Gal-β-1,3-GlcNAc-β-O-octyl | 197390-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Gal-β-1,3-GlcNAc-β-O-octyl
• 英文别名: octyl 2-deoxy-2-acetamido-3-O-β-D-galactopyranosyl-β-D-glucopyranoside；Octyl 2-acetamido-2-deoxy-3-O-(B-D-galactopyranosyl)-B-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-octoxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 197390-85-5
• 化学式: C₂₂H₄₁NO₁₁
• 分子量: 495.568
• InChiKey: LAVIBJFXURBICK-OEUZHLKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  187
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Gal-β-1,3-GlcNAc-β-O-octyl 、 alkaline earth salt of/the/ methylsulfuric acid 在 GDP-Fuc 、 intestine phosphatase 、 manganese(ll) chloride 作用下， 以100%的产率得到N-[(2R,3R,4R,5S,6R)-6-Hydroxymethyl-2-octyloxy-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Outstanding stability of immobilized recombinant α(1→3/4)-fucosyltransferases exploited in the synthesis of Lewis a and Lewis x trisaccharides

  摘要：

  重组人α(1→3/4)-岩藻糖基转移酶（FucT-III）在CHO细胞或被 baculovirus 感染的昆虫细胞中表达，通过6His标签固定在Ni2+-琼脂糖上，表现出显著的稳定性，这在Lewis a和Lewis x 三糖的合成中得到了利用。

  DOI：

  10.1039/b006063l
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 palladium hydroxide - carbon 吡啶 、 N-碘代丁二酰亚胺 、 camphor-10-sulfonic acid 、 氢溴酸 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 氰化汞 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.5h， 生成 Gal-β-1,3-GlcNAc-β-O-octyl
  参考文献：
  名称：

  Screening for Galectin-3 Inhibitors from Synthetic Lacto-N-biose Libraries Using Microscale Affinity Chromatography Coupled to Mass Spectrometry

  摘要：

  The synthesis and screening of two beta-D-Galp-(1-3)-beta-D-GlcpN ( lacto-N-biose) disaccharide libraries are reported. Solution-phase synthetic modifications at the HO-2' and NH positions were performed in an effort to enhance the affinity toward galectin-3, a galactose-binding protein involved in tumor metastasis, apoptosis, and inflammation. The libraries were screened for galectin-3 binding by microscale frontal affinity chromatography coupled to mass spectrometry ( FAC/MS) allowing for rapid ranking of the different inhibitors and the determination of the galectin-3 binding K-d's. Compounds bearing a hydrophobic substituent on the NH group showed the highest affinity for the lectin. The N-naphthoyl derivative ( K-d = 10.6 mu M) was the best inhibitor with a 7 times increased affinity as compared to the N-acetyl parent compound ( K-d = 73.3 mu M).

  DOI：

  10.1021/jo060485v

文献信息

• Fluoridolysis of 5,6-epoxy carbohydrates: application to the synthesis of 5-fluoro lactosamine and isolactosamine glycosides
  作者：Tara L. Hagena、James K. Coward

  DOI：10.1016/j.tetasy.2009.03.025

  日期：2009.5

  The synthesis of 6-selenophenyl derivatives of β-1,3 and β-1,4 disaccharides has been explored for the purpose of extending our epoxide fluoridolysis methodology to the synthesis of 5-fluoro analogues of N-acetyl isolactosamine (isoLacNAc, lacto-N-biose) and N-acetyl lactosamine (LacNAc) glycosides. Successful synthesis of the C-6 selenium-containing disaccharides was achieved via Lewis acid-mediated

  为了将我们的环氧化物荧光分解方法扩展到N-乙酰基异乳糖胺（isoLacNAc，乳酸酯-）的5-氟类似物的合成，已经探索了β-1,3和β-1,4二糖的6-硒苯基衍生物的合成。N-二糖）和N-乙酰基乳糖胺（LacNAc）糖苷。通过路易斯酸介导的供体和受体底物成功合成了含C-6硒的二糖，后者含有选择性保护的C-6羟基，可最终转化为所需的6-硒代苯二糖。相反，在多种条件下使用含硒受体底物不能产生所需的含硒二糖。将6-硒代苯衍生物氧化为相应的亚硒酸盐，然后进行热消除，得到环外烯烃，其被转化为5，6-环氧化物。环氧氟化反应产生所需的目标化合物，即1型和2型聚糖的5-氟β-辛基糖苷类似物。
• Outstanding stability of immobilized recombinant α(1→3/4)-fucosyltransferases exploited in the synthesis of Lewis a and Lewis x trisaccharides
  作者：Claudine Augé、Annie Malleron、André Lubineau、Halima Tahrat、Annie Marc、Jean-Louis Goergen、Martine Cerutti、Wim F. A. Steelant、Philippe Delannoy

  DOI：10.1039/b006063l

  日期：——

  Recombinant human α(1→3/4)-fucosyltransferases (FucT-III) expressed in CHO cells or baculovirus-infected insect cells, immobilized on Ni2+-agarose through a 6His tag, exhibit a marked stability, which was exploited in the synthesis of Lewis a and Lewis x trisaccharides.

  重组人α(1→3/4)-岩藻糖基转移酶（FucT-III）在CHO细胞或被 baculovirus 感染的昆虫细胞中表达，通过6His标签固定在Ni2+-琼脂糖上，表现出显著的稳定性，这在Lewis a和Lewis x 三糖的合成中得到了利用。
• Screening for Galectin-3 Inhibitors from Synthetic Lacto-<i>N</i>-biose Libraries Using Microscale Affinity Chromatography Coupled to Mass Spectrometry
  作者：Sébastien Fort、Hyo-Sun Kim、Ole Hindsgaul

  DOI：10.1021/jo060485v

  日期：2006.9.1

  The synthesis and screening of two beta-D-Galp-(1-3)-beta-D-GlcpN ( lacto-N-biose) disaccharide libraries are reported. Solution-phase synthetic modifications at the HO-2' and NH positions were performed in an effort to enhance the affinity toward galectin-3, a galactose-binding protein involved in tumor metastasis, apoptosis, and inflammation. The libraries were screened for galectin-3 binding by microscale frontal affinity chromatography coupled to mass spectrometry ( FAC/MS) allowing for rapid ranking of the different inhibitors and the determination of the galectin-3 binding K-d's. Compounds bearing a hydrophobic substituent on the NH group showed the highest affinity for the lectin. The N-naphthoyl derivative ( K-d = 10.6 mu M) was the best inhibitor with a 7 times increased affinity as compared to the N-acetyl parent compound ( K-d = 73.3 mu M).