1-isobutyl-β-D-galactose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-isobutyl-β-D-galactose
• 英文别名: isobutyl-C-galactoside；(2R,3R,4R,5R,6S)-2-(hydroxymethyl)-6-(2-methylpropyl)oxane-3,4,5-triol
• 化学式: C₁₀H₂₀O₅
• 分子量: 220.266
• InChiKey: KBGLKGRFOLNGPJ-CVPUBMOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 palladium dihydroxide sodium hydroxide 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 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

文献信息

• Multigram Synthesis of Isobutyl-β-<i>C</i>-galactoside as a Substitute of Isopropylthiogalactoside for Exogenous Gene Induction in Mammalian Cells
  作者：Lin Liu、Basma Abdel Motaal、Marc Schmidt-Supprian、Nicola L. B. Pohl

  DOI：10.1021/jo2024569

  日期：2012.2.3

  Herein we report that isobutyl-beta-C-galactoside (IBCG) is also a promising inducer of gene expression in mammalian cells and report a new synthetic route to the compound that should make obtaining the multigram quantities of material required for animal studies more feasible. A convenient synthesis of IBCG, an inducer of genes controlled by the lac operon system in bacterial cells, was achieved in 5 steps from galactose in 81% overall yield without any chromatographic separation steps. An optimized microwave-assisted reaction at high concentration was key to making the C-glycosidic linkage. A Wittig reaction on a per-O-silylated rather than per-O-acetylated or -benzylated substrate proved most effective in installing the final carbon atom.
• US9062313B2
  申请人：——

  公开号：US9062313B2

  公开（公告）日：2015-06-23
• Synthesis of Isobutyl-<i>C</i>-galactoside (IBCG) as an Isopropylthiogalactoside (IPTG) Substitute for Increased Induction of Protein Expression
  作者：Kwang-Seuk Ko、Jerrid Kruse、Nicola L. Pohl

  DOI：10.1021/ol034444m

  日期：2003.5.1

  [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.