(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)-3-(1H-imidazol-5-yl)-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 | 1316801-03-2

• 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)-3-(1H-imidazol-5-yl)-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: 1316801-03-2
• 化学式: C₅₃H₈₃N₁₅O₁₂
• 分子量: 1122.34
• InChiKey: RVSJFKOFMRVNFL-XBDBAUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  80
• 可旋转键数：
  35
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  380
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-pent-4-ynoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 、 (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)-3-(1H-imidazol-5-yl)-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 4.0h， 以36%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-[4-[3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypropyl]triazol-1-yl]propylamino]-3-(1H-imidazol-5-yl)-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
• 作为产物：
  描述：

  3-azido-1-propanamine hydrochloride 、 (E)-N-(4-((12-oxo-3-(3-(piperidin-1-yl)propanamido)-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-6(12H)-ylidene)methyl)phenyl)-3-(piperidin-1-yl)propanamide 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4%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)-3-(1H-imidazol-5-yl)-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