CN1173042C - Method for preparing D-pantothenic alcohol by using microbial enzyme method - Google Patents
Method for preparing D-pantothenic alcohol by using microbial enzyme method Download PDFInfo
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- CN1173042C CN1173042C CNB021005168A CN02100516A CN1173042C CN 1173042 C CN1173042 C CN 1173042C CN B021005168 A CNB021005168 A CN B021005168A CN 02100516 A CN02100516 A CN 02100516A CN 1173042 C CN1173042 C CN 1173042C
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- panthenol
- lactone
- beta
- alcohol
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- 238000000034 method Methods 0.000 title claims abstract description 20
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 19
- 102000004190 Enzymes Human genes 0.000 title claims abstract description 19
- 230000000813 microbial effect Effects 0.000 title claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- -1 beta-aminopropyl alcohol Chemical compound 0.000 claims abstract description 11
- 241000233732 Fusarium verticillioides Species 0.000 claims abstract description 6
- 239000011703 D-panthenol Substances 0.000 claims description 23
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 claims description 23
- 235000004866 D-panthenol Nutrition 0.000 claims description 23
- 229960003949 dexpanthenol Drugs 0.000 claims description 21
- SERHXTVXHNVDKA-UHFFFAOYSA-N pantolactone Chemical compound CC1(C)COC(=O)C1O SERHXTVXHNVDKA-UHFFFAOYSA-N 0.000 claims description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 9
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 5
- 241000223218 Fusarium Species 0.000 claims description 5
- 239000000413 hydrolysate Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 230000002255 enzymatic effect Effects 0.000 abstract description 5
- SERHXTVXHNVDKA-BYPYZUCNSA-N (R)-pantolactone Chemical compound CC1(C)COC(=O)[C@@H]1O SERHXTVXHNVDKA-BYPYZUCNSA-N 0.000 abstract description 3
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- OTOIIPJYVQJATP-BYPYZUCNSA-N (R)-pantoic acid Chemical compound OCC(C)(C)[C@@H](O)C(O)=O OTOIIPJYVQJATP-BYPYZUCNSA-N 0.000 abstract description 2
- 229940070710 valerate Drugs 0.000 abstract 3
- 230000007071 enzymatic hydrolysis Effects 0.000 abstract 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 abstract 1
- 238000007273 lactonization reaction Methods 0.000 abstract 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N pantothenic acid Chemical compound OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 4
- FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
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- 241001465754 Metazoa Species 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
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- 230000003287 optical effect Effects 0.000 description 2
- 229940055726 pantothenic acid Drugs 0.000 description 2
- 239000011713 pantothenic acid Substances 0.000 description 2
- 235000019161 pantothenic acid Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- FAPWYRCQGJNNSJ-UHFFFAOYSA-L Calcium DL-pantothenate Chemical compound [Ca+2].OCC(C)(C)C(O)C(=O)NCCC([O-])=O.OCC(C)(C)C(O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UHFFFAOYSA-L 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
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- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005516 coenzyme A Substances 0.000 description 1
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- 230000007812 deficiency Effects 0.000 description 1
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
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- 235000013305 food Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000003814 hair luster Effects 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
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- 230000004060 metabolic process Effects 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The present invention relates to a method for producing D-pantothenic alcohol by the reaction of D- Pantolactone which is prepared from the microbe enzymatic hydrolysis, and beta-aminopropyl alcohol. In the method, microbe strain fusarium moniliforme fungi SW-902 (i.e. CGMCCNO. 0536) of high yield D-lactone valerate hydrolase which is sieved and conserved are used for fermenting to produce enzymes; the enzymes are used for the hydrolysis of DL-lactone valerate, and the pure D-lactone valerate which is obtained after the lactonization of D-pantoic acid in enzymatic conversion liquor and the beta-aminopropyl alcohol react to produce the D-pantothenic alcohol. A main mass index [alpha][D]<20> is equal to +29.0DEG C to plus 31.5 DEG C.
Description
Technical field
The present invention relates to the method that microbial enzyme method prepares D-panthenol, relate in particular to and utilize beading Fusarium (Fusarium moniliforme) SW-902 CGMCC No.0536 enzymatic production and carry out enzymic hydrolysis fractionation manufacturing D-pantoyl lactone, react the method for producing D-panthenol with the beta-amino propyl alcohol again.
Background technology
D-pantothenic acid claims pantothenic acid, vitamins B again
5Or B
3, be a kind of important medicine, foodstuff additive and fodder additives.The mankind and animal have physiological demand to D-pantothenic acid; and D-pantothenic acid is extremely unstable; its commercial form is the D-calcium pantothenate; but the D-calcium pantothenate is a solid; range of application is restricted; and D-panthenol; claim pro-vitamin B5 again; be the same effect thing of the D-calcium pantothenate that exists with liquid form, can remedy the deficiency of the Application Areas of D-calcium pantothenate, D-panthenol enters in the human body can be converted into pantothenic acid; and then synthetic coenzyme A; promote human body protein; fat; the metabolism of carbohydrate, the mucous membrane and the hair luster of protection skin surface, the generation that wards off disease; therefore; D-panthenol is specially adapted to medicine as nutritional supplement; food; cosmetic industry is as oral liquid; collyrium; compound VB injection; shampoo; mousse; skin cream etc.
D-panthenol (pro-vitamin B5) is again important makeup and medicinal raw material, and market is in short supply.The production of D-panthenol can not be adopted calcium salt induced crystallization method, and the intermediate pantoyl lactone of synthetic D-panthenol requires to have higher optical purity.
The D-panthenol product of existing market supply all adopts chemical method to split the preparation of D-pantoyl lactone.Chemical method prepares pantoyl lactone and splits with resolving agents such as Chiral Amine, quinine, brucine and the mould ammonia of chlorine, its maximum problem is that operation steps is many, the product purification trouble might have in the product impurity such as the healthy disadvantageous chemical agent of humans and animals, solvents.Also have the resolving agent rate of recovery low, caused a large amount of resolving agents, for example the mould ammonia of chlorine enters waste water, makes that the mould ammonia of chlorine has accounted for 70%～80% of waste water total amount in the waste water, causes that wastewater treatment capacity is big, easily causes environmental pollution.
Though Japan first drugmaker produces the D-pantoyl lactone and adopted the microbial enzyme working system, do not see the report of relevant its synthetic D-panthenol.
Summary of the invention
Purpose of the present invention provides a kind of method that directly prepares D-panthenol with microbial enzyme method, promptly utilize the microorganism strains of high-yield D-pantolactone hydrolytic enzyme, enzyme process splits the DL-pantoyl lactone, the optical purity of D-pantoyl lactone reaches more than the 99%e.e. in the resulting enzymic hydrolysate, reacts the method for producing the high-optical-purity D-panthenol with the beta-amino propyl alcohol again.
A kind of method of microbial enzyme manufactured D-panthenol, comprise and utilize beading Fusarium (Fusariummoniliforme) SW-902 CGMCC No.0536, enzyme process splits the DL-pantoyl lactone, and resulting enzymic hydrolysate D-pantoyl lactone is produced the high-optical-purity D-panthenol with the reaction of beta-amino propyl alcohol again; Described enzymic hydrolysate and beta-amino propyl alcohol with etc. volumetric molar concentration react; 20～80 ℃ of described temperature of reaction, 2～40 hours reaction times.
Description of drawings
Accompanying drawing 1 is a process flow diagram of the present invention.
The present invention realizes by following scheme:
(1) the present invention adopts microorganism strains beading Fusarium (Fusarium moniliforme) the SW-902 CGMCC No.0536 (this bacterial strain has been kept at Zhong Guan-cun, BeiJing, China China Committee for Culture Collection of Microorganisms common micro-organisms preservation center February 12 calendar year 2001) of high-yield D-pantolactone hydrolytic enzyme, enzymatic production, DL-pantoyl lactone with chemosynthesis, refining back is as the enzymatic conversion substrate, enzymatic conversion generates the D-pantoic acid, through lactonizing, the D-pantoyl lactone is made in solvent extraction, decolouring, concentrated, crystallization;
(2) with D-pantoyl lactone and beta-amino propyl alcohol with etc. volumetric molar concentration under certain solvent and 20～80 ℃ of temperature condition, reacted 2～40 hours, through separating, purifying, obtain the D-panthenol of high-optical-purity.
The method of microbial enzyme hydrolysis manufacturing D-pantoyl lactone that the present invention adopts and beta-amino propyl alcohol reaction production D-panthenol has overcome induced crystallization method fractionation DL-calcium pantothenate can not be used for the shortcoming that D-panthenol is produced, it is expensive to have overcome the chemical resolution method resolving agent, the cost height, separation difficulty has problems such as pollution and toxicity.Advantage of the present invention is advantages such as cost is low, technology is simple and easy to control, reaction conditions is gentle, the product safety quality is good, environmental sound.
Embodiment
Below by specific embodiment the present invention is elaborated.
Embodiment 1
Slant culture: substratum is that potato is soaked juice (20%) 100ml, glucose 2g, agar 2g, pH6.5, sterilized 20 minutes for 121 ℃, the inoculation of sterilization postcooling, bacterial classification is beading Fusarium (Fusariummoniliforme) SW-902 CGMCC No.0536, cultivated 5～7 days at 25 ℃, as the slant activation seed.
The product enzyme is cultivated: substratum is a glycerol 3%, peptone 0.5%, yeast extract paste 0.5%, corn steep liquor 0.5%, pH6.0, liquid amount is the bottled liquid 100ml of 500ml triangle, sterilizes 20 minutes sterilization postcooling inoculation inclined-plane seed for 121 ℃, cultivated 1～5 day for 28 ℃, filtering fermentation liquor or centrifugal, the wet thallus that obtains (D-pantoic acid lactone hydrolase) is as the enzyme source.
By the DL-pantoyl lactone of chemosynthesis preparation, with containing 50mmolCaCl
2The aqueous solution to be mixed with 30% concentration be substrate; Enzyme concentration is the 0.3U/g pantoyl lactone, puts 28 ℃ of shaking tables, 150r/min reaction, and high pressure liquid chromatographic analysis is carried out in sampling in per 20 minutes, and is 7.0 with the pH value of strong aqua conditioned reaction liquid.Enzymolysis time is 5～10 hours.After the enzyme hydrolyzate extracting and separating that obtains, the specific rotatory power of the product D-pantoyl lactone through lactonizing is [α]
D 20=-49 °.
Embodiment 2
In reactor, add anhydrous methanol 2,000Kg, beta-amino propyl alcohol 750Kg starts and stirs, and drops into the D-pantoyl lactone 1 that obtains by example 1 method, 300Kg keeps 40～50 ℃, reaction 24hr, be evaporated to till no methyl alcohol steams, discharging obtains water white transparency thick liquid D-panthenol 2,051Kg, mol yield to input D-pantoyl lactone is 99.93%, and measuring specific rotatory power is [α]
D 20=+30.1 °.
Claims (1)
1. the method for a microbial enzyme manufactured D-panthenol, comprise and utilize beading Fusarium (Fusarium moniliforme) SW-902 CGMCC No.0536, enzyme process splits the DL-pantoyl lactone, and resulting enzymic hydrolysate D-pantoyl lactone is produced the high-optical-purity D-panthenol with the reaction of beta-amino propyl alcohol again; Described enzymic hydrolysate and beta-amino propyl alcohol with etc. volumetric molar concentration react; 20～80 ℃ of described temperature of reaction, 2～40 hours reaction times.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021005168A CN1173042C (en) | 2002-01-29 | 2002-01-29 | Method for preparing D-pantothenic alcohol by using microbial enzyme method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021005168A CN1173042C (en) | 2002-01-29 | 2002-01-29 | Method for preparing D-pantothenic alcohol by using microbial enzyme method |
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| CN1367253A CN1367253A (en) | 2002-09-04 |
| CN1173042C true CN1173042C (en) | 2004-10-27 |
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100351369C (en) * | 2005-11-22 | 2007-11-28 | 浙江杭州鑫富药业股份有限公司 | Microorganism of producing D-pantothenic acid enternal ester hydrolase and process for preparing D-pantothenic acid thereof |
| CN101448950B (en) * | 2006-05-16 | 2014-02-12 | 帝斯曼知识产权资产管理有限公司 | Process for production of panthenol |
| CN1900297B (en) * | 2006-07-27 | 2010-05-12 | 浙江杭州鑫富药业股份有限公司 | Method for preparing D-pan-ethyl ether by microbial enzyme method |
| CN101392278B (en) * | 2008-06-11 | 2011-07-20 | 济南大华广济畜牧发展有限公司 | Method for preparing D-pantolactone by microbe mixed fermentation method |
| CN101851171B (en) * | 2010-05-06 | 2012-09-19 | 北京京卫信康医药科技发展有限公司 | Preparation method of D-panthenol |
| CN107446966A (en) * | 2017-08-01 | 2017-12-08 | 南京金浩医药科技有限公司 | A kind of preparation method of D pantolactones |
| CN112174845B (en) * | 2020-09-27 | 2024-01-12 | 安徽泰格生物科技有限公司 | Preparation method of D-panthenol |
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- 2002-01-29 CN CNB021005168A patent/CN1173042C/en not_active Expired - Lifetime
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Owner name: ZHEJIANG HANGZHOU XINFU PHARMACEUTICAL CO., LTD. Free format text: FORMER NAME OR ADDRESS: XINFU BIO-CHEMICAL CO LTD, ZHEJIANG |
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Address after: 311301 Ling'an Economic Development Zone, Zhejiang Patentee after: YIFAN XINFU PHARMACEUTICAL Co.,Ltd. Address before: 311301 Ling'an Economic Development Zone, Zhejiang Patentee before: ZHEJIANG HANGZHOU XINFU PHARMACEUTICAL Co.,Ltd. |
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Effective date of registration: 20160623 Address after: Hangzhou City, Zhejiang province 311300 Ling'an City Kam South Street No. 9 Gua fan Patentee after: HANGZHOU XINFU SCIENCE & TECHNOLOGY Co.,Ltd. Address before: 311301 Ling'an Economic Development Zone, Zhejiang Patentee before: YIFAN XINFU PHARMACEUTICAL Co.,Ltd. |
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Granted publication date: 20041027 |
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