O²,O³,O⁴-Triacetyl-L-fucose | 141607-28-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O²,O³,O⁴-Triacetyl-L-fucose
• 英文别名: tri-O-acetyl-L-fucose；[(2S,3R,4R,5S)-3,4-diacetyloxy-5-hydroxy-1-oxohexan-2-yl] acetate
• CAS: 141607-28-5
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: MUKQRIORUXMVIO-KNFQTBNASA-N

物化性质

• 沸点：
  411.0±45.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  sodium acetate 、 乙酸酐 、 alkaline earth salt of/the/ methylsulfuric acid 在 coppered zinc 、 氢溴酸 、 溶剂黄146 作用下， 生成 O²,O³,O⁴-Triacetyl-L-fucose 、 2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯
  参考文献：
  名称：

  合成d-地高糖。Desoxyzucker。4.米特隆

  摘要：

  DOI：

  10.1002/hlca.194402701156

文献信息

• METHODS AND COMPOSITIONS FOR MAKING ANTIBODIES AND ANTIBODY DERIVATIVES WITH REDUCED CORE FUCOSYLATION
  申请人：Seattle Genetics, Inc.

  公开号：US20140031536A1

  公开（公告）日：2014-01-30

  The invention provides methods and compositions for preparing antibodies and antibody derivatives with reduced core fucosylation.

  这项发明提供了一种减少核心岩藻糖基化的抗体和抗体衍生物制备的方法和组合物。
• Production of fucosylated carbohydrates by enzymatic fucosylation synthesis of sugar nucleotides; and in situ regeneration of GDP-fucose
  申请人：——

  公开号：US20020068331A1

  公开（公告）日：2002-06-06

  This invention contemplates improved methods of enzymatic production of carbohydrates especially fucosylated carbohydrates. Improved syntheses of glycosyl 1- or 2-phosphates using both chemical and enzymatic means are also contemplated. The phosphorylated glycosides are then used to produce sugar nucleotides that are in turn used as donor sugars for glycosylation of acceptor carbohydrates. Especially preferred herein is the use of a disclosed method for fucosylation.

  本发明涉及改进的酶制糖类特别是富含岩藻糖的生产方法。同时，本发明还考虑利用化学和酶法改进糖基1-或2-磷酸的合成方法。然后，将磷酸化糖苷用于生产糖核苷，进而用作供体糖，用于受体糖的糖基化。在此，特别偏爱使用揭示的富含岩藻糖的方法。
• Ellipticine derivative and production process thereof
  申请人：SUNTORY LIMITED

  公开号：EP0173462A2

  公开（公告）日：1986-03-05

  An ellipticine derivative having the general formula: wherein R represents a hydrogen atom, a hydroxyl group, an alkoxyl group having 1 to 4 carbon atoms, or an acyloxy group having 2 to 7 carbon atoms; R2 represents an aldose residue, a deoxyaldose residue, an N-acylaminoaldose residue having a substituted acyl group with 2 to 4 carbon atoms bonded to the N atom, an aldohexuronic amide residue, and aldohexuronic acid residue, an acylated aldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated deoxyaldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated N-acylaminoaldose residue having an amino group substituted with an acyl group with 2 to 4carbon atoms and having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated aldohexuronic amide residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated aldohexuronic acid residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated aldohexuronic acid ester residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an arylalkylated aldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated deoxyaldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 7 to 8 carbon atoms, an arylalkylated N-acylaminoaldose residue having an amino group with an acyl group with 2 to 4 carbon atoms and having, substituted for the hydrogen of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated aldohexuronic amide residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated aldohexuronic acid residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated aldohexuronic acid ester residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms; and R3 represents a hydrogen atom, a linear, branched, cyclic, or cyclic-linear alkyl group having 1 to 5 carbon atoms; X0 represents a pharmaceutically acceptable inorganic or organic acid anion; and the bond represented by N⊕ - R2 in the general formula (I) represents a glycoside bond between a nitrogen atom in the 2-position of the ellipticine and a carbon atom in the 1-position of the sugar. These ellipticine derivatives have a strong antineoplastic or antitumor activity and, therefore, are expected to be effective as an antineoplastic or antitumor agent.

  一种具有通式的鞣花碱衍生物： 其中 R 代表氢原子、羟基、具有 1 至 4 个碳原子的烷氧基或具有 2 至 7 个碳原子的酰氧基； R2 代表醛糖残基、脱氧醛糖残基、N-酰氨基醛糖残基（其 N 原子上键有 2 至 4 个碳原子的取代酰基）、醛缩脲酰胺残基、醛缩脲酸残基、酰化醛糖残基（其糖羟基的氢原子被取代）、一种酰化脱醛糖残基，其糖羟基的氢原子被 2 至 4 个碳原子的烷酰基或 7 至 9 个碳原子的芳酰基取代、酰化的 N-酰氨基醛糖残基，其氨基被 2 至 4 个碳原子的酰基取代，并具有 2 至 4 个碳原子的烷酰基或 7 至 9 个碳原子的芳酰基取代糖羟基的氢原子；酰化的醛缩酰胺残基，其具有一种酰化的醛缩己脲酰胺残基，其糖的羟基的氢原子被 2 至 4 个碳原子的烷酰基或 7 至 9 个碳原子的芳酰基取代、酰化醛缩醛酸酯残基，其糖羟基的氢原子被 2 至 4 个碳原子的烷基酰基或 7 至 9 个碳原子的芳基酰基取代、芳烷基化脱醛糖残基，其糖的羟基的氢原子被 7 至 8 个碳原子的烷酰基取代；芳烷基化 N-酰氨基醛糖残基，其氨基带有 2 至 4 个碳原子的酰基，并具有一种芳烷基化的醛缩脲酰胺残基，其氨基具有 2 至 4 个碳原子的酰基，并具有 7 至 8 个碳原子的芳烷基取代糖的羟基的氢原子、一种芳烷基化的醛缩脲酸酯残基，其糖的羟基的氢原子被具有 7 至 8 个碳原子的芳烷基取代；和 R3 代表氢原子、具有 1 至 5 个碳原子的直链、支链、环状或环状直链烷基； X0 代表药学上可接受的无机或有机酸阴离子；以及 通式（I）中 N⊕ - R2 所代表的键代表鞣花碱 2 位上的氮原子与糖 1 位上的碳原子之间的糖苷键。这些鞣花碱衍生物具有很强的抗肿瘤或抗肿瘤活性，因此有望成为有效的抗肿瘤或抗肿瘤药物。
• Verfahren zur stereoselektiven Herstellung von beta-Fucopyranosylphosphaten und sehr reiner GDP-Fucose
  申请人：MERCK PATENT GmbH

  公开号：EP0502298A2

  公开（公告）日：1992-09-09

  Die Erfindung betrifft ein Verfahren zur stereoselektiven Herstellung von β-L-Fucopyranosyl-phosphaten über die Trichloracetimidate der geschützten L-Fucose und die Synthese und Aufreinigung von sehr reiner GDP-Fucose aus den β-L-Fucopyranosyl-phosphaten.

  本发明涉及一种通过受保护 L-岩藻糖的三氯乙酰亚氨酸盐立体选择性生产 β-L-岩藻糖基磷酸酯的工艺，以及从 β-L-岩藻糖基磷酸酯合成和纯化高纯度 GDP-岩藻糖的工艺。
• FUCOSE ANALOGS FOR INHIBITION OF PROTEIN FUCOSYLATION IN VIVO
  申请人：Seattle Genetics, Inc.

  公开号：EP3513794A2

  公开（公告）日：2019-07-24

  The invention provides compositions for the inhibition of fucosylation of proteins, including antibodies, in vivo by administration of a fucose analog.

  本发明提供了通过服用岩藻糖类似物抑制体内蛋白质（包括抗体）岩藻糖基化的组合物。