GB2106912A - Process for producing high-purity maltose - Google Patents
Process for producing high-purity maltose Download PDFInfo
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- GB2106912A GB2106912A GB08222390A GB8222390A GB2106912A GB 2106912 A GB2106912 A GB 2106912A GB 08222390 A GB08222390 A GB 08222390A GB 8222390 A GB8222390 A GB 8222390A GB 2106912 A GB2106912 A GB 2106912A
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- 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
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- 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
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- Engineering & Computer Science (AREA)
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Abstract
A process for producing high-purity maltose comprises applying a starch sugar solution having a maltose content of at least 70% to a column packed with a strongly-acidic cation exchange resin of alkali metal- of alkaline earth metal-form; separating the constituents of the starch sugar solution by eluting the column with water thereby to fractionate 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 (as hereinbefore defined), in that order, and recovering the high maltose fraction.
Description
SPECIFICATION
Process for producing high purity maltose
The present invention relates to a process for
producing high-purity maltose.
Recently, various advantages of maltose in food
products and pharmaceuticals have been estab
lished, and there is now an increasing demand for
maltose of high-purity.
Conventionally, maltose has been available as a
saccharified starch product with a maltose content
of about 40-50 w/w % on a dry solids basis. Such
maltose is generally obtained by subjecting a liquefied starch solution to the action of malt enzyme.
Unless stated otherwise, percentages given in this specification are weight percentages on a dry solids
basis.
Recent advances in starch saccharification techniques have provided a relatively easier method of production of a saccharified starch product having a maltose content of 50% or higher by using a combination of, for example,j3-amylase with a starch debranching enzyme.
However, from economical and technical points of view, the direct production of high-purity maltose having a maltose content of 90% or more is much more difficult.
Some recent attempts to obtain high-purity maltose are based on the use of a column of an anion exchange resin to separate maltose from a starch sugar solution. For example, Japan Patent Publication No.46,290/77 discloses a process for producing 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. However, in this process the starch sugar solution must be applied to the resin at the lowest possible temperature, preferably, below 20on, to prevent the izomerization of the maltose constituent.As a result an increase in viscosity and microbial contamination, as well as low purification capability, are unavoidable, and render the practice of this method on an industrial-scale very difficult.
Further, Japan 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 S032-- or SO3H--form, to fractionate the solution into the glucose- and maltose-constituents. This process is inadequate as a process for the industrial-scale production of high-purity maltose because the bonding of S032-- or SO3H--group is labile.
We have investigated processes for producing high-purity maltose using a strongly-acidic cation exchange resin, more particularly, an exchange resin of alkali metal- or alkaline earth metal-form and we have found that a high-purity maltose is easily obtainable by using such an exchange resin.
Accordingly, the present invention provides a
process for producing high-purity maltose, which
process comprises applying a starch sugar solution
having a maltose content of at least 70% to a column
packed with a strongly-acidic cation exchange resin
of alkali metal- or alkaline earth metal-form; separat
ing the constituents of the starch sugar solution by eluting the column with water thereby to fractionate 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 (as hereinafter defined), in that order; and
recovering the high maltose fraction.
The terms "high A fraction" and "high A/B fraction" used in this specification are used to mean eluted fractions containing substance A, or substances A and B as the predominant constituent(s), respectively.
We have also found that high-purity maltose can
readily be obtained in higher concentration and at higher recovery yield by employing a method in which a mixture of a said starch sugar solution together with previously obtained high dextrin maltose and/or high maltose/glucose fractions is applied to the column. The resultant high dextrin/ maltose fraction and/or high maltose/glucose fractions can, of course, be used in a subsequent separation process together with fresh starch sugar solution.
The starch sugar solution for use in the present process may be any substantially-ketose-free solution of aldoses derived from starch, which gives fractions having a maltose content of at least 90%, preferably at least 93%, in a high recovery yield when subjected to the fractionation according to the invention. For example, the starch sugar solution may be a saccharified starch solution which is obtainable by subjecting starch to the action of starch-degrading enzymes, e.g. a- and (3-amylases, and a starch-debranching enzyme, or may be an aqueous solution of a commercially-available starch sugar product, with the proviso that the maltose content of the solution is at least 70%.
The strongly-acidic cation exchange resin of alkali metal- or alkaline earth metal form usable in the present invention may be any styrene-divinylbenzene copolymer resin, for example, bearing sulphonyl groups of alkali metal- or alkaline earth metal-form, such as Na+, K+, Ca2F, or Mg2+. Examples of suitable commercially available resins are "Dowex 50WX2", "Dowex 50WX4", and "Dowex 50WX8", products of Dow Chemical Company, Midland, Michigan, U.S.A.; "Amberlite CG-120", a product of Rohm & Haas Company, Philadelphia, Pennsylvania, U.S.A.; "XT-1022E", a product of Tokyo
Chemical Industries, Kita-ku, Tokyo, Japan; and "Diaion SK 1B", "Diaion SK 102", and "Diaion SK 104", products of Mitsubishi Chemical Industries
Limited, Tokyo, Japan.All of these resins have excellent fractionating capability to obtain the high -maltose fractions, and as they are highly heat- and abrasion-resistant, they are particularly suitable for producing high-purity maltose on an industrial-scale.
Preferably a resin having a nominal particle size of 0.01-0.5 mm is used and this 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.
As regards the column usable in the invention, any column can be used regardless of its material, size, and shape as long as the objectives of the invention can be attained therewith. The column may be, for example, of glass, plastics or stainless steel; and its cross-section may be, for example, cylindrical or square form, but is preferably shaped to give the most effective laminarflow when the starch sugar solution is applied to the column packed with the resin.
A preferred embodiment of the present process will be described below.
After packing the strongly-acidic cation exchange resin of alkali metal- or alkaline earth metal-form in an aqueous suspension, in one or more columns to give a total bed depth of 7 m or longer, while keeping the temperature in the column(s) at 45"-85"C, the starch sugar solution is applied to the column(s) art a concentration of 10-70 w/w %, in an amount of 1-60 v/v % against the bed volume, and then charged upwards or downwards with water at a flow rate of SV 0.1-2.0 to effect fractionation of the starch sugar solution into a number of fractions including a high dextrin fraction, a high dextrin/ maltose fraction, a high maitose fraction, a high maltose/glucose fraction, and a high glucose fraction, in that order, followed by harvesting of the high maltose fraction.
Although the eluted fractions are generally collected in batches of 1-20 v/v % against the bed volume, they may be partitioned automatically into the particular fractions specified above.
When the starch sugar solution is applied to the column prior to, after, or together with the application of previously obtained high dextrin/maltose and/or high maltose/glucose fractions, the amount of water required for substantial fractionation of the starch sugar solution can be very much reduced, and the maltose constituent in the solution can be recovered in higher purity, higher concentration, and higher recovery yield. Preferably, the previously obtained high dextrin/maltose fraction is applied to the column first, followed by the starch sugar solution, and then finally by the previously obtained high maltose/glucose fraction. This order of application enhances the separation of the maltose.
Although the high maltose fraction thus obtained can be used intact, it may be, if necessary, purified further. Thus, the fraction may be subjected to conventional purification steps, e.g., filtration, decolorization and/or deionization. Then, the purified product may be, 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 suitable for various uses, e.g.,forthe production of food products or pharmaceuticals.
The following Experiments further illustrate the present invention.
EXPERIMENT 1
Starch sugar solution
The starch sugar solutions used in this EXPERI
MENT, were prepared with 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 %.
"Dowex 50WX4 (Na+)", a commercially-available strongly-acidic cation exchange resin of alkali metal-form, a product of Dow Chemical Company,
Midland, Michigan, U.S.A., in an aqueous suspension, was packed in a jacketted stainless steel column, inside diameter, 5.4 cm, to give a bed depth of10m.
While keeping the temperature in the column at 75"C, each starch sugar solution listed in TABLE I was applied to the column in an amount of 5 v/v % against the bed volume, and fractionated by charging thereto 75"C hot water at a flow rate of SV 0.4.
The high maltose fractions having a maltose content of at least 93% were harvested. The results are given in TABLE II.
The experimental results, as shown in TABLE II, confirm that when the maltose content in the starch sugar solution is at least 70%, a high maltose fraction having a maltose content of at least 93% is easily obtainable in a high yield, i.e. at least 80%, based on the maltose content of the starch sugar solution.
TABLE I
jugar composition (%) A B C D Maltrup 7.1 48.0 44.9 Malstar 3.2 66.0 30.8 HM-75 1.0 76.8 22.2 Sunmalt 4.3 85.0 10.7 Maltose H 0.6 91.5 7.9 Note: A is the starch sugar solution (trade
name or Registered Trade Mark); B,
glucose; C, maltose; and D, maltot
riose and higher oligosaccharides.
TABLE II
A B C D E Maltrup 48.0 132.2 44.2 control Malstar 66.0 231.7 56.3 control HM-75 76.8 403.6 84.3 present invention Sunmalt 85.0 483.8 91.3 present invention Maltose H 91.5 548.8 96.2 present invention Note: A is the starch sugar solution (trade name or Registered
Trade Mark); B, maltose content in the starch sugar solution
(%); C, maltose yield in the high maltose fraction (g); D,
maltose yield based on the maltose content of the starch
sugar solution (%); and E, remarks.
EXPERIMENT 2
Bed depth
In a manner similar to that described in EXPERI
MENT 1, a strongly-acidic cation exchange resin of alkali metal-form was packed in one or two columns to give respective total bed depths in the range of 1-20 m, as shown in TABLE Ill.
While keeping the temperature in the columns of different bed depths at 750C, 45 w/w % aqueous solution aliquots of "Sunmalt", a commerciallyavailable starch sugar powder with a maltose content of 85.0 %, Registered Trade Mark of Hayashibara
Company, Limited, Okayama, Japan, were applied to the columns in an amount of 5 v/v % against the bed volume, and then fractionated by charging thereto 75"C hot water at a flow rate of SV 0.4, followed by harvesting of the high maltose fraction having a maltose content of at least 93%. The results are given in TABLE Ill.
The experimental results, as shown in TABLE Ill, confirm that when the bed depth is 7 m or longer, a high maltose fraction having a maltose content of at least 93% is easily obtainable in a high yield, i.e. at least 80%, based on the maltose content of the starch sugar solution.
Note: A is total bed depth (m); B, number of
columns; C, amount ofthe starch sugar
solution applied (ml); D, maltose yield in
the high maltose fraction (g); E, maltose
yield based on the maltose content of the
starch sugar solution (%); and * means
two columns were cascaded.
EXPERIMENT3
Fractionation temperature
As described in Experiment 1, a strongly-acidic cation exchange resin of alkali metal-form was packed in columns to give bed depths of 10 m, and starch sugar solution aliquots, prepared as described in Experiment 2, were applied thereto, and fractionated as described in Experiment 2. However, the columns were kept at different temperatures (in the range of 35495"C) during the fractionation. The high maltose fractions having a maltose content of at least 93% were harvested. The results are given in
TABLE IV.
The experimental results, as shown in TABLE IV, confirm that when the column is kept at a temperature in the range of 45"-85"C, a high maltose fraction having a maltose content of at least 93% is easily obtainable in a high yield, i.e., at least 80%, based on the maltose content of the starch sugar solution, with less fear of causing a browing reaction.
TABLE 111
A B C D E 1 1 114.5 30.1 56.9 3 1 343.5 102.1 64.2 5 1 572.5 192.9 72.8 7 1 801.5 324.9 87.6 10 1 1145.0 483.8 91.3 15 1 1715.5 739.3 93.0 20 2* 2290.0 994.1 93.8 TABLE IV
A B C D E 35 374.7 70.7 0.023 easy 45 430.2 81.2 0.059 easy 55 471.1 88.9 0.105 easy 65 476.9 90.0 0.150 easy 75 483.8 91.3 0.176 easy 85 485.9 I 91.7 0.205 easy 95 472.2 89.1 0.496 difficult Note: A is the fractionation temperature ("C); B,
total yield of sugar constituents with a
maltose content of 93% or higher (g); C,
maltose yield based on the maltose con
tent of the starch sugar solution (%); D,
coiourization degree, obtained by measur
ing the absorbance of the high maltose
fraction in 10 cm cell (A420 nm-A720 nm), and
reducing the obtained value into that in 30
w/w % solution; and E, decolourization
using 0.1% activated carbon against sugar
constituents.
The following Examples illustrate the present invention.
EXAMPLE 1
A 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 fourjacketted 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.
While keeping the temperature in the columns at 55C, the starch sugar solution was applied thereto in an amount of 5 v/v % against the bed volume, and then fractionated by charging thereto 55"C hot water at a flow rate of SV 0.13. A high maltose fraction having a maltose content of at least 93% was harvested. The fraction contained 808.2 g maltose, and the recovery yield of maltose was very high, i.e., 84.3%, based on the maltose content of the starch sugar solution.
EXAMPLE 2
A 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 Kt-form in usual way, and packed in a jacketed stainless steel column, inside diameter, 2.2 cm, to give a bed depth of 10 m.
While keeping the temperature in the column at 60 C, the starch sugar solution was applied thereto in an amount of 3 v/v % against the bed volume, and then fractionated by charging thereto 60"C hot water at a flow rate of SV 0.2. A high maltose fraction having a maltose content of at least 93% was harvested. The fraction contained 65.7 g maltose, and the recovery yield of maltose was very high, i.e., 88.3%, based on the maltose content of the starch sugar solution.
EXAMPLE 3
A 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 Harashibara Company,
Limited, Okayama, Japan, in water to give a concentration of 45 w/w %.
"Dowex 50WX4 (mg2+)", a commercially available strongly-acidic cation exchange resin of alkaline earth metal-form, a product of Dow Chemical Company, Midland, Michigan, U.S.A., in an aqueous suspension, was packed in fresh columns of the same material and dimensions as used in Example 1 to give a total bed depth of 15 m.
While keeping the temperature in the columns at 75"C, the starch sugar solution was applied thereto in an amount of 6.6 v/v % against the bed volume, and then fractionated by charging thereto 75"C hot water at a flow rate of SV 0.13, and a high maltose fraction having a maltose content of 93% or more was harvested. The fraction contained 913.7 g maltose, and the recovery yield of maltose was very high, i.e., 87.1 %, based on the maltose content of the starch sugar solution.
EXAMPLE 4
In this example, a dual-stage fractionation was carried out.
The first fractionation was carried out as follows:
In a manner similar to that described in Example 1, a starch sugar solution was applied to a column, and fractionated except that the starch sugar solution was applied to the column in an amount of 20 v/v % against the bed volume. The elution pattern is illustrated in the Figure of the accompanying drawings, which shows a graph of sugar concentration plotted against fraction number. In the Figure,
Fractions A to E respectively correspond to the high dextrin fraction, the high dextrin/maltose fraction, the high maltose fraction, the high maltose/glucose fraction and the high glucose fraction, the fractions being eluted in that order. Fraction C, the high maltose fraction, was harvested, and Fractions A and E were removed from the fractionation system.
The additional fractionation was carried out as follows: The column was applied successively with
Fraction B, the starch sugar solution in an amount of about 10 v/v % against the bed volume, and Fraction
D, in that order, then charged with 750C hot water as described in Example 3 to effect fractionation, followed by harvesting of the high maltose fractions having a maltose content of 94% or more. 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 maitose, and the maltose recovery yield was extremely high, i.e., 93.3%, based on the maltose content of the starch sugar solution.
EXAMPLE 5
A starch sugar solution was prepared by dissolv
ing "Maltose H", trade name of a commerciallyavailable 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 (Ca2+)", a commercially-available strongly-acidic cation exchange resin of alkaline earth metal-form, a product of Rohm & Haas Company, Philadelphia, Pennsylvania, 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.
In this example 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 starch sugar solution was applied thereto in an amount of 20 v/v % against the bed volume, and then fractionated by charging thereto 80"C hot water at a flow rate of SV 0.6 to obtain a similar elution pattern as in Example 4. As in
Example 4, Fraction C, the high maltose fraction, was harvested, and Fractions A and E were removed from the fractionation system.
The additional fractionation was carried out as follows: The column was applied successively with
Fraction B, the starch sugar solution in an amount of 10 v/v % against the bed volume, and Fraction D, in the given order, and then charged with 80"C hot water at a flow rate of SV 0.6 to effect fractionation, followed by harvesting of the resultant high maltose fractions a maltose content of 96% or more. 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 of recovered maltose was extremely high, i.e., 95%, based on the maltose content of the starch sugar solution.
Claims (10)
1. A process for producing high-purity maltose, which process comprises applying a starch sugar solution having a maltose content of at least 70% to a column packed with a strongly-acidic cation exchange resin of alkali metal- or alkaline earth metal-form; separating the constituents of the starch sugar solution by eluting the column with water thereby to fractionate 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 (as hereinbefore defined), in that order, and recovering the high maltose fraction.
2. A process as set forth in Claim 1, wherein the bed depth of the resin in the column is at least 7 m.
3. A process as set forth in Claim 1 or 2, wherein the temperature in the column is kept at 45 -85 C.
4. A process as set forth in Claim 1,2 or 3, wherein the maltose content of the high maltose fraction is at least 93%.
5. A process as set forth in any one of the preceding Claims, wherein a strongly-acidic cation exchange resin bearing sulphonyl group of alkali metal- or alkaline earth metal-form is used.
6. A process as set forth in Claim 5, wherein the alkali metal or alkaline earth metal ions are Na+, K+,
Ca2+, or Mg2+.
7. A process as set forth in any one of the preceding Claims, wherein the starch sugar solution is applied to the column together with a high dextrin/maltose fraction and/or a high maltose/glucose fraction obtained from an earlier separation.
8. A process as set forth in Claim 7, wherein the high dextrin/maltose fraction which has been obtained previously, the starch sugar solution, and the high maltose/glucose fraction which has been obtained previously, are applied successively to the column in the stated order.
9. A process for producing a high-purity maltose substantially as hereinbefore described with reference to any one of the Experiments or of the
Examples.
10. A high-purity maltose whenever obtained by a process as claimed in any one of the preceding
Claims.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56121725A JPS5823799A (en) | 1981-08-03 | 1981-08-03 | Production of high purity maltose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2106912A true GB2106912A (en) | 1983-04-20 |
| GB2106912B GB2106912B (en) | 1986-03-12 |
Family
ID=14818330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08222390A Expired GB2106912B (en) | 1981-08-03 | 1982-08-03 | Process for producing high purity maltose |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | USRE33047E (en) |
| JP (1) | JPS5823799A (en) |
| CA (1) | CA1215361A (en) |
| DE (1) | DE3228838A1 (en) |
| FR (1) | FR2510581B1 (en) |
| GB (1) | GB2106912B (en) |
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| US5747300A (en) * | 1994-07-19 | 1998-05-05 | Kabushiki Kaisha Hayashibara Seibutsu Kaguku Kenkyujo | Trehalose and its production and use |
| US5763228A (en) * | 1994-06-16 | 1998-06-09 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Recombinant enzyme for converting maltose into trehalose from pimelobacter sp. |
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| US8324375B2 (en) | 2007-04-26 | 2012-12-04 | Hayashibara Co., Ltd. | Branched α-glucan, α-glucosyltransferase which forms the glucan, their preparation and uses |
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|---|---|---|---|---|
| JPS6067000A (en) * | 1983-09-19 | 1985-04-17 | 三菱化学株式会社 | Maltose separating method |
| JPH0631285B2 (en) * | 1984-02-09 | 1994-04-27 | 株式会社林原生物化学研究所 | Method for producing high-purity oligoglucosylfructoside |
| JPS61205494A (en) * | 1985-03-11 | 1986-09-11 | Sanmatsu Kogyo Kk | Production of branched dextrin and straight-chain oligosaccharide |
| JPH0693840B2 (en) * | 1985-10-04 | 1994-11-24 | 昭和産業株式会社 | Sugar liquid purification method |
| JPH0198601A (en) * | 1987-10-13 | 1989-04-17 | Gunei Kagaku Kogyo Kk | Method for producing high-purity isomalto-oligosaccharide |
| JP2838798B2 (en) * | 1988-02-04 | 1998-12-16 | 株式会社林原生物化学研究所 | Polypeptide having isoamylase activity and its use |
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| JP3072535B2 (en) * | 1991-10-21 | 2000-07-31 | 株式会社林原生物化学研究所 | 5-O-α-D-glucopyranosyl-L-ascorbic acid, its production method and use |
| JP3134235B2 (en) * | 1991-10-23 | 2001-02-13 | 株式会社林原生物化学研究所 | Method for producing 2-O-α-D-glucopyranosyl-L-ascorbic acid high content |
| JP3172925B2 (en) * | 1992-02-25 | 2001-06-04 | 株式会社林原生物化学研究所 | Method for producing neotrehalose and its use |
| JP3605129B2 (en) * | 1993-12-15 | 2004-12-22 | 株式会社林原生物化学研究所 | Non-reducing oligosaccharide having neotrehalose structure, method for producing the same and use thereof |
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| DE69731016T2 (en) * | 1996-03-04 | 2005-10-06 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Preparation of a trehalulose-containing polysaccharide composition. |
| JP3778991B2 (en) * | 1996-03-04 | 2006-05-24 | 株式会社林原生物化学研究所 | Maltooligosyl turranose and maltooligosyl palatinose-containing saccharides, production method and use thereof |
| US5962297A (en) * | 1996-06-10 | 1999-10-05 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Polypeptides having β-fructofuranosidase activity |
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| JP5184768B2 (en) * | 2006-09-05 | 2013-04-17 | 株式会社林原 | Method for recovering sugar solution with high trehalose content and method for producing crystalline trehalose |
| KR20080049924A (en) * | 2006-12-01 | 2008-06-05 | 주식회사 신동방씨피 | Method for preparing high purity crystal powder maltitol |
| JP4830031B2 (en) * | 2010-03-02 | 2011-12-07 | 昭和産業株式会社 | Transferase, sugar production method, glycoside production method, transferase production method |
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| US3565765A (en) * | 1966-12-27 | 1971-02-23 | Cpc International Inc | Preparation of high maltose conversion products |
| IT1050155B (en) * | 1967-06-30 | 1981-03-10 | Hayashibara Co | PROCESS FOR THE PRODUCTION OF HIGH PURITY MALTOSE |
| JPS5420578B1 (en) * | 1970-12-09 | 1979-07-24 | ||
| JPS5617078B1 (en) * | 1971-05-31 | 1981-04-20 | ||
| US3817787A (en) * | 1972-01-26 | 1974-06-18 | Suomen Sokeri Oy | Method for separating monosaccharides from mixtures including di-, and higher saccharides |
| JPS5246290B2 (en) * | 1973-06-05 | 1977-11-24 | ||
| JPS5186143A (en) * | 1975-01-21 | 1976-07-28 | Tokai Togyo Kk | Katono seizohoho |
| US4022637A (en) * | 1976-02-23 | 1977-05-10 | Standard Brands Incorporated | Method for separation of water soluble carbohydrates |
| US4109075A (en) * | 1976-06-09 | 1978-08-22 | Cpc International Inc. | Separation of saccharides by exclusion chromatography |
| ZA774573B (en) * | 1976-08-02 | 1978-06-28 | Uop Inc | Process for separating a monosaccharide from an oligosaccharide by selective adsorption |
| JPS5246290A (en) * | 1976-09-17 | 1977-04-12 | Erepon Kakoki Kk | Ph control system of waste fluid |
| JPS5577896A (en) * | 1978-12-07 | 1980-06-12 | Meiji Seika Kaisha Ltd | Preparation of high-purity maltose |
| JPS5585395A (en) * | 1978-12-21 | 1980-06-27 | Nippon Shiryo Kogyo Kk | Preparation of crystalline maltose |
| JPS6026482B2 (en) * | 1980-07-31 | 1985-06-24 | 日本食品化工株式会社 | Method for producing cyclodextrin |
| JPS5759641A (en) * | 1980-09-26 | 1982-04-10 | Japan Organo Co Ltd | Regenerating method for strong acidic cation exchange resin |
| JPS57209000A (en) * | 1981-06-17 | 1982-12-22 | Organo Kk | Decomposition of maltose |
-
1981
- 1981-08-03 JP JP56121725A patent/JPS5823799A/en active Granted
-
1982
- 1982-08-02 DE DE19823228838 patent/DE3228838A1/en active Granted
- 1982-08-03 CA CA000408629A patent/CA1215361A/en not_active Expired
- 1982-08-03 FR FR8213526A patent/FR2510581B1/en not_active Expired
- 1982-08-03 GB GB08222390A patent/GB2106912B/en not_active Expired
-
1988
- 1988-06-06 US US07/202,249 patent/USRE33047E/en not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| CA1215361A (en) | 1986-12-16 |
| DE3228838C2 (en) | 1990-03-29 |
| DE3228838A1 (en) | 1983-03-24 |
| GB2106912B (en) | 1986-03-12 |
| USRE33047E (en) | 1989-09-05 |
| JPS5823799A (en) | 1983-02-12 |
| FR2510581B1 (en) | 1987-10-16 |
| JPS6251120B2 (en) | 1987-10-28 |
| FR2510581A1 (en) | 1983-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19980803 |
