Fmoc-L-蛋氨酸亚砜 | 76265-70-8

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-L-蛋氨酸亚砜
• 中文别名: N-芴甲氧羰基-L-蛋氨酸亚砜；Fmoc-Met(O)-OH
• 英文名称: Fmoc-Met(O)-OH
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfinylbutanoic acid
• CAS: 76265-70-8
• 化学式: C₂₀H₂₁NO₅S
• 分子量: 387.456
• InChiKey: CEHRSUBRZOGRSW-HSYKDVHTSA-N

物化性质

• 沸点：
  698.0±55.0 °C(Predicted)
• 密度：
  1.358±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)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  2930909090
• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R36/37/38

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-Met(o)-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: Fmoc-Met(o)-OH
CAS number: 76265-70-8

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C20H21NO5S
Molecular weight: 387.5

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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, sulfur 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：

  Fmoc-L-蛋氨酸亚砜 在 三甲基氯硅烷 、 2-巯基咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到Fmoc-L-蛋氨酸
  参考文献：
  名称：

  重新利用 Pummerer 重排：测定肽中的甲硫氨酸亚砜。

  摘要：

  蛋白质中蛋氨酸残基的可逆氧化已成为生物学上重要的翻译后修饰。然而，蛋白质中甲硫氨酸亚砜的检测和定量是困难的。我们的目标是开发一种专门衍生甲硫氨酸亚砜残基的方法。我们报告了用三甲基氯硅烷依次处理的甲硫氨酸亚砜的 Pummerer 重排，然后是 2-巯基咪唑或吡啶-2-硫醇，以产生二硫缩醛产物。该衍生物在标准质谱条件下是稳定的，并且其形成鉴定了氧化的蛋氨酸残基。报告了甲硫氨酸亚砜和模型底物的二硫缩醛形成的范围和要求。反应中间体已通过计算技术和 13 C NMR 光谱学进行了研究。这些为α-氯化中间体提供了证据。衍生化允许通过质谱和可能通过免疫化学方法检测和定量蛋白质中的甲硫氨酸亚砜。

  DOI：

  10.1002/cbic.201900463
• 作为产物：
  描述：

  Fmoc-L-蛋氨酸 在 4,7-二苯基-2,1,3-苯并噻二唑 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以82%的产率得到Fmoc-L-蛋氨酸亚砜
  参考文献：
  名称：

  扩展自动流动合成的工具包：在线快速色谱纯化的开发

  摘要：

  在线提取和纯化技术的最新进展使连续流反应器系统中的复杂多步合成成为可能。然而，对于产生产物混合物或残留起始材料的大范围化学反应，仍需要离线纯化以分离所需化合物。我们展示了商业自动化快速色谱系统与流动反应器的在线集成，用于产品的连续合成和分离。进行了一项原理验证研究以验证系统并测试色谱柱小柱的耐用性，在 2 天内执行 100 次运行的自动化序列。三种突出流动合成优势的不同反应系统已成功应用于在线正相或反相快速色谱，连续分离纯度为 97-99% 的产品。实现了高达 9.9 mmol/h 的生产率，从粗反应混合物的进料中分离出克量的纯产物。在此，我们描述了系统的开发和优化，并提出了选择非常适合在线快速色谱的反应的指南。

  DOI：

  10.1021/acs.joc.1c01151

文献信息

• [EN] SELENO-COMPOUNDS AND THERAPEUTIC USES THEREOF<br/>[FR] COMPOSÉS SÉLÉNO ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：UNIV MELBOURNE

  公开号：WO2012054988A1

  公开（公告）日：2012-05-03

  The present invention relates to compounds and compositions useful as antioxidants and in particular to selenium containing compounds of formula (I): wherein n is 1, 2, or 3; m is 2, 3, 4, or 5; and each R] is independently -(optionally substituted C 1 -C3 alkylene) p-OH, where p is 0 or 1, or a salt thereof. The invention also relates to the use of these seleno-compounds in the treatment of diseases or conditions associated with increased levels of oxidants produced by myeloperoxidase (MPO), such as for instance, atherosclerosis.

  本发明涉及作为抗氧化剂有用的化合物和组合物，特别是公式(I)中含硒的化合物，其中n为1、2或3；m为2、3、4或5；每个R]独立地为-(可选择地取代的C1-C3烷基) p-OH，其中p为0或1，或其盐。该发明还涉及在治疗由髓过氧化物酶(MPO)产生的氧化剂水平增加引起的疾病或症状中使用这些硒化合物，例如动脉粥样硬化。
• [EN] REDOX DEHYDRATION COUPLING CATALYSTS AND METHODS RELATED THERETO<br/>[FR] CATALYSEURS DE COUPLAGE DE DÉSHYDRATATION RÉDOX ET PROCÉDÉS ASSOCIÉS À CEUX-CI
  申请人：UNIV EMORY

  公开号：WO2017070157A1

  公开（公告）日：2017-04-27

  This disclosure relates to synthetic coupling methods using catalytic molecules. In certain embodiments, the catalytic molecules comprise heterocyclic thiolamide, S-acylthiosalicylamide, disulfide, selenium containing heterocycle, diselenide compound, ditelluride compound or tellurium containing heterocycle. Catalytic molecules disclosed herein are useful as catalysts in the transformation of hydroxy group containing compounds to amides, esters, ketones, and other carbon to heteroatom or carbon to carbon transformations.

  这份披露涉及使用催化分子的合成偶联方法。在某些实施例中，这些催化分子包括杂环硫酰胺、S-酰基硫代水杨酰胺、二硫化物、含硒杂环、二硒化合物、二碲化合物或含碲杂环。本文披露的催化分子可用作催化剂，用于将含羟基化合物转化为酰胺、酯、酮和其他碳到杂原子或碳到碳的转化过程中。
• O-Acyl isopeptide method: efficient synthesis of isopeptide segment and application to racemization-free segment condensation
  作者：Taku Yoshiya、Hiroyuki Kawashima、Youhei Sohma、Tooru Kimura、Yoshiaki Kiso

  DOI：10.1039/b903624e

  日期：——

  We report the establishment of the O-acyl isopeptide method-based racemization-free segment condensation reaction toward future chemical protein synthesis. Peptide segments containing C-terminal O-acyl Ser/Thr residues were successfully synthesized by use of a lower nucleophilic base cocktail for Fmoc removal, and then coupled to an amino group of a peptide-resin without side reactions or epimerization

  我们报告了对未来化学蛋白质合成的基于O-酰基异肽方法的无消旋片段缩合反应的建立。通过使用较低的亲核碱基混合物进行Fmoc去除，成功合成了包含C末端O-酰基Ser / Thr残基的肽段，然后将其偶联到肽树脂的氨基上，而没有副反应或差向异构化。我们还成功地以顺序方式以及在固溶相条件下进行了段缩合。
• Selective Substrates and Activity-Based Probes for Imaging of the Human Constitutive 20S Proteasome in Cells and Blood Samples
  作者：Wioletta Rut、Marcin Poręba、Paulina Kasperkiewicz、Scott J. Snipas、Marcin Drąg

  DOI：10.1021/acs.jmedchem.8b00026

  日期：2018.6.28

  the HyCoSuL approach, we designed and synthesized novel and selective fluorogenic substrates for each of these three constitutive 20S proteasome activities and applied them to assess inhibition of proteasome subunits by MG-132 and a clinically used inhibitor bortezomib. Our results confirm the utility of designed substrates in biochemical assays. Furthermore, selective peptide sequences obtained in this

  蛋白酶体是维持蛋白质稳态的关键酶复合物。蛋白酶体功能紊乱导致包括癌症，自身免疫和神经退行性疾病在内的病理。因此，蛋白酶体构成药物开发的极好的分子靶标。在这里，我们使用HyCoSuL方法为这三个20S组成型蛋白酶体活性中的每一个设计和合成了新颖的选择性荧光底物，并将它们应用于评估MG-132和临床使用的硼替佐米对蛋白酶体亚基的抑制作用。我们的结果证实了设计的底物在生化分析中的实用性。此外，以此方式获得的选择性肽序列用于构建荧光团标记的基于活性的探针，然后用于同时检测HEK-293F细胞和红细胞裂解液中的每个20S组成型蛋白酶体亚基。总体而言，我们描述了一种简单而快速的方法，可用于测量全血样本中20S组成型蛋白酶体的活性，该方法可以早期诊断与异常上调的蛋白酶体活性有关的病理状态。
• Diethyl Selenodiglycolate: An Eco-Friendly Synthetic Antioxidant with Potential Application to Inflammatory Disorders
  作者：Marcos Pinatto-Botelho、Railmara da Silva、Marcos Archilha、Lilian Giroldo、Aleksey Kuznetsov、Flávia Meotti、Alcindo dos Santos

  DOI：10.21577/0103-5053.20200009

  日期：——

  procedure to prepare a selenium derivative (diethyl selenodiglycolate). Diethyl selenodiglycolate rapidly reduces hypochlorous acid (HOCl, second-order rate constant of 7 × 10 M s−1) to generate its corresponding selenoxide. In activated HL-60 cells, diethyl selenodiglycolate selectively reacted with HOCl (half maximal inhibitory concentration (IC50) = 23.07 μM) but not with superoxide anion radical or hydrogen

  这项研究描述了制备硒衍生物（硒代二甘醇二酸二乙酯）的单一步骤，高收率和纯度，生态友好且可扩展的程序。亚硒酸二乙酯快速还原次氯酸（HOCl，二级速率常数为7×10 M s-1），生成相应的亚硒酸盐。在活化的HL-60细胞中，亚硒二酸二乙酯与HOCl（半数最大抑制浓度（IC50）= 23.07μM）选择性反应，但不与超氧化物阴离子自由基或过氧化氢反应，而没有任何细胞毒性。这些结果表明，这种合成上简单的硒化物以非常有效和特定的方式反应，有害的促氧化剂HOCl是一种有希望的化合物，可用于氧化性炎症相关疾病。