1-isobutyl-β-D-galactose tetraacetate | 546084-23-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-isobutyl-β-D-galactose tetraacetate
• 英文别名: [(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-(2-methylpropyl)oxan-2-yl]methyl acetate
• CAS: 546084-23-5
• 化学式: C₁₈H₂₈O₉
• 分子量: 388.415
• InChiKey: JTQJFPTUJRWBGB-FLXSYLCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-isobutyl-β-D-galactose tetraacetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以99%的产率得到1-isobutyl-β-D-galactose
  参考文献：
  名称：

  Synthesis of Isobutyl-C-galactoside (IBCG) as an Isopropylthiogalactoside (IPTG) Substitute for Increased Induction of Protein Expression

  摘要：

  [GRAPHICS]Addition of isopropyl-beta-D-thiogalactopyranoside (IPTG) to bacterial cultures is often used to induce expression of plasmid-based genes for the production of recombinant proteins under control of the lac promoter, but a simple method to circumvent the inherent instability of this compound has not been addressed experimentally. Herein we report the first synthesis of isobutyl-C-galactoside (IBCG), the C-glycoside analogue of IPTG, and show that IBCG is superior to IPTG in inducing protein expression over long induction times.

  DOI：

  10.1021/ol034444m
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 palladium dihydroxide 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-isobutyl-β-D-galactose tetraacetate
  参考文献：
  名称：

  Synthesis of Isobutyl-C-galactoside (IBCG) as an Isopropylthiogalactoside (IPTG) Substitute for Increased Induction of Protein Expression

  摘要：

  [GRAPHICS]Addition of isopropyl-beta-D-thiogalactopyranoside (IPTG) to bacterial cultures is often used to induce expression of plasmid-based genes for the production of recombinant proteins under control of the lac promoter, but a simple method to circumvent the inherent instability of this compound has not been addressed experimentally. Herein we report the first synthesis of isobutyl-C-galactoside (IBCG), the C-glycoside analogue of IPTG, and show that IBCG is superior to IPTG in inducing protein expression over long induction times.

  DOI：

  10.1021/ol034444m