JP6262047B2 - 5−アミノレブリン酸又はその塩の製造方法 - Google Patents
5−アミノレブリン酸又はその塩の製造方法 Download PDFInfo
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- JP6262047B2 JP6262047B2 JP2014063330A JP2014063330A JP6262047B2 JP 6262047 B2 JP6262047 B2 JP 6262047B2 JP 2014063330 A JP2014063330 A JP 2014063330A JP 2014063330 A JP2014063330 A JP 2014063330A JP 6262047 B2 JP6262047 B2 JP 6262047B2
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- aminolevulinic acid
- acid
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- salt
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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
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
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- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000012262 fermentative production Methods 0.000 description 1
- VEPSWGHMGZQCIN-UHFFFAOYSA-H ferric oxalate Chemical compound [Fe+3].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O VEPSWGHMGZQCIN-UHFFFAOYSA-H 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
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- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
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- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- CPSYWNLKRDURMG-UHFFFAOYSA-L hydron;manganese(2+);phosphate Chemical compound [Mn+2].OP([O-])([O-])=O CPSYWNLKRDURMG-UHFFFAOYSA-L 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
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- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- NPFOYSMITVOQOS-UHFFFAOYSA-K iron(III) citrate Chemical compound [Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NPFOYSMITVOQOS-UHFFFAOYSA-K 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
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- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- JESHZQPNPCJVNG-UHFFFAOYSA-L magnesium;sulfite Chemical compound [Mg+2].[O-]S([O-])=O JESHZQPNPCJVNG-UHFFFAOYSA-L 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
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- 150000002696 manganese Chemical class 0.000 description 1
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- 235000002867 manganese chloride Nutrition 0.000 description 1
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- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
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- 229930182817 methionine Natural products 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
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- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
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- 230000002688 persistence Effects 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
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- 235000014786 phosphorus Nutrition 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229940048084 pyrophosphate Drugs 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 230000001954 sterilising effect Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- VNOYUJKHFWYWIR-ITIYDSSPSA-N succinyl-CoA 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)NCCSC(=O)CCC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 VNOYUJKHFWYWIR-ITIYDSSPSA-N 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
〔1〕硫酸類を0.5〜1.9mMと含硫アミノ酸を0.1〜1.0mMを含有する培地により5−アミノレブリン酸生産微生物を培養して得られた菌体を用いて5−アミノレブリン酸を発酵生産することを特徴とする、5−アミノレブリン酸又はその塩の製造方法。
〔2〕5−アミノレブリン酸生産微生物が光合成細菌である、〔1〕記載の5−アミノレブリン酸又はその塩の製造方法。
〔3〕5−アミノレブリン酸生産微生物がRhodobacter属の微生物である、〔1〕又は〔2〕記載の5−アミノレブリン酸又はその塩の製造方法。
〔4〕5−アミノレブリン酸生産微生物がロドバクター・スフェロイデスCR0072009(FERM BP−6320)である、〔1〕〜〔3〕のいずれかに記載の5−アミノレブリン酸又はその塩の製造方法。
培地中の含硫アミノ酸とは、システイン、シスチン、メチオニン、タウリンなど、その分子内に硫黄原子を有するアミノ酸のことを指す。
培地中の含硫アミノ酸の濃度は、5−アミノレブリン酸の蓄積濃度の点から、0.1〜1.0mMが好ましく、0.1〜0.8mMがより好ましく、0.1〜0.3mMが更に好ましい。また、5−アミノレブリン酸の生産安定性の点から、1.0mM以下が好ましく、0.8mM以下がより好ましく、0.3mM以下が更に好ましい。従って、5−アミノレブリン酸の蓄積濃度及び生産安定性の両者の点から、培地中の含硫アミノ酸の濃度は、0.1〜1.0mMが好ましく、0.1〜0.8mMがより好ましく、0.1〜0.3mMが更に好ましい。培地への含硫アミノ酸の添加は、酵母エキスなどの栄養成分に含まれる成分として添加しても良いが、精製したアミノ酸として添加することもできる。
また、本発明の製造方法で用いる培地には、さらに、グルタミン酸、アラニン、バリン、ロイシン、イソロイシン、プロリン、フェニルアラニン、トリプトファン、グリシン、セリン、トレオニン、グルタミン、アスパラギン、チロシン、リジン、ヒスチジン、アスパラギン酸、アルギニン等のアミノ酸等を適宜添加することができる。
加熱又は加圧する混合物には、媒体を用いてもよく、その媒体としては、実質的に培地成分を含有しない液体が挙げられ、好ましくは、水である。
のであって、本発明はこれら実施例に限定されるものではない。
(製造例)
200mLの表1に示す培地を2L容三角フラスコに分注し、121℃で20分間滅菌した後、放冷した。これにロドバクター・スフェロイデスCR0072009(FERM BP−6320)を植菌後、32℃、暗所にて26時間振盪培養した。
得られた培養物を再び、2L容三角フラスコに200mLの表1に示す培地を調製したところへ、初期菌体濃度(OD660nm)が0.2となるように植菌し、32℃、暗所にて24時間撹拌培養した。
500mL容の三角フラスコに50mLの表2記載の培地を調製したところへ、製造例で得られた培養物を、初期菌体濃度(OD660nm)が0.5となるように植菌し、28℃、暗所にて撹拌培養した。培養開始24〜26時間後に、グリシンを60mM、レブリン酸を5mMになるように添加し、硫酸を用いてpHを6.4〜6.5に調整した。次いで、この培養液を5本の20mmφ試験管に5mLずつ分注して、100rpmにて往復しんとう培養を行い、培養開始18時間後に培養を止めた。各試験管における5−アミノレブリン酸蓄積量を表3に示す。
5−アミノレブリン酸の生産性の判定については、5−アミノレブリン酸蓄積量が20mMを超える場合を良(○)とし、20mM未満の場合を不良(×)とした。また、5−アミノレブリン酸の生産安定性の判定については、同一の生育培養条件での5回の繰り返し試験における5−アミノレブリン酸蓄積量のCV値を算出し、CV値(変動係数)が10%未満の場合を良(○)とし、10%以上の場合を不良(×)とした。
Claims (2)
- 硫酸類を0.5〜1.9mMと含硫アミノ酸を0.1〜0.3mMを含有する培地によりRhodobacter属の微生物である5−アミノレブリン酸生産微生物を暗所にて培養して得られた菌体を用いて5−アミノレブリン酸を発酵生産することを特徴とする、5−アミノレブリン酸又はその塩の製造方法。
- Rhodobacter属の微生物である5−アミノレブリン酸生産微生物がロドバクター・スフェロイデスCR0072009(FERM BP−6320)である、請求項1に記載の5−アミノレブリン酸又はその塩の製造方法。
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