6-tetramethylrhodamine-(N-hydroxysuccinimidyl-β-alanine)-amide | 933058-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-tetramethylrhodamine-(N-hydroxysuccinimidyl-β-alanine)-amide
• CAS: 933058-16-3
• 化学式: C₃₂H₃₀N₄O₈
• 分子量: 598.612
• InChiKey: IVXVXPWEQKYRLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  152.3
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-tetramethylrhodamine-(N-hydroxysuccinimidyl-β-alanine)-amide 、 C₁₈-lyso-GM1 在 N,N-二异丙基乙胺 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以87%的产率得到
  参考文献：
  名称：

  Synthesis of reference standards to enable single cell metabolomic studies of tetramethylrhodamine-labeled ganglioside GM1

  摘要：

  Ganglioside GM1 and its seven potential catabolic products: asialo-GM1, GM2, asialo-GM2, GM3, Lac-Cer, Glc-Cer and Cer, were labeled with tetramethylrhodamine (TMR) to permit ultra-sensitive analysis using laser-induced fluorescence (LIF) detection. The preparation involved acylation of the homogenous C-18 lyso-forms of GM1, Lac-Cer, Glc-Cer and Cer with the N-hydroxysuccinimide ester of a beta-alanine-tethered 6-TMR derivative, followed by conversion of these labeled products using galactosidase, sialidase, and sialyltransferase enzymes. The TMR-glycolipid analogs produced are detectable on TLC down to the I ng level by the naked eye. All eight compounds could be separated within 4 min in capillary electrophoresis where they could be detected at the zeptomole (ca. 1000 molecule) level using LIF. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.002
• 作为产物：
  描述：

  6-tetramethylrhodamine-(β-alanine)-amide 、 N,N'-二琥珀酰亚胺基碳酸酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 6-tetramethylrhodamine-(N-hydroxysuccinimidyl-β-alanine)-amide
  参考文献：
  名称：

  A concise chemical synthesis of a fluorescent βGal-(1,4)-S-βGlc-Cer derivative and its enzymatic elongation by glycosyltransferases

  摘要：

  A straightforward chemical synthesis of lyso-lactosylceramide with the terminal galactose linked to glucose through a beta-S-glycosidic bond is reported. The product is labeled on the amino-group with tetramethylrhodamine enabling its ultrasensitive detection in capillary electrophoresis using laser-induced fluorescence. The fluorescent product disaccharide is resistant to hydrolysis by glycosidases but is shown to remain as an acceptor substrate for glycosyltransferases for the conversion into the trisaccharides GM3 and Gb3. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.119