JP2016501016A - 糖誘導体を得るためのプロセス - Google Patents
糖誘導体を得るためのプロセス Download PDFInfo
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- JP2016501016A JP2016501016A JP2015542228A JP2015542228A JP2016501016A JP 2016501016 A JP2016501016 A JP 2016501016A JP 2015542228 A JP2015542228 A JP 2015542228A JP 2015542228 A JP2015542228 A JP 2015542228A JP 2016501016 A JP2016501016 A JP 2016501016A
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- JP
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- Prior art keywords
- acid
- sugar
- process according
- arabinose
- xylose
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims abstract description 23
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- 238000006731 degradation reaction Methods 0.000 claims abstract description 5
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- 239000002253 acid Substances 0.000 claims description 44
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 28
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- 239000007983 Tris buffer Substances 0.000 description 1
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- 244000177175 Typha elephantina Species 0.000 description 1
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- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
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- 230000002210 biocatalytic effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
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- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
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- 239000010903 husk Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
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- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- JCQLYHFGKNRPGE-FCVZTGTOSA-N lactulose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 JCQLYHFGKNRPGE-FCVZTGTOSA-N 0.000 description 1
- 229960000511 lactulose Drugs 0.000 description 1
- PFCRQPBOOFTZGQ-UHFFFAOYSA-N lactulose keto form Natural products OCC(=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O PFCRQPBOOFTZGQ-UHFFFAOYSA-N 0.000 description 1
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- 150000002891 organic anions Chemical class 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
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- 230000004260 plant-type cell wall biogenesis Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
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Abstract
Description
キシランの加水分解は、糖重合体を糖オリゴマーまたは糖モノマーに切断するのに役立つ。その点で、それぞれの目的が差別化されてもよい。一部の用途では、セルロースおよびキシロースの両方の糖重合体をモノマーに切断することが適当である。特に、これには、バイオマスから発酵性糖を生成する場合が当てはまる。一方、他の用途では、セルロースは重合体として維持されるべきであるが、キシランは、オリゴマーまたはモノマーに切断されるべきである。キシランの加水分解は、化学的または酵素的に行うことができる。さらに、キシランの加水分解は、リグノセルロース系材料の分離と同時に行われてもよく、または別個の工程で行われてもよい。
(A)リグノスルホン酸もしくはその塩;アルドヘキソン酸もしくはその塩;ヘキスロン酸もしくはその塩、ヘキサル酸もしくはその塩;またはそれらの混合物;および
(B)少なくとも1つのアルドペントン酸またはその塩、
を含む組成物について記載されている。
アラビノース、特にL−アラビノース、
キシロース、特にD−キシロースまたは
アラビノース、特にL−アラビノースと、キシロース、特にD−キシロースとの混合物
のいずれかを構成することを特徴とする本発明によるプロセスを提供する。
キシランをpH4.3で濃度が8%(w/v)の酢酸塩緩衝液に懸濁し、Genencor companyのACCELLERASE(登録商標)TRIO(商標)とキシラン1gあたり酵素溶液1gの濃度で混合する。このバッチを50℃で24時間撹拌する。pH値を確認し、4.5超または4.1未満にずれた場合は再調整する。このバッチをブフナー漏斗によりろ過し、ろ液(加水分解産物)を、モノマーの組成およびそれらの濃度に関してHPLC−LEX−DADにより分析する。このろ液には、濃度が約6%のキシロース、0.43%のアラビノースおよび0.27%のグルコースが含まれる。この方法では、キシランにおいて得られるキシロースの約85%がモノマーの形態で得られる。
実施例1によるキシランの加水分解のろ液500μlを遠心分離し、その後、上清を0.2μMのPVDF(ポリ−ビニリデン−ジフルオリド)フィルターに通し、HPLC−LEX−RID(Agilent Technologies Inc.)によって分析する。それにより、80℃で流速が0.5ml/分の水(VWR:HPLC Grade)を用いてShodex Denko K.K.の鉛カラム(Shodex(登録商標)Sugar SP0810)により糖が分離される。Agilent RIDによって検出を行う。Agilent Technologies Inc.のインライン式フィルターならびにプレカラムとして、Showa Denko K.K.によって供給された逆相カラム(Axpak−WA−G)、陰イオン交換カラム(Shodex(登録商標)Asahipak(登録商標)ODP−50 6E)および糖プレカラム(Shodex(登録商標)SP−G)を使用する。
バッチ0.5mlには、50mg/mlのアラビノース、5U/mlのBurkholderia vietnamiensis由来の組換え型アラビノースデヒドロゲナーゼおよび0.5mMのNADP+と0.5mMのNADPHの混合物を含める。補酵素の再生のために、2.5%(w/v)のアセトンおよび5U/mlのLactobacillus kefir由来の組換え型アルコールデヒドロゲナーゼを添加する。細胞ライセートの形態の酵素を使用する。反応は、40℃、pH10で24時間、連続的に振盪(900rpm)しながら行う。24h後、酵素を不活性化するために反応容器を60℃で10分間インキュベートする。その後、2MのNaOHを5μl添加する。
バッチ0.5mlには、50mg/mlのアラビノース、5U/mlのBurkholderia vietnamiensis由来の組換え型アラビノースデヒドロゲナーゼならびに0.5mMのNADP+および0.5mMのNADPHの混合物を含める。補酵素の再生のために、2.5%(v/v)のアセトンおよび5U/mlのLactobacillus kefir由来の組換え型アルコールデヒドロゲナーゼを添加する。細胞ライセートの形態の酵素を使用する。反応は、40℃およびpH10で24時間、連続的に振盪(900rpm)しながら行う。24h後、酵素を不活性化するために反応容器を60℃で10分間インキュベートする。冷却後、大腸菌(E.coli)細胞ライセート50μlをAzospirillum brasiliense由来の過剰発現させたL−アラビノラクトナーゼとともに添加し、反応を40℃(900rpm)で、さらに24時間振盪する。その後、酵素を不活性化するために反応容器を60℃で10分間インキュベートする。
GC−MSによる酸化反応の分析のために、基質および生成物を誘導体化しなければならない。バッチを遠心分離し、0.2μMのPVDFフィルターを通過させ、1:30に希釈する。20μlの希釈液を0.5mlのバイアルに移し、Speedvac内で乾燥させる。誘導体化のために、その後、ピリジンを150μlおよびN,O−ビス(トリメチルシリル)−トリフルオロアセトアミドとトリメチルクロロシランの99:1混合物を50μl添加する。内部標準として、ピリジン中に0.1mg/mlの濃度でソルビトールを含ませる。60℃で16時間誘導体化を行う。その後、GC−MSによりサンプルを分析する。その際、ガスクロマトグラフの分離カラムHP−5ms(5%−フェニル)−メチルポリシロキサンによりサンプルを分離し、Shimadzuの質量分析計GCMS QP210 Plusを用いて分析する。
D−キシロース180mgおよびL−アラビノース20mgを、2UのBurkholderia vietnamiensis由来のL−アラビノースデヒドロゲナーゼおよび2UのCandida parapsilosis由来のD−キシロースレダクターゼとともに50mMのTris緩衝水溶液(pH=7.0、25℃)に溶解させて総量を500μlにした。反応を密閉反応容器中、40℃で撹拌下(900rpm、Eppendorf Thermomix(登録商標))において行った。30分後、65℃で15分間インキュベーションすることによって酵素を不活性化し、遠心分離(21000g、5分)によって変性タンパク質を分離し、GC−MSによって糖を定量した。使用したL−アラビノースを完全に変換した。そのうちの92%は、L−アラボネートまたはL−アラビノ−γ−ラクトンになり、残りの8%は、L−アラビトールになった。使用したD−キシロースのうち約89.5%が残ったが、10.4%がキシリトールに変換された。使用したD−キシロースのうち0.1%未満がD−キシロネート/D−キシロノ−γ−ラクトンに酸化された。
Claims (13)
- ヘミセルロース含有材料由来の糖、特にバイオマスから得られた糖を、少なくとも1つのイオン結合部位を有する化合物の形態に変換するためのプロセスであって、ヘミセルロース含有材料は、酵素的または非酵素的に加水分解され、得られた加水分解産物は、少なくとも1つの酵素的工程を含む変換に供され、ここで、糖が遊離され、遊離された糖は、少なくとも1つのイオン結合部位を有する化合物に変換されることを特徴とする、プロセス。
- 少なくとも1つのイオン結合部位を有する化合物に変換される遊離された糖は、
アラビノース、特にL−アラビノース、
キシロース、特にD−キシロースまたは
アラビノース、特にL−アラビノースと、キシロース、特にD−キシロースとの混合物
のいずれかを構成することを特徴とする、請求項1に記載のプロセス。 - 遊離された糖、特にC5糖は、オキシドレダクターゼによってラクトン、特にγ−ラクトンに変換され、これが、特に、酵素的、非酵素的および/または自発的加水分解によって、対応するカルボン酸に加水分解されることを特徴とする、請求項1または2に記載のプロセス。
- 得られたカルボン酸は、特にデヒドラターゼによって、ケトカルボン酸に脱水されることを特徴とする、請求項3に記載のプロセス。
- 得られたケトカルボン酸は、特にデヒドラターゼによって、さらにケトカルボン酸セミアルデヒドに脱水されることを特徴とする、請求項4に記載のプロセス。
- 得られたケトカルボン酸セミアルデヒドは、特にオキシドレダクターゼによって、ジカルボン酸に酸化されることを特徴とする、請求項5に記載のプロセス。
- 請求項1または2に記載の糖はアラビノースであり、
請求項3に記載のラクトンはアラビノ−γ−ラクトンであり、
請求項3および4に記載のカルボン酸はアラボン酸であり、
請求項4および5に記載のケトカルボン酸は2−ケト−3−デオキシアラボン酸であり、
請求項5および6に記載のケトカルボン酸セミアルデヒドはα−ケトグルタル酸セミアルデヒドであり、
請求項6に記載のジカルボン酸はα−ケトグルタル酸であることを特徴とする、請求項1から6のいずれかに記載のプロセス。 - 1つまたはいくつかのオキシドレダクターゼによって還元された酸化還元補酵素NADHおよび/またはNADPHは、同じ反応バッチにおいて、少なくとも1つの別のオキシドレダクターゼ活性、特に、アルコールデヒドロゲナーゼ、キシロースレダクターゼ、ラクタートデヒドロゲナーゼ、オキシダーゼまたは電極に固定された1つもしくはいくつかの酸化還元酵素によって、酸化された形態のNAD+および/またはNADP+に変換されることを特徴とする、請求項2から7のいずれかに記載のプロセス。
- 得られたイオン結合部位を有する化合物は、特にイオン交換クロマトグラフィーおよび/または電気透析によって、反応混合物から分離されることを特徴とする、請求項1から8のいずれかに記載のプロセス。
- ヘミセルロース含有材料は、リグノセルロース系材料から得られたものであることを特徴とする、請求項1から9のいずれかに記載のプロセス。
- ヘミセルロース含有材料は、好ましくは50から100℃の温度で、リグノセルロース系材料をアルカリ性アルコール水溶液を用いて処理することによって得られたものであることを特徴とする、請求項10に記載のプロセス。
- リグノセルロース含有材料は、リグノセルロース含有バイオマス、特に、一年生植物、ワラ、エネルギーグラス、サイザル麻、バガス、または殻などの特殊なリグノセルロース基質、特にワラまたはバガスに由来することを特徴とする、請求項10または11のいずれかに記載のプロセス。
- リグノセルロース含有材料からアラビノース、キシロース、特に、アラビノース、アラビノ−γ−ラクトン、アラボン酸、2−ケト−3−デオキシアラボン酸、α−ケトグルタル酸セミアルデヒドおよび/またはα−ケトグルタル酸を得るための、請求項1から12のいずれかに記載のプロセスの使用。
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