(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-6-aminohexanoyl]amino]-5-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-(3-azidopropylamino)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-oxopentanoic acid | 1316800-97-1

• 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: (4S)-4-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-6-aminohexanoyl]amino]-5-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-(3-azidopropylamino)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-oxopentanoic acid
• CAS: 1316800-97-1
• 化学式: C₅₀H₈₁N₁₃O₁₂
• 分子量: 1056.27
• InChiKey: CSBIHSCXHPIGIE-ZHAIIWHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  75
• 可旋转键数：
  33
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  351
• 氢给体数：
  11
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  4-苯基-1-丁炔 、 (4S)-4-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-6-aminohexanoyl]amino]-5-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-(3-azidopropylamino)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-oxopentanoic acid 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 20.0h， 以89%的产率得到(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-6-aminohexanoyl]amino]-5-[(2S)-2-[[(2S)-1-[[(2S)-3-(4-hydroxyphenyl)-1-oxo-1-[[(2S)-1-oxo-1-[3-[4-(2-phenylethyl)triazol-1-yl]propylamino]propan-2-yl]amino]propan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-oxopentanoic acid
  参考文献：
  名称：

  Three-Component Synthesis of Neoglycopeptides Using a Cu(II)-Triggered Aminolysis of Peptide Hydrazide Resin and an Azide–Alkyne Cycloaddition Sequence

  摘要：

  Copper(II)-induced oxidative aminolysis of hydrazides generates Cu(I), the catalyst of the azide-alkyne cycloaddition. This feature was exploited to design a novel solid phase detaching three-component reaction permitting the conversion of supported peptide hydrazides into 1,2,3-triazole linked C-terminal neoglycopeptides.

  DOI：

  10.1021/ol201659x
• 作为产物：
  描述：

  3-azido-1-propanamine hydrochloride 、 C₅₃H₈₀N₁₁O₁₂Pol 在 吡啶 、 氧气 、 copper diacetate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以29%的产率得到(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]-6-aminohexanoyl]amino]-5-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-(3-azidopropylamino)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-oxopentanoic acid
  参考文献：
  名称：

  Three-Component Synthesis of Neoglycopeptides Using a Cu(II)-Triggered Aminolysis of Peptide Hydrazide Resin and an Azide–Alkyne Cycloaddition Sequence

  摘要：

  Copper(II)-induced oxidative aminolysis of hydrazides generates Cu(I), the catalyst of the azide-alkyne cycloaddition. This feature was exploited to design a novel solid phase detaching three-component reaction permitting the conversion of supported peptide hydrazides into 1,2,3-triazole linked C-terminal neoglycopeptides.

  DOI：

  10.1021/ol201659x

文献信息

• Three-Component Synthesis of Neoglycopeptides Using a Cu(II)-Triggered Aminolysis of Peptide Hydrazide Resin and an Azide–Alkyne Cycloaddition Sequence
  作者：Jean-Philippe Ebran、Nabil Dendane、Oleg Melnyk

  DOI：10.1021/ol201659x

  日期：2011.8.19

  Copper(II)-induced oxidative aminolysis of hydrazides generates Cu(I), the catalyst of the azide-alkyne cycloaddition. This feature was exploited to design a novel solid phase detaching three-component reaction permitting the conversion of supported peptide hydrazides into 1,2,3-triazole linked C-terminal neoglycopeptides.