JP6195296B2 - 低分子量ポリヒドロキシアルカン酸の製造方法 - Google Patents
低分子量ポリヒドロキシアルカン酸の製造方法 Download PDFInfo
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- JP6195296B2 JP6195296B2 JP2013162731A JP2013162731A JP6195296B2 JP 6195296 B2 JP6195296 B2 JP 6195296B2 JP 2013162731 A JP2013162731 A JP 2013162731A JP 2013162731 A JP2013162731 A JP 2013162731A JP 6195296 B2 JP6195296 B2 JP 6195296B2
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- 239000012159 carrier gas Substances 0.000 description 1
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- 210000003850 cellular structure Anatomy 0.000 description 1
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- AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 description 1
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- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
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- 238000000855 fermentation Methods 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
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- 235000001727 glucose Nutrition 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
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- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
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- 239000011159 matrix material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000009629 microbiological culture Methods 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 108010078304 poly-beta-hydroxybutyrate polymerase Proteins 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 238000007711 solidification Methods 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
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- 230000002194 synthesizing effect Effects 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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- 229940124024 weight reducing agent Drugs 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
PHAは、微生物が菌体内に蓄積する熱可塑性の生分解性プラスチックである。PHAとしては、例えば3−ヒドロキシアルカン酸や4−ヒドロキシアルカン酸などのモノマー成分を構成単位とするホモポリマーまたは共重合ポリマーが知られている。なかでも共重合ポリマーは、モノマー成分の組成比によって硬質から軟質の幅広い性質を発揮し得るため、広範な用途に適用することができる。なお共重合ポリマーは、一般的にはホモポリマーに比べて結晶化度が低下するという不具合があるが、本発明の結晶核剤を使用することでこの不具合を克服できるため、本発明では共重合ポリマーが好ましい。
次に、PHA樹脂の結晶核剤として有用な、本発明に係るカルボキシ末端修飾低分子量PHA(sPHA)の製造方法を詳しく説明する。
上述した本発明の方法によって得られるsPHAは、重量平均分子量(Mw)が5,000〜40,000と非常に低く、カルボキシ末端が修飾されたものである。
以下の実施例では、sPHA生産株として、前述した非特許文献2などに記載のBacillus cereus YB−4を用いた。この菌株は、北九州市の土壌から単離されたPHA合成細菌であり、北九州工業高等専門学校の水野康平准教授より提供されたものである。
本実施例および後記する実施例2では、アルコール添加培地にて上記sPHA生産株を培養したときのアルコール添加による分子量低減効果を調べるため、培地へのアルコール添加時期を変えて実験を行なった。
本実施例では、培養初期はアルコールを添加せず、培養中期〜後期にかけてアルコールを添加した培地中で培養を行ったときの、アルコール添加による分子量低減効果を調べた。
本実施例では、前述した実施例2のsPHAのうち、エタノール添加培地(エタノール濃度10mL/L)で培養して得られたsPHAについて、その骨格(繰り返し構造)およびカルボキシ末端の構造を解析した。
本実施例では、前述した実施例2のsPHAのうち、ブタノール添加培地(ブタノール濃度5mL/L)で培養して得られたsPHAについて、その骨格およびカルボキシ末端の構造を解析した。
前述した実施例1において、エタノール(5mL/L)添加培地で培養して得られたMn9,000、Mw20,000のsPHBを結晶核剤として用いたときの、PHA樹脂の結晶化速度を測定し、成形加工上効果を調べた。ここでは、PHA樹脂としてPHBHを用い、上記sPHBとPHA樹脂を溶融混錬して樹脂組成物(本発明例)とし、当該樹脂組成物の結晶化速度を測定した。
(PHA樹脂の製造)
ここでは、KNK−005株(US7384766を参照)を用いて培養した。培養に用いた種母培地、前培養培地、PHA生産培地の各組成は以下のとおりである。
1w/v%のMeat−extract、1w/v%のBacto−Tryptone、0.2w/v%のYeast−extract、0.9w/v%のNa2HPO4・12H2O、0.15w/v%のKH2PO4を用いた(pH6.8)。
1.1w/v%のNa2HPO4・12H2O、0.19w/v%のKH2PO4、1.29w/v%の(NH4)2SO4、0.1w/v%のMgSO4・7H2O、0.5v/v%の微量金属塩溶液(0.1N塩酸に1.6w/v%のFeCl3・6H2O、1w/v%のCaCl2・2H2O、0.02w/v%のCoCl2・6H2O、0.016w/v%のCuSO4・5H2O、0.012w/v%のNiCl2・6H2Oを溶かしたもの)を用いた。炭素源は、パーム油を10g/Lの濃度で一括添加した。
0.385w/v%のNa2HPO4・12H2O、0.067w/v%のKH2PO4、0.291w/v%の(NH4)2SO4、0.1w/v%のMgSO4・7H2O、0.5v/v%の微量金属塩溶液(0.1N塩酸に1.6w/v%のFeCl3・6H2O、1w/v%のCaCl2・2H2O、0.02w/v%のCoCl2・6H2O、0.016w/v%のCuSO4・5H2O、0.012w/v%のNiCl2・6H2Oを溶かしたもの)、0.05w/v%のBIOSPUREX200K(消泡剤:コグニスジャパン社製)を用いた。
次に、上記のようにして得られたPHBHと、前述したsPHBを用い、以下のようにして樹脂組成物を製造した。
次に、偏光顕微鏡を用いて、上記樹脂組成物の結晶化の程度を目視評価した。偏光顕微鏡として、LINKAM社製の顕微鏡用急冷加熱ステージLK300Bを用いた。詳細には、まず、上記樹脂組成物を190℃で溶融させて5分間保持した。その後、60℃に急冷した。急冷した直後から、偏光顕微鏡にて倍率400倍で目視観察を行った。上記樹脂組成物の結晶が認められた時間を結晶開始時間とし、結晶がこれ以上成長しない時間を結晶化完了時間とした。測定はそれぞれ、3回繰り返して行い、3回の平均値を算出した。
ここでは、低分子量の結晶核剤が有効であることを示す目的で、分子量が十分に高いPHB(Mw=68万)を下記方法により作製し、前述した方法と同様にして樹脂組成物を作製し、結晶化を評価した。
種母培地の組成
1w/v%のMeat−extract、1w/v%のBacto−Trypton、0.2w/v%のYeast−extract、0.9w/v%のNa2HPO4・12H2O、0.15w/v%のKH2PO4、5×10−6w/v%のカナマイシンとした。
1.1w/v%のNa2HPO4・12H2O、0.19w/v%のKH2PO4、1.29w/v%の(NH4)2SO4、0.1w/v%のMgSO4・7H2O、2.5w/v%のパームWオレイン油、0.5v/v%の微量金属塩溶液(0.1N塩酸に1.6w/v%のFeCl3・6H2O、1w/v%のCaCl2・2H2O、0.02w/v%のCoCl2・6H2O、0.016w/v%のCuSO4・5H2O、0.012w/v%のNiCl2・6H2Oを溶かしたもの)とした。
0.385w/v%のNa2HPO4・12H2O、0.067w/v%のKH2PO4、0・291w/v%の(NH4)2SO4、0.1w/v%のMgSO4・7H2O、0.5v/v%の微量金属塩溶液(0.1N塩酸に1.6w/v%のFeCl3・6H2O、1w/v%のCaCl2・2H2O、0.02w/v%のCoCl2・6H2O、0.016w/v%のCuSO4・5H2O、0.012w/v%のNiCl2・6H2Oを溶かしたもの)とした。炭素源として、パーム核油を分別した低融点画分であるパーム核油オレインのみを用いた。
Claims (11)
- IV型のポリヒドロキシアルカン酸合成酵素遺伝子を有する微生物としてBacillus属細菌を用いるか、または、
IV型のポリヒドロキシアルカン酸合成酵素遺伝子を有する微生物としてBacillus属細菌以外の微生物に、Bacillus属細菌由来のIV型のポリヒドロキシアルカン酸合成酵素遺伝子、ケトチオラーゼ遺伝子、およびアセトアセチル−CoA還元酵素遺伝子を組み込んだ形質転換体を用いて、
炭素数が1〜6の低級アルコールの存在下で培養することを特徴とする、重量平均分子量が5,000〜40,000であり、カルボキシ末端が修飾されたポリヒドロキシアルカン酸を製造する方法。 - 前記アルコールを加えた培地でBacillus属細菌または形質転換体を培養するものである請求項1に記載の製造方法。
- 前記アルコールは、エタノールである請求項2に記載の製造方法。
- 前記培地中のアルコール濃度は、0.01〜5体積%である請求項2または3に記載の製造方法。
- 前記カルボキシ末端がエステル化されたものである請求項1〜4のいずれかに記載の製造方法。
- 前記カルボキシ末端が、炭素数が1〜6の低級アルキルによってエステル化されたものである請求項5に記載の製造方法。
- 前記カルボキシ末端が、エチルエステル化されたものである請求項6に記載の製造方法。
- ポリ(3−ヒドロキシ酪酸)を少なくとも含むポリヒドロキシアルカン酸を製造するものである請求項1〜7のいずれかに記載の製造方法。
- ポリ(3−ヒドロキシ酪酸)またはポリ(3−ヒドロキシ酪酸−co−3−ヒドロキシ吉草酸)を製造するものである請求項1〜8のいずれかに記載の製造方法。
- 前記Bacillus属細菌が、Bacillus cereusである請求項1〜9のいずれかに記載の製造方法。
- 前記Bacillus属細菌以外の微生物が大腸菌である請求項1〜10のいずれかに記載の製造方法。
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