JP7156594B2 - 1ステップ発酵による(r)-3-ヒドロキシ酪酸またはその塩の調製 - Google Patents
1ステップ発酵による(r)-3-ヒドロキシ酪酸またはその塩の調製 Download PDFInfo
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- JP7156594B2 JP7156594B2 JP2019545910A JP2019545910A JP7156594B2 JP 7156594 B2 JP7156594 B2 JP 7156594B2 JP 2019545910 A JP2019545910 A JP 2019545910A JP 2019545910 A JP2019545910 A JP 2019545910A JP 7156594 B2 JP7156594 B2 JP 7156594B2
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- hydroxybutyric acid
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/124—Acids containing four carbon atoms
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- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
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- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/1025—Acyltransferases (2.3)
- C12N9/1029—Acyltransferases (2.3) transferring groups other than amino-acyl groups (2.3.1)
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/13—Transferases (2.) transferring sulfur containing groups (2.8)
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- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/15—Corynebacterium
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Description
-80℃で保管しておいたグリセロールストックCGMCC No.13111を解凍し、500mL種培地(75g/Lのグルコース、25~30g/Lのコーンスティープリカー、20g/Lの(NH4)2SO4、1.5g/LのKH2PO4、0.5g/LのMgSO4・7H2O、1.0g/Lの尿素、30mg/Lのヒスチジン、25g/Lの糖蜜、100μg/Lのビオチン、pH7.0)を入れた5000mLフラスコに接種し、30℃で18時間培養した。OD=0.4~0.5のときに種培養物の培養を終了した。
実施例1で得られた5.2Lの発酵ブロスを、4500rpmで遠心分離し、細胞を廃棄した。上清は1%珪藻土でろ過した。1%活性炭を混合して30分間撹拌した後、清澄なろ液を回収した。
実施例2で得られた5gの(R)-3-ヒドロキシ酪酸と同量の2.0N水酸化ナトリウム溶液とを25℃以下で混合し、中和反応を行った。回転濃縮し、2時間静置してから、吸引ろ過で回収し、60℃で乾燥させて、最終的に81%の収率で4.9gのナトリウム(R)-3-ヒドロキシ酪酸塩粉末を得た。塩の融点は152℃で、特定光学値は[α]D20=-14.1°(C=10%、H2O)であった。
10gの(R)-3-ヒドロキシ酪酸を100mLの2.0N水酸化ナトリウム溶液にゆっくり添加し、混合物を60℃で4時間加熱した。生成物の光学値は室温で0°であった。塩酸を添加し、混合物のpHを7.0に調整して中和反応を行った。固形物が認められるまで回転蒸発を行い、2時間静置させ、その後ろ過を行って、85%の収率で10.3gのナトリウム3-ヒドロキシ酪酸塩粉末を得た。その結果、ラセミ3-ヒドロキシ酪酸塩が得られることがわかった。
Claims (13)
- 操作した非病原性微生物を用いて発酵ブロスを発酵させるステップを含む(R)-3-ヒドロキシ酪酸の生成プロセスであって、前記発酵ブロスが、炭素源と、窒素源と、を含み、前記炭素源と窒素源が、前記非病原性微生物を用いた1ステップ発酵によって(R)-3-ヒドロキシ酪酸に直接変換され、前記(R)-3-ヒドロキシ酪酸が、発酵中に排出された後に発酵ブロスから回収され、このとき、前記非病原性微生物が、China General Microbiological Culture Collection Centerに受託番号CGMCC No.13111で寄託されているコリネバクテリウム・グルタミカム菌株であり、前記非病原性微生物が、少なくとも1つの過剰発現させた酵素を有し、かつ前記非病原性微生物が、ピルビン酸と補酵素AをアセチルCoAに変換し、アセチルCoAをアセトアセチルCoAに変換し、アセトアセチルCoAをアセト酢酸に変換し、かつアセト酢酸を(R)-3-ヒドロキシ酪酸に変換する生体内変化能を有しているプロセス。
- 前記非病原性微生物を用いて過剰発現させた酵素が、スクシニルCoAトランスフェラーゼ、アセトアセチルCoAシンターゼ、または3-HBデヒドロゲナーゼを含む、請求項1に記載のプロセス。
- 前記微生物が、スクシニルCoAトランスフェラーゼと3-HBデヒドロゲナーゼとを過剰発現させる、請求項1または2に記載のプロセス。
- 前記炭素源が、グルコース、スクロース、マルトース、糖蜜、デンプン、およびグリセロールから成る群から選択される要素を含む、請求項1~3のうちいずれか一項に記載のプロセス。
- 前記窒素源が、有機窒素源と無機窒素源から成る群から選択される要素を含む、請求項1~3のうちいずれか一項に記載のプロセス。
- 前記有機窒素源が、コーンスティープリカー、糠加水分解物、大豆かす加水分解物、酵母抽出物、酵母粉末、ペプトン、および尿素から成る群から選択される要素を含む、請求項5に記載のプロセス。
- 前記無機窒素源が、硫酸アンモニウム、硝酸アンモニウム、およびアンモニア水から成
る群から選択される要素を含む、請求項5に記載のプロセス。 - 前記(R)-3-ヒドロキシ酪酸が細菌性エンドトキシンを含まず、95%以上の純度を有する、請求項1~7のうちいずれか一項に記載のプロセス。
- 前記(R)-3-ヒドロキシ酪酸が、(R)-3-ヒドロキシ酪酸塩ナトリウム塩、(R)-3-ヒドロキシ酪酸塩カリウム塩、(R)-3-ヒドロキシ酪酸塩マグネシウム塩、または(R)-3-ヒドロキシ酪酸塩カルシウム塩の形態で調製される、請求項1~8のうちいずれか一項に記載のプロセス。
- (R)-3-ヒドロキシ酪酸がラセミ化されて、ラセミ3-ヒドロキシ酪酸を生成する、請求項8に記載のプロセス。
- (R)-3-ヒドロキシ酪酸塩ナトリウム塩、(R)-3-ヒドロキシ酪酸塩カリウム塩、(R)-3-ヒドロキシ酪酸塩マグネシウム塩、または(R)-3-ヒドロキシ酪酸塩カルシウム塩がラセミ化されて、ラセミ3-ヒドロキシ酪酸を生成する、請求項9に記載のプロセス。
- China General Microbiological Culture Collection Centerに受託番号CGMCC No.13111で寄託されているコリネバクテリウム・グルタミカム菌株である、遺伝子操作した非病原性微生物であって、前記非病原性微生物が、ピルビン酸と補酵素AをアセチルCoAに変換し、アセチルCoAをアセトアセチルCoAに変換し、アセトアセチルCoAをアセト酢酸に変換し、かつアセト酢酸を(R)-3-ヒドロキシ酪酸に変換する生体内変化能を有する、非病原性微生物。
- 前記非病原性微生物が、請求項1~9のうちいずれか一項に記載の1ステップ発酵プロセスで(R)-3-ヒドロキシ酪酸を生成する、請求項12に記載の非病原性微生物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US201762481476P | 2017-04-04 | 2017-04-04 | |
US62/481,476 | 2017-04-04 | ||
PCT/US2018/025879 WO2018187324A1 (en) | 2017-04-04 | 2018-04-03 | Preparation of (r)-3-hydroxybutyric acid or its salts by one-step fermentation |
Publications (2)
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JP2019536478A JP2019536478A (ja) | 2019-12-19 |
JP7156594B2 true JP7156594B2 (ja) | 2022-10-19 |
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US (3) | US10428357B2 (ja) |
EP (1) | EP3507272A1 (ja) |
JP (1) | JP7156594B2 (ja) |
KR (1) | KR102480436B1 (ja) |
CN (1) | CN110035991B (ja) |
AU (1) | AU2018250146B2 (ja) |
CA (1) | CA3039255C (ja) |
MX (1) | MX2019005420A (ja) |
WO (1) | WO2018187324A1 (ja) |
Families Citing this family (15)
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US11241403B2 (en) | 2016-03-11 | 2022-02-08 | Axcess Global Sciences, Llc | Beta-hydroxybutyrate mixed salt compositions and methods of use |
US11103470B2 (en) | 2017-11-22 | 2021-08-31 | Axcess Global Sciences, Llc | Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use |
US10925843B2 (en) | 2018-04-18 | 2021-02-23 | Axcess Global Sciences, Llc | Compositions and methods for keto stacking with beta-hydroxybutyrate and acetoacetate |
US11202769B2 (en) | 2017-11-22 | 2021-12-21 | Axcess Global Sciences, Llc | Ketone body esters of s-beta-hydroxybutyrate and/or s-1,3-butanediol for modifying metabolic function |
US11944598B2 (en) | 2017-12-19 | 2024-04-02 | Axcess Global Sciences, Llc | Compositions containing s-beta-hydroxybutyrate or non-racemic mixtures enriched with the s-enatiomer |
US11806324B2 (en) | 2018-04-18 | 2023-11-07 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies |
CN110862316A (zh) * | 2018-08-27 | 2020-03-06 | 浙江华睿生物技术有限公司 | 一种(r)-3-羟基丁酸的晶型及其应用 |
CN109369372A (zh) * | 2018-11-28 | 2019-02-22 | 上海欣海国际贸易有限公司 | 一种制备3-羟基丁酸盐的方法 |
CN111944853A (zh) * | 2019-05-17 | 2020-11-17 | 南京纽邦生物科技有限公司 | 一种微生物发酵生产(r)-3-羟基丁酸的方法 |
US11950616B2 (en) | 2019-06-21 | 2024-04-09 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
CN111534561A (zh) * | 2020-05-19 | 2020-08-14 | 南京纽邦生物科技有限公司 | 一种(r)-3-羟基丁酸的制备方法 |
WO2022040644A2 (en) * | 2020-08-18 | 2022-02-24 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies |
AU2021367387A1 (en) * | 2021-04-16 | 2022-11-03 | Nanjing Nutrabuilding Bio-Tech Co., Ltd. | Low-lead and low-arsenic beta-hydroxybutyrate salts and methods for producing the same |
CN114436807B (zh) * | 2022-01-24 | 2023-12-22 | 珠海麦得发生物科技股份有限公司 | 一种(r)-3-羟基丁酸盐的制备方法 |
US11969430B1 (en) | 2023-03-10 | 2024-04-30 | Axcess Global Sciences, Llc | Compositions containing paraxanthine and beta-hydroxybutyrate or precursor for increasing neurological and physiological performance |
Citations (2)
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US20030203459A1 (en) | 2002-01-04 | 2003-10-30 | Guoqiang Chen | Method for the production of D-(-)-3-hydroxybutyric acid by recombinant esherichia coli |
WO2014190251A1 (en) | 2013-05-24 | 2014-11-27 | Genomatica, Inc. | Microorganisms and methods for producing (3r)-hydroxybutyl (3r)-hydroxybutyrate |
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JP2761063B2 (ja) * | 1989-12-12 | 1998-06-04 | ダイセル化学工業株式会社 | 光学活性3―ヒドロキシ酪酸の製造法 |
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IL157495A0 (en) * | 2001-02-21 | 2004-03-28 | Basf Ag | Method for the production of d-panthothenic acid and/or salts thereof as adjunct for animal feedstuffs |
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- 2018-04-03 AU AU2018250146A patent/AU2018250146B2/en active Active
- 2018-04-03 CN CN201880004349.9A patent/CN110035991B/zh active Active
- 2018-04-03 EP EP18781496.7A patent/EP3507272A1/en not_active Withdrawn
- 2018-04-03 MX MX2019005420A patent/MX2019005420A/es unknown
- 2018-04-03 KR KR1020197010395A patent/KR102480436B1/ko active IP Right Grant
- 2018-04-03 CA CA3039255A patent/CA3039255C/en active Active
- 2018-04-03 US US15/944,331 patent/US10428357B2/en active Active
- 2018-04-03 JP JP2019545910A patent/JP7156594B2/ja active Active
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- 2019-08-15 US US16/542,044 patent/US11198890B2/en active Active
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US20030203459A1 (en) | 2002-01-04 | 2003-10-30 | Guoqiang Chen | Method for the production of D-(-)-3-hydroxybutyric acid by recombinant esherichia coli |
WO2014190251A1 (en) | 2013-05-24 | 2014-11-27 | Genomatica, Inc. | Microorganisms and methods for producing (3r)-hydroxybutyl (3r)-hydroxybutyrate |
Also Published As
Publication number | Publication date |
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CN110035991A (zh) | 2019-07-19 |
JP2019536478A (ja) | 2019-12-19 |
US20180282767A1 (en) | 2018-10-04 |
US20220162653A1 (en) | 2022-05-26 |
EP3507272A4 (en) | 2019-07-10 |
US11198890B2 (en) | 2021-12-14 |
MX2019005420A (es) | 2019-11-18 |
CN110035991B (zh) | 2022-06-17 |
EP3507272A1 (en) | 2019-07-10 |
AU2018250146A1 (en) | 2019-04-18 |
WO2018187324A1 (en) | 2018-10-11 |
AU2018250146B2 (en) | 2020-11-05 |
US20190376098A1 (en) | 2019-12-12 |
CA3039255C (en) | 2022-11-29 |
CA3039255A1 (en) | 2018-10-11 |
KR20190137060A (ko) | 2019-12-10 |
KR102480436B1 (ko) | 2022-12-21 |
US10428357B2 (en) | 2019-10-01 |
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