JPH0262890A - Polyacetyloligosaccharide derivative - Google Patents
Polyacetyloligosaccharide derivativeInfo
- Publication number
- JPH0262890A JPH0262890A JP21452088A JP21452088A JPH0262890A JP H0262890 A JPH0262890 A JP H0262890A JP 21452088 A JP21452088 A JP 21452088A JP 21452088 A JP21452088 A JP 21452088A JP H0262890 A JPH0262890 A JP H0262890A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- added
- alpha
- compound expressed
- derivative
- 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
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 229920001542 oligosaccharide Polymers 0.000 claims description 5
- 150000002482 oligosaccharides Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000758 substrate Substances 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000002243 precursor Substances 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 abstract description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- 238000010898 silica gel chromatography Methods 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000011369 resultant mixture Substances 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229930182470 glycoside Natural products 0.000 description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000007788 liquid Substances 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
- 241000282994 Cervidae Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- IAYJZWFYUSNIPN-LTHBGAKLSA-N (2r,3r,4s,5s,6r)-2-[(2r,3s,4r,5r,6r)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 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](OC=2C=CC(=CC=2)[N+]([O-])=O)[C@H](O)[C@H]1O IAYJZWFYUSNIPN-LTHBGAKLSA-N 0.000 description 1
- WMXFNCKPYCAIQW-UHFFFAOYSA-N 1,2-dimethoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1OC WMXFNCKPYCAIQW-UHFFFAOYSA-N 0.000 description 1
- 101000737090 Agrotis ipsilon Neuropeptide CCHamide-2 Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 239000005457 ice water Substances 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
- -1 one with bioaffinity Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing 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)
Abstract
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≠、を位が保換され、還元末端に
ｐ−アミノフェニルグルコシド結合ｔＭしたポリアセチ
ルオリゴ糖誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of the Invention) The present invention relates to a non-reducing end sugar that is useful as a precursor for a substrate for measuring enzyme activity, in which the ≠ position is conserved, and p-amino at the reducing end. The present invention relates to a polyacetyl oligosaccharide derivative with phenyl glucoside bonds.
（従来の技術）
非還元末端糖の≠、６位のみが水酸基の１まで他の水酸
基が保護されたオリゴ糖誘導体は、ＩＪ−ビツヒ アナ
レン デエア ケミ−（ＬｉｂｉｇｓＡｎｎａｌｅｎ
ｄｅｒ Ｃｈｅｍｉｅ ）／りｒ３、／り／θ〜／
り／夕に記載されている。この文献においては、還元末
端がフェニルグリコシド結合となっている。(Prior art) Oligosaccharide derivatives in which ≠ and other hydroxyl groups are protected at only the 6th position of the non-reducing terminal sugar are IJ-Annalen Deer Chemie (LibigsAnnalen Deer Chemie).
der Chemie )/ri r3,/ri/θ~/
It is written in the evening. In this document, the reducing end is a phenyl glycoside bond.
又、非還元末端糖の≠、６位の水酸基を他の水酸基と区
別し、還元末端かに一アミノフェニルグリコシド結合金
有したオリゴ糖誘導体は特開昭６０−ｊ≠３りｊ１特開
昭１．０−４７２２７、特開昭Ａ／−４３１タタに記載
されている。こｎらの公報においては、非還元末端糖の
≠、乙位の水酸基だけしか保護されていない。In addition, the hydroxyl group at the ≠ and 6-position of the non-reducing end sugar is distinguished from other hydroxyl groups, and oligosaccharide derivatives having a monoaminophenyl glycoside bond at the reducing end are disclosed in JP-A-60-J≠3-J1. 1.0-47227, and is described in Japanese Patent Application Laid-open No. 1999-431 Tata. In these publications, only the hydroxyl groups at the ≠ and B positions of the non-reducing terminal sugar are protected.
いずれの場合も非還元末端部分音さらに官能基で修飾す
るために弘、６位の非還元末端位と他の水酸基を別々の
形で保護し７′ｃｐ−アミノフェニルグルコシド結合全
市したポリアセチルオリゴ糖誘導体に関しては、１つた
く記載がない。In both cases, in order to modify the non-reducing terminal partial with a functional group, the non-reducing terminal position at the 6-position and other hydroxyl groups were protected separately, and the polyacetyl oligomer was bonded with a 7'cp-aminophenyl glucoside bond. Regarding sugar derivatives, there is no mention at all.
（発明の目的）
本発明の目的は非還元末端抛の≠、乙位が保護され、還
元末端にｐ−アミノフェニルグリ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) The object of the present invention is to provide a polyacetyl oligosaccharide derivative in which the ≠ and ≠ positions of the non-reducing end are protected and have a p-aminophenyl glycosidic bond at the reducing end.
（発明の構成） い。(Structure of the invention) stomach.
以下に本発明の好ましい具体例を物性値と共に列接する
。Preferred specific examples of the present invention are listed below along with physical property values.
（／］
式中ｎはＯ〜りの整数を表わし、Ａｃは−ＣＣＨｓ基を
表わす。Ｒ％ｌ（１は水素原子、アルキル基、フェニル
基を表わす。ｎは好ましくはｎ＝／、コ、≠、！である
。ＪＲＩのアルキル基としてはメチル基が好ましい。Ｒ
，Ｒ’としては片方が水素原子で他方がメチル基または
フェニル基の場合、及び両方がメチル基の場合が好１し
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。(/] In the formula, n represents an integer from O to 2, and Ac represents a -CCHs group. R%l (1 represents a hydrogen atom, an alkyl group, or a phenyl group. n is preferably n=/, co, ≠,!.The alkyl group of JRI is preferably a methyl group.R
, R' is preferably a hydrogen atom and the other is a methyl group or a phenyl group, or both are methyl groups. An example of the route for synthesizing the compound of the present invention is shown below. The method of synthesizing the compounds of the invention is not limited to this route.
（市販品）
〕２
ニージメ
トキシトルエン、
ｐ−）ルエンスルホン酸
一ルホルムアミ
ド
５ン、無水酢酸、ジメチルアミノピリジン；パラジウム
炭素、
メタノール、
水素
（発明の効果）
本発明の化合物〔ｌ〕の脱アセチル体は、特定の酵素に
より’、≠のグリコシド結合が切断される基質である。(Commercially available product) 2 dimethoxytoluene, p-)luenesulfonic acid monolformamide, acetic anhydride, dimethylaminopyridine; palladium on carbon, methanol, hydrogen (effects of the invention) Deacetylation of the compound [l] of the present invention The body is a substrate whose glycosidic bond is cleaved by a specific enzyme.
この際、非還元末端糖のび位、６位の水酸基の両方もし
くは一方に機能性化合物、例えばバイオアフィニティー
をもっ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−アミノフェニルグリコシド結合を有
す糖部分とをバイオアフィニティーを利用して分けるこ
とができる。At this time, a functional compound, such as one with bioaffinity, is bonded to both or one of the hydroxyl group at the 6-position and the non-reducing end sugar position, and the non-reducing end portion is enzymatically cleaved and p-aminophenyl. Sugar moieties with glycosidic bonds can be separated using bioaffinity.
即ち、同−ｍ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、って切断された生成物の中でｐ−アミ
ノフェニルグリコシド結合ｔ［−した糖部分だけを分離
できることになる。分離されたｐ−アミノフェニルグリ
コシド結合ヲ有した糖部分は、更に酵素で処理すればｐ
−アミンフェノールだけが遊離する。このｐ−アミノフ
ェノール誘導体することで酵素の定量ができることにな
る（なおｐ−アミンフェノールの定量法としては、ジャ
ーナル バイオロジカル ケミストリー（Ｊｏｕｒｎａ
ｌＢｉｏｌｏｇｉｃａｌ Ｃｈｅｍｉｓｔｒｙ ）
Ａ ７、ｌＯ（／９ｊ７）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）。In other words, even if there is an excess of substrate in the same solution, only the sugar moiety with the p-aminophenyl glycoside bond t[- is removed in the product cleaved by the enzyme, depending on the amount of the enzyme. It will be possible to separate. The separated sugar moiety with a p-aminophenyl glycoside bond can be further treated with an enzyme to form a p-aminophenyl glycoside bond.
-Only the amine phenol is liberated. Enzymes can be quantified by using this p-aminophenol derivative (a method for quantifying p-aminophenol is described in the Journal Biological Chemistry).
lBiological Chemistry)
The ninhydrin method described in A7, IO(/9j7), etc. 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、微葉のｐ−アミノフェノール誘導
体が測定できることになる。Furthermore, if a highly sensitive dye, fluorescent substance, or photochemical nucleating agent is bonded to the amino group, p-aminophenol derivatives in microphytes can be measured.
よっ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 compounds of the present invention are also very useful as substrate precursors for highly sensitive enzyme detection methods.
実施例１−数式（１）の化合物人−≠の合成人）非還元
末端糖の≠、６位の選択的保護法≠−ニトロフェニル−
α−Ｄ−マルトヘプタオシドジメチルホルムアミド
ジメチルホルムアミド（Ｄ）ｉＦ）λ００ｒｎｔ中にα
、α−ジメトキシトルエンＪ、ｊｒが（／、ｊｅｑ）、
ｋ−トルエンスルホン酸ｓａ弘Ｆｎ９（ｏ、／ｅｑ）、
≠−ニトロフェニルーα−Ｄ−ｖルトヘゾタオシド（市
販品） （Ｇ７−ＰＮＰ ）２０ ？ｋｍｌ１４させ、
減圧（約２０１１１Ｈ？）下ｊＯ°Ｃ〜４０”Ｃにて≠
時間攪拌した。Example 1 - Synthesis of the compound of formula (1) -≠) Selective protection method for the ≠, 6-position of the non-reducing terminal sugar≠-nitrophenyl-
α-D-maltoheptaoside dimethylformamide dimethylformamide (D) iF) α in λ00rnt
, α-dimethoxytoluene J, jr (/, jeq),
k-toluenesulfonic acid sahiro Fn9 (o, /eq),
≠-Nitrophenyl α-D-v rutohesotaoside (commercial product) (G7-PNP) 20? kml14,
Under reduced pressure (approximately 20111H?) at 0°C to 40"C≠
Stir for hours.
反応液を室温まで冷却し、ピリジン７００ｍ！、無水酢
酸ｌλＯｍｌ、ジメチルアミノピリジンｊ００〜を加え
室温にて２０時間放置した。The reaction solution was cooled to room temperature, and 700 m! of pyridine was added. , lλOml of acetic anhydride, and dimethylaminopyridine j00~ were added, and the mixture was left at room temperature for 20 hours.
反応液を氷水ｒｏｏｒｙｔｔに圧加し、酢酸エチル！ｏ
ｏｃｃにて２回抽出した。有機ＩＩを飽和炭酸水素ナト
リウム水ｒＯｑｍｔにて２回、水ｒ００ｒｔｔｌ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
を口別して除去し、口液を減圧濃縮し、淡黄色の無定形
固体物を得た。The reaction solution was pressurized into ice water and ethyl acetate! o
Extracted twice with occ. Organic II was dissolved twice in saturated sodium bicarbonate water rOqmt and once in water r00rttl.
After washing twice, it was dried with sodium sulfate. The sodium sulfate was removed by portion, and the oral liquid was concentrated under reduced pressure to obtain 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ィー
（耐離液ヘキサン／酢酸エチル＝／／２（ｖ／ｖｌ）
にて精製し、化合物■全白色粉末としてＡ−！−■２
０ ｒ （Ｇ７−ＰＮＰ カらの収率！ｔ％）を得た
。This reaction mixture was subjected to silica gel column chromatography (separating liquid: hexane/ethyl acetate=//2 (v/vl)).
The compound ■A-! was purified as a completely white powder. −■2
0 r (yield from G7-PNP! t%) was obtained.
以下に物性値を示す。The physical property values are shown below.
ｍ、ｐ、 ／ ＩＩ ／ 〜／ ４ｔｊ ’Ｃ（
α〕 ＋／７／ （ＣＨＱ！ｓ、０．９１）Ｆ
ＡＢ−ＭＳ ２．２λＡｍ／ｅ ［Ｍ＋Ｎ ａ 〕”
Ｂ）ニトロ基の還元
Ａ−≠−■
化合物Ａ−≠−■０．３２をメタノール−０ｒｔｄに浴
解し、よ％パラジウムー炭素０．ＯＪｆを加え、水素雰
囲気下常圧１時間反応させた。m, p, / II / ~ / 4tj 'C (
α] +/7/ (CHQ!s, 0.91)F
AB-MS 2.2λAm/e [M+N a ]”
B) Reduction of nitro group A-≠-■ Compound A-≠-■ 0.32% was dissolved in methanol-0rtd, and 0% palladium-carbon was dissolved. OJf was added, and the mixture was reacted for 1 hour at normal pressure under a hydrogen atmosphere.
不溶性固体をセライトを用いて口過にて除去しメタノー
ルにて洗浄し、口液を集めて減圧濃縮した。Insoluble solids were removed by filtration using Celite, washed with methanol, and the oral liquid 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−≠を白色結晶として０．ＪＰ（定電的）得た。The obtained solid was recrystallized from ethanol, and the target compound A-≠ was converted into white crystals with a 0.0. JP (static) was obtained.
以下に物性値を示す。The physical property values are shown below.
ｍ、ｐ、 ； ／ｊコ〜／Ｉｔ °Ｃ（α〕Ｄ、
＋ ／ ｔｌ ！ （ＣＨＣＪａ、Ｏ６りよ）ＦＡ
Ｂ−ＭＳ ； ２ｒ／タ （Ｍ＋Ｎ ａ ）”２０
０ＭＨｚ−ＦＩＮＭＲ（爵媒ＣＤＣｔａ、標準物質ＴＭ
Ｓ）δ；２．Ｏコ〜２．２弘 （ＣＣＨａ、ｓ１４０Ｍ
）７、／２〜７．２タ （０−ＣｓＨ＋−（ｋ−ＮＨｚ
）、邑弘Ｈ）
実施例λ
実施例１Ｋ記載の方法に準じて、出発物質をそレソｔｔ
ｐ−ニトロフェニル−α−Ｄ−マルトシド、ｐ−ニト
ロフェニル−α−Ｄ−マルトトリオシト、ｐ−二）ｏフ
ェニル−α−Ｄ−マルトハンタオシドに変更することに
よって（１＝／、ｎ＝コ、ｎ＝３である一般式〔ｌ〕の
化合物Ａ−／１Ａ−２、Ａ−Ｊ１＆：合成した。物性値
は前述の通りである。m, p, ; /jko~/It °C(α]D,
+/tl! (CHCJa, O6 Riyo) FA
B-MS; 2r/ta (M+N a )”20
0MHz-FINMR (medium CDCta, standard material TM
S) δ;2. Oko ~ 2.2 Hiro (CCHa, s140M
)7, /2~7.2ta (0-CsH+-(k-NHz
), Hiromu H) Example λ The starting materials were prepared according to the method described in Example 1K.
By changing to p-nitrophenyl-α-D-maltoside, p-nitrophenyl-α-D-maltotriosito, p-di)o-phenyl-α-D-maltohantaoside (1=/, n Compounds A-/1A-2 and A-J1& of the general formula [l] where = co, n = 3 were synthesized.The physical properties 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人
−≠−［相］）の赤外吸収スペクトル（ＫＢｒ法）のグ
ラフである。
特許出願人 富士写真フィルム株式会社４、補正の対象
明細書の「発明の詳細な説明」の慎FIG. 1 is a graph of the infrared absorption spectrum (KBr method) of the compound (-≠-[phase]) used to synthesize the compound of the present invention. Patent applicant Fuji Photo Film Co., Ltd.4, subject of amendment
Claims (1)
＾１は水素原子、アルキル基またはフェニル基を表わす
。[Claims] Polyacetyl oligosaccharide derivative represented by formula [1] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [1] In the formula, n represents an integer from 0 to 9, and Ac represents ▲ mathematical formula, chemical formula, There are tables, etc. ▼ Represents a group. R, R
^1 represents 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 true JPH0262890A (en) | 1990-03-02 |
| JPH0692432B2 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 |
|---|---|
| JPH0692432B2 (en) | 1994-11-16 |
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