JPH0249796A - Polyacetyloligosaccharide derivative - Google Patents
Polyacetyloligosaccharide derivativeInfo
- Publication number
- JPH0249796A JPH0249796A JP9787489A JP9787489A JPH0249796A JP H0249796 A JPH0249796 A JP H0249796A JP 9787489 A JP9787489 A JP 9787489A JP 9787489 A JP9787489 A JP 9787489A JP H0249796 A JPH0249796 A JP H0249796A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- under reduced
- purified
- stirred
- reduced pressure
- 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.)
- Pending
Links
- 229920001542 oligosaccharide Polymers 0.000 claims description 3
- 150000002482 oligosaccharides Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 9
- 102000004190 Enzymes Human genes 0.000 abstract description 7
- 108090000790 Enzymes Proteins 0.000 abstract description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 239000000758 substrate Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 238000010898 silica gel chromatography Methods 0.000 abstract description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000843 powder Substances 0.000 abstract description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 2
- 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
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229940093499 ethyl acetate Drugs 0.000 abstract 1
- 235000019439 ethyl acetate Nutrition 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000005259 measurement Methods 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 239000011369 resultant mixture Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 235000000346 sugar Nutrition 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 4
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- -1 one with bioaffinity Chemical class 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
- 239000007787 solid Substances 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 102000004139 alpha-Amylases Human genes 0.000 description 1
- 108090000637 alpha-Amylases Proteins 0.000 description 1
- 229940024171 alpha-amylase Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000003028 enzyme activity measurement method Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture 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
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000008163 sugars Chemical group 0.000 description 1
- 238000003786 synthesis reaction 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、非還元末端糖の弘、６位に水酸基を有し、還元末
端にｐ−二トロフェニルグリ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。Detailed Description of the Invention (Field of the Invention) The present invention relates to a non-reducing terminal sugar having a hydroxyl group at the 6-position and a p- This invention relates to polyacetyl oligosaccharide derivatives having ditrophenyl glycosidic bonds.
（背景技術）
非還元末端糖の≠、乙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塘誘導体は、ＩＪ−ビノヒ アナ
レノ デエア ケミ−（４，ｉｂｉｇｓＡｎｎａｌｅｎ
ｄｅｒ Ｃｈｅｍｉｅ ）／ ９１−？、／り１
０〜／り／？頁に記載されている。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。(Background Art) Oligotang derivatives in which only the ≠ and ≠ positions of the non-reducing terminal sugars remain hydroxyl groups and the other hydroxyl groups are protected are IJ-Binohi Analenodea Chemi-(4, ibigsAnnalen
der Chemie) / 91-? ,/ri1
0~/ri/? It is written on the page. In this document, the reducing end is a phenyl glycoside bond.
又、非還元末端糖のび、６位の水酸基を他の水酸基と区
別し、還元末端がｐ−ニトロフェニルグリコシド結合を
有したオリゴ糖誘導体は特開昭６Ｏ−ｊ４ｔ３？！号、
特開昭ＡＯ−ｆ７２９７号、特開昭４ ／ −Ｉ Ｊ
、２タタ号に記載されている。これらの公報においては
、非還元末端糖の≠、６位の水酸基だけが保護されてい
ることを特徴としている。In addition, oligosaccharide derivatives in which the non-reducing terminal sugar extends, the hydroxyl group at the 6-position is distinguished from other hydroxyl groups, and the reducing terminal has a p-nitrophenyl glycosidic bond are disclosed in JP-A-6O-j4t3? ! issue,
JP-A No. AO-f7297, JP-A No. 4 / -I J
, described in the 2nd Tata issue. These publications are characterized in that only the hydroxyl group at the ≠ and 6-position of the non-reducing terminal sugar is protected.
いずれの場合も、非還元末端糖の≠、乙位に水酸基を有
し、還元末端にｐ−ニトロフェニルグリコンド結合金有
したポリアセチルオリゴｆｆＡ９導体に関しては、まっ
たく記載がない。In either case, there is no description at all of the polyacetyl oligo ffA9 conductor which has hydroxyl groups at the ≠ and B positions of the non-reducing terminal sugar and has a p-nitrophenyl glycondo bond at the reducing terminal.
（発明の目的）
本発明の目的は非還元末端糖の弘、２位に水酸基を有し
、還元末端にｐ−ニトロフェニルグリコシド結合を有す
るポリアセチルグリゴ糖誘導体を提供することにある。(Objective of the Invention) The object of the present invention is to provide a polyacetyl glycosaccharide derivative having a hydroxyl group at the first and second positions of the non-reducing end sugar and a p-nitrophenyl glycosidic bond at the reducing end.
（発明の構成） 本発明の化合物は式〔１〕で表わされる。(Structure of the invention) The compound of the present invention is represented by formula [1].
〔１〕
式中ｎはＯ−♂の整数を表わし、Ａｃは−ＣＣＨ３基を
表わす。ｎは好ましくはＯ２／。[1] In the formula, n represents an integer of O-♂, and Ac represents a -CCH3 group. n is preferably O2/.
２．３．ｊである。2.3. It is j.
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 a route for synthesizing the compound of the present invention is shown below, but the method for synthesizing 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／、弘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 compound [1] of the present invention is a substrate whose glycosidic bond is cleaved by a specific enzyme.
この際、非還元末端糖のｊ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切断された非還元末端
ｓ１部分と、ｐ−ニトロフェニルグリコンド、結合を有
す糖部分とをバイオアフィニティーをオ）ｊ用して分け
ることができる。部ち、同−溶液内に過剰の基質が存在
しても酵素の量に応じ、酵素によって切断てれた生成物
の中でｐ−ニトロフェニルグリコン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−二トロ
フェニルグリコンド結合全有した糖部分は、更に酵素で
処理すればｐ−二トロフェノールだけが遊離する。この
ｐ−二トロフェ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。At this time, the non-reducing terminal s1 moiety is cleaved by binding a functional compound, such as one with bioaffinity, to both or one of the hydroxyl groups at the j-position and the 6-position of the non-reducing terminal sugar, and p-nitrophenyl. Glycondos and sugar moieties with bonds can be separated using bioaffinity. However, even if there is an excess of substrate in the same solution, it is possible to separate only the sugar moiety with a p-nitrophenyl glycondo bond from the product cleaved by the enzyme, depending on the amount of enzyme. Become. If the separated sugar moiety having all p-nitrophenyl glycondo bonds is further treated with an enzyme, only p-nitrophenol will be released. By quantifying this p-nitrophenol, the enzyme can be quantitatively determined.
（なおα−アミラーゼの活性を測定するためにｐニトロ
フェノールを定量することは知られてお９、特開昭ｊｊ
−／２１３／号に記載されている。(It is known that p-nitrophenol is quantified in order to measure the activity of α-amylase.9
-/213/ issue.
このよりに、本発明の化合物〔１〕は特定酵素による／
、弘のグリコシド結合切断を利用した酵素活性測定法に
用いる基質の中間体として有用である。Accordingly, the compound [1] of the present invention is produced by a specific enzyme.
, is useful as a substrate intermediate for enzyme activity measurement methods that utilize the glycosidic bond cleavage of Hiromu.
（実施例）
実施例／（ｎ−ｊの一般式〔１〕の化合物の合成）
Ａ）非還元末端糖の≠、６位の選択的保護法ジメチルホ
ルムアミド（ＤＭＦ ） ｘ ｏ ｏｗｌ中にα、α−
ジメトキシトルエン３．よＷＬｔ（／ 、 ！ ｅｑｐ
−トルエンスルホン酸ＪＩＣＩＬＬＩＩ９（０、／ ｅ
、ｑ ）、弘−ニトロフェニル−α−Ｄ−マルトヘプタ
オシド（市販品、Ｇ７−ＰＮＰ ）、２ｏ ｇを溶解さ
せ、減圧（約、ｚ ｏ ｍｍＨｇ ）下ｊＯ°Ｃ−乙ｏ
’Ｃにて弘時間攪拌した。(Example) Example/(Synthesis of compound of general formula [1] of n-j) A) Selective protection method of ≠, 6-position of non-reducing terminal sugar α, in dimethylformamide (DMF) x o owl α−
Dimethoxytoluene 3. YoWLt(/ , ! eqp
-Toluenesulfonic acid JICILLII9 (0, / e
, q), Hiro-nitrophenyl-α-D-maltoheptaoside (commercial product, G7-PNP), 2 o g was dissolved and heated at 0 °C under reduced pressure (approximately 0 mmHg).
The mixture was stirred for a long time at 'C.
反応液を室温まで冷却し、ピリジン３００罰、無水酢酸
／、２θ罰、ジメチルアミノピリジン５００■を加え室
温にて２０時間放置した。The reaction solution was cooled to room temperature, and 300 μm of pyridine, 500 μm of acetic anhydride/2θ, and 500 μm of dimethylaminopyridine were added, and the mixture was allowed to stand at room temperature for 20 hours.
反応ｇ、を氷水に００ｒｔｔｌに注加し、酢酸エチルｊ
ＯＯＣｃにて２回抽出した。有機層を飽和炭酸水素ナト
リウム水１００−にて２回、水１００ｒｔｌにて７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
日別して除去し、口銭を減酸濃縮し、淡黄色の無定形固
体物を得た。Pour reaction g into 00rttl of ice water and add ethyl acetate j
Extracted twice with OOCc. The organic layer was washed twice with 100 ml of saturated sodium bicarbonate water and 7 times with 100 rtl of water, and then dried over sodium sulfate. Sodium sulfate was removed every day, and the solution was concentrated under reduced acid 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
（溶離液ヘキサン／酢酸エチル−／／２（ｖ／ｖ））に
て精製し、化合物■を白色粉末として、２０ｇ（Ｇ７−
ＰＮＰから）収率！ｒ％）をバ
得た。This reaction mixture was purified by silica gel column chromatography (eluent: hexane/ethyl acetate-//2 (v/v)), and 20 g (G7-
from PNP) yield! r%) was obtained.
以下に物性値を示す。The physical property values are shown below.
ｍ、 り、 ／≠／〜／弘５０Ｃ〔α：ｌ、
＋／７／（ＣＨＱ！３、０．９ｒ ）Ｆ
ＡＢ−ＭＳ ２２２１．ｍ／ｅ （Ｍ ＋Ｎａ）”
Ｂ）非還元末端のび、６位の選択的脱保護７０％酢酸水
溶液７罰に化合物■ｔ、７ｇを溶解させ、りｏ ０Ｃに
て７時間攪拌した。m, ri, /≠/～/Hiro50C [α:l,
+/7/(CHQ!3,0.9r)F
AB-MS 2221. m/e (M+Na)”
B) Selective deprotection of the non-reducing terminal and the 6-position 7 g of compound t was dissolved in a 70% aqueous acetic acid solution, and the mixture was stirred at 0°C for 7 hours.
反応液を減圧濃縮し得られた白色固体をシリカゲルカラ
ムクロマトグラフィー（溶離液、ヘキサン、酢酸エチル
＝／：ｚＯ（ｖ／ｖ））にて精製し白色粉末を３．２ｇ
（収率１０％）得た。The reaction solution was concentrated under reduced pressure, and the resulting white solid was purified by silica gel column chromatography (eluent: hexane, ethyl acetate =/:zO (v/v)) to obtain 3.2 g of white powder.
(yield 10%).
以下に物性値を示す。The physical property values are shown below.
ｍ、ｐ、 ； ／ ４”Ｉ 〜／ ｕり０Ｃ〔α
）、 ；＋／ざＡ （ＣＨα３、ｔ、ｏ２）〜ｌ
５（ＦＡＢ）；ｕ／ＪＡｍ／ｅ（（Ｍ＋Ｎａ））’Ｈ−
ＮＭＲ（２ｏ ｏ ＭＨｚ、溶媒ＣＤα３、標準物質Ｔ
ＭＳ ）
δ／、りよ〜λ、ｌに（Ｃ見工３．５１ＡＯＨ）
δ ｒ、ｙｉ （アノマー炭素上Ｈ、ｄ 、
Ｊ −２Ｈｚ 、 ／ Ｈ）δ７．２ｔ１１．２３（０
−Ｃ６Ｈ４
（ｐ−ＮＯ２）、ＡＢ−ｑｕａｒｔｅｔｌＪ ＝ Ｊ
Ｈｚ％≠Ｈ）
ＩＲ（ＫＢｒ法）第１図器照
実施例コ
実施例／に記載の方法に準じて出発物質を各々ｐ−ニト
ロフェニル−α−Ｄ−マルトシド、ｐ−二トロフェニル
ーα−Ｄ−マルトトリオシト、ｐ−ニトロフェニルーα
−Ｄ−マルトハンタオ７ド、ｐ−ニトロフェニル−α−
Ｄ−マルトヘフタオシドに変えて、各々ｎ＝０．ｎ＝／
、ｎ＝３である一般式（Ｉ）の化合物を合成した。以下
にそれらの物性値を記述する。m, p, ; / 4”I ~ / uri0C [α
), ;+/zaA (CHα3, t, o2) ~l
5(FAB); u/JAm/e((M+Na))'H-
NMR (2 o MHz, solvent CDα3, standard substance T
MS) δ/, riyo ~ λ, l (C 3.51 AOH) δ r, yi (H, d on anomeric carbon,
J -2Hz, /H) δ7.2t11.23(0
-C6H4 (p-NO2), AB-quartetlJ = J
Hz%≠H) IR (KBr method) Starting materials were prepared as p-nitrophenyl-α-D-maltoside and p-nitrophenyl-α-D according to the method described in Example 1. -maltotriocyto, p-nitrophenyl α
-D-maltohantao 7-do, p-nitrophenyl-α-
D-maltohephtaoside, each n=0. n=/
, n=3, a compound of general formula (I) was synthesized. The physical property values are described below.
第７図は実施例／で合成されたｎ＝夕の一般式（１）の
化合物のＦＴ−ＩＲスはクトルのグラフである。図中横
軸は波数（Ｃｍ）を、縦軸は吸収を衣わす。FIG. 7 is an FT-IR graph of the compound of general formula (1), where n = 1, synthesized in Example/. In the figure, the horizontal axis represents wave number (Cm), and the vertical axis represents absorption.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9787489A JPH0249796A (en) | 1988-05-20 | 1989-04-18 | Polyacetyloligosaccharide derivative |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12304588 | 1988-05-20 | ||
| JP63-123045 | 1988-05-20 | ||
| JP9787489A JPH0249796A (en) | 1988-05-20 | 1989-04-18 | Polyacetyloligosaccharide derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0249796A true JPH0249796A (en) | 1990-02-20 |
Family
ID=26439015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9787489A Pending JPH0249796A (en) | 1988-05-20 | 1989-04-18 | Polyacetyloligosaccharide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0249796A (en) |
-
1989
- 1989-04-18 JP JP9787489A patent/JPH0249796A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3642576B2 (en) | Method for producing morphine-6-glucuronide or substituted morphine-6-glucuronide | |
| JPS6345293A (en) | Sialosylceramide compound and production thereof | |
| JPS6056994A (en) | Tocopherol derivative | |
| US5011923A (en) | Polyacetyl oligosaccharide derivatives | |
| JPH0249796A (en) | Polyacetyloligosaccharide derivative | |
| Benzing-Nguyen et al. | Stepwise synthesis of N-acetylneuraminic acid and N-acetyl [1-13C] neuraminic acid | |
| Curtis et al. | The Synthesis of 3-O-β-D-Xylopyranosyl-D-Xylose and the Recharacterization of Some Benzylidene Derivatives of D-Xylose | |
| JPH0655753B2 (en) | Novel oligoglucoside derivative, measuring method and measuring reagent for α-amylase | |
| SU514573A3 (en) | The method of obtaining derivatives pregnana | |
| JPS61129197A (en) | Manufacture of pregnane derivative and ester of novel androstane derivative | |
| JPH07508017A (en) | Method for producing steroid-β-O-cellobioside heptaalkanoate | |
| US4496485A (en) | Asymmetric 7-O-(substituted acetyl)-4-demethoxydaunomycinones | |
| JP3016099B2 (en) | Oligosaccharide compound and method for producing the same | |
| JPS61282390A (en) | S-neuraminic acid derivative | |
| JPH0692431B2 (en) | Polyacetyl oligosaccharide derivative | |
| JPS6092300A (en) | Production of soyasapogenol b derivative | |
| JP3029925B2 (en) | Maltooligosaccharide derivatives and their production | |
| JPS62289595A (en) | Production of alpha,beta-nuclear substituted phenylglucoside and alpha,beta-nuclear substituted phenylmalto oligoside | |
| JPH0692432B2 (en) | Polyacetyl oligosaccharide derivative | |
| JP4115066B2 (en) | Carbohydrate amidine derivatives | |
| Flekhter et al. | Synthesis of methyl esters of betulinic acid 2-deoxy-α-glycosides and 28-oxo-19, 28-epoxyoleanane. | |
| JP3070709B2 (en) | Method for producing maltooligosaccharide derivatives | |
| KR850001961B1 (en) | Process for manufacturing 3'-acylated macrolide antibiotics | |
| Jailer et al. | 4β-Acetoxy-Δ5-cholestene-3β, 7α-diol | |
| JPH0283390A (en) | P-nitrophenyl cellooligosaccharide derivative and production thereof |