2-acetamido-1,3,4,6-tetra-O-butanoyl-2-deoxy-α,β-D-galactopyranose | 1146970-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-1,3,4,6-tetra-O-butanoyl-2-deoxy-α,β-D-galactopyranose
• CAS: 1146970-10-6
• 化学式: C₂₄H₃₉NO₁₀
• 分子量: 501.574
• InChiKey: WUQBGYXGTNZCPW-XDLWQIPNSA-N

物化性质

• 沸点：
  608.5±55.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  143.53
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-1,3,4,6-tetra-O-butanoyl-2-deoxy-α,β-D-galactopyranose 以 甲醇 为溶剂， 反应 12.0h， 以82%的产率得到2-acetamido-3,4,6-tri-O-butanoyl-2-deoxy-α,β-D-galactopyranose
  参考文献：
  名称：

  Hexosamine Template. A Platform for Modulating Gene Expression and for Sugar-Based Drug Discovery

  摘要：

  This study investigates the breadth of cellular responses engendered by short chain fatty acid (SCFA)-hexosamine hybrid molecules, a class of compounds long used in "metabolic glycoengineering" that are now emerging as drug candidates. First, a "mix and match" strategy showed that different SCFA (n-butyrate and acetate) appended to the same core sugar altered biological activity, complementing previous results [Campbell et al. J. Med. Chem. 2008, 51, 8135-8147] where a single type of SCFA elicited distinct responses. Microarray profiling then compared transcriptional responses engendered by regioisomerically modified ManNAc, GlcNAc, and GalNAc analogues in MDA-MB-231 cells. These data, which were validated by qRT-PCR or Western analysis for IDI, TP53, HPSE, NQO1, EGR1, and VEGFA, showed a two-pronged response where a core set of genes was coordinately regulated by all analogues while each analogue simultaneously uniquely regulated a larger number of genes. Finally, AutoDock modeling supported a mechanism where the analogues directly interact with elements of the NF-kappa B pathway. Together, these results establish the SCFA-hexosamine template as a versatile platform for modulating biological activity and developing new therapeutics.

  DOI：

  10.1021/jm801661m
• 作为产物：
  描述：

  丁酸酐 、 2-乙酰氨基-2-脱氧-D-吡喃半乳糖 在 吡啶 、 4-二甲氨基吡啶 作用下， 以79%的产率得到2-acetamido-1,3,4,6-tetra-O-butanoyl-2-deoxy-α,β-D-galactopyranose
  参考文献：
  名称：

  Hexosamine Template. A Platform for Modulating Gene Expression and for Sugar-Based Drug Discovery

  摘要：

  This study investigates the breadth of cellular responses engendered by short chain fatty acid (SCFA)-hexosamine hybrid molecules, a class of compounds long used in "metabolic glycoengineering" that are now emerging as drug candidates. First, a "mix and match" strategy showed that different SCFA (n-butyrate and acetate) appended to the same core sugar altered biological activity, complementing previous results [Campbell et al. J. Med. Chem. 2008, 51, 8135-8147] where a single type of SCFA elicited distinct responses. Microarray profiling then compared transcriptional responses engendered by regioisomerically modified ManNAc, GlcNAc, and GalNAc analogues in MDA-MB-231 cells. These data, which were validated by qRT-PCR or Western analysis for IDI, TP53, HPSE, NQO1, EGR1, and VEGFA, showed a two-pronged response where a core set of genes was coordinately regulated by all analogues while each analogue simultaneously uniquely regulated a larger number of genes. Finally, AutoDock modeling supported a mechanism where the analogues directly interact with elements of the NF-kappa B pathway. Together, these results establish the SCFA-hexosamine template as a versatile platform for modulating biological activity and developing new therapeutics.

  DOI：

  10.1021/jm801661m