ethyl (3S)-3-amino-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate | 104274-42-2

• 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: ethyl (3S)-3-amino-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
• CAS: 104274-42-2
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: MTYUKKZPMRVUEO-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (3S)-3-amino-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 Montmorillonite K₁₀ 、 氢气 、 戴斯-马丁氧化剂 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 119.0h， 生成 (4S)-5-[[(2S)-6-amino-1-[[(2S)-1-carboxy-4-(2,6-dimethylbenzoyl)oxy-3-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid
  参考文献：
  名称：

  Synthesis of Novel Caspase Inhibitors for Characterization of the Active Caspase Proteome in Vitro and in Vivo

  摘要：

  Caspases are cysteine proteases that are essential for cytokine maturation and apoptosis. To facilitate the dissection of caspase function in vitro and in vivo, we have synthesized irreversible caspase inhibitors with biotin attached via linker arms of various lengths (12a-d) and a 2,4-dinitrophenyl labeled inhibitor (13). Affinity labeling of apoptotic extracts followed by blotting reveals that these affinity probes detect active caspases. Using the strong affinity of avidin for biotin, we have isolated affinity-labeled caspase 6 from apoptotic cytosolic extracts of cells overexpressing procaspase 6 by treatment with 12c, which contains biotin attached to the N-epsilon-lysine of the inhibitor by a 22.5 A linker arm, followed by affinity purification on monomeric avidin-sepharose beads. Compound 13 has proven sufficiently cell permeable to rescue cells from apoptotic execution. These novel caspase inhibitors should provide powerful probes for the study of the active caspase proteome during apoptosis both in vitro and in vivo.

  DOI：

  10.1021/jm060385h
• 作为产物：
  描述：

  ethyl (E)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate 在 palladium on activated charcoal 氢气 、 苄胺 作用下， 生成 ethyl (3S)-3-amino-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
  参考文献：
  名称：

  基于P1天冬氨酸的肽酰氧基甲基和氟甲基酮的合成，作为白介素1β转化酶的抑制剂

  摘要：

  已经开发出用于合成基于天冬氨酸的P1的2，6-二氯苯甲酰氧基甲基酮1和氟甲基酮2的改进方法，这是两种有效的ICE抑制剂的前药。1由（R）-反式-4,5-O-异亚丙基-4,5-二羟基-2-戊烯基羧酸乙酯制备；2从经由硝基-羟醛缩合为关键步骤中获得原位生成fluoroacetaldehyde。

  DOI：

  10.1016/0040-4039(94)88361-0

文献信息

• Synthesis of P1 aspartate-based peptide acyloxymethyl and fluoromethyl ketones as inhibitors of interleukin-1β-converting enzyme
  作者：Laszlo Revesz、Chantal Briswalter、Richard Heng、Albert Leutwiler、Rudolf Mueller、Hans-Juerg Wuethrich

  DOI：10.1016/0040-4039(94)88361-0

  日期：1994.12

  Improved procedures have been developed for the synthesis of P1 aspartate-based 2,6-dichlorobenzoyloxymethyl ketone 1 and fluoromethyl ketone 2, the prodrugs of two potent ICE-inhibitors. 1 was prepared from (R)-trans-4,5-O-isopropylidene-4,5-dihydroxy-2-pentenecarboxylic acid ethyl ester; 2 was obtained via a nitro-aldol condensation as key step from in situ generated fluoroacetaldehyde.

  已经开发出用于合成基于天冬氨酸的P1的2，6-二氯苯甲酰氧基甲基酮1和氟甲基酮2的改进方法，这是两种有效的ICE抑制剂的前药。1由（R）-反式-4,5-O-异亚丙基-4,5-二羟基-2-戊烯基羧酸乙酯制备；2从经由硝基-羟醛缩合为关键步骤中获得原位生成fluoroacetaldehyde。
• Synthesis of Novel Caspase Inhibitors for Characterization of the Active Caspase Proteome in Vitro and in Vivo
  作者：Alexander J. Henzing、Helen Dodson、Joel M. Reid、Scott H. Kaufmann、Robert L. Baxter、William C. Earnshaw

  DOI：10.1021/jm060385h

  日期：2006.12.1

  Caspases are cysteine proteases that are essential for cytokine maturation and apoptosis. To facilitate the dissection of caspase function in vitro and in vivo, we have synthesized irreversible caspase inhibitors with biotin attached via linker arms of various lengths (12a-d) and a 2,4-dinitrophenyl labeled inhibitor (13). Affinity labeling of apoptotic extracts followed by blotting reveals that these affinity probes detect active caspases. Using the strong affinity of avidin for biotin, we have isolated affinity-labeled caspase 6 from apoptotic cytosolic extracts of cells overexpressing procaspase 6 by treatment with 12c, which contains biotin attached to the N-epsilon-lysine of the inhibitor by a 22.5 A linker arm, followed by affinity purification on monomeric avidin-sepharose beads. Compound 13 has proven sufficiently cell permeable to rescue cells from apoptotic execution. These novel caspase inhibitors should provide powerful probes for the study of the active caspase proteome during apoptosis both in vitro and in vivo.