2-mercaptoethyl O-β-D-galactopyranoside | 304439-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-mercaptoethyl O-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(2-mercaptoethoxy)tetrahydro-2H-pyran-3,4,5-triol；Methanethiosulfonyl-Galactoside；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(2-sulfanylethoxy)oxane-3,4,5-triol
• CAS: 304439-16-5
• 化学式: C₈H₁₆O₆S
• 分子量: 240.277
• InChiKey: HUYFGRHVKQZODJ-DWOUCZDBSA-N

物化性质

• 沸点：
  459.6±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  100
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  溴乙酸 N-羟基琥珀酰亚胺酯 、 2-mercaptoethyl O-β-D-galactopyranoside 、 12,12-Bis-[(5-[2-allyloxycarbonylamino-1-(allyloxycarbonylamino-methyl)-ethoxy]-1-{4-[2-allyloxycarbonylamino-1-(allyloxycarbonylamino-methyl)-ethoxy]-but-2-ynyl}-pent-3-ynyloxycarbonylmethyl)-carbamoyl]-dodecanoic acid 以72%的产率得到
  参考文献：
  名称：

  Solid-Phase Synthesis of Carbohydrate Cluster on Tree-Type Linker with Three Types of Orthogonally Cleavable Part

  摘要：

  我们采用三种正交裂解方法（光裂解、碱裂解和酸裂解），从具有三种可正交裂解部分的固体支撑树型连接体中同时合成了八乳糖苷、四乳糖苷和二乳糖苷。

  DOI：

  10.1055/s-2004-815413
• 作为产物：
  描述：

  (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(acetylthio)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 sodium methylate 作用下， 以10%的产率得到2-mercaptoethyl O-β-D-galactopyranoside
  参考文献：
  名称：

  固相辅助二硫键合连接亲水和疏水成分的有效方法

  摘要：

  亲水性和疏水性成分之间的化学共轭是困难的，因为它们的溶解度极为不同。本文中，我们报道了一种新的通用方法，该方法具有固相辅助的二硫键连接，可以克服由于溶解性引起的结合困难。该方法涉及一个一锅法过程中的两个步骤：1）将疏水性分子负载到有机溶剂中的树脂上，以及2）将与亲水性分子结合的固体负载疏水性分子释放到水性溶剂中。该策略允许在每个步骤中为基材使用合适的溶剂系统。以中等产率（29–45％）获得了水不溶性药物匹林布林与无法通过溶液相反应制备的亲水性载体的结合物。

  DOI：

  10.1002/anie.201712324

文献信息

• Galactosylation of Thiol Group by β-Galactosidase
  作者：Hirofumi NAKANO、Motohiro SHIZUMA、Taro KISO、Sumio KITAHATA

  DOI：10.1271/bbb.64.735

  日期：2000.1

  β-Galactosidase catalyzed β-galactosylation not only of a hydroxyl group but also of a thiol group in the condensation reaction of D-galactose and 2-mercaptoethanol. The thio-galactosylation product was confirmed as 2-hydroxyethyl S-β-D-galactoside on the bases of fast atom bombardment mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectorometry. Aspergillus oryzae β-galactosidase hydrolyzed p-nitrophenyl S-β-D-galactoside most rapidly among several β-galactosidases and produced the thio-galactosylation product most efficiently. The Penicillim multicolor enzyme was as effective as the A. oryzae enzyme. However the enzymes from Escherichia coli, Saccharomyces fragilis, Kluyveromyces lactis, and Bacillus circulans galactosylated hydroxyl groups predominantly to produce O-galactoside. The thio-galactoside was synthesized most effectively at a 2-mercaptoethanol concentration of about 1.25 M. Galactose concentration at 0.8-2.8 M did not affect the synthetic yield of the thio-galactoside so greatly.

  在 D-半乳糖和 2-巯基乙醇的缩合反应中，β-半乳糖苷酶不仅催化了羟基，还催化了硫醇基的 β-半乳糖基化。根据快速原子轰击质谱法、红外光谱法和核磁共振谱法，确认了硫代半乳糖苷化产物为 2-羟乙基 S-β-D-半乳糖苷。在几种β-半乳糖苷酶中，黑曲霉β-半乳糖苷酶水解对硝基苯基 S-β-D-半乳糖苷的速度最快，生成硫代半乳糖苷产物的效率最高。Penicillim 多色酶与 A. oryzae 酶一样有效。然而，大肠杆菌、脆弱酵母菌、乳酸克鲁维酵母菌和环状芽孢杆菌的酶主要对羟基进行半乳糖基化，生成 O-半乳糖苷。在 2-巯基乙醇浓度约为 1.25 M 时，合成硫代半乳糖苷的效果最好；半乳糖浓度为 0.8-2.8 M 时，对硫代半乳糖苷的合成产量影响不大。
• Combinatorial Synthesis of Carbohydrate Cluster on Tree-Type Linker with Orthogonally Cleavable Parts
  作者：Takashi Takahashi、Toru Amaya、Hiroshi Tanaka

  DOI：10.1055/s-2004-815421

  日期：——

  We have successfully developed a synthetic strategy for the combinatorial solid-phase synthesis of carbohydrate clusters on a tree-type linker with two types of orthogonally cleavable parts. The combination of three types of spacers, two types of carbohydrate ligands, and two types of orthogonal cleavage provided a 12-member carbohydrate cluster library (6 dimers and 6 tetramers).

  我们成功开发了一种在具有两种正交可裂解部分的树型连接体上组合固相合成碳水化合物簇的合成策略。三种类型的间隔基、两种类型的碳水化合物配体和两种类型的正交切割的组合提供了12成员碳水化合物簇文库（6个二聚体和6个四聚体）。
• [EN] PRODRUGS WITH 1-(DISULFANYL)ALKYLOXY-CARBONYL UNITS<br/>[FR] PROMÉDICAMENTS À MOTIFS 1-(DISULFANYL)ALKYLOXY-CARBONYLE
  申请人：[en]PHARMACYTICS B.V.

  公开号：WO2022271018A1

  公开（公告）日：2022-12-29

  The invention is in the field of medical sciences. It provides new pharmaceutical methods and preparations. The invention relates to methods for improving the pharmacokinetic, physicochemical or pharmaceutical properties of drugs by converting the drug into a promoiety-containing 1-substituted disulfanylalkyl carbonate, thiocarbamate or carbamate prodrug. In particular, the invention relates to methods for improving the solubility, permeability, stability and/or oral bioavailability of a drug by converting the drug into a promoiety-containing 1-(disulfanylalkyl) carbonate, thiocarbonate or carbamate prodrug. The invention also provides new compositions comprising a drug covalently attached to a promoiety-containing 1-(disulfanylalkyl) carbonate, thiocarbonate or carbamate. More in particular, the invention relates to a method for increasing the oral bioavailability of a drug by covalently attaching a promoiety-containing 1-disulfanylalkyloxycarbonyl unit to a hydroxyl or amine containing drug in which the promoiety contains a 1-0-, 1-S-, 6-0- or 6-S-linked monosaccharide. Formula I
• An Efficient Method for the Conjugation of Hydrophilic and Hydrophobic Components by Solid-Phase-Assisted Disulfide Ligation
  作者：Kyohei Muguruma、Takuya Shirasaka、Daichi Akiyama、Kentarou Fukumoto、Akihiro Taguchi、Kentaro Takayama、Atsuhiko Taniguchi、Yoshio Hayashi

  DOI：10.1002/anie.201712324

  日期：2018.2.19

  in a one‐pot process: 1) loading of a hydrophobic molecule onto a resin in an organic solvent, and 2) release of the solid‐supported hydrophobic molecule as a conjugate with a hydrophilic molecule into an aqueous solvent. This strategy allows the use of a suitable solvent system for the substrates in each step. Conjugates of a water‐insoluble drug, plinabulin, with hydrophilic carriers that could not

  亲水性和疏水性成分之间的化学共轭是困难的，因为它们的溶解度极为不同。本文中，我们报道了一种新的通用方法，该方法具有固相辅助的二硫键连接，可以克服由于溶解性引起的结合困难。该方法涉及一个一锅法过程中的两个步骤：1）将疏水性分子负载到有机溶剂中的树脂上，以及2）将与亲水性分子结合的固体负载疏水性分子释放到水性溶剂中。该策略允许在每个步骤中为基材使用合适的溶剂系统。以中等产率（29–45％）获得了水不溶性药物匹林布林与无法通过溶液相反应制备的亲水性载体的结合物。
• Solid-Phase Synthesis of Carbohydrate Cluster on Tree-Type Linker with Three Types of Orthogonally Cleavable Part
  作者：Takashi Takahashi、Toru Amaya、Hiroshi Tanaka

  DOI：10.1055/s-2004-815413

  日期：——

  We have synthesized octa-, tetra-, and digalactoside based on the three methods of orthogonal cleavage (photo-, base, and acid cleavage) from the solid-supported tree-type linker with three types of orthogonally cleavable parts, simultaneously.

  我们采用三种正交裂解方法（光裂解、碱裂解和酸裂解），从具有三种可正交裂解部分的固体支撑树型连接体中同时合成了八乳糖苷、四乳糖苷和二乳糖苷。