JPH01152105A - Polysaccharide composite containing amino acid or its polymer bonded thereto - Google Patents
Polysaccharide composite containing amino acid or its polymer bonded theretoInfo
- Publication number
- JPH01152105A JPH01152105A JP26572788A JP26572788A JPH01152105A JP H01152105 A JPH01152105 A JP H01152105A JP 26572788 A JP26572788 A JP 26572788A JP 26572788 A JP26572788 A JP 26572788A JP H01152105 A JPH01152105 A JP H01152105A
- Authority
- JP
- Japan
- Prior art keywords
- amino acid
- polysaccharide
- amino
- polymer
- composite
- 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.)
- Granted
Links
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 29
- 150000004676 glycans Chemical class 0.000 title claims abstract description 23
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 23
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 23
- 229920000642 polymer Polymers 0.000 title claims abstract description 17
- 239000002131 composite material Substances 0.000 title abstract description 9
- 125000003277 amino group Chemical group 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 229920002101 Chitin Polymers 0.000 abstract description 12
- -1 N-carboxy amino acid anhydride Chemical class 0.000 abstract description 9
- 102000004190 Enzymes Human genes 0.000 abstract description 6
- 108090000790 Enzymes Proteins 0.000 abstract description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 abstract description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract description 2
- 229940088597 hormone Drugs 0.000 abstract description 2
- 239000005556 hormone Substances 0.000 abstract description 2
- 230000003993 interaction Effects 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000004587 chromatography analysis Methods 0.000 abstract 2
- 239000000470 constituent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000012046 mixed solvent Substances 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229920001661 Chitosan Polymers 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MEALETCBCJNEFX-LURJTMIESA-N (2s)-5-amino-2-(3-hydroxypropylamino)-5-oxopentanoic acid Chemical compound NC(=O)CC[C@@H](C(O)=O)NCCCO MEALETCBCJNEFX-LURJTMIESA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Chemical compound CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229960004452 methionine Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OJTJKAUNOLVMDX-LBPRGKRZSA-N (2s)-6-amino-2-(phenylmethoxycarbonylamino)hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 OJTJKAUNOLVMDX-LBPRGKRZSA-N 0.000 description 1
- HFZKKJHBHCZXTQ-JTQLQIEISA-N (4s)-4-azaniumyl-5-oxo-5-phenylmethoxypentanoate Chemical compound OC(=O)CC[C@H](N)C(=O)OCC1=CC=CC=C1 HFZKKJHBHCZXTQ-JTQLQIEISA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- 239000004395 L-leucine Substances 0.000 description 1
- 235000019454 L-leucine Nutrition 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- GNWDDDINCIDABX-UHFFFAOYSA-N [1-[2-(carboxyamino)propanoyloxy]-1-oxopropan-2-yl]carbamic acid Chemical compound OC(=O)NC(C)C(=O)OC(=O)C(C)NC(O)=O GNWDDDINCIDABX-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229950010030 dl-alanine Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229960005190 phenylalanine Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、アミノ酸及びアミノ酸重合体の結合した多糖
類複合体に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a polysaccharide complex of amino acids and amino acid polymers.
多糖、アミノ酸及びアミノ酸重合体は、生物の体を構成
する物質であり、生体との親和性が良好であり、また場
合によっては、生体内吸収分解性を有する。また、多糖
とアミノ酸との複合体は、生体成分（酵素、抗体、ホル
モン等）と特異的な相互作用が期待され、免疫吸着剤、
酵素精製用クロマト担体等に応用できる。Polysaccharides, amino acids, and amino acid polymers are substances that constitute the bodies of living organisms, have good affinity with living organisms, and, in some cases, are bioabsorbable and decomposable. In addition, complexes of polysaccharides and amino acids are expected to have specific interactions with biological components (enzymes, antibodies, hormones, etc.), and immunoadsorbents,
It can be applied to chromatographic carriers for enzyme purification, etc.
本発明者らは、アミノ酸又はアミノ酸重合体と多糖との
複合体の調製に鋭意努力した結果、Ｎ−カルボキシアミ
ノ酸無水物とアミノ基を有する多糖とを用いることによ
って、アミノ酸又はアミノ酸重合体をペプチド結合を通
して多糖に結合した複した構造を有するアミノ酸又はそ
の重合体が結合した多糖複合体が提供される。As a result of our earnest efforts to prepare a complex of an amino acid or an amino acid polymer and a polysaccharide, the present inventors have discovered that by using an N-carboxyamino acid anhydride and a polysaccharide having an amino group, an amino acid or an amino acid polymer can be converted into a peptide. A polysaccharide complex is provided in which an amino acid having a complex structure or a polymer thereof is bound to a polysaccharide through a bond.
この複合体において、アミノ酸又はアミノ酸重合体の種
類とアミノ酸結合量を変化させることによって生体内吸
収分解性あるいは、酵素の吸着性を制御することができ
、多糖それ自体では発現できないような、特異的吸着現
象が可能となる。In this complex, by changing the type of amino acid or amino acid polymer and the amount of amino acid bond, it is possible to control bioabsorption and decomposition properties or adsorption properties of enzymes, and it is possible to control specific properties that cannot be expressed with the polysaccharide itself. Adsorption phenomenon becomes possible.
本発明の多糖複合体に結合するアミノ酸重合体としては
、例えば、Ｌ−グルタミン酸ベンジル、Ｌ−アスパラギ
ン酸ベンジル、Ｎ−ベンジルオキシカルボニル−し−リ
ジン、Ｌ−メチオニン、Ｌ−ロイシン、し−フェニルア
ラニン、Ｌ−バリン、Ｎ−ペンジルオキジカルボニル−
し−オルニチン、し−アスパラギン酸。Examples of the amino acid polymer that binds to the polysaccharide complex of the present invention include L-benzyl glutamate, L-benzyl aspartate, N-benzyloxycarbonyl-lysine, L-methionine, L-leucine, and phenylalanine. L-valine, N-penzyloxycarbonyl-
Shi-ornithine, Shi-aspartic acid.
Ｌ−グルタミン酸、Ｎ−ヒドロキシ止チル−し一グルタ
ミン、Ｎ−ヒドロキシプロピル−し−グルタミン、ＤＬ
−アラニン、ＤＬ−ロイシン、ＯＬ−メチオニン等の単
独重合体、またはそれらの２種以上が混合した共重合体
が挙げられる。もう一方の成分であるアミノ基を有する
多糖は、部分的脱アセチル化キチン、キトサン、アミノ
エチルアガロース、グリシルスノ基を有する多糖と、ア
ミノ酸又はその重合体の構成比は、多糖が１０〜９０重
量でである。L-glutamic acid, N-hydroxypropyl-glutamine, N-hydroxypropyl-glutamine, DL
Examples include homopolymers of -alanine, DL-leucine, OL-methionine, and copolymers of two or more thereof. The other component, the polysaccharide having an amino group, is composed of partially deacetylated chitin, chitosan, aminoethyl agarose, a polysaccharide having a glycylsuino group, and an amino acid or its polymer in a composition ratio of 10 to 90% by weight. It is.
本発明の複合体の製造は以下のように行う０例えば、部
分的脱アセチル化キチンをジメチルアセトアミド、メチ
ルピロリドン、塩化リチウム（１０：１０：１重量比）
の混合溶媒に溶解し、Ｎ−カルボキシアミノ酸無水物を
加えて、撹拌溶解させ、キチンのアミノ基にアミノ酸を
順次結合させていく。The preparation of the composite of the present invention is carried out as follows. For example, partially deacetylated chitin is mixed with dimethylacetamide, methylpyrrolidone and lithium chloride (10:10:1 weight ratio).
N-carboxyamino acid anhydride is added to the mixture, and the mixture is stirred and dissolved to sequentially bond the amino acids to the amino groups of chitin.
Ｎ−カルボキシアミノ酸無水物は、アミノ酸とホスゲン
を反応させることによって、合成される。N-carboxyamino acid anhydride is synthesized by reacting an amino acid with phosgene.
この反応を（１）式で示す、ここでアミノ酸をＮＨ，Ｃ
）ＩＲｃＯＯＨで表わし、Ｒはアミノ酸残基の側鎖であ
る。This reaction is shown by formula (1), where amino acids are NH,C
)IRcOOH, where R is the side chain of the amino acid residue.
多糖になる６部分的脱アセチル化キチンは、Ｎ−アセチ
ルグルコサミンとグルコサミンの共重合体であるので、
この反応は（ＩＩ）式のようになる。6 Partially deacetylated chitin, which becomes a polysaccharide, is a copolymer of N-acetylglucosamine and glucosamine, so
This reaction is as shown in formula (II).
Ｎ−カルボキシアミノ酸無水物が多糖のアミノ基に対し
て過剰量存在すれば、最初に結合したアミノ酸のアミノ
基に更に、Ｎ−カルボキシアミノ酸無水物が反応する。If the N-carboxyamino acid anhydride is present in an excess amount with respect to the amino group of the polysaccharide, the N-carboxyamino acid anhydride further reacts with the amino group of the first bonded amino acid.
これを（ｍ）式で示す。This is shown in equation (m).
ここでＸは１から１００程度にするのが望ましい。Here, it is desirable that X be approximately 1 to 100.
また均一溶液系でなくとも、アミノ基を有する多糖に、
アミノ酸又はその重合体を結合させることができる。こ
の場合には、キトサンの粉末をジメチルスルホキシドに
ケンダクさせ、これに、Ｎ−カルボキシアミノ酸無水物
を加え、撹拌することにより、アミノ酸又はその重合体
を結合したキトサン粉末を得ることができる。この場合
も反応は前式と同じである。In addition, even if it is not a homogeneous solution system, polysaccharides with amino groups,
Amino acids or polymers thereof can be attached. In this case, chitosan powder bonded with amino acids or polymers thereof can be obtained by mixing chitosan powder with dimethyl sulfoxide, adding N-carboxyamino acid anhydride, and stirring. In this case as well, the reaction is the same as in the previous equation.
多糖の濃度は０．１〜３０重量％、 Ｎ−力ルボキシア
ミノ酸無水物の濃度は０．１〜２０重量％が適当であり
、多糖とＮ−カルボキシアミノ酸無水物との比は２０〜
０．０５が適当である。The appropriate concentration of polysaccharide is 0.1 to 30% by weight, the concentration of N-carboxyamino acid anhydride is 0.1 to 20% by weight, and the ratio of polysaccharide to N-carboxyamino acid anhydride is 20 to 30% by weight.
0.05 is appropriate.
次に本発明を実施例に基づき、そらに詳細に説装置した
。これに氷２２５ｇを加え撹拌し、均一なアルカリキチ
ン溶液とし、４４時間室温で放置した。Next, the present invention will be explained in detail based on examples. 225 g of ice was added and stirred to form a homogeneous alkaline chitin solution, which was left at room temperature for 44 hours.
これを５℃に保ちながら濃塩酸６０−を撹拌しながら滴
下し、更に２規定塩酸４０ｍＱを滴下し、ｐＨ７にした
。このとき溶液は白濁し、キチンの沈殿が生じた。これ
を遠心分離し、沈殿を水で洗浄することと遠心分離を４
回おこない、上澄に塩素イオンのないことを硝酸銀によ
って確めた。更に、この沈殿に２９％アンモニア水を加
え、遠心分離し、次に水による洗浄と遠心分離を４回行
い、最後に沈殿を乾燥させ、部分的腕アセチルｊヒキチ
ン１．８７ｇを得た。別にＬ−グルタミン酸ベンジル７
．６５ｇをジオキサン１００−にケンダクさせ、トリク
ロロメチルクロロホーメイト３．０−を活性炭上に滴下
させて発生させたホスゲンガスを、それに導入し、５０
℃。While maintaining the temperature at 5°C, 60 mQ of concentrated hydrochloric acid was added dropwise with stirring, and then 40 mQ of 2N hydrochloric acid was added dropwise to adjust the pH to 7. At this time, the solution became cloudy and chitin precipitated. Centrifuge this, wash the precipitate with water, and centrifuge 4 times.
The absence of chloride ions in the supernatant was confirmed using silver nitrate. Furthermore, 29% ammonia water was added to this precipitate, followed by centrifugation, followed by washing with water and centrifugation four times, and finally drying the precipitate to obtain 1.87 g of partially-armed acetyl jhiquitin. Separately, benzyl L-glutamate 7
．． 65 g of dioxane was mixed with 100 g of dioxane, and phosgene gas generated by dropping 3.0 g of trichloromethyl chloroformate onto activated carbon was introduced therein.
℃.
で２時間反応させ、その後、窒素ガスを１時間通した。The mixture was reacted for 2 hours, and then nitrogen gas was passed through the mixture for 1 hour.
ジオキサンを減圧下で蒸留して除去し、Ｎ−カ温で１週
間撹拌した。沈殿を遠心分離し、ジメチルスルホキシド
で２回洗浄と遠心分離を行った。Dioxane was removed by distillation under reduced pressure and stirred at N-ca temperature for 1 week. The precipitate was centrifuged, washed twice with dimethyl sulfoxide, and centrifuged.
次にジオキサンで同様に３回処理した。得られた沈殿を
乾燥した。Next, it was treated with dioxane three times in the same manner. The resulting precipitate was dried.
このようにして製造した複合体の収率は１．３５ｇで重
量増加率は１７１％であった。The yield of the composite thus produced was 1.35 g, with a weight increase rate of 171%.
部分的脱アセチル化キチンと得られた複合体の赤外線吸
収スペクトルの特性吸収ピークを第１表に示す、カッコ
内のＳ、Ｍ、ｖは吸収の強さ、つまり強い、中位１弱い
をそれぞれ表す。The characteristic absorption peaks of the infrared absorption spectrum of the partially deacetylated chitin and the resulting complex are shown in Table 1, where S, M, and v in parentheses represent the absorption strength, that is, strong and medium 1 weak, respectively. represent.
アミノ酸重合体が結合していることを示す赤外線吸収が
、３２９０．１７３５．７５０．７００ｃｍ−１に現わ
れていた。Infrared absorption indicating that the amino acid polymer was bound appeared at 3290.1735.750.700 cm-1.
第１表
実施例２
アルカリキチンの放置時間を１６３時間にしたことを除
いて実施例１と同様に処理して得た部分的脱アセチル化
キチン０．３６ｇをジメチルスルホキシド７０ｍ１１に
ケンダクさせ、実施例１と同様にして、ＤＬ−アラニン
から合成したＮ−カルボキシ−ＤＬ−アラニン無水物１
．６１ｇを加え、１週間撹拌した。水による洗浄と遠心
分離を数回繰り返し、最後にアセトンを加え、沈殿を濾
過し、複合体０．６６９ｇを得た０重量増加率８６％で
あった。得られた複合体と１６３時間処理した部分的脱
アセチル化キチンの赤外線吸収スペクトルの特性吸収ピ
ークを第２表に示す、カッコ内のＳ、Ｍ、Ｗは実施例１
と同じである。Table 1 Example 2 0.36 g of partially deacetylated chitin obtained by the same treatment as in Example 1 except that the alkali chitin was left for 163 hours was dissolved in 70 ml of dimethyl sulfoxide. N-carboxy-DL-alanine anhydride 1 synthesized from DL-alanine in the same manner as 1
．． 61 g was added and stirred for one week. Washing with water and centrifugation were repeated several times, and finally acetone was added and the precipitate was filtered to obtain 0.669 g of a composite, with a weight increase rate of 86%. The characteristic absorption peaks of the infrared absorption spectra of the obtained composite and partially deacetylated chitin treated for 163 hours are shown in Table 2, S, M, and W in parentheses are those of Example 1.
is the same as
第２表Table 2
Claims (1)
なくとも一部が、アミノ酸又はその重合体のカルボキシ
ル基と反応結合した構造を有するアミノ酸又はその重合
体が結合した多糖複合体。(1) A polysaccharide complex in which an amino acid or a polymer thereof has a structure in which at least a part of the amino group is reactively bonded to a carboxyl group of the amino acid or a polymer thereof in a polysaccharide having an amino group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26572788A JPH01152105A (en) | 1988-10-21 | 1988-10-21 | Polysaccharide composite containing amino acid or its polymer bonded thereto |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26572788A JPH01152105A (en) | 1988-10-21 | 1988-10-21 | Polysaccharide composite containing amino acid or its polymer bonded thereto |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25552484A Division JPS61133232A (en) | 1984-12-03 | 1984-12-03 | Composite polysaccharide bonded with amino acid polymer and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01152105A true JPH01152105A (en) | 1989-06-14 |
| JPH0340041B2 JPH0340041B2 (en) | 1991-06-17 |
Family
ID=17421162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26572788A Granted JPH01152105A (en) | 1988-10-21 | 1988-10-21 | Polysaccharide composite containing amino acid or its polymer bonded thereto |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01152105A (en) |
-
1988
- 1988-10-21 JP JP26572788A patent/JPH01152105A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0340041B2 (en) | 1991-06-17 |
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