1-methoxyl glucuronate 6-methyl ester | 196608-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methoxyl glucuronate 6-methyl ester
• 英文别名: GluA-OMe；Methyl-(methyl-β-D-glucopyranosid)-uronat；methyl (2S,3S,4S,5R)-3,4,5-trihydroxy-6-methoxyoxane-2-carboxylate
• CAS: 196608-06-7
• 化学式: C₈H₁₄O₇
• 分子量: 222.195
• InChiKey: DCXMXXNUXSBWDI-XWBUKDKVSA-N

物化性质

• 沸点：
  361.6±42.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.39
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  105.45
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-methoxyl glucuronate 6-methyl ester 在 盐酸羟胺 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 1-methoxyl-6-glucuronic acid hydroxamate
  参考文献：
  名称：

  Antioxidant and semicarbazide-sensitive amine oxidase inhibitory activities of glucuronic acid hydroxamate

  摘要：

  The antioxidant and inhibitory activities of glucuronic acid (GluA) and its synthesized 1-methoxyl-6-glucuronic acid hydroxamate (GluA-NHOH) against semicarbazide-sensitive amine oxidase (SSAO) were investigated. The scavenging activities of GluA-NHOH against 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) radicals (half-inhibition concentration [IC50], 152 mu M) and hydroxyl radicals (IC50, 70 nM) were determined. The protective activities of GluA-NHOH against hydroxyl radical-mediated calf thymus DNA damage and peroxynitrite-mediated dihydrorhodamine oxidation were also investigated. GluA-NHOH, but not GluA, exhibited close-dependent protective activities. GluA-NHOH, but not GluA, effectively inhibited bovine SSAO activities in a dose-dependent manner, and was further confirmed by AO activity stains on an acrylamide gel. GluA-NHOH showed mixed noncompetitive inhibition of bovine SSAO with respect to benzylamine (substrate) and benzylamine-SSAO (substrate enzyme complex). The V-max' and K-m' values were reduced in the presence of GluA-NHOH (0.04 mM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2011.04.094
• 作为产物：
  描述：

  甲醇 、 D-吡喃葡萄糖醛酸 在 Dowex 50 WX₈ cation exchange resins 作用下， 反应 12.0h， 生成 1-methoxyl glucuronate 6-methyl ester
  参考文献：
  名称：

  Antioxidant and semicarbazide-sensitive amine oxidase inhibitory activities of glucuronic acid hydroxamate

  摘要：

  The antioxidant and inhibitory activities of glucuronic acid (GluA) and its synthesized 1-methoxyl-6-glucuronic acid hydroxamate (GluA-NHOH) against semicarbazide-sensitive amine oxidase (SSAO) were investigated. The scavenging activities of GluA-NHOH against 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) radicals (half-inhibition concentration [IC50], 152 mu M) and hydroxyl radicals (IC50, 70 nM) were determined. The protective activities of GluA-NHOH against hydroxyl radical-mediated calf thymus DNA damage and peroxynitrite-mediated dihydrorhodamine oxidation were also investigated. GluA-NHOH, but not GluA, exhibited close-dependent protective activities. GluA-NHOH, but not GluA, effectively inhibited bovine SSAO activities in a dose-dependent manner, and was further confirmed by AO activity stains on an acrylamide gel. GluA-NHOH showed mixed noncompetitive inhibition of bovine SSAO with respect to benzylamine (substrate) and benzylamine-SSAO (substrate enzyme complex). The V-max' and K-m' values were reduced in the presence of GluA-NHOH (0.04 mM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2011.04.094

文献信息

• Studies on nepalese crude drugs. III. On the saponins of Hedera nepalensis K. Koch.
  作者：HARUHISA KIZU、SHINGO KITAYAMA、FUKIO NAKATANI、TSUYOSHI TOMIMORI、TSUNEO NAMBA

  DOI：10.1248/cpb.33.3324

  日期：——

  Twelve saponins, tentatively named HN-saponins A (I), B (II), D1 (III), D2 (IV), E (V), F (VI), H (VII), I (VIII), K (X), M (XII), N (XIII) and P (XIV), were isolated from the stem and bark of Hedera nepalensis K. KOCH. (Araliaceae). Compounds II, V, XII, XIII and XIV were identified as Kizuta saponins K3, K6, K10, K11 and K12, respectively, which have been isolated from Hedera rhombea BEAN. On the basis of chemical and physicochemical evidence, other saponins were identified as follows : I, a mixture of the β-D-glucopyranosides of campesterol (trace), stigmasterol and β-sitosterol ; III, hederagenin 3-O-β-D-glucopyranoside ; IV, oleanolic acid 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; VI, 3-O-α-L-arabinopyranosyl-hederagenin 28-O-β-D-glucopyranosyl ester ; VII, hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester ; VIII, oleanolic acid 3-O-β-D-glucuronopyranoside ; X, hederagenin 3-O-β-D-glucuronopyranoside. Compounds VI and VII were isolated from nature for the first time, though they had previously been derived from Akebia seed saponin D and Kizuta saponin K12, respectively, by partial hydrolysis.

  从常春藤（Hedera nepalensis K. KOCH.，五加科）的茎和树皮中分离出12种皂苷，暂时命名为HN-皂苷A（I）、B（II）、D1（III）、D2（IV）、E（V）、F（VI）、H（VII）、I（VIII）、K（X）、M（XII）、N（XIII）和P（XIV）。化合物II、V、XII、XIII和XIV分别被鉴定为木通皂苷K3、K6、K10、K11和K12，这些皂苷先前已从木通（Hedera rhombea BEAN）中分离得到。根据化学和物理化学证据，其他皂苷被鉴定如下：I，为菜油固醇（微量）、豆固醇和β-谷固醇的β-D-葡萄糖苷混合物；III，常春藤苷元3-O-β-D-葡萄糖苷；IV，齐墩果酸3-O-α-L-鼠李糖基-(1→2)-α-L-阿拉伯糖苷；VI，3-O-α-L-阿拉伯糖基-常春藤苷元28-O-β-D-葡萄糖苷酯；VII，常春藤苷元28-O-α-L-鼠李糖基-(1→4)-β-D-葡萄糖基-(1→6)-β-D-葡萄糖苷酯；VIII，齐墩果酸3-O-β-D-葡萄糖醛酸苷；X，常春藤苷元3-O-β-D-葡萄糖醛酸苷。化合物VI和VII虽曾分别通过部分水解木通籽皂苷D和木通皂苷K12获得，但这是它们首次从自然界中分离出来。
• Synthesis and evaluation of glucuronic acid derivatives as alkylating agents for the reversible masking of internucleoside groups of antisense oligonucleotides
  作者：Nathalie Mignet、Carole Chaix、Bernard Rayner、Jean-Louis Imbach

  DOI：10.1016/s0008-6215(97)00147-x

  日期：1997.8

  Abstract 2-Iodoethyl (methyl α- d -glucopyranosid)uronate and 2-iodoethyl (methyl β- d -glucopyranosid)thiouronate were prepared in five steps by an efficient synthetic route starting from d -glucuronic acid. Both compounds were used to alkylate dithymidine phosphorothioate and phosphorodithioate diesters, leading to the corresponding phosphotriesters 12 to 15 . Hydrolytic stability of 12–15 was studied

  摘要从d-葡萄糖醛酸开始，通过有效的合成路线，分五步制备了2-碘乙基（α-d-葡萄糖吡喃葡萄糖苷）尿酸碘代酯和2-碘乙基（β-d-吡喃葡萄糖苷甲基）硫脲酸酯。两种化合物都用于烷基化二硫代磷酸硫代磷酸酯和二硫代磷酸二酯，从而生成相应的磷酸三酯12至15。在不同的生物介质中研究了12-15的水解稳定性。12-15的酶促水解伴随着另一反应，导致二胸苷磷酸二酯的形成。提出了这些反应的几种可能的机理。
• Higuchi, Ryuichi; Tokimitsu, Yoshinori; Hamada, Naoko, Liebigs Annalen der Chemie, 1985, # 5, p. 1192 - 1201
  作者：Higuchi, Ryuichi、Tokimitsu, Yoshinori、Hamada, Naoko、Komori, Tetsuya、Kawasaki, Toshio

  DOI：——

  日期：——
• Yahara, Shoji; Ohtsuka, Michiko (nee Ikeda); Nakano, Kimiko, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 7, p. 1802 - 1804
  作者：Yahara, Shoji、Ohtsuka, Michiko (nee Ikeda)、Nakano, Kimiko、Nohara, Toshihiro

  DOI：——

  日期：——
• On the mechanism of the scission of the glycosidic linkage of methyl (methyl D-glucopyranosid)uronate induced by photolysis
  作者：Allan G.W. Bradbury、Clemens von Sonntag

  DOI：10.1016/s0008-6215(00)83476-x

  日期：1978.1