N2-[(苄氧基)羰基]-N6-(三氟乙酰基)-L-赖氨酸 | 14905-30-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N2-[(苄氧基)羰基]-N6-(三氟乙酰基)-L-赖氨酸
• 中文别名: N-(苄氧羰基)-N6-(三氟乙酰基)-L-赖氨酸
• 英文名称: (S)-2-benzyloxycarbonylamino-6-(2,2,2-trifluoroacetylamino)hexanoic acid
• 英文别名: (2S)-2-{[(benzyloxy)carbonyl]amino}-6-[(trifluoroacetyl)amino]hexanoic acid；N-α-carbenzoxy-N-ε-trifluoroacetyl-L-lysine；Z-Lys(TFA)-OH；TFA-Lys(Z)；(2S)-2-(phenylmethoxycarbonylamino)-6-[(2,2,2-trifluoroacetyl)amino]hexanoic acid
• CAS: 14905-30-7
• 化学式: C₁₆H₁₉F₃N₂O₅
• 分子量: 376.332
• InChiKey: KJWAGCTWJDRZLH-LBPRGKRZSA-N

物化性质

• 熔点：
  88-95

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  8

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储温度应保持在0-5°C。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-Lys(tfa)-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: Z-Lys(tfa)-oh
CAS number: 14905-30-7

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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: C16H19F3N2O5
Molecular weight: 376.3

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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, hydrogen fluoride.

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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：

  N2-[(苄氧基)羰基]-N6-(三氟乙酰基)-L-赖氨酸 在 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 TFA-Lys(Z)-Gly
  参考文献：
  名称：

  多肽。第十四部分。一些含有赖氨酸和谷氨酸残基的寡肽的合成

  摘要：

  已经合成了几种通式为A- Ly [省略图形]。（或[省略图形] lu）.Gly n。[图形省略] lu。（或[y省略图形] ys）.Gly n .O B的寡肽；它们用于聚合实验和“加倍”的预期用途对可以使用的保护基施加了限制，因为这些保护基必须可以选择性地除去。在两种情况下，无法删除N-甲酰基基团而不会破坏肽键，而在这些以及另外的情况下，侧链苄基酯基团对碱的不稳定性极大地阻止了其他保护基团的选择性去除。最后，合成了四种所需类型的被保护的寡肽，分别使用苄氧基羰基用于α - N保护，叔丁酯用于ω- C保护以及三氟乙酰基和甲酯用于保护赖氨酸和谷氨酸侧链。 。通过“加倍”方法将其中的三个转变为适合聚合的侧链保护肽，然后转变为游离肽，其中两个转变为八肽和十二肽。

  DOI：

  10.1039/j39660002349
• 作为产物：
  描述：

  L-赖氨酸盐酸盐 在 sodium hydroxide 、 碳酸氢钠 作用下， 生成 N2-[(苄氧基)羰基]-N6-(三氟乙酰基)-L-赖氨酸
  参考文献：
  名称：

  多肽。第十四部分。一些含有赖氨酸和谷氨酸残基的寡肽的合成

  摘要：

  已经合成了几种通式为A- Ly [省略图形]。（或[省略图形] lu）.Gly n。[图形省略] lu。（或[y省略图形] ys）.Gly n .O B的寡肽；它们用于聚合实验和“加倍”的预期用途对可以使用的保护基施加了限制，因为这些保护基必须可以选择性地除去。在两种情况下，无法删除N-甲酰基基团而不会破坏肽键，而在这些以及另外的情况下，侧链苄基酯基团对碱的不稳定性极大地阻止了其他保护基团的选择性去除。最后，合成了四种所需类型的被保护的寡肽，分别使用苄氧基羰基用于α - N保护，叔丁酯用于ω- C保护以及三氟乙酰基和甲酯用于保护赖氨酸和谷氨酸侧链。 。通过“加倍”方法将其中的三个转变为适合聚合的侧链保护肽，然后转变为游离肽，其中两个转变为八肽和十二肽。

  DOI：

  10.1039/j39660002349

文献信息

• Compounds and Compositions as Channel Activating Protease Inhibitors
  申请人：Tully C. David

  公开号：US20070275906A1

  公开（公告）日：2007-11-29

  The invention provides compounds and pharmaceutical compositions thereof, which are useful for modulating channel activating proteases, and methods for, using such compounds to treat, ameliorate or prevent a condition associated with a channel activating protease, including but not limited to prostasin, PRSS22, TMPRSS11 (e.g., TMPRSS11B, TMPRSS11E), TMPRSS2, TMPRSS3, TMPRSS4 (MTSP-2), matriptase (MTSP-1), CAP2, CAP3, trypsin, cathepsin A, or neutrophil elastase.

  该发明提供了化合物及其制药组合物，用于调节通道激活蛋白酶，并使用这些化合物来治疗、改善或预防与通道激活蛋白酶相关的疾病的方法，包括但不限于前列腺蛋白酶、PRSS22、TMPRSS11（例如TMPRSS11B、TMPRSS11E）、TMPRSS2、TMPRSS3、TMPRSS4（MTSP-2）、麦曲蛋白酶（MTSP-1）、CAP2、CAP3、胰蛋白酶、卡特普辛A或中性粒细胞弹性蛋白酶。
• [EN] ALYSINE MONOMETHYLATED DERIVATIVE AND CORRESPONDING ANTIBODY AND USE THEREOF<br/>[FR] DÉRIVÉ MONOMÉTHYLÉ DE LA LYSINE, ANTICORPS CORRESPONDANT ET UTILISATION ASSOCIÉE
  申请人：PMT BIOLABS INC

  公开号：WO2016011920A1

  公开（公告）日：2016-01-28

  Provided are artificially synthesized modified mono-methylated lysines and modified mono-methylated lysine derivatized polypeptides. Also provided is an antibody produced by using this modified mono-methylated lysine and modified mono-methylated lysine derivatized polypeptide as an antigen, the antibody can be used in recognizing and enriching the modified polypeptide after the lysine mono-methylated polypeptide being derivatized in vitro. Also provided are a preparation method of said antibody, a method for identifying and quantifying the lysine mono-methylated modified substrate in cell or tissue by using proteomics approach of affinity enrichment for specific antibody and mass spectrometry.

  提供了人工合成的修饰的单甲基化赖氨酸和修饰的单甲基化赖氨酸衍生的多肽。还提供了一种通过使用这种修饰的单甲基化赖氨酸和修饰的单甲基化赖氨酸衍生的多肽作为抗原而产生的抗体，该抗体可用于在体外将赖氨酸单甲基化多肽衍生化后识别和富集修饰的多肽。还提供了该抗体的制备方法，以及通过亲和富集特异抗体和质谱法的蛋白质组学方法在细胞或组织中识别和定量赖氨酸单甲基化修饰底物的方法。
• Selective Reagent for Detection of<i>N</i>-ε-Monomethylation of a Peptide Lysine Residue through S_NAr Reaction
  作者：Shuichi Mori、Tomoya Hirano、Asuka Takaguchi、Takashi Fujiwara、Yusuke Okazaki、Hiroyuki Kagechika

  DOI：10.1002/ejoc.201700488

  日期：2017.7.7

  and their reliability and reproducibility often depend on the quality of the protein reagents and the reaction conditions. Here, we describe a convenient method to detect N-e-monomethylation of the lysine residue through a simple chemical reaction. We focused on nucleophilic aromatic substitution reaction (SNAr reaction) between an aromatic electrophile and a primary or monomethylated amino group

  组蛋白特定赖氨酸残基的甲基化由组蛋白甲基转移酶 (HMT) 催化，并在基因表达的表观遗传控制中起关键作用。已经建立了几种检测赖氨酸残基 Ne 甲基化的方法，以评估 HMT 的活性、开发抑制剂和鉴定底物。然而，它们大多使用特异性抗体或酶，如肽酶，其可靠性和重现性往往取决于蛋白质试剂的质量和反应条件。在这里，我们描述了一种通过简单的化学反应检测赖氨酸残基 Ne-单甲基化的便捷方法。我们专注于芳香亲电子试剂与伯氨基或单甲基化氨基之间的亲核芳香取代反应（SNAr 反应）。对各种亲电子试剂的筛选表明，4-氟-2-硝基苯乙酮 (1g) 对赖氨酸的 Ne-单甲基化氨基具有高选择性。此外，1g与赖氨酸和Ne-单甲基化赖氨酸的反应产物5g和6g分别显示出不同的吸收光谱，即6g在350nm处的吸光度是5g的13倍。我们表明 1g 的这些特征特性可用于选择性检测 HMT 底物肽中赖氨酸残基的甲基化状态，并用于检测
• Design, Synthesis, and Structure−Activity Relationships of Macrocyclic Hydroxamic Acids That Inhibit Tumor Necrosis Factor α Release in Vitro and in Vivo
  作者：Chu-Biao Xue、Matthew E. Voss、David J. Nelson、James J.-W. Duan、Robert J. Cherney、Irina C. Jacobson、Xiaohua He、John Roderick、Lihua Chen、Ronald L. Corbett、Li Wang、Dayton T. Meyer、Kenneth Kennedy、William F. DeGrado、Karl D. Hardman、Christopher A. Teleha、Bruce D. Jaffee、Rui-Qin Liu、Robert A. Copeland、Maryanne B. Covington、David D. Christ、James M. Trzaskos、Robert C. Newton、Ronald L. Magolda、Ruth R. Wexler、Carl P. Decicco

  DOI：10.1021/jm010127e

  日期：2001.8.1

  To search for TNF-alpha (tumor necrosis factor alpha) converting enzyme (TACE) inhibitors, we designed a new class of macrocyclic hydroxamic acids by linking the PI and P2 ' residues of acyclic anti-succinate-based hydroxamic acids. A variety of residues including amide, carbamate, alkyl, sulfonamido, Boc-amino, and amino were found to be suitable P1-P2 ' linkers. With an N-methylamide at P3 ', the 13-16-membered macrocycles prepared exhibited low micromolar activities in the inhibition of TNF-alpha release from LPS-stimulated human whole blood. Further elaboration in the P3 ' -P4 ' area using the cyclophane and cyclic carbamate templates led to the identification of a number of potent analogues with IC50 values of less than or equal to 0.2 muM in whole blood assay (WBA). Although the P3 ' area can accommodate a broad array of structurally diversified functional groups including polar residues, hydrophobic residues, and amino and carboxylic acid moieties, in both the cyclophane series and the cyclic carbamate series, a glycine residue at P3 ' was identified as a critical structural component to achieve both good in vitro potency and good oral activity. With a glycine residue at P3 ', an N-methylamide at P4 ' provided the best cyclophane analogue, SL422 (WBA IC50 = 0.22 muM, LPS-mouse ED50 = 15 mg/kg, po), whereas a morpholinylamide at P4 ' afforded the most potent and most orally active cyclic carbamate analogue, SP057 (WBA IC50 = 0.067 muM, LPS-mouse ED50 = 2.3 mg/kg, po). Further profiling for SL422 and SP057 showed that these macrocyclic compounds are potent TACE inhibitors, with K-i values of 12 and 4.2 nM in the porcine TACE assay, and are broad-spectrum MMP inhibitors. Pharmacokinetic studies in beagle dogs revealed that SL422 and SP057 are orally bioavailable, with oral bioavailabilities of 11% and 23%, respectively.
• Subtype Selective Substrates for Histone Deacetylases
  作者：Birgit Heltweg、Franck Dequiedt、Brett L. Marshall、Carsten Brauch、Minoru Yoshida、Norikazu Nishino、Eric Verdin、Manfred Jung

  DOI：10.1021/jm0497592

  日期：2004.10.1

  To probe the steric requirements for deacylation, we synthesized lysine-derived small molecule substrates and examined structure -reactivity relationships with various histone deacetylases. Rat liver, human HeLa, and human recombinant class I and II histone deacetylases (HDACs) as well as human recombinant NAD(+)-dependent SIRT1 (class III enzyme) were used in these studies. A benzyloxycarbonyl substituent on the alpha-amino group yielded the highest conversion rates. Replacing the epsilon-acetyl group with larger lipophilic acyl substituents led to a pronounced decrease in conversion by class I and II enzymes; the class III enzyme displayed a greater tolerance. Incubations with recombinant FLAG-tagged human HDACs 1, 3, and 6 showed a distinct subtype selectivity among small molecule substrates. The subtype selectivity of HDAC inhibitors could be predicted with these substrates and an easily obtainable mixture of HDAC subtypes.