乙酰-L-正亮氨酸 | 15891-49-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 亮氨酸类衍生物
• 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: 乙酰-L-正亮氨酸
• 英文名称: N-acetyl-L-norleucine
• 英文别名: (S)-2-Acetamidohexanoic acid；(2S)-2-acetamidohexanoic acid
• CAS: 15891-49-3
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: JDMCEGLQFSOMQH-ZETCQYMHSA-N

物化性质

• 熔点：
  114-115.5℃ (water )
• 沸点：
  378.3±25.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)
• 溶解度：
  0.31 M

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-nle-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-nle-oh
CAS number: 15891-49-3

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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.
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: C8H15NO3
Molecular weight: 173.2

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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：

  乙酰-L-正亮氨酸 在 phosphate buffer 作用下， 生成 L-正亮氨酸
  参考文献：
  名称：

  Calorimetric evaluation of enzyme kinetic parameters

  摘要：

  The measurement of kinetic parameters (k(cat), K(m), K(i)) for a wide range of proteolytic enzymes is vital to contemporary bioorganic and medicinal chemistry. Enzyme assays based on changes in optical properties of the system or changes in concentration of an ion detectable electrochemically are not viable for many enzyme-catalyzed reactions, including proteases and peptidases. Hydrolysis of an amide bond produces no change in the optical properties or pH of the reaction solution, and as a result no general direct method for the evaluation of protease kinetics exists using underivatized substrates. We report here a microcalorimetric assay which provides a general and straightforward technique for the measurement of kinetic parameters of hydrolysis of underivatized peptide substrates by proteases. Using this technique, k(cat) values as high as 10(5) s-1 can be easily measured. We demonstrate the utility of the technique by measuring the kinetics of hydrolysis of several N-acylamino acids by the synthetically useful enzyme hog kidney acylase and the hydrolysis of tetrapeptide p-nitrophenyl anilides by subtilisin BPN'. Although we have used the technique to monitor amide bond hydrolysis, the methodology is applicable to any system with appropriate kinetic and thermodynamic properties.

  DOI：

  10.1021/jo00065a010
• 作为产物：
  描述：

  L-正亮氨酸 、 乙酸酐 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 5.0h， 以31%的产率得到乙酰-L-正亮氨酸
  参考文献：
  名称：

  通过生物启发的立体选择性γ-C-H键键渗法普遍获得修饰的α-氨基酸

  摘要：

  α‐氨基酸代表了宝贵的一类天然产物，被用作生物和化学合成的基础。由于可用的天然氨基酸数量有限，并且它们在蛋白质组学，诊断，药物递送和催化中的广泛应用，对开发制备修饰的类似物的方法的需求日益增加。在这里，我们表明使用了生物启发性的锰催化剂和H 2 O 2在温和的条件下，可通过γ-C-H键内酯化作用获得修饰的α-氨基酸。该系统可有效靶向α-取代的和非手性α，α-二取代的α-氨基酸的1°，2°和3°γ-C-H键，具有出色的位点选择性，良好的非对映选择性和（如果适用）对映选择性。该方法可以被认为是完善的有机金属程序的替代方法。

  DOI：

  10.1002/anie.202007899
• 作为试剂：
  描述：

  反-3-已烯 、 2-(pyrimidin-5-yl)phenyl (m-tolyl)methanesulfonate 在 copper (II)-fluoride 、 乙酰-L-正亮氨酸 、 palladium diacetate 、 silver carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以66%的产率得到(E)-2-(pyrimidin-5-yl)phenyl (3-(hex-4-en-3-yl)-5-methylphenyl)methanesulfonate
  参考文献：
  名称：

  芳烃的钯催化定向亚选择性CH H烯丙基化：未活化的内部烯烃烯丙基替代物

  摘要：

  钯（II）催化的芳烃间选择性CH H烯丙基化反应是利用合成惰性的未活化无环内烯烃作为烯丙基替代物而开发的。嘧啶基导向基团的强大的σ供体和π接受能力通过克服典型的未活化内烯烃的惰性而促进了烯烃的插入。在 较宽的底物范围，宽泛的官能团耐受性以及良好至优异的收率下，实现了烯丙基对苯乙烯基产物的独家选择性以及E立体选择性。证明了药物的后期功能化。实验和计算研究阐明了机理，并指出了palladacycle中关键的空间控制，从而确定了产品的选择性。

  DOI：

  10.1002/anie.201904608

文献信息

• Structure-activity relationship studies of dipeptide-based hepsin inhibitors with Arg bioisosteres
  作者：Hongmok Kwon、Hyunsoo Ha、Hayoung Jeon、Jaebong Jang、Sang-Hyun Son、Kiho Lee、Song-Kyu Park、Youngjoo Byun

  DOI：10.1016/j.bioorg.2020.104521

  日期：2021.2

  as a potential therapeutic and diagnostic biomarker for PCa. Based on the reported Leu-Arg dipeptide-based hepsin inhibitors, we performed structural modification and determined in vitro hepsin- and matriptase-inhibitory activities. Comprehensive structure-activity relationship studies identified that the p-guanidinophenylalanine-based dipeptide analog 22a exhibited a strong hepsin-inhibitory activity

  Hepsin 是一种 II 型跨膜丝氨酸蛋白酶 (TTSP)，与细胞增殖相关，在包括前列腺癌 (PCa) 在内的多种癌症中过度表达。由于其在癌症进展和转移中的重要作用，hepsin 是一种有吸引力的蛋白质，可作为 PCa 的潜在治疗和诊断生物标志物。基于已报道的基于 Leu-Arg 二肽的 hepsin 抑制剂，我们进行了结构修饰并确定了体外 hepsin 和 Matriptase 抑制活性。综合构效关系研究表明，基于对胍基苯丙氨酸的二肽类似物 22a 表现出强烈的 hepsin 抑制活性（K i= 50.5 nM) 和比 Matriptase 高 22 倍的 hepsin 选择性。化合物 22a 可能是基于二肽的 hepsin 抑制剂结构优化的原型分子。
• Peculiar Stability of Amino Acids and Peptides from a Radical Perspective
  作者：Zachary I. Watts、Christopher J. Easton

  DOI：10.1021/ja9027583

  日期：2009.8.19

  Photochemical reactions of free and N-acetyl alpha-amino acids with chlorine and deuterium labeled hydrogen peroxide have been used to determine both the relative rates of reaction of molecules of these classes and the relative reactivity of their different types of hydrogen toward abstraction by chlorine and oxygen centered radicals. The relative rates of reaction of these species range over more than 3 orders

  游离和 N-乙酰α-氨基酸与氯和氘标记的过氧化氢的光化学反应已被用于确定这些类别分子的相对反应速率以及它们不同类型的氢对氯和氢的提取的相对反应性。以氧为中心的自由基。这些物种的相对反应速率范围超过 3 个数量级；然而，对于侧链特定位置上特定类型基团的多个氨基酸的数据，这些值非常相似。这些结果的预测效用已被证明用于三肽的区域选择性氯化。更一般地说，该分析表明氨基酸和肽的主链和相邻侧链位置对氢原子转移具有特殊的抵抗力，并且在异青霉素-N-合成酶催化的修饰底物反应的早期研究中已经注意到类似的反应模式. 这种抗性与 α-氨基酸、肽和蛋白质的自由基反应的常见发生及其在生物学中的重要性形成鲜明对比。然而，它为氨基酸及其衍生物在自然界中避免降解的能力提供了一个理由，因为它们经常暴露于自由基，并且它至少部分地解释了酶催化自由基反应的异常能力而不是被自由基中间体分解。在异青霉素-N-合成酶催化的修饰底物反应
• Novel peptide derivatives, preparation and therapeutic and cosmetic application thereof
  申请人：Pinel Anne-Marie

  公开号：US20050187164A1

  公开（公告）日：2005-08-25

  The invention relates to peptides of formula (I) R-V 1 -Ala 2 -His 3 -X 4 -Y 5 -Trp 5 -NH2 wherein R represents a hydrogen atom or a protective group which can be chosen from among a benzoyl group, a tosyl group, a benzene sulfonyl group, a benzyloxycarbonyl group or a pyridinepropionyl group; V represents a natural amino acid or not chosen from among norleucine, norvaline and 2-N-Me-norleucine, X represents a natural amino acid or not having an aromatic character chosen from among phenylalanine, 1-naphtylalanine, 2-naphtylalanine, phenylglycine, benzothienylalanine, 4,4′-biphenylalanine, 3,3-diphenylalanine, homophenylalanine, indanylglycine, 4-methylphenylalanine, thienylalanine, p-nitrophenylalanine, halogenophenylalanine of configuration L or D; Y represents a natural amino acid of configuration L, having a basic character chosen from among arginine, lysine or ornithine, the enantiometers or diastercoisomers, and the mixtures thereof, including racemic mixtures. The invention also relates to a method for the preparation and application thereof in the field of therapeutics or cosmetics.

  本发明涉及式（I）的肽，其中R代表氢原子或保护基，所述保护基可以选择自苯甲酰基，对甲苯磺酰基，苯磺酰基，苄氧羰基基或吡啶丙酰基中的一种；V代表天然氨基酸或不选自诺亮氨酸，诺瓦林或2-N-甲基诺亮氨酸中的一种；X代表天然氨基酸或不具有芳香性质的氨基酸，所选自苯丙氨酸，1-萘丙氨酸，2-萘丙氨酸，苯基甘氨酸，苯并噻吩丙氨酸，4,4'-双苯基丙氨酸，3,3-二苯基丙氨酸，同型苯丙氨酸，茚基甘氨酸，4-甲基苯丙氨酸，噻吩基丙氨酸，对硝基苯丙氨酸，卤代苯丙氨酸，其构型为L或D；Y代表具有碱性特性的L型天然氨基酸，所选自精氨酸，赖氨酸或鸟氨酸的对映异构体或二对映异构体，以及包括外消旋混合物在内的它们的混合物。本发明还涉及一种在治疗或化妆品领域中的制备和应用方法。
• 一种氨基保护基N-取代手性氨基酸的合成方法
  申请人：马鞍山诺恩特医药科技有限公司

  公开号：CN114195684A

  公开（公告）日：2022-03-18

  本发明涉及一种氨基保护基N‑取代氨基酸的合成方法，包括以下步骤：(1)使进行乙酰化反应生成(2)使在碱的作用下和溶剂的存在下与R1X进行取代反应，然后脱乙酰基，得到(3)使与氨基保护剂在碱和溶剂的存在下进行反应，生成即所述氨基保护基N‑取代手性氨基酸；其中，R1选自C1～6的烷基；X为卤素；R2为氨基保护基，R3选自C1～6的烷基。本发明先将手性氨基酸上的氨基以乙酰基保护，然后与卤代烷R1X进行取代反应，再脱乙酰基，然后氮上连接氨基保护基制得氨基保护基N‑取代手性氨基酸，操作简单，产物不仅产率高，且合成过程中不消选，产物手性好，纯度高。
• Methionine recovery processes
  申请人：Lorbert Steve

  公开号：US20050089975A1

  公开（公告）日：2005-04-28

  The present invention relates to a method of making a methionine preparation, for example for an animal feed additive. The invention also related to methods for increasing the solubility of a methionine preparation.

  本发明涉及一种制备蛋氨酸制剂的方法，例如用于动物饲料添加剂。本发明还涉及一种提高蛋氨酸制剂溶解度的方法。