1,3,4,6-tetra-acetyl-2-thioacetylacetamido-2-deoxy-α/β-D-mannopyranose | 1313864-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-acetyl-2-thioacetylacetamido-2-deoxy-α/β-D-mannopyranose
• 英文别名: Ac5ManNTGc；[(2R,3S,4R,5S)-3,4,6-triacetyloxy-5-[(2-acetylsulfanylacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 1313864-83-3
• 化学式: C₁₈H₂₅NO₁₁S
• 分子量: 463.463
• InChiKey: QIAVTYOXBOYXHI-GAMQSXCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  186
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2-deoxy-2-(chloroacetamido)-D-mannose 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1,3,4,6-tetra-acetyl-2-thioacetylacetamido-2-deoxy-α/β-D-mannopyranose
  参考文献：
  名称：

  Deciphering glycan linkages involved in Jurkat cell interactions with gold-coated nanofibers via sugar-displayed thiols

  摘要：

  Metabolic oligosaccharide engineering (MOE) provides a method to install novel chemical functional groups into the glycocalyx of living cells. In this Letter we use this technology to compare the impact of replacing natural sialic acid, GalNAc, and GlcNAc with their thiol-bearing counterparts in Jurkat and HL-60 cells. When incubated in the presence of gold-coated nanofibers, only Jurkat cells incubated with Ac(5)ManNTGc-an analogue that installs thiols into sialosides-experienced a distinctive 'spreading' morphology. The comparison of Ac(5)ManNTGc with Ac(5)GalNTGc and Ac(5)GlcNTGc in the two cell lines implicated sialosides of N-linked glycans as critical molecular mediators of the unusual responses evoked in the Jurkat line. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.044