JPWO2015019939A1 - 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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- JPWO2015019939A1 JPWO2015019939A1 JP2015530848A JP2015530848A JPWO2015019939A1 JP WO2015019939 A1 JPWO2015019939 A1 JP WO2015019939A1 JP 2015530848 A JP2015530848 A JP 2015530848A JP 2015530848 A JP2015530848 A JP 2015530848A JP WO2015019939 A1 JPWO2015019939 A1 JP WO2015019939A1
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- phosphorylase
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- 150000008494 α-glucosides Chemical class 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 89
- 108090000790 Enzymes Proteins 0.000 claims abstract description 45
- 102000004190 Enzymes Human genes 0.000 claims abstract description 42
- 239000002994 raw material Substances 0.000 claims abstract description 38
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 37
- 108090001003 Beta-phosphoglucomutases Proteins 0.000 claims abstract description 23
- 108010009450 Phosphoglucomutase Proteins 0.000 claims abstract description 19
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- 235000014633 carbohydrates Nutrition 0.000 claims abstract description 14
- 229950010772 glucose-1-phosphate Drugs 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 9
- 230000002441 reversible effect Effects 0.000 claims abstract description 8
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 4
- 239000010452 phosphate Substances 0.000 claims abstract description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 3
- 229920002472 Starch Polymers 0.000 claims description 52
- 235000019698 starch Nutrition 0.000 claims description 52
- 239000008107 starch Substances 0.000 claims description 52
- 108010073135 Phosphorylases Proteins 0.000 claims description 37
- 102000009097 Phosphorylases Human genes 0.000 claims description 37
- 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
- 239000008103 glucose Substances 0.000 claims description 20
- 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 16
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 15
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- 238000000034 method Methods 0.000 claims description 14
- 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 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
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- 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
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- 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
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- 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
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- 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
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- 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 43
- 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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- 238000002360 preparation method Methods 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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- 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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Abstract
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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