JPH0692432B2 - Polyacetyl oligosaccharide derivative - Google Patents
Polyacetyl oligosaccharide derivativeInfo
- Publication number
- JPH0692432B2 JPH0692432B2 JP21452088A JP21452088A JPH0692432B2 JP H0692432 B2 JPH0692432 B2 JP H0692432B2 JP 21452088 A JP21452088 A JP 21452088A JP 21452088 A JP21452088 A JP 21452088A JP H0692432 B2 JPH0692432 B2 JP H0692432B2
- Authority
- JP
- Japan
- Prior art keywords
- polyacetyl
- oligosaccharide derivative
- compound
- positions
- 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 - Fee Related
Links
- 229920001542 oligosaccharide Polymers 0.000 title claims description 6
- 150000002482 oligosaccharides Chemical class 0.000 title claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229930182478 glucoside Natural products 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FSRMLWKBCQFLJA-HTZQGQHSSA-N (2r,3r,4s,5s,6r)-2-[(2r,3s,4r,5r,6r)-6-[(2r,3s,4r,5r,6r)-6-[(2r,3s,4r,5r,6r)-6-[(2r,3s,4r,5r,6r)-6-[(2r,3s,4r,5r,6r)-6-[(2r,3s,4r,5r,6r)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihyd 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]3[C@H](O[C@H](O[C@@H]4[C@H](O[C@H](O[C@@H]5[C@H](O[C@H](O[C@@H]6[C@H](O[C@H](OC=7C=CC(=CC=7)[N+]([O-])=O)[C@H](O)[C@H]6O)CO)[C@H](O)[C@H]5O)CO)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FSRMLWKBCQFLJA-HTZQGQHSSA-N 0.000 description 1
- YXGBAQKCCMQLGH-VQSBMGSQSA-N (2r,3r,4s,5s,6r)-2-[(2r,3s,4r,5r,6r)-6-[(2r,4r,5r,6r)-6-[(2r,3s,4r,5r,6r)-6-[(2r,3s,4r,5r,6r)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dih 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](OC2[C@H](O[C@H](O[C@@H]3[C@H](O[C@H](O[C@@H]4[C@H](O[C@H](OC=5C=CC(=CC=5)[N+]([O-])=O)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O YXGBAQKCCMQLGH-VQSBMGSQSA-N 0.000 description 1
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
【発明の詳細な説明】 （発明の分野） 本発明は、酵素活性測定用基質のための前駆体として有
用な、非還元末端糖の4,6位が保護され、還元末端にｐ
−アミノフエニルグルコシド結合を有したポリアセチル
オリゴ糖誘導体に関する。Description: FIELD OF THE INVENTION The present invention relates to a non-reducing terminal sugar which is protected at the 4 and 6-positions and which is useful as a precursor for a substrate for measuring enzyme activity.
A polyacetyl oligosaccharide derivative having an aminophenyl glucoside bond.
（従来の技術） 非還元末端糖の4,6位のみが水酸基のままで他の水酸基
が保護されたオリゴ糖誘導体は、リービツヒ アナレン
デエア ケミー（Libigs Annalen der Chemie）198
3、1910〜1919に記載されている。この文献において
は、還元末端がフエニルグリコシド結合となつている。(Prior Art) An oligosaccharide derivative in which only the 4- and 6-positions of a non-reducing terminal sugar remain hydroxyl groups and other hydroxyl groups are protected is a Libigs Annalen der Chemie 198.
3, 1910-1919. In this document, the reducing end is a phenylglycoside bond.
又、非還元末端糖の4,6位の水酸基を他の水酸基と区別
し、還元末端がｋ−アミノフエニルグリコシド結合を有
したオリゴ糖誘導体は特開昭60−54395、特開昭50−872
97、特開昭61−63299に記載されている。これらの公報
においては、非還元末端糖の4,6位の水酸基だけしか保
護されていない。Further, oligosaccharide derivatives which distinguish the hydroxyl groups at the 4 and 6-positions of a non-reducing terminal sugar from other hydroxyl groups and have a k-aminophenyl glycoside bond at the reducing terminal are disclosed in JP-A-60-54395 and JP-A-50-395. 872
97, JP-A-61-63299. In these publications, only the hydroxyl groups at the 4th and 6th positions of the non-reducing terminal sugar are protected.
いずれの場合も非還元末端部分をさらに官能基で修飾す
るために4,6位の非還元末端位と他の水酸基を別々の形
で保護したｐ−アミノフエニルグルコシド結合を有した
ポリアセチルオリゴ糖誘導体に関しては、まつたく記載
がない。In any case, a polyacetyl oligo having a p-aminophenyl glucoside bond in which the non-reducing terminal positions at the 4 and 6 positions and other hydroxyl groups are separately protected in order to further modify the non-reducing end portion with a functional group. There is no mention of sugar derivatives.
（発明の目的） 本発明の目的は非還元末端糖の4,6位が保護され、還元
末端にｐ−アミノフエニルグルコシド結合を有するポリ
アセチルオリゴ糖誘導体を提供することにある。(Object of the Invention) An object of the present invention is to provide a polyacetyl oligosaccharide derivative in which the non-reducing terminal sugar is protected at the 4th and 6th positions and has a p-aminophenyl glucoside bond at the reducing end.
（発明の構成） 式中ｎは０〜９の整数を表わし、Acは を表わす。Ｒ、R1は水素原子、アルキル基、フエニル基
を表わす。ｎは好ましくはｎ＝１、２、４、５である。
Ｒ、R1のアルキル基としてはメチル基が好ましい。Ｒ、
R1としては片方が水素原子で他方がメチル基またはフエ
ニル基の場合、及び両方がメチル基の場合が好ましい。(Structure of the invention) In the formula, n represents an integer of 0 to 9, and Ac is Represents R and R 1 represent a hydrogen atom, an alkyl group or a phenyl group. n is preferably n = 1, 2, 4, 5.
The alkyl group of R and R 1 is preferably a methyl group. R,
R 1 is preferably a hydrogen atom on one side and a methyl group or a phenyl group on the other side, and a case where both are methyl groups.
以下に本発明の好ましい具体例を物性値と共に列挙す
る。Preferred specific examples of the present invention are listed below together with physical properties.
本発明の化合物を合成するための経路の一例を次に示す
が、本発明の化合物の合成方法はこの経路に限定される
ものではない。 An example of the route for synthesizing the compound of the present invention is shown below, but the synthetic method of the compound of the present invention is not limited to this route.
（発明の効果） 本発明の化合物〔１〕の脱アセチル体は、特定の酵素に
より1,4のグリコシド結合が切断される基質である。 (Effects of the Invention) The deacetylated form of the compound [1] of the present invention is a substrate in which 1,4 glycoside bonds are cleaved by a specific enzyme.
この際、非還元末端糖の４位、６位の水酸基の両方もし
くは一方に機能性化合物、例えばバイオアフイニテイー
をもつたものを結合させることで酵素で切断された非還
元末端部分と、ｐ−アミノフエニルグルコシド結合を有
す糖部分とをバイオアフイニテイーを利用して分けるこ
とができる。即ち、同一溶液内に過剰の基質が存在して
も酵素の量に応じ、酵素によつて切断された生成物の中
でｐ−アミノフエニルグルコシド結合を有した糖部分だ
けを分離できることになる。分離されたｐ−アミノフエ
ニルグルコシド結合を有した糖部分は、更に酵素で処理
すればｐ−アミノフエノールだけが遊離する。このｐ−
アミノフエノールを定量することで酵素の定量ができる
ことになる（なおｐ−アミノフエノールの定量法として
は、ジヤーナル オブ バイオロジカル ケミストリー
（Journal of Biological Chemistry）67、10（1957）
などに記載されているニンヒドリン法などが知られてい
る）。At this time, a non-reducing end portion cleaved by an enzyme by binding a functional compound, for example, one having bioaffinity to both or one or both of the 4- and 6-hydroxyl groups of the non-reducing terminal sugar, and p -A sugar moiety having an aminophenyl glucoside bond can be separated by utilizing bioaffinity. That is, even if an excess substrate exists in the same solution, only the sugar moiety having a p-aminophenyl glucoside bond can be separated in the product cleaved by the enzyme depending on the amount of the enzyme. . When the separated sugar moiety having a p-aminophenyl glucoside bond is further treated with an enzyme, only p-aminophenol is released. This p-
The enzyme can be quantified by quantifying aminophenol. (As a method for quantifying p-aminophenol, Journal of Biological Chemistry 67, 10 (1957)
The ninhydrin method and the like described in is known).
又、アミノ基に高感度な色素や螢光物質や写真化学的造
核剤を結合させれば、微量のｐ−アミノフエノール誘導
体が測定できることになる。Further, if a highly sensitive dye, a fluorescent substance or a photochemical nucleating agent is bound to the amino group, a trace amount of p-aminophenol derivative can be measured.
よつて本発明の化合物は高感度な酵素検出法の基質の前
駆体としても大変有用である。Therefore, the compound of the present invention is very useful as a precursor of a substrate for a highly sensitive enzyme detection method.
実施例１ 一般式〔１〕の化合物Ａ−４の合成 Ａ）非還元末端糖の４、６位の選択的保護法 ジメチルホルムアミド（DHF）200ml中にα，α−ジメト
キシトルエン3.5ml（1.5eq）、ｋ−トルエンスルホン酸
544mg（0.1eq）、４−ニトロフエニル−α−Ｄ−マルト
ヘプタオシド（市販品）（G7−PNP）20gを溶解させ、減
圧（約20mmHg）下50℃〜60℃にて４時間攪拌した。Example 1 Synthesis of compound A-4 of the general formula [1] A) Selective protection method for 4- and 6-positions of non-reducing terminal sugar Α, α-dimethoxytoluene 3.5 ml (1.5 eq), k-toluenesulfonic acid in 200 ml of dimethylformamide (DHF)
544 mg (0.1 eq), 4-nitrophenyl-α-D-maltoheptaoside (commercially available product) (G 7 -PNP) 20 g was dissolved and stirred at 50 ° C to 60 ° C for 4 hours under reduced pressure (about 20 mmHg). .
反応液を室温まで冷却し、ピリジン300ml、無水酢酸120
ml、ジメチルアミノピリジン500mgを加え室温にて20時
間放置した。The reaction mixture was cooled to room temperature, pyridine 300 ml, acetic anhydride 120
ml and dimethylaminopyridine 500 mg were added and the mixture was allowed to stand at room temperature for 20 hours.
反応液を氷水800mlに注加し、酢酸エチル500ccにて２回
抽出した。有機層を飽和炭酸水素ナトリウム水800mlに
て２回、水800mlにて１回洗浄後硫酸ナトリウムにて乾
燥した。硫酸ナトリウムをロ別して除去し、ロ液を減圧
濃縮し、淡黄色の無定形固体物を得た。The reaction solution was poured into 800 ml of ice water and extracted twice with 500 cc of ethyl acetate. The organic layer was washed twice with 800 ml of saturated aqueous sodium hydrogen carbonate solution and once with 800 ml of water, and dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give a pale yellow amorphous solid.
この反応混合物をシリカゲルカラムクロマトグラフイー
（溶離液ヘキサン／酢酸エチル＝1/2（v/v））にて精製
し、化合物を白色粉末としてＡ−４−20g（G7−PNP
からの収率58％）を得た。The reaction mixture was purified by silica gel column chromatography (eluent hexane / ethyl acetate = 1/2 (v / v)) to give the compound as a white powder, A-4-20 g (G 7 -PNP
Yield 58%) was obtained.
以下に物性値を示す。The physical property values are shown below.
m.p. 141〜145℃ ▲〔α〕31 D▼ ＋171 （CHCl3、0.98） FAB−MS 2226m/e〔Ｍ＋Na〕＋ Ｂ）ニトロ基の還元 化合物Ａ−４−0.3gをメタノール20mlに溶解し、５％
パラジウム−炭素0.03gを加え、水素雰囲気下常圧１時
間反応させた。mp 141-145 ℃ ▲ [α] 31 D ▼ +171 (CHCl 3 , 0.98) FAB-MS 2226m / e [M + Na] + B) Reduction of nitro group Compound A-4-0.3 g was dissolved in 20 ml of methanol to obtain 5%.
Palladium-carbon (0.03 g) was added, and the mixture was reacted under a hydrogen atmosphere at normal pressure for 1 hour.
不溶性固体をセライトを用いてロ過にて除去しメタノー
ルにて洗浄し、ロ液を集めて減圧濃縮した。The insoluble solid was removed by filtration using Celite and washed with methanol, and the filtrate was collected and concentrated under reduced pressure.
得られた固体をエタノールにて再結晶し、目的の化合物
Ａ−４を白色結晶として0.3g（定量的）得た。The obtained solid was recrystallized from ethanol to obtain 0.3 g (quantitative) of the target compound A-4 as white crystals.
以下に物性値を示す。The physical property values are shown below.
m.p.;152〜156℃ ▲〔α〕20 D▼；＋145（CHCl3、0.95） FAB−MS;2219(M+Na)+ 200MHz−HNMR（溶媒CDCl3、標準物質TMS） δ;2.02〜2.24 δ;7.19〜7.29（Ｏ−C6H4−（ｋ−NH2）、ｍ、4H） 実施例２ 実施例１に記載の方法に準じて、出発物質をそれぞれｐ
−ニトロフエニル−α−Ｄ−−マルトトリシド、ｐ−ニ
トロフエニル−α−Ｄ−マルトテトラオシド、ｐ−ニト
ロフエニル−α−Ｄ−マルトペンタオシドに変更するこ
とによつてｎ＝１、ｎ＝２、ｎ＝３である一般式〔１〕
の化合物Ａ−１、Ａ−２、Ａ−３を合成した。物性値は
前述の通りである。mp; 152-156 ° C ▲ [α] 20 D ▼; +145 (CHCl 3 , 0.95) FAB-MS; 2219 (M + Na) + 200MHz-H NMR (solvent CDCl 3 , standard substance TMS) δ; 2.02-2.24 δ; 7.19~7.29 (O-C 6 H 4 - (k-NH 2), m, 4H) according to the method described in Example 1, respectively of the starting material p
By changing to -nitrophenyl-α-D-maltotriside, p-nitrophenyl-α-D-maltotetraoside, p-nitrophenyl-α-D-maltopentaoside, n = 1, n = 2, General formula [1] in which n = 3
Compounds A-1, A-2, and A-3 of Example 1 were synthesized. The physical property values are as described above.
第１図は本発明の化合物を合成するのに用いた化合物Ａ
−４−の赤外吸収スペクトル（KBr法）のグラフであ
る。FIG. 1 shows compound A used to synthesize the compounds of the present invention.
It is a graph of the infrared absorption spectrum (KBr method) of -4-.
Claims (1)
糖誘導体 式中ｎは０〜９の整数を表わし、Acは を表わす。Ｒ、R1は水素原子、アルキル基またはフエニ
ル基を表わす。1. A polyacetyl oligosaccharide derivative represented by the formula [1]. In the formula, n represents an integer of 0 to 9, and Ac is Represents R and R 1 represent a hydrogen atom, an alkyl group or a phenyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21452088A JPH0692432B2 (en) | 1988-08-29 | 1988-08-29 | Polyacetyl oligosaccharide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21452088A JPH0692432B2 (en) | 1988-08-29 | 1988-08-29 | Polyacetyl oligosaccharide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0262890A JPH0262890A (en) | 1990-03-02 |
| JPH0692432B2 true JPH0692432B2 (en) | 1994-11-16 |
Family
ID=16657083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21452088A Expired - Fee Related JPH0692432B2 (en) | 1988-08-29 | 1988-08-29 | Polyacetyl oligosaccharide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0692432B2 (en) |
-
1988
- 1988-08-29 JP JP21452088A patent/JPH0692432B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0262890A (en) | 1990-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |