USRE33047E - Process for producing a high-purity maltose - Google Patents
Process for producing a high-purity maltose Download PDFInfo
- Publication number
- USRE33047E USRE33047E US07/202,249 US20224988A USRE33047E US RE33047 E USRE33047 E US RE33047E US 20224988 A US20224988 A US 20224988A US RE33047 E USRE33047 E US RE33047E
- Authority
- US
- United States
- Prior art keywords
- maltose
- fraction
- column
- glucose
- starch sugar
- 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.)
- Expired - Lifetime
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- 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 title claims abstract description 96
- 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 title claims abstract description 91
- 238000000034 method Methods 0.000 title claims abstract description 24
- 229920001353 Dextrin Polymers 0.000 claims abstract description 20
- 239000004375 Dextrin Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000008103 glucose Substances 0.000 claims abstract description 18
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 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 abstract description 13
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 13
- 239000012527 feed solution Substances 0.000 claims abstract description 8
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 235000019425 dextrin Nutrition 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- -1 sulphonyl groups Chemical group 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001342 alkaline earth metals Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229920002472 Starch Polymers 0.000 abstract description 64
- 235000019698 starch Nutrition 0.000 abstract description 64
- 239000008107 starch Substances 0.000 abstract description 64
- 239000000243 solution Substances 0.000 abstract description 56
- 239000003513 alkali Substances 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000005194 fractionation Methods 0.000 description 20
- 239000000470 constituent Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000003957 anion exchange resin Substances 0.000 description 5
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 210000002196 fr. b Anatomy 0.000 description 2
- 210000000540 fraction c Anatomy 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 1
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 108090000637 alpha-Amylases Proteins 0.000 description 1
- 102000004139 alpha-Amylases Human genes 0.000 description 1
- 108010019077 beta-Amylase Proteins 0.000 description 1
- 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 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
- 210000004027 cell Anatomy 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside 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](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Images
Classifications
-
- 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
- C07H3/04—Disaccharides
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K7/00—Maltose
Definitions
- the present invention relates to a process for producing a high-purity maltose.
- maltose has been available as a saccharified starch product with a maltose content of about 40-50 w/w % based upon the weight of the dry solid solute (all percentages are used in the specification mean "weight percentages on dry solid basis” unless otherwise specified) which is obtainable by subjecting a liquefied starch solution to the action of a malt enzyme.
- a starch sugar solution containing maltose is passed through a column of an anion exchange resin.
- Japanese Patent Publication No. 46,290/77 discloses a process for producing a high-purity maltose comprising preparing a starch sugar solution substantially consisting of dextrin and about 65% maltose, and applying the solution to an anion exchange resin of OH-form to adsorb the maltose constituent and also to remove the dextrin constituent.
- Japanese Patent Publication No. 20,579/79 discloses a process for producing a high-purity maltose which comprises applying a starch sugar solution, containing glucose and maltose, to a column packed with an anion exchange resin of SO 3 2- - or SO.sub.
- the present inventors have investigated processes for producing a high-purity maltose using a strongly-acidic cation exchange resin, more particularly, of alkali metal- or alkaline earth metal-form, instead of an anion exchange resin which has the above described disadvantages.
- a high-purity maltose is easily obtainable by admitting a feed starch sugar solution with a maltose content of at least 70% and water to a column packed with a strongly-acidic cation exchange resin of alkali metal- or alkaline earth metal-form thereby fractionating the solution into a high-dextrin fraction, a high-dextrin, maltose fraction, a high-maltose fraction, a high-maltose.glucose fraction, and a high-glucose fraction (the terms "high-A fraction” and "high-A.B fraction” as used in the specification shall mean the eluted fractions rich in A, or rich in A but highly contaminated with B); and recovering the high-maltose fraction.
- the drawing shows the elution pattern of the feed solution upon the fractionation into fractions A through E, i.e., the high-dextrin fraction, high-dextrin.maltose fraction, high-maltose fraction, high-maltose.glucose fraction, and high-glucose fraction, respectively.
- the feed starch sugar solution usable in the present invention may be almost any substantially-ketose-free solution of aldoses derived from starch. Such a feed solution results in a high-maltose fraction; and with a maltose content of 90%, typically 93% or higher, in a high yield when subjected to the fractionation according to the present invention.
- feed starch sugar solution may be a saccharified starch solution obtained by subjecting starch to the actions of starch-degrading enzymes, e.g., ⁇ - and ⁇ -amylases, and starch-debranching enzyme, or may be an aqueous solution of a commercially-available starch sugar product having a maltose content of at least 70%.
- the strongly-acidic cation exchange resin of alkali metal- or alkaline earth metal-form usable in the invention may be, for example, one or more members of styrene-divinylbenzene copolymer resins bearing sulphonyl groups of alkali metal- or alkaline earth metal-form, such as Na + , K + , Ca 2+ , or Mg 2+ .
- Commercially-available resins are, for example, "Dowex 50WX2", “Dowex 50WX4", and “Dowex 50WX8", products of Dow Chemical Company, Midland, Mich., U.S.A., "Amberlite CG-120", a product of Rohm & Haas Company, Philadelphia, Pa.
- a resin with a nominal particle size of about 0.01-0.5 mm is packed in one or more columns.
- the bed depth preferred in the invention is generally 7 m or longer. If two or more columns are used, they are cascaded to give a total bed depth of 7 m or longer.
- any column can be used regardless of its material, size, and shape so far as the objectives of the invention can be attained therewith.
- the column may be, for example, of glass, plastic or stainless steel, and its shape may be, for example, in cylindrical or square pillar form, but it should be designed to give the most effective laminar flow possible when the feed starch sugar solution is applied to the column packed with the resin.
- One or more column(s) is packed with a strongly-acidic cation exchange resin of alkali metal- or alkaline earth metal-form, in an aqueous suspension, to give a total bed depth of 7 m or longer.
- the feed starch sugar solution While keeping the temperature in the column(s) at 45°-85° C., the feed starch sugar solution, at a concentration of about 10-70 w/w %, in an amount of about 1-60 v/v % against the bed volume, is admitted into the column(s) and then charged upwards or downwards with water at a flow rate of about SV 0.1-2.0 to effect fractionation of the material starch sugar solution into a high-dextrin fraction, a high-dextrin.-maltose fraction, a high-maltose fraction, a high-maltose.glucose fraction, and a high-glucose fraction, in the given order.
- the high maltose-fraction is then recovered.
- the eluted fractions are generally collected in about 1-20 v/v % against the bed volume, they may be distributed automatically into the fractions.
- the amount of water required for substantial fractionation of the feed starch sugar solution can be sharply reduced, and the maltose constituent in the solution can be recovered in higher purity, higher concentration, and higher yield.
- the previously obtained high-dextrin.maltose fraction, the feed starch sugar solution, and the previoiusly obtained high-maltose.glucose fraction are applied successively to the column in the given order.
- the high-maltose fraction thus obtained can be used intact, it may be, if necessary, treated further as follows.
- the high-maltose fraction may be subjected to conventional purification steps, e.g., filtration, decolorization and/or deionization.
- the purified product is, for example, concentrated to obtain a syrup, or crystallized to obtain a mascuit which may be spray-dried into crystalline powder, or separated into mother liquor and maltose crystals of much higher purity.
- the high-purity maltose thus obtained is extremely useful in various applications, e.g., for production of food products or pharmaceuticals.
- the feed starch sugar solutions used in this experiment were prepared from commercially-available starch sugar products as listed in Table I, products of Hayashibara Company, Limited, Okayama, Japan, by dissolving or diluting them in water to give respective concentrations of 45 w/w %.
- each feed starch sugar solution listed in Table I was admitted to the column in an amount of 5 v/v % against the bed volume, and fractionated by charging 75° C. hot water at a flow rate of SV 0.4 through the column and the high-maltose fraction, with a maltose content of 93 % or higher, was recovered.
- Table II The results are given in Table II.
- a feed starch sugar solution was prepared by diluting "HM-75", trade name of a commercially-available starch sugar syrup with a maltose content of 76.8%, a product of Hayashibara Company, Limited, Okayama, Japan, in water to give a concentration of 45 w/w %.
- XT-1022E (Na + ) a commercially-available strongly-acidic cation exchange resin of alkali metal-form, a product of Tokyo Chemical Industries, Kita-ku, Tokyo, Japan, in an aqueous suspension, was packed in four jacketted stainless steel columns, inside diameter, 5.4 cm, to give respective bed depths of 5 m, and the columns were cascaded to give a total bed depth of 20 m.
- the feed starch sugar solution was admitted thereto in an amount of 5 v/v % against the bed volume, and then fractionated by charging 55° C. hot water at a flow rate of SV 0.13 through the columns and the high-maltose fraction, with a maltose content of 93% or higher, was recovered.
- the high-maltose fraction contained 808.2 g maltose, and the yield was extremely high, i.e., 84.3%, against the maltose constituent in the feed starch sugar solution.
- a feed starch sugar solution was prepared by dissolving "Sunmalt", a commercially-available starch sugar powder with a maltose content of 85.0%, Registered Trade Mark of Hayashibara Company, Limited, Okayama, Japan, in water to give a concentration of 60 w/w %.
- the resin, used in Example 1, was converted into K + -form in the usual way and packed in a jacketted stainless steel column, inside diameter, 2.2 cm, to give a bed depth of 10 m.
- the feed starch sugar solution was admitted thereto in an amount of 3 v/v % against the bed volume, and then fractionated by charging 60° C. hot water at a flow rate of SV 0.2 through the column and the high-maltose fraction, with a maltose content of 93% or higher, was recovered.
- the high-maltose fraction contained 65.7 g maltose, and the yield was extremely high, i.e., 88.3% against the maltose constituent in the feed starch sugar solution.
- a feed starch sugar solution was prepared by dissolving "Sunmalt", a commercially-available starch sugar powder with a maltose content of 85.0%, Registered Trade Mark of Hayashibara Company, Limited, Okayama, Japan, in water to give a concentration of 45 w/w %.
- the feed starch sugar solution was applied thereto in an amount of 6.6 v/v % against the bed volume, and then fractionated by charging 75° C. hot water at a flow rate of SV 0.13 through the columns and the high-maltose fraction, with a maltose content of 93% or higher, was recovered.
- the high-maltose fraction contained 913.7 g maltose, and the yield was extremely high, i.e., 87.1%, against the maltose constituent in the feed starch sugar solution.
- the first fractionation was carried out as follows. Similarly as in Example 1, a feed starch sugar solution was applied to a column, and fractionated except that the feed starch sugar solution was applied to the column in an amount of 20 v/v % against the bed volume.
- the elution pattern is given in the drawing, where Fractions A through E show a high-dextrin fraction, a high-dextrin.maltose fraction, a high-maltose fraction, a high-maltose.glucose fraction, and a high-glucose fraction respectively, and where the elution is effected in the given order.
- Fraction C the high-maltose fraction
- Fractions A and E were removed from the fractionation system.
- the additional fractionation was carried out as follows. Fraction B, the feed starch sugar solution in an amount of about 10 v/v % against the bed volume, and Fraction D were admitted into the column successively in the given order, and the column then charged with 75° C. hot water, as in Example 3, to effect fractionation. The high maltose fractions, with a maltose content of 94%, were recovered. The additional fractionation was repeated up to 30 batches in total, and the averaged results per batch were calculated. On an average, one high-maltose fraction contained 1483 g maltose, and the yield was extremely high, i.e., 93.3%, against the maltose constituent in the feed starch sugar solution.
- a feed starch sugar solution was prepared by dissolving "Maltose H", trade name of a commercially-available starch sugar powder with a maltose content of 91.5%, a product of Hayashibara Company, Limited, Okayama, Japan, in water to give a concentration of 45 w/w %.
- Amberlite CG-120 (Ca 2+ ) a commercially-available strongly-acidic cation exchange resin of alkaline earth metal-form, a product of Rohm & Haas Company, Philadelphia, Pa., U.S.A., was packed in fresh columns of the same material and dimensions as used in Example 1 to give a total bed depth of 10 m.
- Example 4 a dual-stage fractionation was carried out.
- the first fractionation was carried out as follows. While keeping the temperature in the columns at 80° C., the feed starch sugar solution was applied thereto in an amount of 20 v/v % against the bed volume, and then fractinated by charging 80° C. hot water at a flow rate of SV 0.6 through the columns to obtain a similar elution pattern as in Example 4. Similarly as in Example 4, Fraction C, the high-maltose fraction, was harvested, and Fractions A and E were removed from the fractionation system.
- Fraction B the feed starch sugar solution in an amount of 10 v/v % against the bed volume, and Fraction D, were admitted into the column successively in the given order, and the column then charged with 80° C. hot water at a flow rate of SV 0.6 to effect fractionation.
- the resultant high-maltose fractions with a maltose content of 96% or higher, was recovered.
- the additional fractionation was repeated up to 100 batches in total, and the averaged results per batch were calculated. On an average, one high-maltose fraction contained 1084 g maltose, and the yield was extremely high, i.e., 95%, against the maltose constituent in the feed starch sugar solution.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56121725A JPS5823799A (ja) | 1981-08-03 | 1981-08-03 | 高純度マルト−スの製造方法 |
JP56-121725 | 1981-08-03 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/402,823 Reissue US4487198A (en) | 1982-07-28 | 1982-07-28 | Process for producing a high-purity maltose |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE33047E true USRE33047E (en) | 1989-09-05 |
Family
ID=14818330
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/202,249 Expired - Lifetime USRE33047E (en) | 1981-08-03 | 1988-06-06 | Process for producing a high-purity maltose |
Country Status (6)
Country | Link |
---|---|
US (1) | USRE33047E (enrdf_load_stackoverflow) |
JP (1) | JPS5823799A (enrdf_load_stackoverflow) |
CA (1) | CA1215361A (enrdf_load_stackoverflow) |
DE (1) | DE3228838A1 (enrdf_load_stackoverflow) |
FR (1) | FR2510581B1 (enrdf_load_stackoverflow) |
GB (1) | GB2106912B (enrdf_load_stackoverflow) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5773282A (en) * | 1994-10-01 | 1998-06-30 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Recombinant thermostable enzyme for converting maltose into trehalose from Thermus aquaticus |
US6066477A (en) | 1996-11-08 | 2000-05-23 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Method of producing glucosylated saccharides with kojibiose phosphorylase |
US6436678B2 (en) | 2000-02-28 | 2002-08-20 | Grain Processing Corporation | High purity maltose process and products |
US20030021866A1 (en) * | 2001-07-24 | 2003-01-30 | Grain Processing Corporation | Method for making wine |
US20050009017A1 (en) * | 2000-05-22 | 2005-01-13 | Michio Kubota | Alpha-isomaltosyltransferase, process for producing the same and use thereof |
US20060188626A1 (en) * | 2003-07-18 | 2006-08-24 | Stouffs Robert H | Process for preparing maltitol enriched products |
US7186535B1 (en) | 1998-09-11 | 2007-03-06 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Non-reducing saccharide-forming enzyme, trehalose-releasing enzyme, and process for producing saccharides using the enzymes |
US7241606B2 (en) | 2000-08-01 | 2007-07-10 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | α-Isomaltosylglucosaccharide synthase, process for producing the same and use thereof |
US7709230B2 (en) | 2001-04-27 | 2010-05-04 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing isomaltose and uses thereof |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6067000A (ja) * | 1983-09-19 | 1985-04-17 | 三菱化学株式会社 | マルト−スの分離法 |
JPH0631285B2 (ja) * | 1984-02-09 | 1994-04-27 | 株式会社林原生物化学研究所 | 高純度オリゴグルコシルフラクトシドの製造方法 |
JPS61205494A (ja) * | 1985-03-11 | 1986-09-11 | Sanmatsu Kogyo Kk | 分枝デキストリン類及び直鎖オリゴ糖類の製造方法 |
JPH0693840B2 (ja) * | 1985-10-04 | 1994-11-24 | 昭和産業株式会社 | 糖液の精製方法 |
JPH0198601A (ja) * | 1987-10-13 | 1989-04-17 | Gunei Kagaku Kogyo Kk | 高純度イソマルトオリゴ糖の製造方法 |
JP2838798B2 (ja) * | 1988-02-04 | 1998-12-16 | 株式会社林原生物化学研究所 | イソアミラーゼ活性を有するポリペプチドとその用途 |
US5272136A (en) * | 1991-10-12 | 1993-12-21 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | 5-0-α-D-Glucopyranosyl-L-ascorbic acid, and its preparation and uses |
JP3072535B2 (ja) * | 1991-10-21 | 2000-07-31 | 株式会社林原生物化学研究所 | 5−O−α−D−グルコピラノシル−L−アスコルビン酸とその製造方法並びに用途 |
JP3134235B2 (ja) * | 1991-10-23 | 2001-02-13 | 株式会社林原生物化学研究所 | 2−O−α−D−グルコピラノシル−L−アスコルビン酸高含有物の製造方法 |
JP3172925B2 (ja) * | 1992-02-25 | 2001-06-04 | 株式会社林原生物化学研究所 | ネオトレハロースの製造方法とその用途 |
ES2194885T3 (es) * | 1992-12-28 | 2003-12-01 | Hayashibara Biochem Lab | Purificacion de trehalosa. |
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Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
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US5773282A (en) * | 1994-10-01 | 1998-06-30 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Recombinant thermostable enzyme for converting maltose into trehalose from Thermus aquaticus |
US6087146A (en) | 1994-10-01 | 2000-07-11 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Recombinant thermostable enzyme for converting maltose into trehalose |
US6066477A (en) | 1996-11-08 | 2000-05-23 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Method of producing glucosylated saccharides with kojibiose phosphorylase |
US6140487A (en) | 1996-11-08 | 2000-10-31 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | DNA encoding kojibiose phosphorylase obtainable from thermoanaerobium, ' its preparation and uses |
US6204377B1 (en) | 1996-11-08 | 2001-03-20 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Kojibiose phosphorylase glucosyl-saccharides produced by transglycosylation |
US7575900B2 (en) | 1998-09-11 | 2009-08-18 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Non-reducing saccharide-forming enzyme, trehalose-releasing enzyme, and process for producing saccharides using the enzymes |
US20070281346A1 (en) * | 1998-09-11 | 2007-12-06 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku | Non-reducing saccharide-forming enzyme, trehalose-releasing enzyme, and process for producing saccharides using the enzymes |
US7582463B2 (en) | 1998-09-11 | 2009-09-01 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Non-reducing saccharide-forming enzyme, trehalose-releasing enzyme, and process for producing saccharides using the enzymes |
US7186535B1 (en) | 1998-09-11 | 2007-03-06 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Non-reducing saccharide-forming enzyme, trehalose-releasing enzyme, and process for producing saccharides using the enzymes |
US20070218529A1 (en) * | 1998-09-11 | 2007-09-20 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku | Non-reducing saccharide-forming enzyme, trehalose-releasing enzyme, and process for producing saccharides using the enzymes |
US6670155B2 (en) | 2000-02-28 | 2003-12-30 | Grain Processing Corporation | Process for preparing dextrins |
US6436678B2 (en) | 2000-02-28 | 2002-08-20 | Grain Processing Corporation | High purity maltose process and products |
US20050009017A1 (en) * | 2000-05-22 | 2005-01-13 | Michio Kubota | Alpha-isomaltosyltransferase, process for producing the same and use thereof |
US7192746B2 (en) | 2000-05-22 | 2007-03-20 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | α-Isomaltosyltransferase, process for producing the same and use thereof |
US7241606B2 (en) | 2000-08-01 | 2007-07-10 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | α-Isomaltosylglucosaccharide synthase, process for producing the same and use thereof |
US7718404B2 (en) | 2000-08-01 | 2010-05-18 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | α-isomaltosylglucosaccharide-forming enzyme, process and uses of the same |
US7811797B2 (en) | 2000-08-01 | 2010-10-12 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | α-isomaltosylglucosaccharide-forming enzyme, process and uses of the same |
US7709230B2 (en) | 2001-04-27 | 2010-05-04 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing isomaltose and uses thereof |
US20030021866A1 (en) * | 2001-07-24 | 2003-01-30 | Grain Processing Corporation | Method for making wine |
US20060188626A1 (en) * | 2003-07-18 | 2006-08-24 | Stouffs Robert H | Process for preparing maltitol enriched products |
US7935190B2 (en) | 2003-07-18 | 2011-05-03 | Cargill, Incorporated | Process for preparing maltitol enriched products |
Also Published As
Publication number | Publication date |
---|---|
FR2510581A1 (fr) | 1983-02-04 |
JPS6251120B2 (enrdf_load_stackoverflow) | 1987-10-28 |
DE3228838A1 (de) | 1983-03-24 |
JPS5823799A (ja) | 1983-02-12 |
FR2510581B1 (fr) | 1987-10-16 |
GB2106912B (en) | 1986-03-12 |
DE3228838C2 (enrdf_load_stackoverflow) | 1990-03-29 |
CA1215361A (en) | 1986-12-16 |
GB2106912A (en) | 1983-04-20 |
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