JPH0253038B2 - - Google Patents
Info
- Publication number
- JPH0253038B2 JPH0253038B2 JP4407184A JP4407184A JPH0253038B2 JP H0253038 B2 JPH0253038 B2 JP H0253038B2 JP 4407184 A JP4407184 A JP 4407184A JP 4407184 A JP4407184 A JP 4407184A JP H0253038 B2 JPH0253038 B2 JP H0253038B2
- Authority
- JP
- Japan
- Prior art keywords
- starch
- cyclodextrin
- butyric acid
- yield
- enzyme
- 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
Links
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 46
- 229920002472 Starch Polymers 0.000 claims description 39
- 239000008107 starch Substances 0.000 claims description 38
- 235000019698 starch Nutrition 0.000 claims description 37
- 229920000858 Cyclodextrin Polymers 0.000 claims description 33
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 21
- 108090000790 Enzymes Proteins 0.000 claims description 11
- 102000004190 Enzymes Human genes 0.000 claims description 11
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229920000881 Modified starch Polymers 0.000 claims description 6
- 235000019426 modified starch Nutrition 0.000 claims description 6
- 229920001353 Dextrin Polymers 0.000 claims description 5
- 239000004375 Dextrin Substances 0.000 claims description 5
- 235000019425 dextrin Nutrition 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 3
- 239000004368 Modified starch Substances 0.000 claims description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 15
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 15
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 15
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 7
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 7
- 239000001116 FEMA 4028 Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229960004853 betadex Drugs 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000178960 Paenibacillus macerans Species 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 241000194107 Bacillus megaterium Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 241000193752 Bacillus circulans Species 0.000 description 1
- 241000194110 Bacillus sp. (in: Bacteria) Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- MKRNVBXERAPZOP-UHFFFAOYSA-N Starch acetate Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OC(C)=O)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 MKRNVBXERAPZOP-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- FYPVXEILSNEKOO-UHFFFAOYSA-L calcium;butanoate Chemical compound [Ca+2].CCCC([O-])=O.CCCC([O-])=O FYPVXEILSNEKOO-UHFFFAOYSA-L 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001254 oxidized starch Substances 0.000 description 1
- 235000013808 oxidized starch Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
本発明はサイクロデキストリンの製法に関す
る。更に詳しくは、でんぷんやその分解反応生成
物などに酪酸および／または酪酸塩の存在下でサ
イクロデキストリン生産酵素を作用させ、α−、
β−、γ−サイクロデキストリンのうちα−サイ
クロデキストリンを選択的に増収するサイクロデ
キストリンの製造方法に関する。
従来法によるサイクロデキストリンの製法には
各種の方法があり、たとえば馬れいしよでんぶ
ん、甘しよでんぷん、トウモロコシでんぷん、モ
チトウモロコシでんぷん、大麦でもぷんにサイク
ロデキストリングルカノトランスフエラーゼを作
用せしめる方法がある。この方法で得られるサイ
クロデキストリンはグルコース６個からなるα−
サイクロデキストリン、７個のβ−サイクロデキ
ストリン、８個のγ−サイクロデキストリンの混
合物よりなり、これらサイクロデキストリンの成
分比率は、サイクロデキストリングルカノトラン
スフエラーゼ産生菌の種類によつて必然的に異な
る。たとえばバチルス・メガテリウム（Bacillus
megaterium）、バチルス属の菌（Bacillus sp.ア
ルカリ生育菌）、バチルス、サーキユランス（B.
circulans）などはβ−サイクロデキストリンを
バチルス・マセランス（B.macerans）はα−サ
イクロデキストリンを主に生成する酵素を産生す
る。バチルス・マセランスの産生する酵素を利用
する場合においても、基質でんぷん濃度が高くな
るにつれてβ−サイクロデキストリンの生成比率
が増加し、αリツチのサイクロデキストリン製品
を経済的に得られないのが現状である。
サイクロデキストリンは種々のゲスト物質を分
子内に取り込み、いわゆる包接化合物を形成する
ため、食品、医薬を問わず用途開発が広く行なわ
れているが、これら各種の用途に応じるために
も、あるいは必要に応じサイクロデキストリン単
品を分別採取する場合においても、成分比率をコ
ントロールできれば非常に好都合である。いずれ
のサイクロデキストリン生産酵素を用いてもβ−
サイクロデキストリンは比較的生成し易すく、ま
た単品分離の場合でも共沈もなく簡単に沈澱、分
離、採取できるが、α−サイクロデキストリンは
分離、採取が困難である。この事実がα−サイク
ロデキストリンの価格をβ−サイクロデキストリ
ンのそれの数十倍に高めている。
α−サイクロデキストリンの含量をβ−サイク
ロデキストリンのそれの二倍程度に高めることに
よつて上記問題の解決につながることから、本発
明者らは酵素反応に際に各種の有機酸および有機
酸塩を用い、α−サイクロデキストリン・リツチ
の反応生成物を得る方法について鋭意研究を重ね
た。その結果、酪酸および／または酪酸塩を使用
することが有効できることを見出し、本発明を完
成するに至つたのである。
本発明はでんぷんまたはその組成画分、焙焼デ
キストリン、化工でんぷん、でんぷん誘導体、物
理的処理でんぷんおよびα−でんぷんよりなる群
から選ばれた１種もしくは２種以上の物質に、酪
酸および／または酪酸塩の存在下でサイクロデキ
ストリン生産酵素を作用させることを特徴とする
サイクロデキストリンの製法である。
すでにアルコール類等の有機溶剤を添加してサ
イクロデキストリンの増収をはかることが提案さ
れているが、この方法ではアルコール類等の回収
再使用が簡単でなく、製造コストが高くなるのが
欠点である。これに対して酪酸および／または酪
酸塩を用いる場合は、各種の方法で酪酸等を容易
に分離再使用することができる。
本発明の方法に用いるでんぷんは、馬れいしよ
でんぷん、甘しよでんぷん、トウモロコシでんぶ
んなど各種のものがあり、特定のでんぷんに限定
されないが、より高収率のα−サイクロデキスト
リンを求める場合には馬れいしよでんぷんが好ま
しい。また、でんぷんの組成画分としては、たと
えばアミロース、アミロペクチンなどがあり、焙
焼デキストリンとしては白色デキストリン、黄色
デキストリン、ブリテイツシユガムなどがある。
化工でんぷんとしては酸化でんぷん、低粘性変性
（酵素、酸、機械高速撹拌等の処理による）でん
ぷん等がある。さらにでんぷん誘導体としては、
たとえばリン酸でんぷん、酢酸でんぷんなどので
んぷんエーテルやでんぷんエステルなどがあり、
物理的処理でんぷんとしては、たとえば放射線や
中性子線を照射したり高周波処理あるいは湿熱処
理したでんぷんなどがある。本発明に用いるでん
ぷん類は単独で用いてもよく、２種以上を組合せ
て用いてもよい。でんぷん濃度は５〜30％の範囲
で任意の濃度を選択でき、酪酸等の添加率５〜20
％（対でんぷん重量、酪酸換算、以下同じ。）好
ましくは５〜10％でα−サイクロデキストリンの
収率を向上させることができるが、α−サイクロ
デキストリン含量を最も高め、かつ総サイクロデ
キストリン含量を最も高める条件ででんぷん濃度
15％、酪酸および／または酪酸塩の添加率10％〜
15％のときである。酪酸等の添加時期は転移反応
開始直後がも好ましいが、反応開始後２時間まで
効果が認めれる。なお酪酸塩としては酪酸テトリ
ウム、酪酸カルシウム等が好ましいものである。
酪酸と酪酸塩以外の有機酸および有機酸塩の添
加効果についても検討した。その結果プロピオン
酸ナトリウムは酪酸に比べてα−サイクロデキス
トリン、総−サイクロデキストリン生成量は少な
いが、α／β比率の改善効果が認められた。ま
た、乳酸、乳酸ナトリウム、プロピオン酸、酢
酸、酢酸ナトリウムも添加条件によつては一部効
果が認められるので、サイクロデキストリンの製
造に利用することは可能であるが、酪酸等の著し
い効果には今一つ及ばない。
次に本発明を実施例によつて詳しく説明する。
実施例 １
馬れいしよでんぷん（水分含量18％）を水で
５、10、15、20％の各濃度に調製し、、マセラン
ス酵素をでんぷんｇ当たり5THU（チルデン−ハ
ドソン単位）加え、65℃で２時間撹拌しながら反
応させたのち、液温を95℃に上げ30分間保つた。
しかるのち液温を50℃に下げ、酪酸をでんぷん重
量あたり０、５、10、15、20、30％加え、水酸化
ナトリウムでPHを6.0に調製したのちに再度マセ
ランス酵素をでんぷんｇ当たり10THU加え、50
℃で24時間撹拌しながら反応させた。反応で得ら
れたサイクロデキストリン成分を高速液体クロマ
トグラフイで定量分析した。分析結果を表−１に
示す。
The present invention relates to a method for producing cyclodextrin. More specifically, starch and its decomposition reaction products are treated with a cyclodextrin-producing enzyme in the presence of butyric acid and/or butyrate to produce α-,
The present invention relates to a method for producing cyclodextrin that selectively increases the yield of α-cyclodextrin among β- and γ-cyclodextrins. There are various conventional methods for producing cyclodextrin, including a method in which cyclodextrin glucanotransferase is applied to horse starch, sweet starch, corn starch, waxy corn starch, and barley starch. . The cyclodextrin obtained by this method is α-
It consists of a mixture of cyclodextrin, 7 β-cyclodextrins, and 8 γ-cyclodextrins, and the component ratio of these cyclodextrins necessarily differs depending on the type of cyclodextrin glucanotransferase-producing bacteria. For example, Bacillus megaterium (Bacillus megaterium)
megaterium), Bacillus sp. alkaline growing bacteria, Bacillus circulans (B.
Bacillus macerans mainly produces enzymes that mainly produce β-cyclodextrin, and B. macerans mainly produces α-cyclodextrin. Even when using the enzyme produced by Bacillus macerans, the ratio of β-cyclodextrin production increases as the substrate starch concentration increases, making it difficult to economically obtain α-rich cyclodextrin products. . Cyclodextrins incorporate various guest substances into their molecules to form so-called clathrate compounds, so they are being developed for a wide range of applications in both food and medicine. Even when separately collecting individual cyclodextrin products, it would be very convenient if the component ratio could be controlled. β-
Cyclodextrin is relatively easy to produce and can be easily precipitated, separated, and collected without coprecipitation even when separated singly, but α-cyclodextrin is difficult to separate and collect. This fact makes the price of α-cyclodextrin several tens of times higher than that of β-cyclodextrin. Since the above problem can be solved by increasing the content of α-cyclodextrin to about twice that of β-cyclodextrin, the present inventors have found that increasing the content of α-cyclodextrin to about twice that of β-cyclodextrin can solve the above problem. We have conducted intensive research on a method for obtaining α-cyclodextrin-rich reaction products using As a result, they found that it is effective to use butyric acid and/or butyrate, and have completed the present invention. The present invention provides for adding butyric acid and/or butyric acid to one or more substances selected from the group consisting of starch or its composition fraction, roasted dextrin, modified starch, starch derivatives, physically treated starch, and α-starch. This is a method for producing cyclodextrin, which is characterized by allowing a cyclodextrin-producing enzyme to act in the presence of salt. It has already been proposed to increase the yield of cyclodextrin by adding organic solvents such as alcohols, but the disadvantage of this method is that it is not easy to recover and reuse the alcohols and the production costs are high. . On the other hand, when butyric acid and/or butyrate is used, butyric acid and the like can be easily separated and reused by various methods. There are various types of starch used in the method of the present invention, such as horse starch, sweet starch, corn starch, etc., and the starch is not limited to a specific one, but if a higher yield of α-cyclodextrin is desired, Horse starch is preferred. Examples of starch composition fractions include amylose and amylopectin, and examples of roasted dextrin include white dextrin, yellow dextrin, and British gum.
Modified starches include oxidized starch, starch modified with low viscosity (by treatment with enzymes, acids, high-speed mechanical stirring, etc.), and the like. Furthermore, as starch derivatives,
Examples include starch ethers and starch esters such as starch phosphate and starch acetate.
Physically treated starch includes, for example, starch that has been irradiated with radiation or neutron beams, high frequency treatment, or moist heat treatment. The starches used in the present invention may be used alone or in combination of two or more. Any starch concentration can be selected within the range of 5 to 30%, and the addition rate of butyric acid, etc. is 5 to 20%.
% (based on starch weight, butyric acid equivalent, the same applies hereinafter) The yield of α-cyclodextrin can be improved preferably at 5 to 10%, but it is preferable to increase the α-cyclodextrin content most and to reduce the total cyclodextrin content. Starch concentration under the highest conditions
15%, addition rate of butyric acid and/or butyrate 10% ~
15%. It is preferable to add butyric acid, etc. immediately after the start of the transfer reaction, but the effect is observed up to 2 hours after the start of the reaction. As the butyrate, tetrium butyrate, calcium butyrate, etc. are preferable. The effects of adding organic acids and organic salts other than butyric acid and butyrate were also investigated. As a result, although sodium propionate produced less α-cyclodextrin and total cyclodextrin than butyric acid, an improvement effect on the α/β ratio was observed. In addition, lactic acid, sodium lactate, propionic acid, acetic acid, and sodium acetate have some effects depending on the addition conditions, so they can be used for the production of cyclodextrin, but the remarkable effects of butyric acid, etc. Not even close. Next, the present invention will be explained in detail with reference to Examples. Example 1 Horse starch (moisture content 18%) was prepared with water to concentrations of 5, 10, 15, and 20%, and 5 THU (Tilden-Hudson units) of maceran enzyme was added per g of starch, and the mixture was heated at 65°C for 2 hours. After reacting with stirring for an hour, the liquid temperature was raised to 95°C and maintained for 30 minutes.
Afterwards, lower the liquid temperature to 50℃, add butyric acid at 0, 5, 10, 15, 20, 30% per starch weight, adjust the pH to 6.0 with sodium hydroxide, and add macerans enzyme again at 10 THU per gram of starch. , 50
The reaction was allowed to proceed at ℃ for 24 hours with stirring. The cyclodextrin component obtained in the reaction was quantitatively analyzed using high performance liquid chromatography. The analysis results are shown in Table-1.
【表】
表−１から明らかなように、でんぷん濃度15
％、酪酸添加率10％のときにα−サイクロデキス
トリン収率は30.2％と最高に近づき、かつ総サイ
クロデキストリン収率も51.9％と最高になる。他
のでんぷん濃度においても酪酸添加率５〜15％で
α−サイクロデキストリンの収率は無添加に比べ
て約1.5〜２倍に向上する。酪酸添加率が15％以
上になると、でんぷん濃度などによるが、逆にサ
イクロデキストリンの生生成は阻害される傾向に
あり、α−サイクロデキストリン、総サイクロデ
キストリン収率も低下してくる。
実施例 ２
トウモロコシでんぷん64ｇを300mlの水に懸濁
し、15％のでんぷん乳を調製した。このでんぷん
乳を120℃、30分間オートクレープした。ついで、
これを70〜80℃に冷却し、酪酸を9.6ｇ添加し水
酸化ナトリウムでPHを6.0に調製したのち再度マ
セランス酵素をでんぷんｇ当たり10THU加え、
50℃で２時間反応させた。反生成物を定量分析し
た結果を表−２に示す。[Table] As is clear from Table 1, starch concentration 15
%, and when the butyric acid addition rate is 10%, the α-cyclodextrin yield approaches the maximum at 30.2%, and the total cyclodextrin yield also reaches the maximum at 51.9%. Even at other starch concentrations, the yield of α-cyclodextrin is improved by about 1.5 to 2 times when butyric acid is added at a rate of 5 to 15% compared to when no addition is made. When the addition rate of butyric acid exceeds 15%, although it depends on the starch concentration, the production of cyclodextrin tends to be inhibited, and the yield of α-cyclodextrin and total cyclodextrin also decreases. Example 2 64 g of corn starch was suspended in 300 ml of water to prepare 15% starch milk. This starch milk was autoclaved at 120°C for 30 minutes. Then,
This was cooled to 70 to 80°C, 9.6 g of butyric acid was added, the pH was adjusted to 6.0 with sodium hydroxide, and macerans enzyme was added again at 10 THU per g of starch.
The reaction was carried out at 50°C for 2 hours. Table 2 shows the results of quantitative analysis of the reaction product.
【表】
表−２から明らかなように、基質にトウモロコ
シでんぷんを用いてもサイクロデキストリンの収
率、とりわけα−サイクロデキストリンの収率が
大幅に向上する。なお、馬れいしよでんぷんに比
較し若干収率は低くなるが、これはマセランス酵
素の作用特性とでんぷん構造の違いによるものと
思われる。[Table] As is clear from Table 2, even when corn starch is used as a substrate, the yield of cyclodextrin, especially the yield of α-cyclodextrin, is significantly improved. The yield is slightly lower than that of horse starch, but this is thought to be due to the difference in the action characteristics of the macerans enzyme and the starch structure.
Claims (1)
リン、化工でんぷん、でんぷん誘導体、物理的処
理でんぷんおよびα−でんぷんよりなる群から選
ばれた１種もしくは２種以上の物質に、酪酸およ
び／または酪酸塩の存在下でサイクロデキストリ
ン生産酵素を作用させることを特徴とするサイク
ロデキストリンの製法。1. Addition of butyric acid and/or butyrate to one or more substances selected from the group consisting of starch or its composition fraction, roasted dextrin, modified starch, starch derivatives, physically treated starch, and α-starch. A method for producing cyclodextrin, which comprises allowing a cyclodextrin-producing enzyme to act in the presence of the enzyme.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4407184A JPS60188088A (en) | 1984-03-09 | 1984-03-09 | Production method of cyclodextrin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4407184A JPS60188088A (en) | 1984-03-09 | 1984-03-09 | Production method of cyclodextrin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60188088A JPS60188088A (en) | 1985-09-25 |
| JPH0253038B2 true JPH0253038B2 (en) | 1990-11-15 |
Family
ID=12681392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4407184A Granted JPS60188088A (en) | 1984-03-09 | 1984-03-09 | Production method of cyclodextrin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60188088A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5571821A (en) * | 1993-05-20 | 1996-11-05 | Texas Biotechnology Corporation | Sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US5594021A (en) * | 1993-05-20 | 1997-01-14 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US5591761A (en) * | 1993-05-20 | 1997-01-07 | Texas Biotechnology Corporation | Thiophenyl-, furyl-and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US6030991A (en) * | 1993-05-20 | 2000-02-29 | Texas Biotechnology Corp. | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| US5804585A (en) * | 1996-04-15 | 1998-09-08 | Texas Biotechnology Corporation | Thieno-pyridine sulfonamides derivatives thereof and related compounds that modulate the activity of endothelin |
| AT410321B (en) * | 1998-08-11 | 2003-03-25 | Tulln Zuckerforschung Gmbh | METHOD FOR PRODUCING CYCLODEXTRIN |
-
1984
- 1984-03-09 JP JP4407184A patent/JPS60188088A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60188088A (en) | 1985-09-25 |
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