| 1415304-68-5

• 分子结构分类: 有机化合物 - 有机聚合物 - 多糖
• CAS: 1415304-68-5
• 化学式: C₁₂₂H₂₀₅N₁₅O₇₅S₃
• 分子量: 3178.22
• InChiKey: MXFWSRFWAGDCLV-FCORFYDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -29.72
• 重原子数：
  215.0
• 可旋转键数：
  74.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  1409.82
• 氢给体数：
  51.0
• 氢受体数：
  76.0

反应信息

• 作为产物：
  描述：

  BOC-甘氨酸 、 3-(叔丁氧羰基)噻唑烷-4-羧酸 、 N-Boc-L-缬氨酸 、 BOC-L-异亮氨酸 、 BOC-L-亮氨酸 、 N-叔丁氧羰基-L-丙氨酸 、 N-叔丁氧羰基-L-谷氨酸 5-苄酯 、 、 N-BOC-O-苄基-L-丝氨酸 、 mesna 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以16%的产率得到
  参考文献：
  名称：

  Efficient synthesis of glycopeptide-α-thioesters with a high-mannose type oligosaccharide by means of tert-Boc-solid phase peptide synthesis

  摘要：

  High-mannose type oligosaccharides consist of nine mannose and two N-acetylglucosamine residues (Man(9)GlcNAc(2):M9) and play an important role in protein folding processes in the endoplasmic reticulum. A highly efficient preparation method of this asparaginyl-M9-oligosaccharide from hen egg yolk was established by a two-step proteolysis with commercially available proteases and subsequent purification using high performance liquid chromatography (HPLC). To avoid the hydrolysis of the desired M9-oligosaccharide during the proteolysis steps, several commercially available proteases were screened for their contamination with mannosidases. The alpha-amino group of the resultant H2N-Asn-(M9-oligosaccharide)OH was protected with 9-fluorenylmethyloxycarbonyl (Fmoc) group for convenient separation by HPLC. The structure of Fmoc-Asn-(M9-oligosaccharide)-OH thus obtained was confirmed by ESI-MS spectrometry and several NMR experiments. Using this Fmoc-Asn-(M9-oligosaccharide)-OH, the synthesis of the M9-glycopeptide-alpha-thioester was demonstrated by means of tert-Boc-solid phase peptide synthesis. These tert-Boc conditions afforded the M9-glycopeptide-alpha-thioester in moderate yield. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.10.011