JP6771458B2 - ムコン酸異性体およびその誘導体からのポリマー - Google Patents
ムコン酸異性体およびその誘導体からのポリマー Download PDFInfo
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Description
本願は、2014年10月28日出願の米国仮出願第62/069,613号に基づく優先権を主張する。
本発明は、特殊および汎用ムコン酸ポリマーを生成する分野である。より具体的には、本発明は、ホモポリマー、縮合ポリマー、開環ポリマーおよびコポリマーへのムコン酸異性体およびその誘導体の変換に関する。
ペトロ-ムコン酸の合成
バイオ-ムコン酸の合成
ムコン酸を生成するように徐々に改変したエシェリヒア・コリ(Escherichia coli)株を、小規模(200ml)微好気性発酵槽において37℃にて、10μg/Lビオチン、1mg/Lナイアシンおよび1mg/Lチアミン塩酸塩を添加した100g/Lグルコースを含む所定の培地を用いて増殖させた。培養フラスコを270RPMで回転振とう機で浸透した。pHを7.0に設定し、必要に応じて2M NH4OHの添加により制御した。15g/lムコン酸が192時間で生成された。発酵ブロスを遠心分離して、細胞集団を除去した。300ミクロンろ紙でプレろ過を用いて、遠心分離後に残った固体を除去した。10KD限外ろ過を行って、タンパク質およびペプチド等のマクロ分子を除去した。色体および色前駆体NF245をナノろ過によりを除去した。5%活性炭での木炭処理がほとんどの残った色を除去して、澄明溶液を得た。ろ過により木炭を除去した後、澄明溶液を氷浴で10℃に冷却し、硫酸で酸性化して、白色のムコン酸の水中懸濁液を得た。ろ過および乾燥は、純粋なムコン酸を無色粉末として産出した。
ジメチルムコネートの合成
塩化ムコニルの合成
ムコン酸ホモポリマーの合成
ムコン酸架橋ポリマーの合成
ムコン酸コポリマーの合成
ムコン酸ラクトンの合成
ムコン酸ラクトン重合
ムコン酸ポリエステル
ムコン酸ポリエステルコポリマー
ムコン酸ポリアミド
ムコン酸ポリアミドコポリマー
ヘキサ-3-エン二酸エステルの合成
2,5ジメチレン-3-エン二酸エステルの合成
2,5ジメチレン-3-エン二酸エステル環化
ジヒドロテレフタル酸の酸化
水素化反応
3,4-ジスルホヘキサン二酸の合成
2,3,4,5テトラブロモヘキサン二酸の合成
[1]
式(i)
--[RO 2 C-C-C=C-C-CO 2 R]-- (i)
で示される繰返し単位を含み、式中、Rの各々が水素、アルキル、アリール、アルキル芳香族または芳香族アルキルである、ポリマー。
[2]
式(i)で示される繰返し単位が、電気化学反応により式(ii)
RO 2 C-C=C-C=C-CO 2 R (ii)
で示される単量体単位からもたらされ、式(ii)で示される単量体単位中のRの各々が水素、アルキル、アリール、アルキル芳香族または芳香族アルキルである、[1]に記載のポリマー。
[3]
繰返し単位がヘキサ-3-エン二酸である、[1]に記載のポリマー。
[4]
繰返し単位がヘキサ-3-エン二酸エステルである、[1]に記載のポリマー。
[5]
式RO 2 C-C=C-C=C-CO 2 Rで示される単量体単位がEZ異性体、EE異性体、ZZ異性体およびZE異性体からなる群より選択される、[3]に記載のポリマー。
[6]
式RO 2 C-C=C-C=C-CO 2 Rで示される単量体単位がバイオマス由来の原料から得られる、[3]に記載のポリマー。
[7]
式RO 2 C-C=C-C=C-CO 2 Rで示される単量体単位が石油化学由来の原料から得られる、[3]に記載のポリマー。
[8]
ブタジエン、イソプレン、メタクリル酸、スチレン、エチレン、プロピレン、アクリル酸またはアクリロニトリルからなる群より選択される少なくとも1のモノマーをさらに含む、[1]に記載のポリマー。
[9]
式(i)
で示される繰返し単位を含み、式中、Rの各々が水素、アルキル、アリール、アルキル芳香族または芳香族アルキルである、ポリマー。
[10]
式(i)で示される繰返し単位がアルデヒドまたはケトンとの縮合反応により式RO 2 C-C-C=C-C-CO 2 Rで示される単量体単位からもたらされ、式RO 2 C-C-C=C-C-CO 2 Rで示される単量体単位中のRの各々が水素、アルキル、アリール、アルキル芳香族または芳香族アルキルである、[9]に記載のポリマー。
[11]
繰返し単位が2,5ジメチレン-3-エン二酸である、[9]に記載のポリマー。
[12]
繰返し単位が2,5ジメチレン-3-エン二酸エステルである、[9]に記載のポリマー。
[13]
式RO 2 C-C-C=C-C-CO 2 Rで示される単量体単位がEZ異性体、EE異性体、ZZ異性体およびZE異性体からなる群より選択される、[10]に記載のポリマー。
[14]
式RO 2 C-C-C=C-C-CO 2 Rで示される単量体単位がバイオマス由来の原料から得られる、[10]に記載のポリマー。
[15]
式RO 2 C-C-C=C-C-CO 2 Rで示される単量体単位が石油化学由来の原料から得られる、[3]に記載のポリマー。
[16]
ブタジエン、イソプレン、メタクリル酸、スチレン、エチレン、プロピレン、アクリル酸またはアクリロニトリルからなる群より選択される少なくとも1のモノマーをさらに含む、[9]に記載のポリマー。
[17]
式(i)で示される分子が式(ii)で示される分子の酸化に由来し、式(ii)で示される分子が式(iii)で示される分子の環化に由来し、式(iii)で示される分子がホルムアルデヒドの式(iv)で示される分子との縮合に由来し、式中、Rの各々が水素、アルキル、アリール、アルキル芳香族または芳香族アルキルである、式(i)で示される分子。
式(i)で示される分子がテレフタル酸である、[17]に記載の式(i)で示される分子。
[19]
テレフタル酸がバイオマス由来の原料から得られる、[18]に記載のテレフタル酸。
[20]
テレフタル酸が石油化学由来の原料から得られる、[18]に記載のテレフタル酸。
[21]
式(i)で示される分子が式(ii)で示される分子の水素化に由来し、該式で示される分子が式(iii)で示される分子の環化に由来し、式(iii)で示される分子がホルムアルデヒドの式(iv)で示される分子との縮合に由来し、式中、Rの各々が水素、アルキル、アリール、アルキル芳香族または芳香族アルキルである、式(i)で示される分子。
分子がシクロヘキサンジカルボン酸エステルである、[21]に記載の式(A)で示される分子。
[23]
分子がシクロヘキサンジカルボン酸である、[21]に記載の式(A)で示される分子。
[24]
シクロヘキサンジカルボン酸がバイオマス由来の原料から得られる、[22]に記載のシクロヘキサンジカルボン酸。
[25]
シクロヘキサンジカルボン酸が石油化学由来の原料から得られる、[22]に記載のシクロヘキサンジカルボン酸。
[26]
[22]に記載のシクロヘキサンジカルボン酸を水素化してシクロヘキサンジメタノールを得る工程を含む、シクロヘキサンジメタノールの製造方法。
[27]
[18]に記載のテレフタル酸を水素化してシクロヘキサンジメタノールを得る工程を含む、シクロヘキサンジメタノールの製造方法。
[28]
式(i)
で示される繰返し単位を含み、式中、Rの各々が水素、アルキル、アリール、アルキル芳香族または芳香族アルキルである、ポリマー。
[29]
繰返し単位がEZ異性体、EE異性体、ZZ異性体およびZE異性体からなる群より選択される、[28]に記載のポリマー。
[30]
繰返し単位が3,4-ジスルホヘキサン二酸または3,4-ジスルホヘキサン二酸の誘導体である、[28]に記載のポリマー。
[31]
3,4-ジスルホヘキサン二酸の誘導体が3,4-ジスルホヘキサン二酸の脂肪族エステル、3,4-ジスルホヘキサン二酸の芳香族エステル、3,4-ジスルホヘキサン二酸のアルキル芳香族エステル、および3,4-ジスルホヘキサン二酸の芳香族アルキルエステルからなる群より選択される、[22]に記載のポリマー。
[32]
式(i)
で示される繰返し単位を含み、式中、Rの各々が水素、アルキル、アリール、アルキル芳香族または芳香族アルキルであり、Xが塩素、臭素、フッ素およびヨウ素からなる群より選択されハロゲンである、ポリマー。
[33]
式(i)で示される繰返し単位がEZ異性体、EE異性体、ZZ異性体およびZE異性体からなる群より選択される、[32]に記載のポリマー。
[34]
繰返し単位が2,3,4,5-テトラハロヘキサン二酸または2,3,4,5-テトラハロヘキサン二酸の誘導体である、[25]に記載のポリマー。
[35]
2,3,4,5-テトラハロヘキサン二酸の誘導体が2,3,4,5-テトラハロヘキサン二酸の脂肪族エステル、2,3,4,5-テトラハロヘキサン二酸の芳香族エステル、2,3,4,5-テトラハロヘキサン二酸のアルキル芳香族エステル、および2,3,4,5-テトラハロヘキサン二酸の芳香族アルキルエステルからなる群より選択される、[34]に記載のポリマー。
[36]
(a)cis-cisムコン酸をラクトン化してムコノビス-ラクトンを生成する工程;および
(b)ムコノビス-ラクトンを重合触媒と接触させて重合反応を開始する工程
を含む、ムコン酸ポリマーの合成方法。
[37]
重合反応触媒がアニオン開始剤またはカチオン開始剤である、[36]に記載のムコン酸ポリマーの合成方法。
[38]
重合反応が開環重合である、[36]に記載のムコン酸ポリマーの合成方法。
(参考文献)
すべての参考文献を読む者の便宜のために記載する。各参考文献は、出典明示によりその全体として本明細書の一部とする。
米国特許第3,429,949号
米国特許第3,497,479号
米国特許第3,562,209号
米国特許第3,615,434号
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米国特許第4,401,795号
米国特許第4,461,887号
米国特許第4,480,034号
米国特許第4,535,059号
米国特許第4,588,688号
米国特許第4,608,338号
米国特許第4,661,588号
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米国特許第5,487,987号
米国特許第5,616,496号
米国特許第6,600,077号
米国特許第6,180,373号
米国特許第6,210,937号
米国特許第6,472,169号
米国特許第6,613,552号
米国特許第6,962,794号
米国特許第7,244,593号
米国特許第7,388,064号
米国特許第7,638,312号
米国特許第7,790,431号
米国特許第7,880,030号
米国特許第8,367,858号
米国特許第8,367,859号
米国特許第8,415,496号
米国特許第8,426,639号
米国特許第8,742,060号
米国特許第8,809,583号
米国特許第8,829,237号
米国特許第8,895,779号
米国特許第8.946,472号
米国特許出願公開第2009/0191610号
米国特許出願公開第2010/0314243号A
米国特許出願公開第2011/0288263号A1
米国特許出願公開第2013/0085255号A1
米国特許出願公開第2013/0085747号A1
米国特許出願公開第2014/0171614号A1
米国特許出願公開第2015/0225329号A1
米国特許出願公開第2014/0171614号A1
米国特許出願公開第2014/0228595号A1
米国特許出願公開第20140302573号A1
米国特許出願公開第2015/0203880号
欧州特許出願第86300748.0号
国際公開第90/10654号
国際公開第2011/017560号
国際公開第2011/085311号
国際公開第2011/123154号
国際公開第2013/085747号
国際公開第2013/109865号
国際公開第2013/116244号
国際公開第2014/047407号
国際公開第2014/102280号
国際公開第2015/069847号
国際公開第2015/086827号
Averesch, N. J. H. and Kromer, J. O. (2014) Tailoring strain construction strategies for muconic acid production in S. cerevisiae and E. coli. Metabol. Engineer. Comm. 1, 19-28.
Chiba, T., Okimoto, M., Nagai, H. and Takata, Y. (1983) Electrocatalytic reduction using raney nickel. Bull. Chem. Soc. Jpn. 56, 719-723.
Choi, W. J., Lee, E. Y., Cho, M. H., and Choi, C. Y. (1997) Enhanced production of cis, cis-muconate in a cell-recycle bioreactor. J. Fermentation and Bioengineering. 84, 70-76.
Curran, K. A., Leavitt, J. M., Karim, A. S. and Alper, H. S. (2012) Metabolic engineering of muconic acid production in Saccharomyces cerevisiae. Metabol. Engineer. 15, 55-66.
Kaneko, A., Ishii, Y., and Kirimura, K. (2011) High-yield production of cis, cis-muconic acid from catechol in aqueous solution by biocatalyst. Chem. Lett. 40, 381-383.
Matsumoto, A. (2003) Polymer structure control based on crystal engineering for materials design. Polymer J. 35, 93-121.
Matsumoto, A., Fujioka, D. and Kunisue, T. (2003) Organic intercalation of unsaturated amiines into layeres polymer crystals and solid-state photoreactivity of the guest molecules in constrained interlayers. Polymer J. 35, 652-661.
Mizuno, S., Yoshikawa, N., Seki, M., Mikawa, T., and Imada, Y. (1988) Microbial production of cis, cis- muconic acid from benzoic acid. Appl Microbiol Biotechnol. 28, 20-25.
Niu, W., Draths, K. M., and Frost, J. W. (2002) Benzene-free synthesis of adipic acid, Biotechnol Prog 18, 201-211.
Odani, T. and Matsumoto, A. (2002) Solvent-free synthesis of layered polymer crystals. Polymer J. 34, 841-846.
Perez-Pantoja, D., De la Iglesia, R., Pieper, D. H., and Gonzalez, B. (2008) Metabolic reconstruction of aromatic compounds degradation from the genome of the amazing pollutant-degrading bacterium Cupriavidus necator JMP134, FEMS Microbiol Rev 32, 736-794.
Perez-Pantoja, D., Donoso, R., Agullo, L., Cordova, M., Seeger, M., Pieper, D. H., and Gonzalez, B. (2011) Genomic analysis of the potential for aromatic compounds biodegradation in Burkholderiales, Environ Microbiol.
Sun, X., Lin, Y., Huang, Q., Yuan, Q. and Yan, Y. (2013) A novel muconic acid biosynthesis approach by shunting tryptophan biosynthesis via anthranilate. App. Environ. Micorbiol. 79, 4024-4030.
Weber, C., Bruckner, C., Weinreb, S., Lehr, C., Essl, C. and Bole, E. (2012) Biosynthesis of cis, cis-muconic acid and its aromatic precursors catechol and proteocatechuic acid, from renewable feedstocks by Saccharomyces cerevisiae, App Environ Microbiol. 78, 8421-8430.
Xie, N-Z., Lilang, H., Huang, R-B. and Xu, P. (2014) Biotechnological produciton of muconic acid: current status and future prospepcts. Biotech. Adv. 32, 615-622.
Yoshikawa, N., Mizuno, S., Ohta, K., and Suzuki, M. (1990) Microbial production of cis, cis-muconic acid. J. Biotechnol. 14, 203-210.
Zhang, H., Li, Z., Pereira, B. and Stephanopoulos (2015) Engineering E. coli-E.coli cocultures for producitn of muconic acid from glycerol. Microb. Cell Fact. 14, 134- 143.
Zhang, H., Pereira, B., Li, Z. and Stephanopoulos (2015) Engineering Excherichia coli coculture system for the production of biochemical products. Proc. Natl. Acad. Sci. USA 112, 8266-8271.
Claims (10)
- 式(i)
--[O2C-C-C=C-C-CO2]-- (i)
で示される繰返し単位を含み、式(i)で示される繰返し単位が、電気化学反応により式(ii)
RO2C-C=C-C=C-CO2R (ii)
で示される単量体単位からもたらされ、式(ii)で示される単量体単位中のRの各々が水素またはアルキルもしくはアリール基であり、式(ii)で示される単量体単位が、微生物発酵プロセスを用いる炭素源として再生可能な生物学的材料に由来する、ポリマー。 - 式(i)で示される繰返し単位が、式(ii)で示される単量体単位からヘキサ-3-エン二酸を経てもたらされる、請求項1に記載のポリマー。
- 式(i)で示される繰返し単位が、式(ii)で示される単量体単位からヘキサ-3-エン二酸エステルを経てもたらされる、請求項1に記載のポリマー。
- 式(ii)で示される単量体単位が、EZ異性体、EE異性体、ZZ異性体およびZE異性体からなる群より選択される、請求項1〜3のいずれかに記載のポリマー。
- ブタジエン、イソプレン、メタクリル酸、スチレン、エチレン、プロピレン、アクリル酸またはアクリロニトリルからなる群より選択される少なくとも1の単量体単位をさらに含む、請求項1〜4のいずれかに記載のポリマー。
- 式(iii)で示される単量体単位が、2,5ジメチレン-3-エン二酸である、請求項6に記載のポリマー。
- 式(iii)で示される単量体単位が、2,5ジメチレン-3-エン二酸エステルである、請求項6に記載のポリマー。
- 式(ii)で示される単量体単位が、EZ異性体、EE異性体、ZZ異性体およびZE異性体からなる群より選択される、請求項6〜8のいずれかに記載のポリマー。
- ブタジエン、イソプレン、メタクリル酸、スチレン、エチレン、プロピレン、アクリル酸またはアクリロニトリルからなる群より選択される少なくとも1の単量体単位をさらに含む、請求項6〜9のいずれかに記載のポリマー。
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