JP2019536478A - 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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Abstract
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 (20)
- 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、非病原性微生物を用いて過剰発現させた酵素とを含み、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、コリネバクテリウム・グルタミカム、枯草菌、ブレビバクテリウム・ラクトフェルメンタム、ブレビバクテリウム・ディフィシル(Brevibacterium difficile)、ブレビバクテリウム・フラバム、およびブレビバクテリウム・ブレベ(Brevibacterium breve)から成る群から選択され、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、および3−HBデヒドロゲナーゼから成る群から選択される要素を含む、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。
- 前記非病原性微生物が、コリネバクテリウム・グルタミカム、グルタミン酸細菌HR057、枯草菌、ブレビバクテリウム・ラクトフェルメンタム、ブレビバクテリウム・ディフィシル、ブレビバクテリウム・フラバム、またはブレビバクテリウム・ブレベである、請求項1〜3のうちいずれか一項に記載のプロセス。
- 前記微生物が、コリネバクテリウム・グルタミカムまたはグルタミン酸細菌HR057である、請求項1〜4のうちいずれか一項に記載のプロセス。
- 前記微生物がコリネバクテリウム・グルタミカムである、請求項1〜5のうちいずれか一項に記載のプロセス。
- 前記コリネバクテリウム・グルタミカムが、China General Microbiological Culture Collection Centerに受託番号CGMCC No.13111で寄託されている、請求項6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1〜7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1〜8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1〜9のうちいずれか一項に記載のプロセス。
- 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1〜10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1〜11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1〜12のうちいずれか一項に記載のプロセス。
- 請求項12に記載のプロセスにおける(R)−3−ヒドロキシ酪酸のラセミ化処理によって調製されるラセミ3−ヒドロキシ酪酸。
- 請求項13に記載のプロセスにおける(R)−3−ヒドロキシ酪酸塩のラセミ化処理によって調製されるラセミ3−ヒドロキシ酪酸。
- コリネバクテリウム・グルタミカム、グルタミン酸細菌HR057、枯草菌、ブレビバクテリウム・ラクトフェルメンタム、ブレビバクテリウム・ディフィシル、ブレビバクテリウム・フラバム、およびブレビバクテリウム・ブレベから成る群から選択される非病原性微生物。
- 前記非病原性微生物が、コリネバクテリウム・グルタミカム菌株またはグルタミン酸細菌HR057菌株である、請求項16に記載の非病原性微生物。
- 前記非病原性微生物がコリネバクテリウム・グルタミカム菌株である、請求項17に記載の非病原性微生物。
- 前記コリネバクテリウム・グルタミカム菌株が、China General Microbiological Culture Collection Centerに受託番号CGMCC No.13111で寄託されている、請求項18に記載の非病原性微生物。
- 前記微生物が、請求項1〜13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できる、請求項16に記載の非病原性微生物。
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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 |
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JP2019536478A true JP2019536478A (ja) | 2019-12-19 |
JP7156594B2 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) |
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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 |
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Patent Citations (5)
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JPS58158190A (ja) * | 1982-03-16 | 1983-09-20 | Kanegafuchi Chem Ind Co Ltd | D(−)−β−ヒドロキシ酪酸の製造法 |
JPS6474999A (en) * | 1987-09-16 | 1989-03-20 | Nissei Kagaku Kogyo Kk | Production of optically active (r)-(-)-beta-hydroxylactic acid |
JPH03183499A (ja) * | 1989-12-12 | 1991-08-09 | Daicel Chem Ind Ltd | 光学活性3―ヒドロキシ酪酸の製造法 |
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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AU2018250146B2 (en) | 2020-11-05 |
KR102480436B1 (ko) | 2022-12-21 |
US20190376098A1 (en) | 2019-12-12 |
CN110035991A (zh) | 2019-07-19 |
US11198890B2 (en) | 2021-12-14 |
KR20190137060A (ko) | 2019-12-10 |
WO2018187324A1 (en) | 2018-10-11 |
CA3039255A1 (en) | 2018-10-11 |
CN110035991B (zh) | 2022-06-17 |
JP7156594B2 (ja) | 2022-10-19 |
AU2018250146A1 (en) | 2019-04-18 |
US20220162653A1 (en) | 2022-05-26 |
MX2019005420A (es) | 2019-11-18 |
CA3039255C (en) | 2022-11-29 |
EP3507272A4 (en) | 2019-07-10 |
US20180282767A1 (en) | 2018-10-04 |
US10428357B2 (en) | 2019-10-01 |
EP3507272A1 (en) | 2019-07-10 |
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