Ac-YVAD-肽核酸 | 149231-66-3

• 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
• 中文名称: Ac-YVAD-肽核酸
• 英文名称: N-α-acetyl-Tyr-Val-Ala-Asp-p-nitroanilide
• 英文别名: Ac-Tyr-Val-Ala-Asp-pNA；N-acetyl-L-Tyr-L-Val-L-Ala-L-Asp-p-nitroanilide；Ac-YVAD-pNA；(3S)-3-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]-4-(4-nitroanilino)-4-oxobutanoic acid
• CAS: 149231-66-3
• 化学式: C₂₉H₃₆N₆O₁₀
• 分子量: 628.639
• InChiKey: YDPNOCSPPGFBPX-XNHCRPTKSA-N

物化性质

• 沸点：
  1108.9±65.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  249
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Ac-YVAD-肽核酸 在 DL-dithiothreitol 、 recombinant human caspase-1 、 三羟甲基氨基甲烷盐酸盐 作用下， 生成 Ac-Tyr-Val-Ala-Asp-H
  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

文献信息

• US6348570B1
  申请人：——

  公开号：US6348570B1

  公开（公告）日：2002-02-19
• [EN] NOVEL CYSTEINE PROTEASE RELATED TO INTERLEUKIN-1 beta CONVERTING ENZYME<br/>[FR] NOUVELLE CYSTEINE PROTEASE APPARENTEE A L'ENZYME DE CONVERSION D'INTERLEUKINE-1 beta
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：WO1996026280A1

  公开（公告）日：1996-08-29

  (EN) A novel human cysteine protease (referred to as Ich-2 or Bih-3) related to interleukin-1$g(b) converting enzyme (ICE) but having an amino acid sequence that differs by 47 % from that of ICE is disclosed. The Ich-2 protein of the invention exhibits proteolytic activity and can induce apoptosis in cells. The invention provides isolated nucleic acid molecules encoding Ich-2 (including proteolytic cleavage products, subunits, fusion proteins and non-naturally occurring homologs thereof), as well as recombinant expression vectors containing these nucleic acid molecules, host cells into which the expression vectors have been introduced and non-human transgenic animals carrying an Ich-2-encoding nucleic acid. The invention further provides isolated Ich-2 proteins (including proteolytic cleavage products, subunits, fusion proteins and non-naturally occurring homologs thereof), as well as anti-Ich-2 antibodies. The invention still further provides methods for identifying modulators of Ich-2 protease activity (e.g., inhibitors and activators) and methods for modulating apoptisis in cells.(FR) L'invention concerne une nouvelle cystéine protéase humaine (appelée Ich-2 Bih-3) apparentée à l'enzyme de conversion d'interleukine-1$g(b) (ICE), mais présentant une séquence d'acides aminés différente à 47 % par rapport à celle de ICE. La protéine Ich-2 de l'invention présente une activité protéolytique et peut induire une apoptose dans les cellules. L'invention concerne des molécules d'acide nucléique isolées codant Ich-2 (y compris des produits de clivage protéolytique, des sous-unités, des protéines de fusion et leurs homologues non naturels), ainsi que des vecteurs d'expression recombinés contenant ces molécules d'acide nucléique, des cellules hôtes dans lesquelles les vecteurs d'expression ont été introduits ainsi que des animaux transgéniques non humains porteurs d'un acide nucléique codant Ich-2. L'invention concerne également des protéines Ich-2 isolées (y compris des produits de clivage protéolytique, des sous-unités, des protéines de fusion et leurs homologues non naturels), ainsi que des anticoprs anti-Ich-2. En outre, l'invention concerne des procédés d'identification de modulateurs de l'activité protéase de Ich-2 (par exemple des inhibiteurs et des activateurs), ainsi que des procédés de modulation de l'apoptose dans les cellules.
• 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.