N⁴-<2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2 | 142699-59-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N⁴-<2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2
• 英文别名: (2S)-N'-[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]-N-[(2S)-1-[[(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-benzamidobutanediamide
• CAS: 142699-59-0
• 化学式: C₃₇H₅₇N₇O₁₆
• 分子量: 855.897
• InChiKey: VGBRBDXBFDJGIR-FTNPJHSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  60
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  367
• 氢给体数：
  13
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  N-Cbz-Asp(β-OtBu)-Leu-Thr-NH2 在 palladium on activated charcoal 水 、 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、165.48 kPa 条件下， 反应 20.91h， 生成 N⁴-<2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranosyl>-N²-benzoyl-Asn-Leu-Thr-NH2
  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

文献信息

• Enzyme-catalyzed glycosylation of peptides using a synthetic lipid disaccharide substrate
  作者：Jung Lee、James K. Coward

  DOI：10.1021/jo00041a015

  日期：1992.7

  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.