JP6332961B2 - ω−アミノ脂肪酸の製造 - Google Patents
ω−アミノ脂肪酸の製造 Download PDFInfo
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- JP6332961B2 JP6332961B2 JP2013265665A JP2013265665A JP6332961B2 JP 6332961 B2 JP6332961 B2 JP 6332961B2 JP 2013265665 A JP2013265665 A JP 2013265665A JP 2013265665 A JP2013265665 A JP 2013265665A JP 6332961 B2 JP6332961 B2 JP 6332961B2
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- cell catalyst
- whole cell
- fatty acid
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- 150000002829 nitrogen Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000005261 phosphopantetheinylation Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000019525 primary metabolic process Effects 0.000 description 1
- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- 229930182852 proteinogenic amino acid Natural products 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000021250 regulation of fatty acid beta-oxidation Effects 0.000 description 1
- 108091008146 restriction endonucleases Proteins 0.000 description 1
- 108060007223 rubredoxin Proteins 0.000 description 1
- 108010060589 rubredoxin-NAD+ reductase Proteins 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000006152 selective media Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
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Description
a)脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルを、アルカンヒドロキシラーゼおよび/またはアルコールデヒドロゲナーゼとの接触によって酸化させて酸化生成物とする工程と、
b)前記酸化生成物と、ホスホパンテテイニル化された脂肪酸レダクターゼまたはα−ジオキシゲナーゼとを接触させてアルデヒドとする工程と、
c)前記アルデヒドとトランスアミナーゼとを接触させる工程と、
を含む前記方法によって解決される。
R1−A−COOR2 (I)
[式中、
R1は、−H、−CHO、−OHおよびCOOR3を含む群から選択され、
R2およびR3は、それぞれ互いに独立して、H、メチル、エチルおよびプロピルを含む群から選択されるが、但し、前記基R2およびR3の少なくとも1つは、Hであり、その際、Aは、少なくとも4個の炭素原子を有する非分枝鎖状の、分枝鎖状の、直鎖状の、環状の、置換もしくは非置換の炭化水素基を表す]の化合物である方法によって解決される。
R1−A−COOR2 (I)
[式中、
R1は、−H、−CHO、−OHおよびCOOR3を含む群から選択され、
R2およびR3は、それぞれ互いに独立して、H、メチル、エチルおよびプロピルを含む群から選択されるが、但し、前記基R2およびR3の少なくとも1つは、Hであり、その際、Aは、少なくとも4個の炭素原子を有する非分枝鎖状の、分枝鎖状の、直鎖状の、環状の、置換もしくは非置換の炭化水素基を、好ましくは式−(CH2)n−を表し、式中、nが少なくとも4であり、特に好ましくは少なくとも10である]の脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルを含む反応混合物によって解決される。
オデッセラ(Odyssella)、アキュムリバクター(Accumulibacter)、
特にB.サチリス(B. subtilis)、B.メガテリウム(B. megaterium)、
C.グルタミクム(C. glutamicum)、E.コリ(E. coli)、シュードモナス・エスピー(Pseudomonas sp.)、シュードモナス・フルオレッセンス(Pseudomonas fluorescens)、シュードモナス・プチダ(Pseudomonas putida)、シュードモナス・スタッツェリ(Pseudomonas stutzeri)、アシネトバクター・エスピー(Acinetobacter sp.)、
ブルクホルデリア・エスピー(Burkholderia sp.)、ブルクホルデリア・タイランデンシス(Burkholderia thailandensis)、藍藻(Cyanobakterien)、クレブシエラ・エスピー(Klebsiella sp.)、クレブシエラ・オキシトカ(Klebsiella oxytoca)、
サルモネラ・エスピー(Salmonella sp.)、リゾビウム・エスピー(Rhizobium sp.)およびリゾビウム・メリロチ(Rhizobium meliloti)を含む群から選択される細菌であってよい。特に好ましい一実施形態においては、腸内細菌、最も好ましくはエシェリキア・コリである。
R1−A−COOR2 (I)
[式中、
R1は、−H、−CHO、−OHおよびCOOR3を含む群から選択され、
R2およびR3は、それぞれ互いに独立して、H、メチル、エチルおよびプロピルを含む群から選択されるが、但し、前記基R2およびR3の少なくとも1つは、Hであり、その際、Aは、少なくとも4個の炭素原子を有する非分枝鎖状の、分枝鎖状の、直鎖状の、環状の、置換もしくは非置換の炭化水素基を表す]の化合物である前記方法で使用できる。好ましい一実施形態においては、前記のAは、式−(CH2)n−の構造であり、式中、nは、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29または30である。好ましい一実施形態においては、前記の脂肪酸、ω−ヒドロキシ脂肪酸またはω−オキソ脂肪酸は、ラウリン酸、ω−ヒドロキシラウリン酸もしくはω−オキソラウリン酸である。更なる好ましい一実施形態においては、前記の脂肪酸、ω−ヒドロキシ脂肪酸またはω−オキソ脂肪酸は、ヘキサン酸、ω−ヒドロキシヘキサン酸もしくはω−オキソヘキサン酸である。更なる好ましい一実施形態においては、前記の脂肪酸、ω−ヒドロキシ脂肪酸またはω−オキソ脂肪酸は、デカン酸、ω−ヒドロキシデカン酸もしくはω−オキソデカン酸である。
脂肪酸レダクターゼをコードする遺伝子と、ノカルディア・エスピー(Nocardia sp.)由来のnptとを同時発現するための発現ベクターの製造
脂肪酸レダクターゼをコードする遺伝子と、ノカルディア・エスピー(Nocardia sp.)由来の、ホスホパンテテイニル−トランスフェラーゼをコードするnpt(配列番号1、ABI83656.1をコードする)とを同時発現するためのベクターの製造のために、それらの遺伝子を、エシェリキア・コリ(Escherichia coli)での発現のためにコドン最適化し、そしてlacuv5−プロモーター(配列番号2)と一緒に合成し、かつ同時にそれぞれ1つの制限切断部位を上流と下流に導入した。以下の脂肪酸レダクターゼ遺伝子を使用した:
・ マイコバクテリウム・スメグマティス(Mycobacterium smegmatis)由来のMSMEG_2956(carA、配列番号3、YP_887275.1をコードする)
・ マイコバクテリウム・スメグマティス(Mycobacterium smegmatis)由来のMSMEG_5739(carB、配列番号4、YP_889972.1をコードする)
・ マイコバクテリウム・イントラセルラレMOTT−64(Mycobacterium intracellulare MOTT-64)由来のfadD9(car_Mint、配列番号5、YP_005349252.1をコードする)
・ マイコバクテリウム・フォルツイツム・サブエスピー・フォルツイツムDSM46621(Mycobacterium fortuitum subsp. fortuitum DSM 46621)由来のMFORT_07381(car_Mfort、配列番号6、ZP_11001941.1をコードする)
・ マイコバクテリウム・アビウム・サブエスピー・パラツベルクロシスK−10(Mycobacterium avium subsp. paratuberculosis K-10)由来のFadD9(car_Mavi、配列番号7、NP_959974.1をコードする)
・ シアノビウム・エスピーPCC7001(Cyanobium sp. PCC 7001)由来のCPCC7001_1320(car_Cs、配列番号8、ZP_05045132.1をコードする)
・ マイコバクテリウム・アブセッサスATCC19977(Mycobacterium abscessus ATCC 19977)由来のMAB_3367(car_Mab、配列番号9、YP_001704097.1をコードする)
・ ノカルディア・ブラシリエンシスATCC700358(Nocardia brasiliensis ATCC 700358)由来のFadD9(car_nbr、配列番号10、ZP_09839660.1をコードする)
・ マイコバクテリウム・インディカス・プラニイMTCC9506(Mycobacterium indicus pranii MTCC 9506)由来のMIP_06852(car_Mip、配列番号11、YP_006731697.1をコードする)
・ ノカルディア・ファルシニカIFM10152(Nocardia farcinica IFM 10152)由来のnfa20150(car_nfa、配列番号12、YP_118225.1をコードする)
・ マイコバクテリウム・ウルセランスAgy99(Mycobacterium ulcerans Agy99)由来のMUL_1722(car_Mul、配列番号13、YP_905678.1をコードする)
・ ストレプトマイセス・アシディスカビエス84−104(Streptomyces acidiscabies 84-104)由来のSaci8_010100039603(car_Sac、配列番号14、ZP_10456477.1をコードする)
・ マイコバクテリウム・コロムビエンスCECT3035(Mycobacterium colombiense CECT 3035)由来のMCOL_V203220(car_Mcol、配列番号15、WP_007769435.1をコードする)
合成されたDNA断片を、制限エンドヌクレアーゼNdeIおよびAvrIIを用いて消化し、そして相応して切断されたベクターpSC101(配列番号16)中にライゲーションした。ベクターpSC101は、非常に低コピーのベクターであって、テトラサイクリン耐性を有し、かつ1細胞あたり約4コピーの低いコピー数を有する。このように、以下の発現ベクターを製造できた:
・ pSC101{Placuv5}[carA_Ms(co_Ec)-npt_Noc(co_Ec)](配列番号17)
・ pSC101{Placuv5}[carB_Ms(co_Ec)-npt_Noc(co_Ec)](配列番号18)
・ pSC101{Placuv5}[car_Mint(co_Ec)-npt_Noc(co_Ec)](配列番号19)
・ pSC101{Placuv5}[car_Mfort(co_Ec)-npt_Noc(co_Ec)](配列番号20)
・ pSC101{Placuv5}[car_Mavi(co_Ec)-npt_Noc(co_Ec)](配列番号21)
・ pSC101{Placuv5}[car_Csp(co_Ec)-npt_Noc(co_Ec)](配列番号22)
・ pSC101{Placuv5}[car_Mab(co_Ec)-npt_Noc(co_Ec)](配列番号23)
・ pSC101{Placuv5}[car_nbr(co_Ec)-npt_Noc(co_Ec)](配列番号24)
・ pSC101{Placuv5}[car_Mip(co_Ec)-npt_Noc(co_Ec)](配列番号25)
・ pSC101{Placuv5}[car_nfa(co_Ec)-npt_Noc(co_Ec)](配列番号26)
・ pSC101{Placuv5}[car_Mul(co_Ec)-npt_Noc(co_Ec)](配列番号27)
・ pSC101{Placuv5}[car_Sac(co_Ec)-npt_Noc(co_Ec)](配列番号28)
・ pSC101{Placuv5}[car_Mcol(co_Ec)-npt_Noc(co_Ec)](配列番号29)
遺伝子産物nptは、脂肪酸レダクターゼの活性化のために、ホスホパンテテイニル基を補酵素Aから脂肪酸レダクターゼ酵素へと転移する。
遺伝子bioHに欠失を有する、アミノラウリン酸メチルエステルをラウリン酸メチルエステルから製造するための、増強された脂肪酸レダクターゼ活性とホスホパンテテイニルトランスフェラーゼ活性とを有するE.コリ菌株の製造
エステラーゼをコードする遺伝子bioHの欠失と、アミノラウリン酸メチルエステルの製造のための増強された脂肪酸レダクターゼ活性を有するE.コリ菌株の作成のために、菌株エシェリキア・コリW3110ΔbioH(製造は、EP12007663を参照のこと)を、プラスミドpBT10_alkL(配列と製造は、WO/2011/131420の例1もしくはそこに挙げられるSeq ID NR: 8と同等)、pJ294_alaDH_B.s._TA_C.v.(Ct)(WO/2013/024114の例1およびそこに挙げられるSEQ ID Nr. 17と同等)および例1で作成された、脂肪酸レダクターゼの発現のためのベクターでエレクトロポレーションによって形質転換し、そしてカナマイシン(50μg/ml)、アンピシリン(100μg/ml)およびテトラサイクリン(5μg/ml)を有するLBアガープレート上にプレーティングした。形質転換体を、プラスミド調製と制限分析によって正確なプラスミドの存在について調べた。こうして以下の菌株を作成した:
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[carA_Ms(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[carB_Ms(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_Mint(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_Mfort(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_Mavi(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_Csp(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_Mab(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_nbr(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_Mip(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_nfa(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_Mul(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_Sac(co_Ec)-npt_Noc(co_Ec)]
・ E.コリ W3110 ΔbioH pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[car_Mcol(co_Ec)-npt_Noc(co_Ec)]
前記の菌株を、ラウリン酸メチルエステルから出発するアミノラウリン酸メチルエステルの製造のためのその能力を調査するために使用した。
アミノラウリン酸メチルエステルをラウリン酸メチルエステルから製造するための、増強された脂肪酸レダクターゼ活性とホスホパンテテイニルトランスフェラーゼ活性とを有するE.コリ菌株の製造
使用される宿主菌株E・コリW3110を、発現ベクタープラスミドpBT10_alkL(配列と製造は、WO/2011/131420の例1もしくはそこに上げられるSeq ID NR: 8と同等)、pJ294_alaDH_B.s._TA_C.v.(Ct)(WO/2013/024114の例1およびそこに挙げられるSEQ ID Nr. 17と同等)およびpSC101{Placuv5}[carB_Ms(co_Ec)-npt_Noc(co_Ec)]もしくはpSC101の空ベクターでエレクトロポレーションによって形質転換し、そしてカナマイシン(50μg/ml)、アンピシリン(100μg/ml)およびテトラサイクリン(5μg/ml)を有するLBアガープレート上にプレーティングした。形質転換体を、プラスミド調製と制限分析によって正確なプラスミドの存在について調べた。こうして、菌株E.コリ W3110 pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101{Placuv5}[carB_Ms(co_Ec)-npt_Noc(co_Ec)]およびE.コリ W3110 pBT10_alkL / pJ294_alaDH_B.s._TA_C.v.(Ct) / pSC101が作成された。
脂肪酸レダクターゼ遺伝子とノカルディア・エスピー(Nocardia sp.)由来の遺伝子nptのための発現ベクターおよびバシラス・サチリス(Bacillus subtilis)由来の遺伝子aldとクロモバクテリウム・ビオラセウム(Chromobacterium violaceum)由来のCv_2025についての発現ベクターを、シュードモナス・プチダ(Pseudomonas putida)由来のalkオペロンからの遺伝子alkB、alkG、alkTおよびalkLについての発現ベクターと組み合わせて有するE.コリ菌株によるアミノラウリン酸の生産
例2および例3で作成された菌株を、アミノラウリン酸メチルエステルの生産のためのその能力を調査するために使用した。
発酵のために、1Lのリアクターを使用した。pHプローブを、pH4.0とpH7.0の基準溶液で二点校正法によって校正した。前記リアクターに、300mLの飲料水を満たし、滅菌性を保証するために121℃で20分にわたりオートクレーブにかけた。引き続き、pO2プローブを、一晩(少なくとも6時間長)にわたりDASGIPシステムで分極させた。翌朝に、水をクリーンベンチのもとで取り除き、100mg/Lのアンピシリン、50mg/Lのカナマイシンおよび5mg/Lのテトラサイクリンを有する300mLの高細胞密度培地に置き換えた。次に、pO2プローブを一点校正法(撹拌機:400rpm/給気:10sL/h空気)により校正し、供給区間、校正剤区間および誘導剤区間を定置洗浄(Clean-in-Place)で洗浄した。そのために、それらのチューブを、70%エタノールで、引き続き1MのNaOHで、次いで滅菌完全脱塩水ですすぎ、最後にその都度の培地で満たした。
発酵試料におけるALS、ALSME、DDS、DDSME、LS、LSME、HLS、HLSME、OLSおよびOLSMEの定量化は、LC−ESI/MS2によって、全ての分析物についての外部校正(0.1〜50mg/L)をもとに、かつアミノウンデカン酸(AUD、これは、HLS、DDS、OLS、HLSME、OLSMEのため)、d4−ALSME(ALSMEのため)、13C−DDSME(DDSMEのため)、d3−LS(LSのため)およびd3−LSME(LSMEのため)といった内部標準を用いて行った。
・ オートサンプラー(G1367E)と、バイナリポンプ(G1312B)と、カラムオーブン(G1316A)とを備えたHPLCシステム1260(Agilent;Boeblingen)
・ ESI源を備えた質量分析計TripelQuad 6410(Agilent;Boeblingen)
・ HPLCカラム:Kinetex C18、100×2.1mm、粒度:2.6μm、細孔サイズ100Å(Phenomenex;Aschaffenburg)
・ プレカラム:KrudKatcher Ultra HPLC In-Line Filter;0.5μmの濾層厚および0.004mmの内径(Phenomenex;Aschaffenburg)
試料を、1900μLの溶剤(80%(v/v)のACN、20%の二回蒸留H2O(v/v)+0.1%のギ酸)および100μLの試料を2mLの反応容器にピペット導入することによって準備した。その混合物を、約10秒間にわたりボルテックスにかけ、引き続き約13000rpmで5分間にわたり遠心分離した。澄明な上清を、ピペットで取り出し、希釈剤(80%(v/v)のACN、20%の二回蒸留H2O(v/v)+0.1%のギ酸)での相応の希釈の後に分析した。それぞれ900μLの試料に対して100μLのISTDを更にピペット導入した(試料容量90μLの場合に10μL)。
・ ガス温度 280℃
・ ガス流速 11L/分
・ ネブライザー圧力 50psi
・ キャピラリー電圧 4000V
化合物ALS、ALSME、DDS、DDSME、HLS、HLSME、OLS、OLSMEの検出および定量化は、以下のMRMパラメータをもって行った。その際、それぞれ1つのプロダクトイオンをクオリファイアとして用い、1つをクオンティファイアとして用いた:
1. 組み換え型のα−ジオキシゲナーゼまたは組み換え型の脂肪酸レダクターゼと該脂肪酸レダクターゼをホスホパンテテイニル化するホスホパンテテイニル−トランスフェラーゼからなる組み合わせを発現し、更にトランスアミナーゼを発現する全細胞触媒であって、前記ホスホパンテテイニル−トランスフェラーゼおよび/またはトランスアミナーゼが好ましくは組み換え型である前記全細胞触媒。
2. 1に記載の全細胞触媒であって、前記全細胞触媒が、更に、好ましくは組み換え型であるアミノ酸デヒドロゲナーゼを発現する前記全細胞触媒。
3. 1または2に記載の全細胞触媒であって、前記全細胞触媒が、更に、好ましくは組み換え型であるアルカンヒドロキシラーゼを発現する前記全細胞触媒。
4. 1から3までのいずれかに記載の全細胞触媒であって、前記全細胞触媒が、更に、好ましくは組み換え型であるAlkLファミリーのポリペプチドを発現する前記全細胞触媒。
5. 1から4までのいずれかに記載の全細胞触媒であって、前記全細胞触媒が、更に、好ましくは組み換え型であるアルコールデヒドロゲナーゼを発現する前記全細胞触媒。
6. 1から5までのいずれかに記載の全細胞触媒であって、β−酸化に関与する少なくとも1つの酵素の活性が、該全細胞触媒の野生型に対して低減されている前記全細胞触媒。
7. 1から6までのいずれかに記載の全細胞触媒であって、BioHまたはその変異体の活性が、該全細胞触媒の野生型に対して低減されている前記全細胞触媒。
8. 1から6までのいずれかに記載の全細胞触媒であって、FadLまたはその変異体の活性が、該全細胞触媒の野生型に対して高められている前記全細胞触媒。
9. 脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルのアミンへの転化方法であって、
a)脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルを、アルカンヒドロキシラーゼおよび/またはアルコールデヒドロゲナーゼとの接触によって酸化させて酸化生成物とする工程と、
b)前記酸化生成物と、ホスホパンテテイニル化された脂肪酸レダクターゼまたはα−ジオキシゲナーゼとを接触させてアルデヒドとする工程と、
c)前記アルデヒドとトランスアミナーゼとを接触させる工程と、
を含む前記方法。
10. 9に記載の方法であって、工程c)においてアミノ酸デヒドロゲナーゼが存在する前記方法。
11. 9または10に記載の方法であって、ホスホパンテテイニル化された脂肪酸レダクターゼ、α−ジオキシゲナーゼ、トランスアミナーゼ、アミノ酸デヒドロゲナーゼおよびアルカンヒドロキシラーゼを含む群からの少なくとも1つの酵素、好ましくは前記の群からの全ての使用される酵素が、1から8までのいずれかに記載の全細胞触媒の形で提供される前記方法。
12. 9から11までのいずれかに記載の方法であって、前記の脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルが、式(I)
R1−A−COOR2 (I)
[式中、
R1は、−H、−CHO、−OHおよびCOOR3を含む群から選択され、
R2およびR3は、それぞれ互いに独立して、H、メチル、エチルおよびプロピルを含む群から選択されるが、但し、前記基R2およびR3の少なくとも1つは、Hであり、その際、Aは、少なくとも4個の炭素原子を有する非分枝鎖状の、分枝鎖状の、直鎖状の、環状の、置換もしくは非置換の炭化水素基を表す]の化合物である前記方法。
13. 9から12までのいずれかに記載の方法であって、Aが式−(CH2)n−を有し、その式中、nが、少なくとも4であり、好ましくは少なくとも10である前記方法。
14. 1から8までのいずれかに記載の全細胞触媒または8から12までのいずれかに記載の方法を、脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのエステルのアミノ化のために用いる使用。
15. 1から8までのいずれかに記載の全細胞触媒を水溶液で含み、かつ式(I)
R1−A−COOR2 (I)
[式中、
R1は、−H、−CHO、−OHおよびCOOR3を含む群から選択され、
R2およびR3は、それぞれ互いに独立して、H、メチル、エチルおよびプロピルを含む群から選択されるが、但し、前記基R2およびR3の少なくとも1つは、Hであり、その際、Aは、少なくとも4個の炭素原子を有する非分枝鎖状の、分枝鎖状の、直鎖状の、環状の、置換もしくは非置換の炭化水素基を、好ましくは式−(CH2)n−を表し、式中、nが少なくとも4であり、特に好ましくは少なくとも10である]の脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルを含む反応混合物。
Claims (14)
- 組み換え型のα−ジオキシゲナーゼを過剰発現するか、または組み換え型の脂肪酸レダクターゼと該脂肪酸レダクターゼをホスホパンテテイニル化するホスホパンテテイニル−トランスフェラーゼからなる組み合わせを過剰発現し、更にトランスアミナーゼを過剰発現する全細胞触媒であって、前記ホスホパンテテイニル−トランスフェラーゼおよびトランスアミナーゼが組み換え型である前記全細胞触媒。
- 請求項1に記載の全細胞触媒であって、前記全細胞触媒が、更に、組み換え型であるアミノ酸デヒドロゲナーゼを発現する前記全細胞触媒。
- 請求項1または2に記載の全細胞触媒であって、前記全細胞触媒が、更に、組み換え型であるアルカンヒドロキシラーゼを発現する前記全細胞触媒。
- 請求項1から3までのいずれか1項に記載の全細胞触媒であって、前記全細胞触媒が、更に、組み換え型であるAlkLファミリーのポリペプチドを発現する前記全細胞触媒。
- 請求項1から4までのいずれか1項に記載の全細胞触媒であって、前記全細胞触媒が、更に、組み換え型であるアルコールデヒドロゲナーゼを発現する前記全細胞触媒。
- 請求項1から5までのいずれか1項に記載の全細胞触媒であって、β−酸化に関与する少なくとも1つの酵素の活性が、該全細胞触媒の野生型に対して低減されている前記全細胞触媒。
- 請求項1から6までのいずれか1項に記載の全細胞触媒であって、BioHまたはその変異体の活性が、該全細胞触媒の野生型に対して低減されている前記全細胞触媒。
- 請求項1から6までのいずれか1項に記載の全細胞触媒であって、FadLまたはその変異体の活性が、該全細胞触媒の野生型に対して高められている前記全細胞触媒。
- 脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルのアミンへの転化方法であって、
a)脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルを、アルカンヒドロキシラーゼおよび/またはアルコールデヒドロゲナーゼとの接触によって酸化させて酸化生成物とする工程と、
b)前記酸化生成物と、ホスホパンテテイニル化された脂肪酸レダクターゼまたはα−ジオキシゲナーゼとを接触させてアルデヒドとする工程と、
c)前記アルデヒドとトランスアミナーゼとを接触させる工程と、
を含み、請求項1から8までのいずれか1項に記載の全細胞触媒を用いて行う前記方法。 - 請求項9に記載の方法であって、工程c)においてアミノ酸デヒドロゲナーゼが存在する前記方法。
- 請求項9から10までのいずれか1項に記載の方法であって、前記の脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルが、式(I)
R1−A−COOR2 (I)
[式中、
R1は、−H、−CHO、−OHおよびCOOR3を含む群から選択され、
R2およびR3は、それぞれ互いに独立して、H、メチル、エチルおよびプロピルを含む群から選択されるが、但し、前記基R2およびR3の少なくとも1つは、Hであり、その際、Aは、少なくとも4個の炭素原子を有する非分枝鎖状の、分枝鎖状の、直鎖状の、環状の、置換もしくは非置換の炭化水素基を表す]の化合物である前記方法。 - 請求項9から11までのいずれか1項に記載の方法であって、Aが式−(CH2)n−を有し、その式中、nが、少なくとも4である前記方法。
- 請求項1から8までのいずれか1項に記載の全細胞触媒または請求項9から12までのいずれか1項に記載の方法を、脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのエステルのアミノ化のために用いる使用。
- 請求項1から8までのいずれか1項に記載の全細胞触媒を水溶液で含み、かつ式(I)
R1−A−COOR2 (I)
[式中、
R1は、−H、−CHO、−OHおよびCOOR3を含む群から選択され、
R2およびR3は、それぞれ互いに独立して、H、メチル、エチルおよびプロピルを含む群から選択されるが、但し、前記基R2およびR3の少なくとも1つは、Hであり、その際、Aは、少なくとも4個の炭素原子を有する非分枝鎖状の、分枝鎖状の、直鎖状の、環状の、置換もしくは非置換の炭化水素基を表す]の脂肪酸、ω−ヒドロキシ脂肪酸、ω−オキソ脂肪酸またはそれらのモノエステルを含む反応混合物。
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CN (1) | CN103881933B (ja) |
AR (1) | AR094464A1 (ja) |
BR (1) | BR102013033208A2 (ja) |
ES (1) | ES2640712T3 (ja) |
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2012
- 2012-12-21 EP EP12199024.6A patent/EP2746397A1/de not_active Withdrawn
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2013
- 2013-11-26 EP EP13194396.1A patent/EP2746399B1/de active Active
- 2013-11-26 ES ES13194396.1T patent/ES2640712T3/es active Active
- 2013-11-26 HU HUE13194396A patent/HUE034426T2/en unknown
- 2013-12-11 SG SG10201605082RA patent/SG10201605082RA/en unknown
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- 2013-12-23 BR BR102013033208A patent/BR102013033208A2/pt not_active Application Discontinuation
- 2013-12-24 JP JP2013265665A patent/JP6332961B2/ja active Active
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SG10201605082RA (en) | 2016-08-30 |
CN103881933B (zh) | 2019-04-09 |
US9719117B2 (en) | 2017-08-01 |
BR102013033208A2 (pt) | 2015-09-22 |
AR094464A1 (es) | 2015-08-05 |
HUE034426T2 (en) | 2018-02-28 |
EP2746399A1 (de) | 2014-06-25 |
US20140178948A1 (en) | 2014-06-26 |
EP2746397A1 (de) | 2014-06-25 |
JP2014121325A (ja) | 2014-07-03 |
KR20140090935A (ko) | 2014-07-18 |
MX349714B (es) | 2017-08-09 |
ES2640712T3 (es) | 2017-11-06 |
SG2013092010A (en) | 2014-07-30 |
KR102252150B1 (ko) | 2021-05-17 |
EP2746399B1 (de) | 2017-07-19 |
CN103881933A (zh) | 2014-06-25 |
MX2013014727A (es) | 2014-06-23 |
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