5 minutes, make sugared spot development in 120 DEG C of bakings; Above-mentioned developing agent is by propyl carbinol, dehydrated alcohol and water 10:3:2 mixed preparing by volume; Developer to be volume percent be 20% sulfuric acid and concentration be the solution of 3, the 5-orcins of 0.5wt%.
To get above-mentioned hydroxyurea rhamnoside dilute with water be mass percent be 1% solution, carry out mass spectroscopy, the characteristic molecular quasi-molecular ions (m/z) of target product is [M+Na]
+245.08, judge that molecular weight of product is 222, structure is hydroxyurea rhamnoside.Above-mentioned mass spectroscopy instrument is Shimadzu LCMS-IT-TOF mass spectrograph (Japan).
Embodiment 3
Enzyme process prepares a method for hydroxyurea rhamnoside, comprises the steps:
(1) preparing rhamnosyl concentration with sodium phosphate buffer is 0.5M, and hydroxyurea concentration is 0.5M, and the alpha-L-Rhamnosidase addition of aminoacid sequence as shown in SEQIDNO.1 is the reaction system of 10 μ g/mL;
Damping fluid in described step (1) is the sodium phosphate buffer of concentration 100mM, pH8;
(2) obtained for step (1) reaction system reacted 48 hours in 60 DEG C of water-baths, 100 DEG C are boiled 5 minutes termination reactions, and 12000 revs/min centrifugal 30 minutes, gets supernatant liquor;
(3) by supernatant liquor obtained for step (2), be separated by the Bio-gelP2 chromatographic column of specification 15mm × 100cm, take water as moving phase, flow velocity 0.3mL/ minute, collect elution samples, thin-layer chromatography detects, and merges the product that migration distance is identical, make powder after lyophilize, be hydroxyurea rhamnoside.
The step that above-mentioned thin-layer chromatography detects is as follows:
Launch in developing agent after thin layer chromatography board point sample, after spray painting developer, within 5 minutes, make sugared spot development in 120 DEG C of bakings; Above-mentioned developing agent is by propyl carbinol, dehydrated alcohol and water 10:3:2 mixed preparing by volume; Developer to be volume percent be 20% sulfuric acid and concentration be the solution of 3, the 5-orcins of 0.5wt%.
To get above-mentioned hydroxyurea rhamnoside dilute with water be mass percent be 1% solution, carry out mass spectroscopy, the characteristic molecular quasi-molecular ions (m/z) of target product is [M+Na]
+245.08, judge that molecular weight of product is 222, structure is hydroxyurea rhamnoside.Above-mentioned mass spectroscopy instrument is Shimadzu LCMS-IT-TOF mass spectrograph (Japan).
Get above-mentioned hydroxyurea rhamnoside 5mg powder and be dissolved in deuterated dimethyl sulfoxide (DMSO), carry out nuclear-magnetism parsing, comprehensive hydrogen spectrum (as shown in Figure 2), carbon spectrum (as shown in Figure 3), hydrogen hydrogen Correlated Spectroscopy (COSY) (as shown in Figure 4), hydrocarbon directly related spectrum (HSQC) (as shown in Figure 5), hydrocarbon long-range Correlated Spectroscopy (HMBC) (as shown in Figure 6), two-dimentional hydrogen hydrogen spatial correlation spectrum (NOESY) (as shown in Figure 7), determine the chemical shiftsum coupling constant that each position is hydrocarbon.Rhamanopyranosyl
1j
cHfor 175.8H
z, infer that rhamanopyranosyl is connected with hydroxyurea molecule by α key, in COSY spectrum, observe rhamnosyl C-2, C-3, C-4 are connected with hydroxyl respectively, and C-1 is not connected with hydroxyl.In NOESY spectrum, NH and NH2 on rhamnosyl H-1 and hydroxyurea has coherent signal, is connected after hydroxyurea rhamanopyranosyl is described with the C-1 position of rhamnosyl, and final to obtain hydroxyl urine rhamnoside structural formula as follows:
Above-mentioned nmr analysis instrument is AVANCE600 type superconduction super shielding fourier transform NMR spectrometer (Bruker company of Switzerland).
Accretion rate is fast in vivo, poor selectivity, toxic side effect are larger for hydroxyurea.The hydroxyurea that rhamnoside is modified is combined with the rhamnosyl lectin of tumor surface by its rhamnoside carried, by targeted drug delivery to tumour cell, thus improve tumour cell recognition specificity and the antitumous effect of medicine, reduce the toxicity of agents on normal cells, reduce toxic side effect.
Claims (10)
1. a hydroxyurea glycosides derivatives, name is called: hydroxyurea rhamnoside (1-Hydroxyureal-α-L-rhamnopyranoside), and chemical structural formula is as follows:
。
2. the application of alpha-L-Rhamnosidase in hydroxyurea rhamnoside described in preparation claim 1, described alpha-L-Rhamnosidase aminoacid sequence is as shown in SEQIDNO.1.
3. enzyme process prepares a method for hydroxyurea rhamnoside described in claim 1, it is characterized in that, comprises the steps:
(1) preparing rhamnosyl concentration with sodium phosphate buffer is 0.3M ~ 0.5M, and hydroxyurea concentration is 0.3M ~ 0.5M, and the alpha-L-Rhamnosidase addition of aminoacid sequence as shown in SEQIDNO.1 is the reaction system of 5 μ g ~ 10 μ g/mL;
(2) obtained for step (1) reaction system is reacted 24 ~ 48 hours in 45 ~ 60 DEG C of water-baths, boil termination reaction, centrifugal, get supernatant liquor;
(3) by the supernatant liquor that step (2) is obtained, after separation, drying, obtained hydroxyurea rhamnoside.
4. method as claimed in claim 3, it is characterized in that, the damping fluid in described step (1) is the sodium phosphate buffer of concentration 10 ~ 100mM, pH6 ~ 8; Preferred further according to the present invention, the damping fluid in described step (1) is the sodium phosphate buffer of 50mM, pH6.5.
5. method as claimed in claim 3, is characterized in that, centrifugal in described step (2) be 10000 ~ 12000 revs/min centrifugal 30 minutes; Preferably, the reaction conditions in described step (2) is 55 DEG C of water-baths 30 hours.
6. method as claimed in claim 3, it is characterized in that, the termination reaction condition of boiling in described step (2) is 100 DEG C and boils 5 minutes.
7. method as claimed in claim 3, is characterized in that, the separation in described step (3) adopts thin-layer chromatography to be separated; Preferred further, described separation adopts preparative thin layer chromatography board to be separated.Preparative thin layer chromatography board can adopt model as the thin layer chromatography board of Silicagel60F254.
8. method as claimed in claim 3, it is characterized in that, the drying in described step (3) is lyophilize;
Preferably, thin-layer chromatography when also comprising separation in described step (3) detects, and merges the step of the identical product of migration distance.
9. method as claimed in claim 8, is characterized in that, the step that described thin-layer chromatography detects is as follows:
Launch in developing agent after thin layer chromatography board point sample, after spray painting developer, within 5 minutes, make sugared spot development in 120 DEG C of bakings;
Above-mentioned developing agent is by propyl carbinol, dehydrated alcohol and water 10:3:2 mixed preparing by volume; Developer to be volume percent be 20% sulfuric acid and concentration be the solution of 3, the 5-orcins of 0.5wt%.
10. the application of hydroxyl urine rhamnoside in preparation control tumour medicine described in claim 1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107236010A (en) * | 2017-06-28 | 2017-10-10 | 山东大学 | A kind of application of α L rhamnosidases in cytarabine derivative is prepared |
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| CN102321645A (en) * | 2011-08-08 | 2012-01-18 | 山东大学 | Alternaria alpha-L-rhamnosidase gene and application thereof |
| CN102965415A (en) * | 2012-11-19 | 2013-03-13 | 华南理工大学 | Regioselective fucosylation modification method of enzymatic nuclear glucoside class medicine |
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2015
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2903446A (en) * | 1957-06-05 | 1959-09-08 | Grace W R & Co | Monoacyl derivatives of substituted carbamides and process of preparation |
| WO1998051303A1 (en) * | 1997-05-16 | 1998-11-19 | The Procter & Gamble Company | Hiv and cancer treatment |
| CN1634586A (en) * | 2004-11-22 | 2005-07-06 | 山东蓝金生物工程有限公司 | Anti-cancer medicine composition |
| CN102321645A (en) * | 2011-08-08 | 2012-01-18 | 山东大学 | Alternaria alpha-L-rhamnosidase gene and application thereof |
| CN102965415A (en) * | 2012-11-19 | 2013-03-13 | 华南理工大学 | Regioselective fucosylation modification method of enzymatic nuclear glucoside class medicine |
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| Title |
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| BERND L. SORG，等: "Synthesis and NMR characterization of hydroxyurea and mesylglycol glycoconjugates as drug candidates for targeted cancer chemotherapy", 《CARBOHYDRATE RESEARCH》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107236010A (en) * | 2017-06-28 | 2017-10-10 | 山东大学 | A kind of application of α L rhamnosidases in cytarabine derivative is prepared |
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