JPH01168292A - Production of d-glyceric acid - Google Patents
Production of d-glyceric acidInfo
- Publication number
- JPH01168292A JPH01168292A JP32727687A JP32727687A JPH01168292A JP H01168292 A JPH01168292 A JP H01168292A JP 32727687 A JP32727687 A JP 32727687A JP 32727687 A JP32727687 A JP 32727687A JP H01168292 A JPH01168292 A JP H01168292A
- Authority
- JP
- Japan
- Prior art keywords
- glyceric acid
- glycerin
- culture
- gluconobacter
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 title claims abstract description 32
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 36
- 235000011187 glycerol Nutrition 0.000 claims abstract description 18
- 244000005700 microbiome Species 0.000 claims abstract description 15
- 241000589236 Gluconobacter Species 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 238000012258 culturing Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 abstract description 7
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001413 amino acids Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000001963 growth medium Substances 0.000 abstract 3
- 241000233866 Fungi Species 0.000 abstract 1
- -1 serine Chemical class 0.000 abstract 1
- 230000001580 bacterial effect Effects 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002609 medium Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000000813 microbial effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000589232 Gluconobacter oxydans Species 0.000 description 2
- 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 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000012136 culture method Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000013587 production medium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 241001518248 Gluconobacter cerinus Species 0.000 description 1
- SKCKOFZKJLZSFA-UHFFFAOYSA-N L-Gulomethylit Natural products CC(O)C(O)C(O)C(O)CO SKCKOFZKJLZSFA-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001061090 Melanonus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明はＤ−グリセリン酸の製造法に関するものである
。さらに具体的には、グルコノバクタ−（Ｇｌｕｃｏｎ
ｏｂａｃｔｅｒ ）属に属する微生物を用いるＤ−グリ
セリン酸の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing D-glyceric acid. More specifically, Gluconobacter (Glucon
The present invention relates to a method for producing D-glyceric acid using microorganisms belonging to the genus P. obacter.
Ｄ−グリセリン酸はセリン等のアミノ酸及び医薬、農薬
の中間体、さらには、樹脂あるいは潤滑剤等への添加剤
あるいはその中間原料等として用いられる有用な化合物
である。D-glyceric acid is a useful compound used as an intermediate for amino acids such as serine, pharmaceuticals, agricultural chemicals, and as an additive for resins, lubricants, etc., or as an intermediate raw material thereof.
（従来技術およυその問題点）
グリセリン酸の製造法としては、従来よりアクリル酸お
よびその誘導体、あるいは、アクロレインを酸化する化
学合成法が知られている（特開昭６０−２２６８４２号
公報、特開昭５１−２３２０９号公報、米国特許第２，
７５２，３９１号、米国特許第２．７３１，５０２号、
Ｊ、 Ｃｈｅｍ、Ｓｏｃ、 ｒ １９５７ 、４３２
１ ＋Ｊ、Ａｍ、Ｃｈｅｍ、、７６．３４８６（１９５
４）。(Prior art and its problems) Chemical synthesis methods that oxidize acrylic acid and its derivatives, or acrolein have been known as methods for producing glyceric acid (Japanese Patent Laid-Open No. 60-226842, JP-A No. 51-23209, U.S. Patent No. 2,
No. 752,391, U.S. Patent No. 2.731,502;
J, Chem, Soc, r 1957, 432
1 +J, Am, Chem, 76.3486 (195
4).
しかしながら光学活性グリセリン酸の製造法にか望まれ
ていた。However, a method for producing optically active glyceric acid has been desired.
（問題点を解決する為の手段）
本発明者等は、光学活性なグリセリン酸全生成する能力
を有する微生物を得る為に研究を行った。(Means for Solving the Problems) The present inventors conducted research to obtain a microorganism capable of producing optically active glyceric acid.
その結果、グルコノバクタ−属に属する微生物がグリセ
リンをＤ−グリセリン酸に転換する能力を有することを
見出し、本研究を完成した。As a result, we found that microorganisms belonging to the genus Gluconobacter have the ability to convert glycerin to D-glyceric acid, and completed this research.
ヅ下に本発明の詳細な説明する。The present invention will be explained in detail below.
本発明は、グルコノバクタ−属に属し、グリセリンをＤ
−グリセリン酸に転換する能力を有する微生物を、グリ
セリンを含有した培地に培養することにより、または、
培地に培養して得られる菌体またはその処理物をグリセ
リンを含有する水溶液中で反応させることによシ、培養
物または、水溶液中にＤ−グリセリン酸を生成させこれ
を採取することを特徴とするＤ−グリセリン酸の製造法
を提供するものである。The present invention belongs to the genus Gluconobacter, and the present invention relates to D.
- by culturing a microorganism capable of converting to glyceric acid in a medium containing glycerin, or
D-glyceric acid is produced in the culture or aqueous solution by reacting bacterial cells obtained by culturing in a medium or a processed product thereof in an aqueous solution containing glycerin, and this is collected. The present invention provides a method for producing D-glyceric acid.
本発明に用いる微生物としては、グルコノバクタ−属に
属し、グリセリンをグリセリン酸に転換する能力を有す
る微生物であれば、いずれも用いることができる。具体
的な例としては、グルコノバクタ−サブオキシダンス（
Ｇｌｕｃｏｎｏｂａｃｔｅｒｓｕｂｏｘｙｄａｎｓ）
ＩＦｏ ３１７２株、グルコノバクターメラノジーナス
（Ｇｌｕｃｏｎｏｂａｃｔｅｒ ｍｅｌａｎｏｇｅｎｕ
ｓ ）ＩＦｏ ３２９２株、３２９４株、グルコノバク
タ−セリナス（Ｇｌｕｃｏｎｏｂａｃｔｅｒ ｃｅｒｉ
ｎｕｓ ） ＩＦＯ３２６２株等が上げられる。本発明
で用いられる微生物としては上記の菌株のみならすこれ
らから、人工的あるいは自然に得られる変異株であって
も、Ｄ−グリセリン酸生産能を有するグルコノバクタ−
属の菌株であれば、すべて本発明に使用することができ
る。As the microorganism used in the present invention, any microorganism that belongs to the genus Gluconobacter and has the ability to convert glycerin to glyceric acid can be used. A specific example is Gluconobacter suboxidans (
Gluconobacter suboxydans)
IFo 3172 strain, Gluconobacter melanogenu
s) IFo 3292 strain, 3294 strain, Gluconobacter ceri
nus) 3262 shares of IFO etc. are listed. The microorganisms used in the present invention include not only the above-mentioned strains, but also mutant strains obtained artificially or naturally from these strains, such as gluconobacter that has the ability to produce D-glyceric acid.
Any strain of the genus can be used in the present invention.
これらの微生物を培養する培地としては、炭素源、窒素
源、無機物などを、程よく含有するものであれば、天然
培地、人工培地のいずれでも良い。The medium for culturing these microorganisms may be either a natural medium or an artificial medium, as long as it contains appropriate amounts of carbon sources, nitrogen sources, inorganic substances, and the like.
例えば、炭素源としてはグルコース、フラクトース、ソ
ルビトール、マンニトール、デキストリン、澱粉、グリ
セリン等が利用できる。窒素源としては、肉エキス、酵
母エキス、コーンステイープリカー等が利用できる。そ
の他、必要に応じて、炭酸カルシウム、塩化カリウム、
リン酸塩等の無機塩類を添加する。また、使用する菌株
の増殖を促進し、グリセリンからＤ−グリセリン酸への
転換能を促進するような有機物および無機物を適当に添
加することもできる。For example, glucose, fructose, sorbitol, mannitol, dextrin, starch, glycerin, etc. can be used as the carbon source. As a nitrogen source, meat extract, yeast extract, corn staple liquor, etc. can be used. In addition, calcium carbonate, potassium chloride,
Add inorganic salts such as phosphates. In addition, organic and inorganic substances that promote the growth of the strain used and the ability to convert glycerin to D-glyceric acid may be appropriately added.
培養法としては、液体培養法、特に深部通気攪拌培養法
が最も適している。培養に適当な温度は２５〜３７℃で
あるが、通常３０℃付近で培養する。−は一般的に中性
から微酸性（ｐＨ４〜７）が望ましい。The most suitable culture method is a liquid culture method, especially a deep aeration agitation culture method. The appropriate temperature for culturing is 25 to 37°C, but it is usually cultured at around 30°C. - is generally desirable to be neutral to slightly acidic (pH 4 to 7).
本発明では、通常、培養に用いられる培地に、グリセリ
ン’！ｒ ０．５〜２０％の濃度になるように添加しま
たは添加しながら１〜７日間培養する。この様にして培
養物中にＤ−グリセリン酸が生成する。In the present invention, glycerin'! Add or add r to a concentration of 0.5 to 20% and culture for 1 to 7 days. In this way, D-glyceric acid is produced in the culture.
一方、微生物菌体またはその処理物とグリセリン全作用
させてＤ−グリセリン酸を得る場合にも、微生物の培養
には前記組成と同様の培地および培養条件が用いられる
。On the other hand, when D-glyceric acid is obtained by fully interacting microorganism cells or their processed product with glycerin, the same medium and culture conditions as those described above are used for culturing the microorganism.
又、この場合、得られる微生物菌体はそのまま反応に使
用できるし、さらに、該菌体を種々処理して得られる処
理物全反応に用いても良い。Further, in this case, the obtained microbial cells can be used as they are for the reaction, or the processed products obtained by various treatments of the microorganism cells may be used for the whole reaction.
微生物菌体としては、菌体そのものまたは、菌体を含む
培養液が用いられる。菌体処理物としては、菌体の機械
的摩砕処理物、超音波処理物、凍結乾燥処理物酵素処理
物、乾燥処理物、界面活性＼
剤処理物、菌体の蛋白質分画、菌体および菌体処理物の
固定化物などが用いられる。As the microbial cells, the microbial cells themselves or a culture solution containing the microbial cells are used. Examples of bacterial cell-treated products include mechanically ground bacterial cells, ultrasonic-treated products, freeze-dried products, enzyme-treated products, dry-treated products, surfactant agent-treated products, protein fractions of bacterial cells, and bacterial cells. and immobilized products of processed bacterial cells.
反応は水溶液中、前記で得られる菌体またはその処理物
を、グリセリンに作用させることによシ行われる。菌体
またはその処理物をグリセリン１〜２０％水溶液、また
は、さらに無機塩類を添加した反応溶液に懸濁して、好
気的条件下で反応させる。反応の適する温度は、２０〜
３７℃であるが、通常３０℃付近で反応させる。The reaction is carried out by allowing the bacterial cells obtained above or a treated product thereof to act on glycerin in an aqueous solution. The bacterial cells or their processed material are suspended in a 1 to 20% glycerin aqueous solution or a reaction solution to which inorganic salts have been added, and reacted under aerobic conditions. The suitable temperature for the reaction is 20~
Although the temperature is 37°C, the reaction is usually carried out at around 30°C.
このようにして、水溶液中にＤ−グリセリン酸が生成す
る。In this way, D-glyceric acid is produced in the aqueous solution.
培養物中あるいは水溶液中に生成蓄積されたＤ−グリセ
リン酸を単離精製するには濾過、遠心分離等の方法によ
り菌体を分離した後通常の有機酸の分離精製法即ち、イ
オン交換樹脂による方法、カルシウムイオン等との金属
塩を作る方法、エステル体にして蒸溜による方法等が用
いられる。To isolate and purify D-glyceric acid produced and accumulated in a culture or an aqueous solution, the bacterial cells are separated by a method such as filtration or centrifugation, and then the usual organic acid separation and purification method is used, that is, using an ion exchange resin. A method of making a metal salt with calcium ion, etc., a method of forming an ester and distilling it, etc. are used.
（発明の効果）
本発明により、微生物を利用した工業的なり一グリセリ
ン酸の製造法が提供された。(Effects of the Invention) The present invention provides an industrial method for producing monoglyceric acid using microorganisms.
以下実施例を上げて本発明を具体的に説明する。The present invention will be specifically described below with reference to Examples.
実施例中Ｄ−グリセリン酸の定量にはイオン交換樹脂カ
ラムを用いる高速液体クロマトグラフイー法を用いた。In the examples, high performance liquid chromatography using an ion exchange resin column was used to quantify D-glyceric acid.
実施例１
グルコノバクタ−サブオキシダンスＩＦ０３１７２株、
グルコノパクターメラノノーナスＩＦ０３２９２株、３
２９４株、グルコノバクタ−セリナスＩＦ０３２６２株
の４菌株をグルコース１チ、酵母エキス０．５％、コー
ンステイープリカー１％、炭酸カルシウム１％の組成を
有する前培養培地（１００ｒｎ１．／坂ロフラスコ）に
植菌し３０℃で２日間往復振盪培養した。次いで下記組
成の生産培地１ｔを入れた２、６を容ミニツヤ−に上記
種培養液２０−ずつ全植菌した。Example 1 Gluconobacter suboxidans IF03172 strain,
Gluconopacter melanonus IF03292 strain, 3
294 strain and Gluconobacter selinus strain IF03262 were inoculated into a preculture medium (100rn1./Sakaro flask) having a composition of 1 g glucose, 0.5% yeast extract, 1% cornstarch liquor, and 1% calcium carbonate. The cells were cultured at 30°C for 2 days with reciprocal shaking. Next, 20 microliters of the above seed culture solution was inoculated into 2 and 6 microliters containing 1 ton of production medium having the following composition.
生産培地組成；グリセリン５チ、コーンステイーグリカ
ー３％、炭酸カルシウム１％
培養条件は、温度３０℃１通気量ｏ、 ５ ｖｖｍ ＋
攪拌４００ ｒｐｍで行った。４８時間後の培養液につ
いて生成したＤ−グリセリン酸の量を定量したところ下
記の表１の通シであった。Production medium composition: 5 t glycerin, 3 % corn stay glycer, 1 % calcium carbonate.Culture conditions: temperature 30°C 1 aeration volume o, 5 vvm +
Stirring was performed at 400 rpm. After 48 hours, the amount of D-glyceric acid produced in the culture solution was quantified, and the results were as shown in Table 1 below.
表 １
実施例２
実施例１で用いた４菌株について実施例１と同様に前培
養、本培養を行なった。本培養開始後２４時間目の培養
液を遠心分離にかけ菌体を得た。Table 1 Example 2 The four bacterial strains used in Example 1 were subjected to preculture and main culture in the same manner as in Example 1. The culture solution 24 hours after the start of the main culture was centrifuged to obtain bacterial cells.
この菌体を１０％グリセリン水溶液１ｔに懸濁し２．６
を容ミニジャーに入れ３０℃、通気量０．５ＶＶｍ ＋
攪拌４００ ｒｐｍの条件下４８時間反応させた。生成
したＤ−グリセリン酸の量を定量したところ表２の通シ
であった。This bacterial cell was suspended in 1 t of 10% glycerin aqueous solution and 2.6
Put it in a mini jar at 30℃, airflow rate 0.5VVm +
The reaction was carried out under conditions of stirring at 400 rpm for 48 hours. The amount of D-glyceric acid produced was quantified and was as shown in Table 2.
表 ２
実施例３
実施例２で得られ−た４菌株についての反応液１０−づ
つを遠心分離にかけ上澄液を得た。この４種のサンプル
をそれぞれダウエソクヌ１−Ｘ８（Ｃｔ型）（ダウケミ
カル社製）のカラム（ＩＸ］０ｃＩｎ）にチャージした
後２０−の蒸留水で洗浄した。しかる後０． Ｉ Ｎ−
ＨＣ６Ｉ ＯｒｎｌでＤ−グリセリン酸全溶出した。Table 2 Example 3 Ten reaction solutions for the four bacterial strains obtained in Example 2 were centrifuged to obtain supernatants. These four types of samples were charged to a column (IX]0 cIn) of Dow Soknu 1-X8 (Ct type) (manufactured by Dow Chemical Company), and then washed with 20-mL distilled water. After that, 0. IN-
All D-glyceric acid was eluted with HC6I Ornl.
この溶出成金それぞれ光学異性体分割用カラム、キラル
・ぐツクＷＨ（ダイセル化学工業製）を装着した高速液
体クロマトグラフィーにかけ分析した。Each of the eluted metals was analyzed by high-performance liquid chromatography equipped with a column for separating optical isomers, Chiral Gutsuku WH (manufactured by Daicel Chemical Industries, Ltd.).
その結果４種のサンプルについていずれも、Ｄ−グリセ
リン酸の標準品（シグマ社より市販）とピークは完全に
一致し光学純度もほぼ１００％であった。As a result, the peaks of all four samples completely matched with the standard D-glyceric acid (commercially available from Sigma), and the optical purity was approximately 100%.
実施例４
実施例２で得られたグルコノバクタ−セリナスの反応液
１００ｍ１を遠心分離にかけ上澄液９０ゴを得た。Example 4 100 ml of the Gluconobacter-serinus reaction solution obtained in Example 2 was centrifuged to obtain 90 ml of supernatant.
この上澄液上ダウエックス１−Ｘ、８ （Ｃｔ型）のカ
ラム（２，５ｘ３０ｃＩｎ）にチャージした後蒸留水３
００ｒｎｌで洗浄した。After charging the supernatant liquid onto a DOWEX 1-X, 8 (Ct type) column (2,5 x 30 cIn), distilled water
Washed with 00rnl.
しかる後０． Ｉ Ｎ・ＨＣｌ２００−でＤ−グリセリ
ン酸を溶出しまた
この溶出液をローターリ−エバポレーターにて濃縮し４
２１のＤ−グリセリン酸を得た。このサンプルを高速液
体クロストグラフィー法により分析したところ純度９５
チでちった。After that, 0. D-glyceric acid was eluted with 200% of IN HCl, and the eluate was concentrated using a rotary evaporator.
21 D-glyceric acid was obtained. When this sample was analyzed by high performance liquid crosstography, the purity was 95.
Chidechita.
Claims (1)
ン酸を生成する能力を有する微生物をグリセリンを含む
培地に培養することにより、または培地に培養して得ら
れる菌体またはその処理物をグリセリンを含有する水溶
液中で反応させることにより、培養物または水溶液中に
Ｄ−グリセリン酸を生成せしめ、これを採取することを
特徴とするＤ−グリセリン酸の製造法。An aqueous solution containing glycerin by culturing a microorganism belonging to the genus Gluconobacter that has the ability to produce D-glyceric acid from glycerin in a medium containing glycerin, or by culturing cells in a medium or a processed product thereof. 1. A method for producing D-glyceric acid, which comprises producing D-glyceric acid in a culture or an aqueous solution by reacting the same in an aqueous solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32727687A JPH0751069B2 (en) | 1987-12-25 | 1987-12-25 | Method for producing D-glyceric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32727687A JPH0751069B2 (en) | 1987-12-25 | 1987-12-25 | Method for producing D-glyceric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01168292A true JPH01168292A (en) | 1989-07-03 |
| JPH0751069B2 JPH0751069B2 (en) | 1995-06-05 |
Family
ID=18197314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32727687A Expired - Lifetime JPH0751069B2 (en) | 1987-12-25 | 1987-12-25 | Method for producing D-glyceric acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0751069B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008143146A3 (en) * | 2007-05-11 | 2009-03-12 | Sumitomo Chemical Co | Method for producing glyceric acid |
| JP2009153507A (en) * | 2007-12-28 | 2009-07-16 | National Institute Of Advanced Industrial & Technology | Process for preparation of d-glyceric acid from glycerol |
| JP2009159826A (en) * | 2007-12-28 | 2009-07-23 | National Institute Of Advanced Industrial & Technology | Method for producing d-glyceric acid from glycerol |
| JP2010130908A (en) * | 2008-12-02 | 2010-06-17 | National Institute Of Advanced Industrial Science & Technology | Method for producing glycerate |
| JP2010273599A (en) * | 2009-05-28 | 2010-12-09 | National Institute Of Advanced Industrial Science & Technology | Method for producing glycerol derivative |
| US8728780B2 (en) | 2004-04-27 | 2014-05-20 | Mitsui Chemicals, Inc. | Process for producing hydroxycarboxylic acid |
-
1987
- 1987-12-25 JP JP32727687A patent/JPH0751069B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8728780B2 (en) | 2004-04-27 | 2014-05-20 | Mitsui Chemicals, Inc. | Process for producing hydroxycarboxylic acid |
| WO2008143146A3 (en) * | 2007-05-11 | 2009-03-12 | Sumitomo Chemical Co | Method for producing glyceric acid |
| JP2009153507A (en) * | 2007-12-28 | 2009-07-16 | National Institute Of Advanced Industrial & Technology | Process for preparation of d-glyceric acid from glycerol |
| JP2009159826A (en) * | 2007-12-28 | 2009-07-23 | National Institute Of Advanced Industrial & Technology | Method for producing d-glyceric acid from glycerol |
| JP2010130908A (en) * | 2008-12-02 | 2010-06-17 | National Institute Of Advanced Industrial Science & Technology | Method for producing glycerate |
| JP2010273599A (en) * | 2009-05-28 | 2010-12-09 | National Institute Of Advanced Industrial Science & Technology | Method for producing glycerol derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0751069B2 (en) | 1995-06-05 |
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