JP6501306B2 - α−グルコシドの製造方法 - Google Patents
α−グルコシドの製造方法 Download PDFInfo
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- JP6501306B2 JP6501306B2 JP2015530848A JP2015530848A JP6501306B2 JP 6501306 B2 JP6501306 B2 JP 6501306B2 JP 2015530848 A JP2015530848 A JP 2015530848A JP 2015530848 A JP2015530848 A JP 2015530848A JP 6501306 B2 JP6501306 B2 JP 6501306B2
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- 150000008494 α-glucosides Chemical class 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 85
- 229920002472 Starch Polymers 0.000 claims description 52
- 235000019698 starch Nutrition 0.000 claims description 52
- 239000008107 starch Substances 0.000 claims description 52
- 108090000790 Enzymes Proteins 0.000 claims description 44
- 102000004190 Enzymes Human genes 0.000 claims description 41
- 108010073135 Phosphorylases Proteins 0.000 claims description 37
- 102000009097 Phosphorylases Human genes 0.000 claims description 37
- 150000001720 carbohydrates Chemical class 0.000 claims description 26
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 22
- 235000014633 carbohydrates Nutrition 0.000 claims description 22
- 108090001003 Beta-phosphoglucomutases Proteins 0.000 claims description 21
- 239000008103 glucose Substances 0.000 claims description 21
- 239000002994 raw material Substances 0.000 claims description 19
- 108010009450 Phosphoglucomutase Proteins 0.000 claims description 18
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 17
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 15
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 14
- 108010048610 cellobiose phosphorylase Proteins 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- HXXFSFRBOHSIMQ-VFUOTHLCSA-N alpha-D-glucose 1-phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O HXXFSFRBOHSIMQ-VFUOTHLCSA-N 0.000 claims description 12
- HXXFSFRBOHSIMQ-DVKNGEFBSA-N beta-D-glucose 1-phosphate Chemical compound OC[C@H]1O[C@@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O HXXFSFRBOHSIMQ-DVKNGEFBSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 11
- 108010074725 Alpha,alpha-trehalose phosphorylase Proteins 0.000 claims description 11
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 11
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 11
- 229950010772 glucose-1-phosphate Drugs 0.000 claims description 11
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 9
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims description 9
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims description 8
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- 108010057899 Maltose phosphorylase Proteins 0.000 claims description 7
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- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 6
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- 108010037131 Laminaribiose phosphorylase Proteins 0.000 claims description 5
- FYGDTMLNYKFZSV-ZWSAEMDYSA-N cellotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-ZWSAEMDYSA-N 0.000 claims description 5
- 235000019425 dextrin Nutrition 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 4
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 3
- 108010077004 Cellodextrin phosphorylase Proteins 0.000 claims description 3
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims description 3
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 3
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 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 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 3
- 229960002442 glucosamine Drugs 0.000 claims description 3
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 108010046163 Glycogen Phosphorylase Proteins 0.000 claims description 2
- HIWPGCMGAMJNRG-ACCAVRKYSA-N Sophorose Natural products O([C@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HIWPGCMGAMJNRG-ACCAVRKYSA-N 0.000 claims description 2
- HIWPGCMGAMJNRG-UHFFFAOYSA-N beta-sophorose Natural products OC1C(O)C(CO)OC(O)C1OC1C(O)C(O)C(O)C(CO)O1 HIWPGCMGAMJNRG-UHFFFAOYSA-N 0.000 claims description 2
- 108010085781 maltodextrin phosphorylase Proteins 0.000 claims description 2
- PZDOWFGHCNHPQD-VNNZMYODSA-N sophorose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PZDOWFGHCNHPQD-VNNZMYODSA-N 0.000 claims description 2
- 125000000185 sucrose group Chemical group 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 56
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- RWHOZGRAXYWRNX-VFUOTHLCSA-N alpha-D-glucose 1,6-bisphosphate Chemical compound O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]1O RWHOZGRAXYWRNX-VFUOTHLCSA-N 0.000 description 15
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- 238000002523 gelfiltration Methods 0.000 description 14
- QIGJYVCQYDKYDW-NSYYTRPSSA-N nigerose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1O QIGJYVCQYDKYDW-NSYYTRPSSA-N 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 14
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- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 7
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
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- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/24—Preparation of compounds containing saccharide radicals produced by the action of an isomerase, e.g. fructose
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- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
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- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
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- Enzymes And Modification Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
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Description
(i)糖質原料、及び該糖質原料を可逆的に加リン酸分解しα−グルコース−1−リン酸を生じる酵素の組合せ;並びに
(ii)α−グルコシドを可逆的に加リン酸分解してβ−グルコース−1−リン酸を生じる酵素及びその逆反応において糖アクセプターとして作用する物質の組合せを作用させることを特徴とする、α−グルコシドの製造方法。
グルコース、10mM 塩化マグネシウム、75mM リン酸−ナトリウム緩衝液(pH7.0)、59μM グルコース−1,6−ビスリン酸からなる基質溶液を調製し、そこにホスホリラーゼ、ニゲロースホスホリラーゼ、α−ホスホグルコムターゼ、β−ホスホグルコムターゼ、イソアミラーゼを1ミリリットル当たり0.96mg、0.02mg、0.0085mg、0.21mg、0.33μg加え、30℃で216時間反応を行った。反応を0.15mLの6N 塩酸を添加することで反応を停止し、反応液のpHを7.0に調整後、グルコアミラーゼ処理を行うことにより残存デンプンを分解した。反応液をTOYOPEARL HW−40Sカラムに供し、ゲル濾過によりニゲロース画分を単離、回収した。回収した画分をエバポレーターで濃縮し、凍結乾燥によりニゲロース標品27mgを得た。(図1)
Claims (3)
- リン酸、α−ホスホグルコムターゼ(EC 5.4.2.2)、β−ホスホグルコムターゼ(EC 5.4.2.6)及びそれらの補因子の存在下で、
(i)糖質原料、及び該糖質原料を可逆的に加リン酸分解しα−グルコース−1−リン酸を生じる酵素の組合せ;並びに
(ii)α−グルコシドを可逆的に加リン酸分解してβ−グルコース−1−リン酸を生じる酵素及びその逆反応において糖アクセプターとして作用する物質の組合せを作用させることを特徴とする、α−グルコシドの製造方法。 - (i)の糖質原料、及び該糖質原料を可逆的に加リン酸分解しα−グルコース−1−リン酸を生じる酵素の組合せが、スクロースとスクロースホスホリラーゼ(EC 2.4.1.7)との組合せ、デンプン若しくはデキストリンとホスホリラーゼ(EC 2.4.1.1)との組合せ、セロビオースとセロビオースホスホリラーゼ(EC 2.4.1.20)との組合せ、セロデキストリンとセロデキストリンホスホリラーゼ(EC 2.4.1.49)及びセロビオースホスホリラーゼ(EC 2.4.1.20)との組合せ、ラミナリオリゴ糖とラミナリビオースホスホリラーゼ(EC 2.4.1.31)及び/若しくはβ−1,3オリゴグルカンホスホリラーゼ(EC 2.4.1.30)との組合せ、ソホロオリゴ糖とソホロースホスホリラーゼ及び/若しくはβ−1,2オリゴグルカンホスホリラーゼとの組合せ、並びにトレハロースとトレハロースホスホリラーゼ(EC 2.4.1.231)との組合せ、よりなる群から選択される1つ以上の組合せである、請求項1に記載の方法。
- (ii)のα−グルコシドを可逆的に加リン酸分解してβ−グルコース−1−リン酸を生じる酵素及びその逆反応において糖アクセプターとして作用する物質の組合せが、ニゲロースホスホリラーゼとグルコース及び/若しくはガラクトース及び/若しくはキシロースとの組合せ、コージビオースホスホリラーゼとグルコースとの組合せ、トレハロースホスホリラーゼとグルコース及び/若しくはガラクトース及び/若しくはキシロース及び/若しくはアラビノース及び/若しくはフコースとの組合せ、グルコシル−α−1,2−グリセロールホスホリラーゼとグリセロールとの組合せ、マルトースホスホリラーゼとグルコース及び/若しくはマンノース及び/若しくはキシロース及び/若しくはフコース及び/若しくはグルコサミン及び/若しくはN−アセチルグルコサミンとの組合せ、よりなる群から選択される1つ以上の組合せである、請求項1に記載の方法。
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