N2-乙酰基-N-(4-甲基-2-氧代-2H-苯并吡喃-7-基)赖氨酰胺 | 156661-42-6

• 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: N2-乙酰基-N-(4-甲基-2-氧代-2H-苯并吡喃-7-基)赖氨酰胺
• 英文名称: Ac-Lys-AMC
• 英文别名: H-(N-acetyl-Lys)-AMC；N²-acetyl-L-lysine 4-methylcoumar-7-ylamide；(2S)-2-acetamido-6-amino-N-(4-methyl-2-oxochromen-7-yl)hexanamide
• CAS: 156661-42-6
• 化学式: C₁₈H₂₃N₃O₄
• 分子量: 345.398
• InChiKey: NBOQAQRQQNJREL-HNNXBMFYSA-N

物化性质

• 沸点：
  666.7±55.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  5

制备方法与用途

生物活性底物 Ac-Lys-AMC（也称为 MAL）是一种用于检测组蛋白去乙酰化酶（HDACs）的荧光底物。

反应信息

• 作为反应物：
  描述：

  N2-乙酰基-N-(4-甲基-2-氧代-2H-苯并吡喃-7-基)赖氨酰胺 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 methyl 4-[[(5S)-5-acetamido-6-[(4-methyl-2-oxochromen-7-yl)amino]-6-oxohexyl]amino]-4-oxobutanoate
  参考文献：
  名称：

  Compounds and methods for detection of enzymes that remove formyl, succinyl, methyl succinyl or myristoyl groups from ε-amino lysine moieties

  摘要：

  提供的是一种包含以下结构的化合物：其中SIG是一个信号分子，R3是一个甲酰基、琥珀酰基、甲基琥珀酰基或肉豆蔻酰基。还提供了一个包含上述化合物的试剂盒，并附有确定酶存在的指导说明。此外，还提供了一种用于确定样品是否具有去除赖氨酸ε-氨基上的琥珀酰基、甲基琥珀酰基、甲酰基或肉豆蔻酰基的酶的方法。还提供了一种确定分子是否抑制去除赖氨酸ε-氨基上的琥珀酰基、甲基琥珀酰基、甲酰基或肉豆蔻酰基的酶的方法。

  公开号：

  US09637773B2
• 作为产物：
  描述：

  7-氨基-4-甲基香豆素 在 盐酸 、 N,N'-羰基二咪唑 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 生成 N2-乙酰基-N-(4-甲基-2-氧代-2H-苯并吡喃-7-基)赖氨酰胺
  参考文献：
  名称：

  Reactivity of Lysine Moieties toward γ-Hydroxy-α,β-unsaturated Epoxides:  A Model Study on Protein−Lipid Oxidation Product Interaction

  摘要：

  Epoxyols are generally accepted as crucial intermediates in lipid oxidation. The reactivity of gamma-hydroxy-alpha,beta-unsaturated epoxides toward lysine moieties is investigated, employing trans-4,epoxy-trans-2-hexen-1-ol (EH) as a model substrate and propylamine or N-2-acetyl-L-lysine 4-methylcoumar-7-ylamide (AcLys-MCA) as model reagents for protein-bound lysine. Independent syntheses are reported for EH and AcLys-MCA. Reaction of the amine components with EH in THF yields 4-(propylamino)-trans-2-hexene-1,5-diol and N-2-acetyl-N-6-(1,5-dihydroxy-trans-2-hexen-4-yl)-L-lysine 4-methylcoumaryl-7-amide, respectively. Unequivocal structural characterization of the products prove the epoxy ring cleavage to proceed by a true S(N)2 mechanism. Incubation bf EH with propylamine and AcLys-MCA in aqueous medium at 37 degrees C shows the turnover to decrease with lower pHs. From reaction of EH (100 mM) with AcLys-MCA (50 mM) under physiological conditions (pH 7.4), 3% of the lysine moieties can be identified in the form of N-2-acetyl-N-6-(1,5-dihydroxy-trans-2-hexen-4-yl)-L-lysine 4-methylcoumar-7-ylamide after 24 h.

  DOI：

  10.1021/jf950837r

文献信息

• Novel hydroxamates as therapeutic agents
  申请人：Setti L. Eduardo

  公开号：US20050227976A1

  公开（公告）日：2005-10-13

  The present invention is directed to certain hydroxamate derivatives that are inhibitors of histone deacetylase and are therefore useful in the treatment of diseases associated with histone deacetylase activity. Pharmaceutical compositions and processes for preparing these compounds are also disclosed.

  本发明涉及某些羟肟酸酯衍生物，它们是组蛋白去乙酰化酶的抑制剂，因此在治疗与组蛋白去乙酰化酶活性相关的疾病方面是有用的。还公开了制备这些化合物的药物组合物和方法。
• Profiling of Substrates for Zinc-dependent Lysine Deacylase Enzymes: HDAC3 Exhibits Decrotonylase Activity In Vitro
  作者：Andreas S. Madsen、Christian A. Olsen

  DOI：10.1002/anie.201203754

  日期：2012.9.3

  of the activities of the eleven human zinc‐dependent lysine deacylases against a series of fluorogenic substrates (see scheme) as well as kinetic evaluation revealed substrates for screenings of histone deacetylases HDAC10 and HDAC11 at reasonably low enzyme concentrations. Furthermore, HDAC3 in complex with nuclear receptor corepressor 1 (HDAC3–NCoR1) was shown to harbor decrotonylase activity in vitro

  系统针对一系列荧光底物的11人的锌依赖性赖氨酸脱酰的活动的筛选（参见方案）以及动力学评价揭示基板组蛋白的脱乙酰放映和HDAC10 HDAC11在合理的低的酶浓度。此外，HDAC3在复合体与核受体辅抑制子1（HDAC3-NCoR1）显示窝藏在体外decrotonylase活性。
• Compounds and methods for detection of enzymes that remove methyl succinyl groups from epsilon-amino lysine moieties
  申请人：Enzo Life Sciences, Inc.

  公开号：US10920265B2

  公开（公告）日：2021-02-16

  Provided is a compound that comprises the structure: where SIG is a signaling molecule and R3 is a formyl, a succinyl, a methyl succinyl, or a myristoyl. Also provided is a kit is provided that comprises the above compound, with instructions for determining the presence of the enzyme. Additionally, a method is provided for determining whether a sample has an enzyme that removes a succinyl, a methyl succinyl, a formyl, or a myristoyl moiety from an ε-amino of a lysine. Also provided is a method of determining whether a molecule inhibits an enzyme that removes a succinyl, a methyl succinyl, a formyl, or a myristoyl moiety from an ε-amino of a lysine.

  本文提供了一种包含以下结构的化合物： 其中 SIG 是信号分子，R3 是甲酰基、琥珀酰基、甲基琥珀酰基或肉豆蔻酰基。还提供了一种试剂盒，其中包含上述化合物，并附有测定酶存在的说明。此外，还提供了一种方法，用于确定样品中是否含有能从赖氨酸的 ε-氨基中去除琥珀酰基、甲基琥珀酰基、甲酰基或肉豆蔻酰基的酶。还提供了一种方法，用于确定一种分子是否抑制从赖氨酸的 ε-氨基中去除琥珀酰基、甲基琥珀酰基、甲酰基或肉豆蔻酰基的酶。
• COMPOUNDS AND METHODS FOR DETECTION OF ENZYMES THAT REMOVE FORMYL, SUCCINYL, METHYL SUCCINYL OR MYRISTOYL GROUPS FROM EPSILON-AMINO LYSINE MOIETIES
  申请人：Enzo Life Sciences, Inc.

  公开号：US20170198333A1

  公开（公告）日：2017-07-13

  Provided is a compound that comprises the structure: where SIG is a signaling molecule and R 3 is a formyl, a succinyl, a methyl succinyl, or a myristoyl. Also provided is a kit is provided that comprises the above compound, with instructions for determining the presence of the enzyme. Additionally, a method is provided for determining whether a sample has an enzyme that removes a succinyl, a methyl succinyl, a formyl, or a myristoyl moiety from an ε-amino of a lysine. Also provided is a method of determining whether a molecule inhibits an enzyme that removes a succinyl, a methyl succinyl, a formyl, or a myristoyl moiety from an ε-amino of a lysine.
• COMPOUNDS AND METHODS FOR DETECTION OF ENZYMES THAT REMOVE METHYL SUCCINYL GROUPS FROM EPSILON-AMINO LYSINE MOIETIES
  申请人：Enzo Life Sciences, Inc.

  公开号：US20200283821A1

  公开（公告）日：2020-09-10

  Provided is a compound that comprises the structure: where SIG is a signaling molecule and R 3 is a formyl, a succinyl, a methyl succinyl, or a myristoyl. Also provided is a kit is provided that comprises the above compound, with instructions for determining the presence of the enzyme. Additionally, a method is provided for determining whether a sample has an enzyme that removes a succinyl, a methyl succinyl, a formyl, or a myristoyl moiety from an ε-amino of a lysine. Also provided is a method of determining whether a molecule inhibits an enzyme that removes a succinyl, a methyl succinyl, a formyl, or a myristoyl moiety from an ε-amino of a lysine.