N-乙酰基-L-谷氨酸 5-叔丁酯 | 84192-88-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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: N-乙酰基-L-谷氨酸 5-叔丁酯
• 中文别名: N-乙酰基-L-谷氨酸5-叔丁酯
• 英文名称: Ac-Glu(OtBu)-OH
• 英文别名: (S)-2-acetamido-5-(tert-butoxy)-5-oxopentanoic acid；acetyl-L-glutamic acid γ-tert-butyl ester；(2S)-2-acetamido-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
• CAS: 84192-88-1
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: FALCCLKESWGSNI-QMMMGPOBSA-N

物化性质

• 沸点：
  464.0±40.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-Glu(OtBu)-OH
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Ac-Glu(OtBu)-OH
CAS number: 84192-88-1

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H19NO5
Molecular weight: 245.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-乙酰基-L-谷氨酸 5-叔丁酯 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 methyl (S)-(2-acetamido-5-oxo-5-(tritylthio)pentanoyl)glycinate
  参考文献：
  名称：

  自由基介导的酰基硫醇-烯反应快速合成生物分子硫酯衍生物

  摘要：

  生物相关烯烃和硫代酸组分之间自由基介导的酰基硫醇-烯反应能够快速、化学选择性和高产率地形成硫酯。该反应与能够进行分子内酰基转移的底物结合，允许获得超出硫醚键的天然和修饰产物。

  DOI：

  10.1002/ejoc.202100615

文献信息

• [EN] TARGETED NOTCH PATHWAY INHIBITORS<br/>[FR] INHIBITEURS DE LA VOIE DE NOTCH CIBLÉE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2016198366A1

  公开（公告）日：2016-12-15

  The instant invention relates to novel conjugates of formula (I): S - L - A (I) or salts thereof, wherein A is a gamma-secretase inhibitor, L is a linker and S is a peptidase-specific substrate, as well as processes for their manufacture, pharmaceutical compositions comprising them, and their use as medicaments, especially for the treatment of renal diseases and tissue damage in the kidney.

  本发明涉及式(I)的新型共轭物：S - L - A (I)或其盐，其中A为γ-分泌酶抑制剂，L为连接子，S为肽酶特异性底物，以及它们的制备方法、包含它们的药物组合物及其作为药物，特别是用于治疗肾脏疾病和肾脏组织损伤的用途。
• Site-Specific Nonenzymatic Peptide S/O-Glutamylation Reveals the Extent of Substrate Promiscuity in Glutamate Elimination Domains
  作者：Alexander A. Vinogradov、Masanobu Nagano、Yuki Goto、Hiroaki Suga

  DOI：10.1021/jacs.1c06470

  日期：2021.8.25

  dissect the substrate recognition requirements of three known EDs. Our results establish that EDs are uniquely promiscuous enzymes capable of acting on substrates with arbitrary amino acid sequences and performing retro-Michael reaction beyond the canonical glutamate elimination. To facilitate substrate recruitment, EDs apparently engage in nonspecific hydrophobic interactions with their substrates. Altogether

  通过 tRNA 依赖性丝氨酸和苏氨酸脱水形成脱氢丙氨酸和脱氢丁氨酸残基是羊毛肽和硫肽 RiPPs 生物合成中的关键翻译后修饰。脱水过程涉及两个反应，其中 O-谷氨酰丝氨酸/苏氨酸中间体通过使用 Glu-tRNA Glu的专用酶获得作为酰基供体，被称为谷氨酸消除结构域（ED）的第二种酶识别，其催化产生脱氢氨基酸的同名反应。ED 催化的许多细节仍未探索，因为可用于测试的底物范围仅限于上游酶可以提供的底物。在这里，我们报告了两种互补策略，用于直接、非酶促访问不同的 ED 底物。我们确定了含有 Cys 的肽和α之间的硫醇 - 硫酯交换反应谷氨酸硫酯导致 S-谷氨酰化中间体，可作为 ED 的底物。此外，我们表明，通过位点特异性 S-to-O 酰基转移反应，可以从 S-谷氨酰化肽中获得天然 O-谷氨酰化底物。结合用于快速肽生产的灵活体外翻译，这些化学物质使我们能够剖析三种已知 ED 的底物识别要求。我们的研究结果表明，EDs
• Acid and Solvent Effects on the Regioselectivity of Minisci-Type Addition to Quinolines Using Amino Acid Derived Redox Active Esters
  作者：Robert J. Phipps、Barbara W. Hadrys

  DOI：10.1055/s-0040-1707888

  日期：2021.1

  Minisci-type reactions comprise an important class of reactions for the direct functionalization of basic heterocyclic compounds. On certain heterocycles, such as quinolines, Minisci-type reactions face a regioselectivity choice which often results in mixtures of regioisomers at the C2 and C4 positions, limiting utility. We present a study of the effect of solvent and Bronsted acid catalyst on regioselectivity

  Minisci 型反应包括一类重要的用于碱性杂环化合物直接官能化的反应。在某些杂环（例如喹啉）上，Minisci 型反应面临区域选择性选择，这通常会导致 C2 和 C4 位置的区域异构体混合，从而限制了实用性。我们研究了溶剂和布朗斯台德酸催化剂对将 N-乙酰基取代的 α-氨基烷基添加到喹啉中的区域选择性的影响。通过调整溶剂和酸的组合，我们确定了强烈支持 C2 和强烈支持 C4 的条件，并提供了小范围的兼容底物。
• A structure-based design approach to advance the allyltyrosine-based series of HIV integrase inhibitors
  作者：Christopher P. Gordon、Neal Dalton、Nicholas Vandegraaff、John Deadman、David I. Rhodes、Jonathan A. Coates、Stephen G. Pyne、Renate Griffith、John B. Bremner、Paul A. Keller

  DOI：10.1016/j.tet.2017.11.052

  日期：2018.3

  of mid-2017, only one structure of the human immunodeficiency virus (HIV) integrase core domain co-crystallised with an active site inhibitor was reported. In this structure (1QS4), integrase is complexed with a diketo-acid based strand-transfer inhibitor (INSTI). This structure has been a preferred platform for the structure-based design of INSTIs despite concerns relating to structural irregularities

  截至2017年中，仅报道了与活性位点抑制剂共结晶的人类免疫缺陷病毒（HIV）整合酶核心结构域的一种结构。在此结构（1QS4）中，整合酶与基于二酮酸的链转移抑制剂（INSTI）复合。尽管担心因晶体堆积效应引起的结构不规则，但该结构已成为INSTI基于结构设计的首选平台。对目前所报告的297个整合酶催化核心结构库的一项调查表明，复杂结构1QS4中活性位点的解剖结构相对于所检查的所有其他结构表现出细微的变化。因此，将1QS4结构用于对接研究。从27个烯丙基酪氨酸类似物的对接中HIV感染的人类T细胞中50 ±10±5μM的值。在3'-加工和链转移试验的结合中，“内部”化合物库的另外对接发现了基于甲基酯的腈衍生物，其IC 50值为0.5μM。
• Sequence-Selective Peptide Recognition with Designed Modules
  作者：Mark Wehner、Dominic Janssen、Gerhard Schäfer、Thomas Schrader

  DOI：10.1002/ejoc.200500393

  日期：2006.1

  A concept for the rational design of sequence-selective peptide receptors has been extended: in addn. to recognition modules for polar, arom. and basic amino acids, the series has now been completed with new receptor units for apolar and acidic amino acids. The underlying strategy uses the intermol. b-sheet stabilization of a dipeptide as a prerequisite to bind its N-terminal amino acid side chain

  合理设计序列选择性肽受体的概念已得到扩展：另外。到 polar、arom 的识别模块。和碱性氨基酸，该系列现在已经完成了新的非极性和酸性氨基酸受体单元。底层策略使用 intermol。二肽的 b 片层稳定性，作为通过从受体部分突出的 U 形转弯末端的战略性放置的识别尖端结合其 N 端氨基酸侧链的先决条件。因此，二氨基吡唑已通过环状酰亚胺共价连接到肯普氏三酸，而间位取代的苯胺作为酰胺偶联到第三个羧酸酯悬垂臂上，形成两个芳基。在紧密的构象锁定中将单位转换为子范德华距离。核磁共振滴定，Karplus 分析和蒙特卡洛模拟证明了丙氨酸-contg 的有效序列选择性识别。二肽。以前不存在这样一组合理设计的肽受体的例子。