Nα-fluorenylmethoxycarbonyl-Nβ-β-D-mannopyranosyl-L-aspargine tert-butyl ester | 146388-47-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Nα-fluorenylmethoxycarbonyl-Nβ-β-D-mannopyranosyl-L-aspargine tert-butyl ester
• 英文别名: N^α-fluorenylmethoxycarbonyl-N^β-β-D-mannopyranosyl-L-aspargine tert-butyl ester
• CAS: 146388-47-8
• 化学式: C₂₉H₃₆N₂O₁₀
• 分子量: 572.612
• InChiKey: ZUTBUNDIRGKULK-MIVGUHOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  183.88
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Nα-fluorenylmethoxycarbonyl-Nβ-β-D-mannopyranosyl-L-aspargine tert-butyl ester 在 三氟乙酸 作用下， 反应 0.33h， 生成 Nα-fluorenylmethoxycarbonyl-Nβ-β-D-mannopyranosyl-L-aspargine
  参考文献：
  名称：

  Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides

  摘要：

  I-Amino 1-deoxy derivatives of unprotected O-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-glucopyranose, 2-acetamido-2-deoxy-D-galactose, D-galactose, lactose, D-fucose, D-mannose, and 2-deoxy-D-arabino-hexose were prepared and acylated with N-fluorenylmethoxycarbonylaspartic acid alpha-tert-butyl ester. The anomeric configuration of the N-glycosyl bond (including that of the mannose derivative) in each of the purified compounds was shown to be beta. The probable stability of the N-glycosyl and glycosidic bonds during the conditions of solid-phase peptide synthesis was investigated by treatment of the glycosylated asparagine derivatives with different concentrations of trifluoroacetic acid. Based on their stability, we found that Fmoc-Asn(sugar)-OH derivatives are excellent candidates for automated synthesis of biologically active glycopeptides.

  DOI：

  10.1016/0008-6215(92)80080-k
• 作为产物：
  描述：

  甘露糖 在 碳酸氢铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 172.0h， 生成 Nα-fluorenylmethoxycarbonyl-Nβ-β-D-mannopyranosyl-L-aspargine tert-butyl ester
  参考文献：
  名称：

  Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides

  摘要：

  I-Amino 1-deoxy derivatives of unprotected O-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-glucopyranose, 2-acetamido-2-deoxy-D-galactose, D-galactose, lactose, D-fucose, D-mannose, and 2-deoxy-D-arabino-hexose were prepared and acylated with N-fluorenylmethoxycarbonylaspartic acid alpha-tert-butyl ester. The anomeric configuration of the N-glycosyl bond (including that of the mannose derivative) in each of the purified compounds was shown to be beta. The probable stability of the N-glycosyl and glycosidic bonds during the conditions of solid-phase peptide synthesis was investigated by treatment of the glycosylated asparagine derivatives with different concentrations of trifluoroacetic acid. Based on their stability, we found that Fmoc-Asn(sugar)-OH derivatives are excellent candidates for automated synthesis of biologically active glycopeptides.

  DOI：

  10.1016/0008-6215(92)80080-k

文献信息

• Preparation of S‐ and N‐Linked Glycosylated Amino Acid Building Blocks for Solid‐phase Glycopeptide Library Synthesis*
  作者：C. Maljaars、Koen Halkes、Wim de Oude、Seléne van der Poel、Niels Pijnenburg、Johannis Kamerling

  DOI：10.1081/car-200066915

  日期：2005.8.1

  A general route for the preparation of 1,2-trans-linked S-glycosylated amino acid building blocks by a Lewis-acid-promoted condensation of peracetylated glycosyl donors and N-alpha-Fmoc-Cys-OH, in good overall yield, is described. In addition, a short and time-efficient route was applied for the synthesis of N-glycosylated amino acid building blocks in good overall yields by coupling unprotected glycosylamines and N-alpha-Fmoc-Asp(OH)-(OBu)-Bu-t using TBTU activation.