L-glutaminyl-glycyl-glycyl-{N-[α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl]}-L-asparaginyl-L-tyrosyl-glycyl-glycine methyl ester

• 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: L-glutaminyl-glycyl-glycyl-{N-[α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl]}-L-asparaginyl-L-tyrosyl-glycyl-glycine methyl ester
• 英文别名: methyl 2-[[2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2,5-diamino-5-oxopentanoyl]amino]acetyl]amino]acetyl]amino]-4-[[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-4-oxobutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetate
• 化学式: C₄₅H₆₉N₉O₂₆
• 分子量: 1152.09
• InChiKey: JFDOHGWLUYNSLQ-SGSBLQDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11
• 重原子数：
  80
• 可旋转键数：
  29
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  568
• 氢给体数：
  20
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  L-酪氨酰甘氨酰甘氨酸 在 哌啶 、 氯化亚砜 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 L-glutaminyl-glycyl-glycyl-{N-[α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl]}-L-asparaginyl-L-tyrosyl-glycyl-glycine methyl ester
  参考文献：
  名称：

  Efficient Synthesis of Complex Glycopeptides Based on Unprotected Oligosaccharides

  摘要：

  N-Glycopeptides containing 1 to 4 trisaccharide chains, with the carbohydrates vicinal to each other in the multivalent glycopeptides, were efficiently synthesized by using the glycosylated Fmoc-asparagine as a key building block. While the couplings of amino acids with glycopeptides could be achieved in the homogeneous solutions in N-methylpyrrolidinone (NMP) to give excellent yields, all products were conveniently isolated from the reaction mixtures through a precipitation method by using the free carbohydrate chains as phase tags. Commercially available pentafluorophenyl (Pfp) esters of amino acids were employed for the glycopeptide elongation. Longer glycopeptides were constructed by means of a highly convergent synthetic design that is based on the coupling of glycopeptide/peptide fragments. Hydrogen bond interactions between free oligosaccharides were proposed to explain the exceptionally high efficiency of the couplings between two glycosylated building blocks.

  DOI：

  10.1021/jo020570c

文献信息

• Efficient Synthesis of Complex Glycopeptides Based on Unprotected Oligosaccharides
  作者：Jie Xue、Zhongwu Guo

  DOI：10.1021/jo020570c

  日期：2003.4.1

  N-Glycopeptides containing 1 to 4 trisaccharide chains, with the carbohydrates vicinal to each other in the multivalent glycopeptides, were efficiently synthesized by using the glycosylated Fmoc-asparagine as a key building block. While the couplings of amino acids with glycopeptides could be achieved in the homogeneous solutions in N-methylpyrrolidinone (NMP) to give excellent yields, all products were conveniently isolated from the reaction mixtures through a precipitation method by using the free carbohydrate chains as phase tags. Commercially available pentafluorophenyl (Pfp) esters of amino acids were employed for the glycopeptide elongation. Longer glycopeptides were constructed by means of a highly convergent synthetic design that is based on the coupling of glycopeptide/peptide fragments. Hydrogen bond interactions between free oligosaccharides were proposed to explain the exceptionally high efficiency of the couplings between two glycosylated building blocks.