JPH01299294A - 4,8-anhydro-n-acetyleuramic acid derivative - Google Patents
4,8-anhydro-n-acetyleuramic acid derivativeInfo
- Publication number
- JPH01299294A JPH01299294A JP12633188A JP12633188A JPH01299294A JP H01299294 A JPH01299294 A JP H01299294A JP 12633188 A JP12633188 A JP 12633188A JP 12633188 A JP12633188 A JP 12633188A JP H01299294 A JPH01299294 A JP H01299294A
- Authority
- JP
- Japan
- Prior art keywords
- anhydro
- acid
- compound
- formula
- ammonium
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 8
- XMUBGQUTGWCNOC-LUWBGTNYSA-N (1R,5S,7R,8S,9R)-9-acetamido-3,8-dihydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.1]nonane-3-carboxylic acid Chemical class C1C(O)(C(O)=O)O[C@@]2([H])[C@H](O)[C@@H](CO)O[C@]1([H])[C@H]2NC(C)=O XMUBGQUTGWCNOC-LUWBGTNYSA-N 0.000 claims description 9
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical class CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- 230000001518 anti-nephritic effect Effects 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 229910052700 potassium Inorganic materials 0.000 abstract description 4
- 239000011591 potassium Substances 0.000 abstract description 4
- SQVRNKJHWKZAKO-LUWBGTNYSA-N N-acetylneuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-LUWBGTNYSA-N 0.000 abstract description 3
- 239000012670 alkaline solution Substances 0.000 abstract description 2
- VSELSKPNZNRYFH-VAPHQMJDSA-N C(C)(=O)N[C@@H]1[C@H](CC(C(=O)O)=O)O[C@@H]([C@H]([C@@H]1O)O)CO Chemical compound C(C)(=O)N[C@@H]1[C@H](CC(C(=O)O)=O)O[C@@H]([C@H]([C@@H]1O)O)CO VSELSKPNZNRYFH-VAPHQMJDSA-N 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 6
- 229910001868 water Inorganic materials 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000004108 freeze drying Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229940125682 antidementia agent Drugs 0.000 description 3
- 239000003443 antiviral agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000002664 nootropic agent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- QKFTYFYIYXTFBX-BKSOAOGQSA-M sodium;(2s,4s,5r,6r)-5-acetamido-2,4-dihydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylate Chemical compound [Na+].CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C([O-])=O)O[C@H]1[C@H](O)[C@H](O)CO QKFTYFYIYXTFBX-BKSOAOGQSA-M 0.000 description 3
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000005770 birds nest Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- -1 magnesium Chemical compound 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000005765 wild carrot Nutrition 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、抗ウィルス剤、抗腎炎剤及び抗痴呆剤として
有用な新規４．８−アンハイドロ−Ｎ−アセチルノイラ
ミン酸塩に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel 4,8-anhydro-N-acetylneuraminic acid salt useful as an antiviral agent, an anti-nephritis agent, and an anti-dementia agent.
従来より、４．８−アンハイドロ−Ｎ−アセチルノイラ
ミン酸が、鳥巣に含まれていることはεｕｒ、Ｊ、 Ｂ
ｉｏｃｈｅｍ、 １６２、ｐ４４５〜４５０（１９８
７）により公知である。しかしながら、その抽出量は非
常に微量であり、その生理活性等の検討はこれまで十分
になされていなかった。It has been known that 4,8-anhydro-N-acetylneuraminic acid is contained in bird's nest.
iochem, 162, p445-450 (198
7). However, the amount extracted is extremely small, and its physiological activity has not been sufficiently investigated.
本発明者は上記４．８−アンハイドロ−Ｎ−アセチルノ
イラミン酸塩を多量に得るべく鋭意検討し、その製法を
確豆するとともに、４，８−アンハイドロ−Ｎ−アセチ
ルノイラミン酸塩が抗ウィルス剤、抗腎炎剤及び抗痴呆
剤として有用であることを見い出し、本発明に至ったも
のである。なお、この４，８−アンハイドロ−Ｎ−アセ
チルノイラミン酸塩が各種の重要な細胞表面糖鎖の構成
成分であるＮ−アセチルノイラミン酸塩類及びＮ−アセ
チ、ルマンノサミンの合成中間体としても有用であるこ
とが分った。The present inventor has made extensive studies to obtain a large amount of the above-mentioned 4,8-anhydro-N-acetylneuraminic acid salt, and has confirmed the production method. The inventors have discovered that the compound is useful as an antiviral agent, an anti-nephritis agent, and an anti-dementia agent, leading to the present invention. In addition, this 4,8-anhydro-N-acetylneuraminate is also used as a synthetic intermediate for N-acetylneuraminates, N-acetyl, and lumannosamine, which are constituent components of various important cell surface sugar chains. I found it useful.
本発明は、抗ウィルス剤、抗腎炎剤及び抗痴呆剤として
有用性を有する４、８−アンハイドロ−Ｎ−アセチルノ
イラミン酸塩を提供することを目的とする。An object of the present invention is to provide 4,8-anhydro-N-acetylneuraminic acid salt, which has utility as an antiviral agent, an anti-nephritis agent, and an anti-dementia agent.
本発明は、
一般式：
（ただし、Ｍはアルカリ金属、アルカリ土類金属又はア
ンモニウムでアル）
で表わされる４、８−アンハイドロ−Ｎ−アセチルノイ
ラミン酸塩、及び
上記４．８−アンハイドロ−Ｎ−アセチルノイラミン酸
塩の製造方法であって、
Ｈ
（ただし、Ｍは上記の定義の通りである）で表わされる
Ｎ−アセチルノイラミン酸塩を、酸あるいはアルカリ又
は熱で処理する方法、に関する。The present invention provides a 4,8-anhydro-N-acetylneuraminic acid salt represented by the general formula: (M is alkali metal, alkaline earth metal, or ammonium); - A method for producing N-acetylneuraminic acid salt, comprising treating N-acetylneuraminic acid salt represented by H (where M is as defined above) with acid, alkali, or heat. , regarding.
以下、本発明について詳述する。The present invention will be explained in detail below.
本発明の４．８−アンハイドロ−Ｎ−アセチルノイラミ
ン酸塩は以下の一般式（Ｉ）で表わされる。The 4,8-anhydro-N-acetylneuraminic acid salt of the present invention is represented by the following general formula (I).
ここで、Ｍはアルカリ金属、アルカリ土類金属又はアン
モニウムである。例えば、ナトリウム、カリウムなどの
アルカリ金属、マグネシウムなどのアルカリ土類金属、
更にはアンモニウムが挙げられる。なお、Ａｃはアセチ
ル基を表わｔ′。Here, M is an alkali metal, an alkaline earth metal or ammonium. For example, alkali metals such as sodium and potassium, alkaline earth metals such as magnesium,
Further examples include ammonium. Note that Ac represents an acetyl group and t'.
この化合物は、例えば、次式（■）：
Ｈ
（ここで、Ｍ及びＡＣは上記定義通りである。）で表わ
されるＮ−アセチルノイラミン酸塩を酸、アルカリ、又
は熱で処理することによって製造することかできる。This compound can be produced, for example, by treating N-acetylneuraminate represented by the following formula (■): H (where M and AC are as defined above) with acid, alkali, or heat. Can be manufactured.
ここで、上記化合物（ＩＩ）は公知であり、容易に人手
可能な化合物である。Here, the above-mentioned compound (II) is a known compound and can be easily produced manually.
化合物（ｎ）の処理に使用する酸としては、塩酸、硫酸
等が挙げられる。ｐＨとしては１〜２が適当である。Examples of the acid used for treating compound (n) include hydrochloric acid and sulfuric acid. A suitable pH is 1 to 2.
アルカリ処理としては、水酸化ナトリウム、水酸化カリ
ウムなどのアルカリ溶液による処理が挙げられる。ｐＨ
としては１０〜１１が適当である。Examples of the alkaline treatment include treatment with alkaline solutions such as sodium hydroxide and potassium hydroxide. pH
10 to 11 is appropriate.
化合ｙＡ（１）は上記化合物（ＩＩ）を加熱することに
よっても得られる。通常、４０〜１８０℃で行なわれ、
一般ｉご溶媒が使用される。溶媒としては、水、及びＮ
ａ、Ｃｏ、、ＮａＨＣＯｓ、クラークールブスなどの各
種緩衝液等が使用される。Compound yA (1) can also be obtained by heating the above compound (II). Usually carried out at 40-180℃,
General solvents are used. As a solvent, water and N
Various buffer solutions such as a, Co, NaHCOs, and Clarke Cools are used.
化合物（ＩＩ）の酸、アルカリ又は熱処理時間は一般に
２０分〜３０時間である。The acid, alkali or heat treatment time of compound (II) is generally 20 minutes to 30 hours.
以下、本発明について実施例により更に詳述する。 Hereinafter, the present invention will be explained in more detail with reference to Examples.
実施例１
Ｎ−アセチルノイラミン酸ナトリウム１０ｇを水１５０
ｍｆに゛溶かし、水酸化ナトリウムＯ，ｌ ｇを加えた
後、８０℃にて１時間撹はんした。反応液を凍結乾燥し
た後、残留物にメタノールを加えて溶かし、アセトニト
リル−水（６：１）を用いてセルロースカラムクロマト
グラフィーにて分離精製し溶媒を留去した。残留物をメ
タノールにて再結晶化し、無色結晶３．３４０ ｇを得
た（収率３５．３％、原料回収２４．４％）。Example 1 10 g of sodium N-acetylneuraminate in 150 g of water
After dissolving the mixture in mf and adding 0.1 g of sodium hydroxide, the mixture was stirred at 80°C for 1 hour. After freeze-drying the reaction solution, the residue was dissolved in methanol, separated and purified by cellulose column chromatography using acetonitrile-water (6:1), and the solvent was distilled off. The residue was recrystallized from methanol to obtain 3.340 g of colorless crystals (yield 35.3%, raw material recovery 24.4%).
元素分析 Ｃ＋＋ｔｌ＋５ＮＯ８Ｎａ
計算値 Ｃ：４２．１８． Ｈ：５．１５． Ｎ：
４．４７゜実測値 Ｃ：４１．９０． Ｈ：５．３６
． Ｎ：４．５３゜分子量 ３１３．２５
〔α〕。−３４，１°（ｃｍ０．５０． Ｈ２Ｏ）融
点 ２１７℃（分解）
’Ｈ−Ｎ！ＪＲ（５００Ｌ４Ｈｚ、 ロ２０）。
δ（４，７５ｐｐ＋ｎ、 Ｉｔ、Ｏ）２．１４ （
３Ｈ，ｓ、 ＮＡｃ）
２．９１ （１）１． ｄｄ、 Ｊ＝４．４および１７
．６１１ｚ、 ３−）り３．０５ （１）１． ｄｄ、
Ｊ＝８．４および１７．６Ｈｚ、 ３−Ｈ）３．４４
（ＩＨ，ｄｄｄ、 Ｊ＝２．２．４．８および９．９
Ｈｚ、 ８−）１）３．５７ （ＬＨ，ｔ、 Ｊ＝９．
９および９．９Ｈｚ、７−Ｈ）３．８１ （１）１．
ｄｄ、 Ｊ＝４．８および１２．５Ｈｚ、 ９−１４）
３．８９ （ＬＨ，ｄｄ、 Ｊ＝２．２および１２．５
Ｈｚ、 ９−ｔｌ）３．９２ （１）！、 ｄｄ、 Ｊ
＝４．４および９．９Ｈｚ、 ６−Ｈ）４．２７ （１
１（、ｄｄｄ、 Ｊ＝１．８，４．４および８．４Ｈｚ
、 ４−Ｈ）４．４０ （１）１． ｄｄ、 Ｊ＝１．
８および４．４Ｈｚ、 ５−Ｈ）ＩＲｖ、、、 ｃｍ−
’ ：３４４０． ３３８０． ３２３６． ３０６４
（Ｎ−Ｈ，Ｄ−Ｈ）３６００〜２８００ （０−Ｈ）
１７０３、 １６５５． １６３８ （Ｃ＝Ｏ）１５
６８ （ＮＨ）
１０７５、 １０５５． １０２９ （Ｃ−０）１９
３１ｍ （ε＝９０００）
実施例２
Ｎ−アセチルノイラミン酸ナトリウム１０ｇをクラーク
ールブスのｐ）１２．０の緩衝液１００−に溶かし、８
０℃にて７時間撹はんした。反応液を凍結乾燥した後、
残留物にメタノールを加えて溶かし、アセトニトリル−
水（６： １）を用いてセルロースカラムクロマトグラ
フィーにて分離精製し溶媒を留去した。残留物をメタノ
ールにて再結晶化し、無色結晶３．１００ ｇを得た（
収率３２．８％、原料回収１７．１％）。Elemental analysis C++tl+5NO8Na Calculated value C:42.18. H:5.15. N:
4.47° Actual value C: 41.90. H:5.36
．． N: 4.53°Molecular weight 313.25 [α]. -34,1° (cm0.50. H2O) melting
Point 217℃ (decomposition) 'H-N! JR (500L4Hz, Ro20).
δ(4,75pp+n, It, O)2.14 (
3H,s, NAc) 2.91 (1)1. dd, J=4.4 and 17
．． 611z, 3-)ri3.05 (1)1. dd,
J=8.4 and 17.6Hz, 3-H) 3.44
(IH, ddd, J=2.2.4.8 and 9.9
Hz, 8-)1) 3.57 (LH, t, J=9.
9 and 9.9Hz, 7-H) 3.81 (1)1.
dd, J=4.8 and 12.5Hz, 9-14)
3.89 (LH, dd, J=2.2 and 12.5
Hz, 9-tl) 3.92 (1)! , dd, J
=4.4 and 9.9Hz, 6-H)4.27 (1
1(,ddd, J=1.8, 4.4 and 8.4Hz
, 4-H) 4.40 (1)1. dd, J=1.
8 and 4.4Hz, 5-H) IRv, , cm-
' :3440. 3380. 3236. 3064
(NH, D-H) 3600-2800 (0-H) 1703, 1655. 1638 (C=O)15
68 (NH) 1075, 1055. 1029 (C-0)19
31 m (ε=9000) Example 2 10 g of sodium N-acetylneuraminate was dissolved in Clark Koolbus p) 12.0 buffer 100-.
The mixture was stirred at 0°C for 7 hours. After freeze-drying the reaction solution,
Dissolve the residue in methanol and dilute with acetonitrile.
The mixture was separated and purified by cellulose column chromatography using water (6:1), and the solvent was distilled off. The residue was recrystallized from methanol to obtain 3.100 g of colorless crystals (
Yield: 32.8%, raw material recovery: 17.1%).
化合物の物性値は実施例１のものと同一であった。The physical properties of the compound were the same as those of Example 1.
実施例３
Ｎ−アセチルノイラミン酸ナトリウム１０ｇを１４０℃
にて３時間加熱後、メタノールを加えて溶かし、アセト
ニトリル−水（６：１）を用いてセルロースカラムクロ
マトグラフィーにて分離精製し溶媒を留去した。残留物
をメタノールにて再結晶し、無色結晶３．９８０ ｇを
得た（収率４２．１％、原料回収４．３．０％）。Example 3 10g of sodium N-acetylneuraminate at 140°C
After heating for 3 hours, methanol was added to dissolve the mixture, and the mixture was separated and purified by cellulose column chromatography using acetonitrile-water (6:1), and the solvent was distilled off. The residue was recrystallized from methanol to obtain 3.980 g of colorless crystals (yield 42.1%, raw material recovery 4.3.0%).
化合物の物性値は実施例１のものと同一であった。The physical properties of the compound were the same as those of Example 1.
実施例４
５−アセトアミド−４，８−アンヒドロ−３゜５−ジデ
オキシ−Ｄ−グリセロ−〇−ガラクトーノニュロソン酸
のカリウム、マグネシウム、アンモニウム等の各種塩に
ついて各々実施例１．２および３と同様にして製造した
。すなわち、Ｎ−アセチルノイラミン酸の対応するそれ
ぞれの塩を粉体加熱、アルカリ又は酸性の水溶液中で扱
い、反応させたものをアセトニトリル−水（６：１）を
用いてセルロースカラムクロマトグラフィーにて分離精
製し、凍結乾燥して相当する塩を得た。Example 4 Examples 1.2 and 3 were prepared for various salts of 5-acetamido-4,8-anhydro-3゜5-dideoxy-D-glycero-〇-galactononeurosonic acid such as potassium, magnesium, and ammonium, respectively. It was manufactured in the same manner. That is, each corresponding salt of N-acetylneuraminic acid was heated as a powder, treated in an alkaline or acidic aqueous solution, and the reacted product was subjected to cellulose column chromatography using acetonitrile-water (6:1). The corresponding salt was obtained by separating and purifying and freeze-drying.
５−アセトアミド−４，８−アンヒドロ−３゜５−ジデ
オキシ−Ｄ−グリセロ−Ｄ−ガラクトーノニュロソン酸
カリウム
ＩＲ１’ａｍ、ＩＣｍ−’ ：３３００ （０−Ｈ）１
７２０、１６３２．１５４５ （Ｃ＝０）１０７８ （
Ｃ−０）
５−アセトアミド−４，８−アンヒドロ−３゜５−ジデ
オキシ−Ｄ−グリセロ−Ｄ−ガラクトーノニュロソン酸
マグネシウム
ＩＲｖ−ａｘ ｃｍ−’ ： ３３５０ （Ｄ−Ｈ）１
７１０、 １６４０． １５４９ （Ｃ＝０）１０８
０ （Ｃ−０）
５−アセトアミド−４，８−アンヒドロ−３゜５−ジテ
゛オキシーＤ−グリセローＤ−ガラクトーノニュロソン
酸アンモニウム
１７１８、１６２５．１５４５ （Ｃ＝Ｏ）１０７８
（Ｃ−０）
参考例１
〈５−アセトアミド−３，５−ジデオキシ−Ｄ−グリセ
ロ−〇−ガラクトーノニニロソン酸（Ｎ−アセチルノイ
ラミン酸）ナトリウムの合成〉
５−アセトアミド−４，８−アンヒドロ−３゜５−ジデ
オキシ−Ｄ−グリセロ−Ｄ−ガラクトーノニュロソン酸
ナトリウム３０ｍｇを０．ＩＮ水酸化ナトリウム水溶液
１０ｍ１に溶解し、室温にて１５日間攬はんした。反応
液を凍結乾燥後、残留物を水に溶かし、アセトニトリル
−水（６：１）を用いてセルロース薄層クロマトグラフ
ィーにて分離精製し、白色粉末４．６ ｍｇを得たく収
率１５．１％、＠料回収３０，８％）。5-acetamido-4,8-anhydro-3゜5-dideoxy-D-glycero-D-galactononeurosonic acid potassium IR1'am, ICm-': 3300 (0-H)1
720, 1632.1545 (C=0) 1078 (
C-0) 5-acetamido-4,8-anhydro-3゜5-dideoxy-D-glycero-D-galactononeurosonic acid magnesium IRv-ax cm-': 3350 (D-H)1
710, 1640. 1549 (C=0)108
0 (C-0) Ammonium 5-acetamido-4,8-anhydro-3゜5-ditoxy-D-glycerol D-galactononeurosonic acid 1718, 1625.1545 (C=O) 1078
(C-0) Reference Example 1 <Synthesis of sodium 5-acetamido-3,5-dideoxy-D-glycero-〇-galactononinilosonic acid (N-acetylneuraminic acid)> 5-acetamido-4,8- 30 mg of sodium anhydro-3゜5-dideoxy-D-glycero-D-galactononeurosonate at 0. It was dissolved in 10 ml of IN aqueous sodium hydroxide solution and stirred at room temperature for 15 days. After freeze-drying the reaction solution, the residue was dissolved in water and purified by cellulose thin layer chromatography using acetonitrile-water (6:1) to obtain 4.6 mg of white powder with a yield of 15.1. %, @ fee recovery 30.8%).
元素分析 Ｃ＋ ＋Ｎ＋ｅＮ（］ｓＮａ計算値 Ｃ：３
９．８８． Ｈ：５．４８． Ｎ：４．２３゜実測
値 Ｃ：３９．８１． Ｈ：５．７７、 Ｎ：４．
２１゜分子量 ３３１．２５
（α：ｌｏ ２７．５°（ｃ ＝ １．００． Ｈ
２Ｏ）融 点 １６９〜１７０℃（分解）
’１（−ＮＩＩＲ（５００Ｍ）Ｉｚ、 Ｄ、０）。 δ
（４，７，＋ｐｐＩＩｌ、Ｈ２０）１．８７ （ＩＨ，
ｄｄ、 Ｊ＝１１．６および１３．０）１ｚ、 ３−Ｈ
）２．０３ （３Ｈ，ｓ、 ＮＡｃ）
２．２５ （ＬＨ，ｄｄ、 、ｈ４．９ ｂよび１３
．ＯＨｚ、 ３−１（）３．５５ （１）１． ｄｄ、
Ｊ＝０．９および９．３ Ｈｚ、 ７−）１）３．６
５ （ＬＨ，ｄｄ、 Ｊ＝６．５および１１．８）１ｚ
、 ９−）１）３．８０ （ＩＨ，ｄｄｄ、 Ｊ＝２．
８．６．５および９．３８２．８−Ｈ）３．８８ （１
Ｎ、 ｄｄ、 Ｊ＝２．８および１１．８）１ｚ、 ９
−Ｈ）３．９５ （ＩＨ，ｄｄ、 Ｊ＝１０．ｌよびｌ
ｏ、２Ｈｚ、 ５−Ｈ）４．０２ （ＩＨ，ｄｄ、 Ｊ
＝０．９および１０．１１（ｚ、 ６−Ｈ）４．０７
（［、ｄｄｄ、Ｊ＝４．９．１０．２およびｉｌ、 ６
ｔｌｚ、 ４−Ｈ）１６１８ （Ｃ＝０）Elemental analysis C+ +N+eN(]sNa calculated value C:3
9.88. H:5.48. N: 4.23° Actual value C: 39.81. H:5.77, N:4.
21° Molecular weight 331.25 (α: lo 27.5° (c = 1.00. H
2O) Melting point 169-170°C (decomposition) '1 (-NIIR (500M) Iz, D, 0). δ
(4,7,+ppIIl, H20) 1.87 (IH,
dd, J=11.6 and 13.0) 1z, 3-H
) 2.03 (3H, s, NAc) 2.25 (LH, dd, , h4.9 b and 13
．． OHz, 3-1()3.55 (1)1. dd,
J=0.9 and 9.3 Hz, 7-)1) 3.6
5 (LH, dd, J=6.5 and 11.8)1z
, 9-)1) 3.80 (IH, ddd, J=2.
8.6.5 and 9.382.8-H) 3.88 (1
N, dd, J=2.8 and 11.8) 1z, 9
-H) 3.95 (IH, dd, J=10.l and l
o, 2Hz, 5-H) 4.02 (IH, dd, J
=0.9 and 10.11 (z, 6-H) 4.07
([, ddd, J=4.9.10.2 and il, 6
tlz, 4-H) 1618 (C=0)
Claims (2)
ンモニウムである） で表わされる４，８−アンハイドロ−Ｎ−アセチルノイ
ラミン酸塩。(1) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (where M is an alkali metal, alkaline earth metal, or ammonium) 4,8-anhydro-N-acetylneuraminic acid salt represented by .
ンモニウムである） で表わされる４，８−アンハイドロ−Ｎ−アセチルノイ
ラミン酸塩を製造する方法であって、▲数式、化学式、
表等があります▼ （ただし、Ｍは上記の定義の通りである） で示されるＮ−アセチルノイラミン酸塩を、酸あるいは
アルカリ又は熱で処理する方法。(2) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (where M is an alkali metal, alkaline earth metal, or ammonium) 4,8-anhydro-N-acetylneuraminic acid salt represented by A method for producing ▲mathematical formula, chemical formula,
There are tables, etc.▼ (However, M is as defined above.) A method of treating N-acetylneuraminic acid salt shown by with acid, alkali, or heat.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12633188A JPH01299294A (en) | 1988-05-24 | 1988-05-24 | 4,8-anhydro-n-acetyleuramic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12633188A JPH01299294A (en) | 1988-05-24 | 1988-05-24 | 4,8-anhydro-n-acetyleuramic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01299294A true JPH01299294A (en) | 1989-12-04 |
Family
ID=14932541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12633188A Pending JPH01299294A (en) | 1988-05-24 | 1988-05-24 | 4,8-anhydro-n-acetyleuramic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01299294A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0473108A2 (en) * | 1990-08-30 | 1992-03-04 | Mect Corporation | Preparation for treating renal disease |
| US5231177A (en) * | 1989-03-08 | 1993-07-27 | Mect Corporation | Sodium n-acetylneuraminate trihydrate |
| US5393742A (en) * | 1990-08-30 | 1995-02-28 | Mect Corporation | Preparation for treating renal disease |
| US5516764A (en) * | 1991-03-07 | 1996-05-14 | Mect Corporation | Anti-inflammatory agent |
-
1988
- 1988-05-24 JP JP12633188A patent/JPH01299294A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231177A (en) * | 1989-03-08 | 1993-07-27 | Mect Corporation | Sodium n-acetylneuraminate trihydrate |
| EP0473108A2 (en) * | 1990-08-30 | 1992-03-04 | Mect Corporation | Preparation for treating renal disease |
| US5393742A (en) * | 1990-08-30 | 1995-02-28 | Mect Corporation | Preparation for treating renal disease |
| US5516764A (en) * | 1991-03-07 | 1996-05-14 | Mect Corporation | Anti-inflammatory agent |
| US5763420A (en) * | 1991-03-07 | 1998-06-09 | Mect Corporation | Method for modulating the immune system |
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