(S)-2-乙酰胺基-6-((叔丁氧羰基)氨基)己酸 | 23500-04-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天然氨基酸及其衍生物
• 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: (S)-2-乙酰胺基-6-((叔丁氧羰基)氨基)己酸
• 英文名称: N²-acetyl-N⁶-(tert-butoxycarbonyl)-L-lysine
• 英文别名: (S)-2-acetamido-6-((tert-butoxycarbonyl)amino)hexanoic acid；Ac-Lys(Boc)-OH；(2S)-2-acetamido-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 23500-04-1
• 化学式: C₁₃H₂₄N₂O₅
• 分子量: 288.344
• InChiKey: NZAMQYCOJSWUAO-JTQLQIEISA-N

物化性质

• 熔点：
  128 °C
• 沸点：
  528.8±45.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

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
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-Lys(Boc)-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-Lys(Boc)-OH
CAS number: 23500-04-1

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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.
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: C13H24N2O5
Molecular weight: 288.3

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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：

  (S)-2-乙酰胺基-6-((叔丁氧羰基)氨基)己酸 在 N-甲基吗啉 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 Nα-acetyl-Nε-Boc-(S)-lysine-mexiletine
  参考文献：
  名称：

  [EN] MEXILETINE PRODRUGS
  [FR] PROMÉDICAMENTS DE MÉXILÉTINE

  摘要：

  本发明涉及美西利汀（及美西利汀的活性代谢物）的前药，包含这些前药的药物组合物。还提供了用于治疗肌张力疾病的方法，同时减少与美西利汀相关的固有不良G1副作用，增加美西利汀的生物利用度，并通过上述前药改善美西利汀的药代动力学可重复性。

  公开号：

  WO2012085586A1
• 作为产物：
  描述：

  L-赖氨酸盐酸盐 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 生成 (S)-2-乙酰胺基-6-((叔丁氧羰基)氨基)己酸
  参考文献：
  名称：

  A Magnetic Biomimetic Nanocatalyst for Cleaving Phosphoester and Carboxylic Ester Bonds under Mild Conditions

  摘要：

  As a result of the unique surface structure of nanospheres, Asp and His residues supported on a 12 nm maghemite nanoparticle worked collaboratively as a biomimetic nanocatalyst for hydrolyzing paraoxon (phosphoester) and 4-nitrophenyl acetate (carboxylic ester) in Milli-Q water (pH 7.0) at 37 degrees C, without employing extremes of pH or heavy metals. Our nanocatalyst could be facilely recovered via magnetic concentration. The isolated catalyst exhibited long-term stability, showing no significant loss of its catalytic activity for repeated uses after 3 months.

  DOI：

  10.1021/ol061098a

文献信息

• ¹⁸F-Trifluoromethylation of Unmodified Peptides with 5-¹⁸F-(Trifluoromethyl)dibenzothiophenium Trifluoromethanesulfonate
  作者：Stefan Verhoog、Choon Wee Kee、Yanlan Wang、Tanatorn Khotavivattana、Thomas C. Wilson、Veerle Kersemans、Sean Smart、Matthew Tredwell、Benjamin G. Davis、Véronique Gouverneur

  DOI：10.1021/jacs.7b10227

  日期：2018.2.7

  18F-labeling of 5-(trifluoromethyl)-dibenzothiophenium trifluoromethanesulfonate, commonly referred to as the Umemoto reagent, has been accomplished applying a halogen exchange 18F-fluorination with 18F-fluoride, followed by oxidative cyclization with Oxone and trifluoromethanesulfonic anhydride. This new 18F-reagent allows for the direct chemoselective 18F-labeling of unmodified peptides at the thiol cysteine

  5-(三氟甲基)-二苯并噻吩三氟甲磺酸盐的 18F 标记，通常称为 Umemoto 试剂，已通过卤素交换 18F-氟化与 18F-氟化物，然后与 Oxone 和三氟甲磺酸酐氧化环化来完成。这种新的 18F 试剂允许在硫醇半胱氨酸残基处对未修饰的肽进行直接化学选择性 18F 标记。
• Visible‐Light‐Mediated S−H Bond Insertion Reactions of Diazoalkanes with Cysteine Residues in Batch and Flow
  作者：Long‐Zhou Qin、Xin Yuan、Yu‐Sheng Cui、Qi Sun、Xiu Duan、Kai‐Qiang Zhuang、Lin Chen、Jiang‐Kai Qiu、Kai Guo

  DOI：10.1002/adsc.202000716

  日期：2020.11.18

  diazoacetates with cysteine residues that enabled metal‐free, S−H functionalization under visible‐light conditions. Moreover, this process could be intensified by a continuous‐flow photomicroreactor on the acceleration of the reaction (6.5 min residence time). The batch and flow protocols described were applied to obtain a wide range of functionalized cysteine derivatives and cysteine‐containing dipeptides

  我们描述了芳基重氮乙酸酯与半胱氨酸残基的S-H键插入反应的应用，该反应可在可见光条件下实现无金属的S-H功能化。此外，连续反应光微反应器可加快反应速度（6.5分钟的停留时间），从而增强该过程。所描述的批次和流程方案可用于获得各种功能化的半胱氨酸衍生物和含半胱氨酸的二肽，从而为其在温和条件下的功能化提供了一个简单而通用的平台。
• Continuous-flow processes for the <i>S</i>-alkynylation of cysteine-containing peptides and thioglycosides under catalyst-free, oxidant-free and mild conditions
  作者：Long-Zhou Qin、Xin Yuan、Jie Liu、Meng-Yu Wu、Qi Sun、Xiu Duan、Xin-Peng Zhang、Jiang-Kai Qiu、Kai Guo

  DOI：10.1039/d1gc01937f

  日期：——

  Selective S-alkynylation of cysteine-containing peptides and 1-thioglycoside residues was developed using continuous flow.

  含半胱氨酸肽和1-硫代糖苷残基的选择性S-炔基化反应已经在连续流条件下开发。
• [EN] SPLICEOSTATIN ANALOGS<br/>[FR] ANALOGUES DE SPLICÉOSTATINE
  申请人：PFIZER

  公开号：WO2014068443A1

  公开（公告）日：2014-05-08

  The present invention is directed to novel cytotoxic spliceostatin analogs (I) and derivatives, to antibody drug conjugates thereof, and to methods for using the same to treat medical conditions including cancer.

  本发明涉及新型细胞毒性剪接抑制素类似物（I）及其衍生物，涉及其抗体药物结合物，以及使用它们治疗包括癌症在内的医疗状况的方法。
• Biocompatible Photoinduced Alkylation of Dehydroalanine for the Synthesis of Unnatural α-Amino Acids
  作者：José A. C. Delgado、José T. M. Correia、Emanuele F. Pissinati、Márcio W. Paixão

  DOI：10.1021/acs.orglett.1c01781

  日期：2021.7.2

  A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is described. The protocol is characterized by the wide nature of alkyl radicals employed, mild conditions, and functional group compatibility. This protocol is further extended to access peptides, late-stage functionalization of pharmaceuticals, and enantioenriched amino acids.

  描述了脱氢丙氨酸的位点选择性烷基化以获取受保护的非天然氨基酸。该协议的特点是所用烷基的广泛性质、温和的条件和官能团兼容性。该协议进一步扩展到访问肽、药物的后期功能化和对映体富集的氨基酸。