N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-Cbz-L-aspartic acid α-tert-butyl ester | 142699-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-Cbz-L-aspartic acid α-tert-butyl ester
• 英文别名: N⁴-[2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl]-N²-Cbz-L-aspartic acid α-tert-butyl ester；tert-butyl (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4-acetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-4-oxo-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 142699-60-3
• 化学式: C₄₂H₅₈N₄O₂₀
• 分子量: 938.937
• InChiKey: HKTDEDKAPSYKOL-KCYFUBDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  66.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  311.12
• 氢给体数：
  4.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-Cbz-L-aspartic acid α-tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以87 mg的产率得到N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-Cbz-L-aspartic acid
  参考文献：
  名称：

  Enzyme-catalyzed glycosylation of peptides using a synthetic lipid disaccharide substrate

  摘要：

  A lipid disaccharide, consisting of chitobiose linked to dilichol via an alpha-1-pyrophosphate, has been synthesized for use as a substrate in the enzyme-catalyzed glycosylation of peptides. For the purpose of confirming the structure of the reaction product, the expected glycopeptide was synthesized via an unambiguous, convergent method. Chromatographic and spectral comparison of the synthetic vs biosynthetic glycopeptides showed that they were identical. Thus, glycosylation of synthetic peptides by a synthetically accessible lipid disaccharide can be effected using oligosaccharyltransferase isolated from yeast.

  DOI：

  10.1021/jo00041a015
• 作为产物：
  描述：

  (S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester 、 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosylamine 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以68%的产率得到N⁴-<2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl>-N²-Cbz-L-aspartic acid α-tert-butyl ester
  参考文献：
  名称：

  Enzyme-catalyzed glycosylation of peptides using a synthetic lipid disaccharide substrate

  摘要：

  A lipid disaccharide, consisting of chitobiose linked to dilichol via an alpha-1-pyrophosphate, has been synthesized for use as a substrate in the enzyme-catalyzed glycosylation of peptides. For the purpose of confirming the structure of the reaction product, the expected glycopeptide was synthesized via an unambiguous, convergent method. Chromatographic and spectral comparison of the synthetic vs biosynthetic glycopeptides showed that they were identical. Thus, glycosylation of synthetic peptides by a synthetically accessible lipid disaccharide can be effected using oligosaccharyltransferase isolated from yeast.

  DOI：

  10.1021/jo00041a015