CN109880818A - A kind of novel cyanalcohol enzyme and its synthetic method for chiral cyanohydrin - Google Patents
A kind of novel cyanalcohol enzyme and its synthetic method for chiral cyanohydrin Download PDFInfo
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- CN109880818A CN109880818A CN201910284339.1A CN201910284339A CN109880818A CN 109880818 A CN109880818 A CN 109880818A CN 201910284339 A CN201910284339 A CN 201910284339A CN 109880818 A CN109880818 A CN 109880818A
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Abstract
The invention discloses a kind of novel cyanalcohol enzyme and its for the synthetic method of chiral cyanohydrin, more particularly to field of biotechnology, the novel cyanalcohol enzyme is that the 103rd amino acids residue, the 128th amino acids residue, 141 amino acids residues and the 220th amino acids residue of wild cyanalcohol lyases mutate and generate, and the 103rd amino acids residue mutations are alanine, arginine, asparagine or asparatate, and the 128th amino acids residue mutations are alanine, cysteine or glutamine.The present invention replaces the chiral cyanalcohol semi-finished product of mode that dry concentration substep carries out in the prior art to process by using the mode of freeze-drying, in practice, effectively shorten the time required for preparing chiral cyanohydrin, reduce the preparation difficulty of chiral cyanohydrin semi-finished product, while can be used for laboratory preparation, industrialized production can also be effectively applicable to.
Description
Technical field
The present invention relates to field of biotechnology, it is more particularly related to a kind of novel cyanalcohol enzyme and its be used for
The synthetic method of chiral cyanohydrin.
Background technique
Chiral cyanohydrin and its ester are a kind of chiral sources for having Important Academic to be worth in modern asymmetric syntheses research.This
Outside, it is easily converted to chiral 'alpha '-hydroxy acids (ester), a-amino acid, beta-alkamine etc. have important commercial value medicine and
Pesticide intermediate.Therefore, its synthesis is constantly subjected to the great attention of academia and industry.The synthesis of chiral cyanohydrin is always
Challenging project in the field of asymmetric synthesis.The asymmetric syntheses of chiral cyanohydrin generally requires chiral catalyst: chemistry
Chiral catalyst or biocatalyst.The latter is due to abundance, and high catalytic efficiency, reaction condition is mild, yield and optics
The features such as purity is high, wide application range of substrates and be taken seriously.
The patent of invention of patent application publication CN102417917B discloses a kind of enzyme for directly using cyanogen salt as cyanogens source
The method of catalytically synthesizing chiral acetic cyanhydrin ester, this method are: sequentially adding enzyme, cyanogen salt, water, organic solvent in the reaction vessel
With acetic acid and stir evenly, aldehyde compound is added dropwise, reaction carries out at room temperature, reaction time 6-100h；Reaction knot
The organic phase obtained after liquid separation is added drop-wise in the mixed liquor for filling acetic anhydride and pyridine by Shu Hou, reacts at room temperature 3-24h；Through
After saturated sodium bicarbonate and washing, dry, concentration and the processing of column chromatographic purifying, corresponding target compound is obtained.The invention is straight
It connects and uses cyanogen salt as cyanogen source；It uses acetic acid cheap and easy to get as proton donor, controls the organic Phase Proportion of water-, effectively inhibit
The chemical addition reaction of the spontaneous progress of HCN and aldehyde ketone, enables the enzymatic reaction of hydroxynitrile lyases efficiently to carry out.The invented party
Method is simple, safe, obtains the chiral acetic cyanhydrin ester of high-optical-purity, industrial application value with higher in high yield.
But it is in actual use, still there are some disadvantages, as it is when chiral cyanalcohol semi-finished product are handled
It needs to be dried and be concentrated, i.e. two steps carry out, and thus extend the time required for preparing chiral cyanohydrin, increase simultaneously
The step difficulty for preparing chiral cyanohydrin can be used for laboratory preparation, but can not be suitable for industrialized production.
Summary of the invention
The present invention overcomes the shortcomings of the prior art, technical problem to be solved are as follows: provides a kind of novel cyanogen
Alcoholase and its synthetic method for chiral cyanohydrin replace dry concentration in the prior art by using the mode of freeze-drying
The chiral cyanalcohol semi-finished product of mode that substep carries out are processed, and in practice, are effectively shortened and are prepared chiral cyanohydrin institute
The time needed reduces the preparation difficulty of chiral cyanohydrin semi-finished product, while can be used for laboratory preparation, can also effectively fit
For industrialized production, to solve the problems mentioned in the above background technology.
To achieve the above object, the invention provides the following technical scheme: a kind of novel cyanalcohol enzyme, the novel cyanalcohol
Enzyme is the 103rd amino acids residue of wild cyanalcohol lyases, the 128th amino acids residue, 141 amino acids residues and the
220 amino acids residues mutate and generate, and the 103rd amino acids residue mutations are alanine, arginine, lucid asparagus
Amide or asparatate, the 128th amino acids residue mutations are alanine, cysteine or glutamine, the 141st bit amino
Sour residue mutations are serine, glutamic acid or lysine, and the 220th amino acids are residual to sport leucine, serine or tryptophan.
The novel specific preparation method of the specific preparation method of cyanalcohol enzyme the following steps are included:
S1: under the suitable conditions, cultivating host cell, to give expression to the novel cyanalcohol enzyme；
S2: the novel cyanalcohol enzyme is separated.
The wild cyanalcohol lyases is set as cassava cyanalcohol lyases MeHNL.
The 103rd amino acids residue mutations are asparagine, and the 128th amino acids residue mutations are the third ammonia
Acid, the 141 amino acids residue mutations are serine, and the 220th amino acids residue mutations are leucine.
The host cell contains carrier.
The carrier contains polynucleotide molecule.
The polynucleotide molecule encodes novel cyanalcohol enzyme described in claim 1.
The present invention also provides the synthetic methods that a kind of novel cyanalcohol enzyme is used for chiral cyanohydrin, specifically include following step
It is rapid:
S1, primary first-order equation: sequentially adding the enzyme preparation containing the novel cyanalcohol enzyme in the reaction vessel, then to
Water, organic solvent and acetic acid are added in enzyme preparation and stirs evenly, aldehyde compound is then added dropwise and is reacted, reaction temperature is set
15-25 DEG C is set, reaction time 12-24h；
S2, secondary response: after reaction, the organic phase obtained after liquid separation is added drop-wise to and fills acetic anhydride and pyridine
In mixed liquor, 2-12h is reacted at room temperature；
S3, freeze-drying: through saturated sodium bicarbonate and washing obtained chiral cyanohydrin semi-finished product, then carries out to semi-finished product cold
Be lyophilized it is dry, then by after freeze-drying product carry out the processing of column chromatographic purifying, obtain corresponding chiral cyanohydrin finished product.
In parts by mass, the ratio of the enzyme preparation, water, organic solvent, acetic acid and aldehyde compound is 1:12:0.7:2:
0.14。
Technical effect and advantage of the invention: the present invention replaces by using the mode of freeze-drying to be dried in the prior art
The chiral cyanalcohol semi-finished product of mode that concentration substep carries out are processed, and in practice, effectively shorten the chiral cyanogen of preparation
Time required for alcohol reduces the preparation difficulty of chiral cyanohydrin semi-finished product, while can be used for laboratory preparation, can also have
Effect is suitable for industrialized production.
Detailed description of the invention
The present invention will be further described in detail with reference to the accompanying drawing.
Fig. 1 is chiral cyanohydrin preparation flow schematic diagram of the invention.
Specific embodiment
In order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below in conjunction with the embodiment of the present invention
In attached drawing, technical scheme in the embodiment of the invention is clearly and completely described, it is clear that described embodiment is
A part of the embodiments of the present invention, instead of all the embodiments；Based on the embodiments of the present invention, ordinary skill people
Member's every other embodiment obtained without creative efforts, shall fall within the protection scope of the present invention.
Embodiment 1
A kind of novel cyanalcohol enzyme, the novel cyanalcohol enzyme be wild cyanalcohol lyases the 103rd amino acids residue,
128th amino acids residue, 141 amino acids residues and the 220th amino acids residue mutate and generate, and the 103rd
Amino acids residue mutations are alanine, arginine, asparagine or asparatate, the 128th amino acids residue mutations
For alanine, cysteine or glutamine, the 141st amino acids residue mutations are serine, glutamic acid or lysine, the
220 amino acids are residual to sport leucine, serine or tryptophan.
The novel specific preparation method of cyanalcohol enzyme the following steps are included:
S1: under the suitable conditions, cultivating host cell, to give expression to the novel cyanalcohol enzyme；
S2: the novel cyanalcohol enzyme is separated.
The wild cyanalcohol lyases is set as cassava cyanalcohol lyases MeHNL；
The 103rd amino acids residue mutations are asparagine, and the 128th amino acids residue mutations are the third ammonia
Acid, the 141 amino acids residue mutations are serine, and the 220th amino acids residue mutations are leucine；
The host cell contains carrier, and the carrier contains polynucleotide molecule, the polynucleotide molecule coding power
Benefit require 1 described in novel cyanalcohol enzyme.
The present invention also provides the synthetic methods that a kind of novel cyanalcohol enzyme is used for chiral cyanohydrin, specifically include following step
It is rapid:
S1, primary first-order equation: sequentially adding the enzyme preparation containing the novel cyanalcohol enzyme in the reaction vessel, then to
Water, organic solvent and acetic acid are added in enzyme preparation and stirs evenly, aldehyde compound is then added dropwise and is reacted, reaction temperature is set
15 DEG C are set, reaction time 12h；
S2, secondary response: after reaction, the organic phase obtained after liquid separation is added drop-wise to and fills acetic anhydride and pyridine
In mixed liquor, 2h is reacted at room temperature；
S3, freeze-drying: through saturated sodium bicarbonate and washing obtained chiral cyanohydrin semi-finished product, then carries out to semi-finished product cold
Be lyophilized it is dry, then by after freeze-drying product carry out the processing of column chromatographic purifying, obtain corresponding chiral cyanohydrin finished product.
In parts by mass, the ratio of the enzyme preparation, water, organic solvent, acetic acid and aldehyde compound is 1:12:0.7:2:
0.14。
As can be seen from the above embodiments: reaction temperature is set as 15 DEG C in the present embodiment, and the reaction time, (one) was set as 12h,
Reaction time (two) is set as 2h, and dry condensing mode is set as being freeze-dried, after actual experiment, chiral cyanohydrin conversion ratio
97.4%.
Embodiment 2
A kind of novel cyanalcohol enzyme, the novel cyanalcohol enzyme be wild cyanalcohol lyases the 103rd amino acids residue,
128th amino acids residue, 141 amino acids residues and the 220th amino acids residue mutate and generate, and the 103rd
Amino acids residue mutations are alanine, arginine, asparagine or asparatate, the 128th amino acids residue mutations
For alanine, cysteine or glutamine, the 141st amino acids residue mutations are serine, glutamic acid or lysine, the
220 amino acids are residual to sport leucine, serine or tryptophan.
The novel specific preparation method of cyanalcohol enzyme the following steps are included:
S1: under the suitable conditions, cultivating host cell, to give expression to the novel cyanalcohol enzyme；
S2: the novel cyanalcohol enzyme is separated.
The wild cyanalcohol lyases is set as cassava cyanalcohol lyases MeHNL；
The 103rd amino acids residue mutations are asparagine, and the 128th amino acids residue mutations are the third ammonia
Acid, the 141 amino acids residue mutations are serine, and the 220th amino acids residue mutations are leucine；
The host cell contains carrier, and the carrier contains polynucleotide molecule, the polynucleotide molecule coding power
Benefit require 1 described in novel cyanalcohol enzyme.
The present invention also provides the synthetic methods that a kind of novel cyanalcohol enzyme is used for chiral cyanohydrin, specifically include following step
It is rapid:
S1, primary first-order equation: sequentially adding the enzyme preparation containing the novel cyanalcohol enzyme in the reaction vessel, then to
Water, organic solvent and acetic acid are added in enzyme preparation and stirs evenly, aldehyde compound is then added dropwise and is reacted, reaction temperature is set
20 DEG C are set, reaction time 18h；
S2, secondary response: after reaction, the organic phase obtained after liquid separation is added drop-wise to and fills acetic anhydride and pyridine
In mixed liquor, 7h is reacted at room temperature；
S3, freeze-drying: through saturated sodium bicarbonate and washing obtained chiral cyanohydrin semi-finished product, then carries out to semi-finished product cold
Be lyophilized it is dry, then by after freeze-drying product carry out the processing of column chromatographic purifying, obtain corresponding chiral cyanohydrin finished product.
In parts by mass, the ratio of the enzyme preparation, water, organic solvent, acetic acid and aldehyde compound is 1:12:0.7:2:
0.14。
As can be seen from the above embodiments: reaction temperature is set as 20 DEG C in the present embodiment, and the reaction time, (one) was set as 18h,
Reaction time (two) is set as 7h, and dry condensing mode is set as being freeze-dried, after actual experiment, chiral cyanohydrin conversion ratio
99.2%.
Embodiment 3
A kind of novel cyanalcohol enzyme, the novel cyanalcohol enzyme be wild cyanalcohol lyases the 103rd amino acids residue,
128th amino acids residue, 141 amino acids residues and the 220th amino acids residue mutate and generate, and the 103rd
Amino acids residue mutations are alanine, arginine, asparagine or asparatate, the 128th amino acids residue mutations
For alanine, cysteine or glutamine, the 141st amino acids residue mutations are serine, glutamic acid or lysine, the
220 amino acids are residual to sport leucine, serine or tryptophan.
The novel specific preparation method of cyanalcohol enzyme the following steps are included:
S1: under the suitable conditions, cultivating host cell, to give expression to the novel cyanalcohol enzyme；
S2: the novel cyanalcohol enzyme is separated.
The wild cyanalcohol lyases is set as cassava cyanalcohol lyases MeHNL；
The 103rd amino acids residue mutations are asparagine, and the 128th amino acids residue mutations are the third ammonia
Acid, the 141 amino acids residue mutations are serine, and the 220th amino acids residue mutations are leucine；
The host cell contains carrier, and the carrier contains polynucleotide molecule, the polynucleotide molecule coding power
Benefit require 1 described in novel cyanalcohol enzyme.
The present invention also provides the synthetic methods that a kind of novel cyanalcohol enzyme is used for chiral cyanohydrin, specifically include following step
It is rapid:
S1, primary first-order equation: sequentially adding the enzyme preparation containing the novel cyanalcohol enzyme in the reaction vessel, then to
Water, organic solvent and acetic acid are added in enzyme preparation and stirs evenly, aldehyde compound is then added dropwise and is reacted, reaction temperature is set
25 DEG C are set, the reaction time is for 24 hours；
S2, secondary response: after reaction, the organic phase obtained after liquid separation is added drop-wise to and fills acetic anhydride and pyridine
In mixed liquor, 12h is reacted at room temperature；
S3, freeze-drying: through saturated sodium bicarbonate and washing obtained chiral cyanohydrin semi-finished product, then carries out to semi-finished product cold
Be lyophilized it is dry, then by after freeze-drying product carry out the processing of column chromatographic purifying, obtain corresponding chiral cyanohydrin finished product.
In parts by mass, the ratio of the enzyme preparation, water, organic solvent, acetic acid and aldehyde compound is 1:12:0.7:2:
0.14。
As can be seen from the above embodiments: reaction temperature is set as 25 DEG C in the present embodiment, and the reaction time, (one) was set as 24 hours,
Reaction time (two) is set as 12h, and dry condensing mode is set as being freeze-dried, after actual experiment, chiral cyanohydrin conversion ratio
96.6%.
Following table can be obtained by above-described embodiment 1-3:
As seen from the above table: the mode that freeze-drying is all made of in embodiment 1-3 replaces dry concentration substep in the prior art
The chiral cyanalcohol semi-finished product of the mode of progress are processed, and in practice, are effectively shortened required for preparing chiral cyanohydrin
Time, reduce the preparation difficulty of chiral cyanohydrin semi-finished product, can be used for laboratory preparation while, can also be effectively applicable to
Industrialized production；All data is preparing chiral cyanohydrin by higher conversion ratio in embodiment 1-3 simultaneously, wherein embodiment 2
Middle all data conversion ratio highest when preparing chiral cyanohydrin is 99.2%.
Finally, it should be noted that the above embodiments are only used to illustrate the technical solution of the present invention., rather than its limitations；To the greatest extent
Pipe present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that: its according to
So be possible to modify the technical solutions described in the foregoing embodiments, or to some or all of the technical features into
Row equivalent replacement；And these are modified or replaceed, various embodiments of the present invention technology that it does not separate the essence of the corresponding technical solution
The range of scheme.
Claims (9)
1. a kind of novel cyanalcohol enzyme, it is characterised in that: the novel cyanalcohol enzyme is the 103rd ammonia of wild cyanalcohol lyases
Base acid residue, the 128th amino acids residue, 141 amino acids residues and the 220th amino acids residue mutate and generate,
And the 103rd amino acids residue mutations are alanine, arginine, asparagine or asparatate, the 128th amino acids
Residue mutations are alanine, cysteine or glutamine, and the 141st amino acids residue mutations are serine, glutamic acid or rely
Propylhomoserin, the 220th amino acids are residual to sport leucine, serine or tryptophan.
2. the novel cyanalcohol enzyme of one kind according to claim 1, it is characterised in that: the novel cyanalcohol enzyme is specifically prepared
Method the following steps are included:
S1: under the suitable conditions, cultivating host cell, to give expression to the novel cyanalcohol enzyme；
S2: the novel cyanalcohol enzyme is separated.
3. the novel cyanalcohol enzyme of one kind according to claim 1, it is characterised in that: the wild cyanalcohol lyases is set as
Cassava cyanalcohol lyases MeHNL.
4. the novel cyanalcohol enzyme of one kind according to claim 1, it is characterised in that: the 103rd amino acids residue is prominent
Become asparagine, the 128th amino acids residue mutations are alanine, and the 141 amino acids residue mutations are silk
Propylhomoserin, the 220th amino acids residue mutations are leucine.
5. the novel cyanalcohol enzyme of one kind according to claim 2, it is characterised in that: the host cell contains carrier.
6. the novel cyanalcohol enzyme of one kind according to claim 5, it is characterised in that: the carrier contains polynucleotides point
Son.
7. the novel cyanalcohol enzyme of one kind according to claim 6, it is characterised in that: the polynucleotide molecule encodes right
It is required that cyanalcohol enzyme novel described in 1.
8. the synthetic method that a kind of novel cyanalcohol enzyme is used for chiral cyanohydrin, which is characterized in that specifically includes the following steps:
S1, primary first-order equation: the enzyme preparation containing the novel cyanalcohol enzyme is sequentially added in the reaction vessel, then to enzyme system
Water, organic solvent and acetic acid are added in agent and stirs evenly, aldehyde compound is then added dropwise and is reacted, reaction temperature setting
15-25 DEG C, reaction time 12-24h；
S2, secondary response: after reaction, the organic phase obtained after liquid separation is added drop-wise to the mixing for filling acetic anhydride and pyridine
In liquid, 2-12h is reacted at room temperature；
S3, freeze-drying: through saturated sodium bicarbonate and washing obtained chiral cyanohydrin semi-finished product, and it is dry then to carry out freezing to semi-finished product
It is dry, the product after freeze-drying is then subjected to the processing of column chromatographic purifying, obtains corresponding chiral cyanohydrin finished product.
9. the synthetic method that the novel cyanalcohol enzyme of one kind according to claim 7 is used for chiral cyanohydrin, it is characterised in that:
In parts by mass, the ratio of the enzyme preparation, water, organic solvent, acetic acid and aldehyde compound is 1:12:0.7:2:0.14.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111057696A (en) * | 2019-12-26 | 2020-04-24 | 华东理工大学 | Hydroxynitrile lyase mutant and application thereof in synthesis of (R) -salmeterol |
| CN113528498A (en) * | 2021-08-12 | 2021-10-22 | 江西科苑生物股份有限公司 | Preparation method of S-cyanohydrin lyase and product thereof |
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| CN102417917A (en) * | 2011-10-20 | 2012-04-18 | 华东师范大学 | Method for enzymatically synthesizing chiral acetic cyanhydrin ester by directly using cyanogen salt as cyanogens source |
| WO2018127143A1 (en) * | 2017-01-06 | 2018-07-12 | 上海弈柯莱生物医药科技有限公司 | Highly active s-cyanohydrin lyase and application thereof |
| CN108277216A (en) * | 2017-01-06 | 2018-07-13 | 上海弈柯莱生物医药科技有限公司 | High activity S- cyanalcohols lyases and its application |
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2019
- 2019-04-10 CN CN201910284339.1A patent/CN109880818A/en active Pending
Patent Citations (3)
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|---|---|---|---|---|
| CN102417917A (en) * | 2011-10-20 | 2012-04-18 | 华东师范大学 | Method for enzymatically synthesizing chiral acetic cyanhydrin ester by directly using cyanogen salt as cyanogens source |
| WO2018127143A1 (en) * | 2017-01-06 | 2018-07-12 | 上海弈柯莱生物医药科技有限公司 | Highly active s-cyanohydrin lyase and application thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111057696A (en) * | 2019-12-26 | 2020-04-24 | 华东理工大学 | Hydroxynitrile lyase mutant and application thereof in synthesis of (R) -salmeterol |
| CN111057696B (en) * | 2019-12-26 | 2022-11-11 | 华东理工大学 | Hydroxynitrile lyase mutant and application thereof in synthesis of (R) -salmeterol |
| CN113528498A (en) * | 2021-08-12 | 2021-10-22 | 江西科苑生物股份有限公司 | Preparation method of S-cyanohydrin lyase and product thereof |
| CN113528498B (en) * | 2021-08-12 | 2022-05-03 | 江西科苑生物股份有限公司 | Preparation method of S-cyanohydrin lyase and product thereof |
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