NL194441C - Werkwijze voor isomerisatie van een aldose in een ketose. - Google Patents
Werkwijze voor isomerisatie van een aldose in een ketose. Download PDFInfo
- Publication number
- NL194441C NL194441C NL9320024A NL9320024A NL194441C NL 194441 C NL194441 C NL 194441C NL 9320024 A NL9320024 A NL 9320024A NL 9320024 A NL9320024 A NL 9320024A NL 194441 C NL194441 C NL 194441C
- Authority
- NL
- Netherlands
- Prior art keywords
- compound
- isomerization
- organogermanium
- glucose
- fructose
- Prior art date
Links
- 238000006317 isomerization reaction Methods 0.000 title claims description 66
- 238000000034 method Methods 0.000 title claims description 19
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 title claims description 9
- 150000002584 ketoses Chemical class 0.000 title claims description 9
- 208000007976 Ketosis Diseases 0.000 title description 5
- -1 organogermanium compound Chemical class 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 38
- 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 37
- 239000008103 glucose Substances 0.000 claims description 35
- 239000005715 Fructose Substances 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 229930091371 Fructose Natural products 0.000 claims description 25
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 108090000790 Enzymes Proteins 0.000 claims description 15
- 102000004190 Enzymes Human genes 0.000 claims description 15
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 11
- 125000000082 organogermanium group Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 8
- 150000002291 germanium compounds Chemical class 0.000 claims description 6
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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 claims description 4
- 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 claims description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 4
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- 238000004128 high performance liquid chromatography Methods 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
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- 230000015572 biosynthetic process Effects 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- 150000003839 salts Chemical group 0.000 description 2
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- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 description 1
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- ZAQJHHRNXZUBTE-NQXXGFSBSA-N D-ribulose Chemical compound OC[C@@H](O)[C@@H](O)C(=O)CO ZAQJHHRNXZUBTE-NQXXGFSBSA-N 0.000 description 1
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- ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 description 1
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- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VSOAQEOCSA-N L-altropyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-VSOAQEOCSA-N 0.000 description 1
- 240000001929 Lactobacillus brevis Species 0.000 description 1
- 235000013957 Lactobacillus brevis Nutrition 0.000 description 1
- 239000007993 MOPS buffer Substances 0.000 description 1
- NBGXQZRRLOGAJF-UHFFFAOYSA-N Maltulose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)(CO)OCC1O NBGXQZRRLOGAJF-UHFFFAOYSA-N 0.000 description 1
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- 206010044565 Tremor Diseases 0.000 description 1
- FPAMXKYNBQIRKS-UHFFFAOYSA-N [Sn].[Ge]=O Chemical compound [Sn].[Ge]=O FPAMXKYNBQIRKS-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 108090000637 alpha-Amylases Proteins 0.000 description 1
- 102000004139 alpha-Amylases Human genes 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 description 1
- 229940024171 alpha-amylase Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
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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 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
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- 239000007853 buffer solution Substances 0.000 description 1
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- 229930182830 galactose Natural products 0.000 description 1
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- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
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- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
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- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
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- MUDDKLJPADVVKF-UHFFFAOYSA-N trichlorogermane Chemical compound Cl[GeH](Cl)Cl MUDDKLJPADVVKF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/30—Germanium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP36034392 | 1992-12-28 | ||
| JP4360343A JPH06315391A (ja) | 1992-12-28 | 1992-12-28 | グルコースの異性化方法及び異性化促進剤 |
| JP5188877A JPH0717991A (ja) | 1993-06-30 | 1993-06-30 | アルドース構造を有する化合物をケトース構造を有する化合物へ異性化する方法、異性化或いはその促進剤 |
| JP18887793 | 1993-06-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL9320024A NL9320024A (nl) | 1995-03-01 |
| NL194441B NL194441B (nl) | 2001-12-03 |
| NL194441C true NL194441C (nl) | 2002-04-04 |
Family
ID=26505202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL9320024A NL194441C (nl) | 1992-12-28 | 1993-12-27 | Werkwijze voor isomerisatie van een aldose in een ketose. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5679787A (zh) |
| EP (1) | EP0628050B1 (zh) |
| JP (1) | JP3524094B2 (zh) |
| KR (1) | KR100344966B1 (zh) |
| CN (1) | CN1036922C (zh) |
| AU (1) | AU672865B2 (zh) |
| CH (1) | CH685701A5 (zh) |
| DE (2) | DE4396846B4 (zh) |
| GB (1) | GB2279650B (zh) |
| NL (1) | NL194441C (zh) |
| NZ (1) | NZ250367A (zh) |
| SE (1) | SE519168C2 (zh) |
| WO (1) | WO1994014826A1 (zh) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3668262B2 (ja) * | 1994-06-28 | 2005-07-06 | 株式会社浅井ゲルマニウム研究所 | 有機ゲルマニウム化合物の分離回収方法 |
| RU2476436C1 (ru) * | 2012-01-25 | 2013-02-27 | Общество С Ограниченной Ответственностью "Вдс Фарма" | Комплексные соединения германия с аминокислотами и карбоновыми кислотами |
| CN106032386B (zh) * | 2015-03-16 | 2019-03-15 | 中国科学院宁波材料技术与工程研究所 | 一种醛酮糖的催化转化方法 |
| WO2018148939A1 (zh) * | 2017-02-17 | 2018-08-23 | 中国科学院宁波材料技术与工程研究所 | 一种单糖差向异构化反应催化剂 |
| WO2021142019A1 (en) * | 2020-01-06 | 2021-07-15 | Solugen, Inc. | Compositions, systems and methods for production of value-added chemicals |
| JP7416016B2 (ja) * | 2021-06-01 | 2024-01-17 | 株式会社豊田中央研究所 | 製造方法、使用方法及び反応システム |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1497888A (en) * | 1975-06-17 | 1978-01-12 | Ici Ltd | Aldose to ketose conversion |
| BE834794A (fr) * | 1975-10-23 | 1976-02-16 | Acide 3-trihydroxygermano-propionique | |
| GB1585174A (en) * | 1976-06-16 | 1981-02-25 | Ici Ltd | Separation of sugars from mixtures |
| JPS5632485A (en) * | 1979-08-24 | 1981-04-01 | Pola Chem Ind Inc | Preparation of organogermanium compound |
| CA1314210C (en) * | 1987-10-29 | 1993-03-09 | Norihiro Kakimoto | Agent for improving reduced functions of organs caused by inhibited blood circulation |
| JP3270969B2 (ja) * | 1990-04-13 | 2002-04-02 | 株式会社浅井ゲルマニウム研究所 | 光学活性な有機ゲルマニウム化合物の製造方法 |
| US5418298A (en) * | 1993-03-19 | 1995-05-23 | Regents Of The University Of Michigan | Neutral and mixed neutral/anionic polymetallooxanes |
-
1993
- 1993-12-06 NZ NZ250367A patent/NZ250367A/en not_active IP Right Cessation
- 1993-12-27 WO PCT/JP1993/001896 patent/WO1994014826A1/en active IP Right Grant
- 1993-12-27 EP EP94903072A patent/EP0628050B1/en not_active Expired - Lifetime
- 1993-12-27 CH CH2654/94A patent/CH685701A5/fr not_active IP Right Cessation
- 1993-12-27 KR KR1019940702868A patent/KR100344966B1/ko not_active IP Right Cessation
- 1993-12-27 DE DE4396846A patent/DE4396846B4/de not_active Expired - Fee Related
- 1993-12-27 NL NL9320024A patent/NL194441C/nl not_active IP Right Cessation
- 1993-12-27 AU AU57163/94A patent/AU672865B2/en not_active Ceased
- 1993-12-27 CN CN93121222A patent/CN1036922C/zh not_active Expired - Fee Related
- 1993-12-27 DE DE4396846T patent/DE4396846T1/de not_active Withdrawn
- 1993-12-27 GB GB9416016A patent/GB2279650B/en not_active Expired - Fee Related
- 1993-12-27 US US08/295,739 patent/US5679787A/en not_active Expired - Lifetime
- 1993-12-27 JP JP51501394A patent/JP3524094B2/ja not_active Expired - Fee Related
-
1994
- 1994-08-16 SE SE9402735A patent/SE519168C2/sv unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1994014826A1 (en) | 1994-07-07 |
| US5679787A (en) | 1997-10-21 |
| KR100344966B1 (ko) | 2002-12-31 |
| AU672865B2 (en) | 1996-10-17 |
| NZ250367A (en) | 1995-10-26 |
| EP0628050A1 (en) | 1994-12-14 |
| SE519168C2 (sv) | 2003-01-21 |
| AU5716394A (en) | 1994-07-19 |
| DE4396846T1 (de) | 1995-01-26 |
| CN1094053A (zh) | 1994-10-26 |
| DE4396846B4 (de) | 2005-11-17 |
| GB2279650A (en) | 1995-01-11 |
| GB9416016D0 (en) | 1994-09-28 |
| NL9320024A (nl) | 1995-03-01 |
| NL194441B (nl) | 2001-12-03 |
| SE9402735L (sv) | 1994-08-16 |
| GB2279650B (en) | 1996-11-20 |
| SE9402735D0 (sv) | 1994-08-16 |
| JPH08502999A (ja) | 1996-04-02 |
| JP3524094B2 (ja) | 2004-04-26 |
| CN1036922C (zh) | 1998-01-07 |
| EP0628050B1 (en) | 1998-04-08 |
| CH685701A5 (fr) | 1995-09-15 |
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| BA | A request for search or an international-type search has been filed | ||
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| V1 | Lapsed because of non-payment of the annual fee |
Effective date: 20120701 |