(N-琥珀酰亚胺基氧代羰基甲基)三(2,4,6-三甲氧苯基)溴化膦 | 226409-58-1

• 物质功能分类: 分析化学 - 标准品 - 光谱标准品
• 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: (N-琥珀酰亚胺基氧代羰基甲基)三(2,4,6-三甲氧苯基)溴化膦
• 中文别名: N-琥珀酰亚胺基[三(2,4,6-三甲氧苯基)磷基]溴乙酸酯
• 英文名称: (N-succinimidyloxycarbonylmethyl) tris(2,4,6-trimethoxyphenyl)phosphonium bromide
• 英文别名: (N-succinimidyloxycarbonylmethyl)tris(2,4,6-trimethoxyphenyl)phosphonium bromide；(succinimidyloxycarbonylmethyl)tris(2,4,6-trimethoxyphenyl)phosphonium bromide；TMPP-Ac-OSu；TMPP；(N-Succinimidyloxycarbonyl-methyl)tris(2,4,6-trimethoxyphenyl)phosphonium Bromide；[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethyl]-tris(2,4,6-trimethoxyphenyl)phosphanium;bromide
• CAS: 226409-58-1
• 化学式: Br*C₃₃H₃₉NO₁₃P
• 分子量: 768.549
• InChiKey: YKMSQZIYVKTUHI-UHFFFAOYSA-M

物化性质

• 熔点：
  201-205 °C (dec.)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  14

安全信息

• WGK Germany：
  3
• 海关编码：
  29251900
• 储存条件：
  -20°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : (N-Succinimidyloxycarbonylmethyl)tris(2,4,6-
trimethoxyphenyl)phosphonium bromide
CAS-No. : 226409-58-1
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : TMPP-Ac-OSu
N-Succinimidyl [tris(2,4,6-trimethoxyphenyl)phosphonio]acetate bromide
Formula : C33H39BrNO13P
Molecular Weight : 768,54 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Oxides of phosphorus, Hydrogen bromide gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Keep in a dry place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 199 - 205 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (N-琥珀酰亚胺基氧代羰基甲基)三(2,4,6-三甲氧苯基)溴化膦 在 水 作用下， 生成 Carboxymethyl-tris-(2,4,6-trimethoxy-phenyl)-phosphonium; bromide
  参考文献：
  名称：

  Qualitative and Quantitative Analysis of Small Amine Molecules by MALDI-TOF Mass Spectrometry through Charge Derivatization

  摘要：

  我们合成了一对同位素编码的轻、重试剂--三(2,4,6-三甲氧基苯基)膦乙酸 N-羟基琥珀酰亚胺酯（1 和 2），用于衍生含有伯胺或仲胺官能团的低分子量（<500 Da）分子，以进行 MALDI-TOF MS 分析。轻试剂和重试剂分别为每种分析物添加了 573 Da 和 600 Da 的正电荷标签。在标记试剂过量 10 倍的情况下，偶联反应在 10 分钟内接近完成。衍生化大大促进了对小分子的 MALDI 分析，并显著提高了分析灵敏度，使检测限达到了低飞摩尔范围。此外，反应混合物可直接用 MALDI 进行分析，无需进行样品清理。通过分析同位素编码的轻质和重质衍生物，成功实现了 MALDI-TOF MS 对小分子的定量分析。对抗生素混合物的 MALDI-TOF 定量分析得出了浓度范围为 0.3 至 30 pmol/μL 的校准曲线，其 r2 值大于 0.9995。

  DOI：

  10.1021/ac035537k
• 作为产物：
  描述：

  三(2,4,6-三甲氧基苯基)磷 、 溴乙酸 N-羟基琥珀酰亚胺酯 以 甲苯 为溶剂， 反应 0.5h， 生成 (N-琥珀酰亚胺基氧代羰基甲基)三(2,4,6-三甲氧苯基)溴化膦
  参考文献：
  名称：

  Qualitative and Quantitative Analysis of Small Amine Molecules by MALDI-TOF Mass Spectrometry through Charge Derivatization

  摘要：

  我们合成了一对同位素编码的轻、重试剂--三(2,4,6-三甲氧基苯基)膦乙酸 N-羟基琥珀酰亚胺酯（1 和 2），用于衍生含有伯胺或仲胺官能团的低分子量（<500 Da）分子，以进行 MALDI-TOF MS 分析。轻试剂和重试剂分别为每种分析物添加了 573 Da 和 600 Da 的正电荷标签。在标记试剂过量 10 倍的情况下，偶联反应在 10 分钟内接近完成。衍生化大大促进了对小分子的 MALDI 分析，并显著提高了分析灵敏度，使检测限达到了低飞摩尔范围。此外，反应混合物可直接用 MALDI 进行分析，无需进行样品清理。通过分析同位素编码的轻质和重质衍生物，成功实现了 MALDI-TOF MS 对小分子的定量分析。对抗生素混合物的 MALDI-TOF 定量分析得出了浓度范围为 0.3 至 30 pmol/μL 的校准曲线，其 r2 值大于 0.9995。

  DOI：

  10.1021/ac035537k

文献信息

• 3-ARYL PROPIOLONITRILE COMPOUNDS FOR THIOL LABELING
  申请人：UNIVERSITE DE STRASBOURG

  公开号：US20160145199A1

  公开（公告）日：2016-05-26

  The present invention relates to a process for labeling compounds comprising thiol moieties with 3-arylpropiolonitrile compounds, to 3-arylpropiolonitrile compounds substituted with tag moieties and to specific 3-arylpropiolonitrile linkers.

  本发明涉及一种将含硫醇基团的化合物用3-芳基丙炔腈化合物标记的方法，以及用标记基团取代的3-芳基丙炔腈化合物和特定的3-芳基丙炔腈连接剂。
• Reagent Precoated Targets for Rapid In-Tissue Derivatization of the Anti-Tuberculosis Drug Isoniazid Followed by MALDI Imaging Mass Spectrometry
  作者：M. Lisa Manier、Michelle L. Reyzer、Anne Goh、Veronique Dartois、Laura E. Via、Clifton E. Barry、Richard M. Caprioli

  DOI：10.1007/s13361-011-0150-8

  日期：2011.8.1

  Isoniazid (INH) is an important component of front-line anti-tuberculosis therapy with good serum pharmacokinetics but unknown ability to penetrate tuberculous lesions. However, endogenous background interferences hinder our ability to directly analyze INH in tissues. Chemical derivatization has been successfully used to measure isoniazid directly from tissue samples using matrix-assisted laser desorption/ionization (MALDI) imaging mass spectrometry (IMS). MALDI targets were pretreated with trans-cinnamaldehyde (CA) prior to mounting tissue slices. Isoniazid present in the tissues was efficiently derivatized and the INH-CA product measured by MS/MS. Precoating of MALDI targets allows the tissues to be directly thaw-mounted and derivatized, thus simplifying the preparation. A time-course series of tissues from tuberculosis infected/INH dosed animals were assayed and the MALDI MS/MS response correlates well with the amount of INH determined to be in the tissues by high-performance liquid chromatography (HPLC)-MS/MS.

  异烟肼（INH）是治疗肺结核的一线药物的重要组成部分，具有良好的血清药代动力学特性，但其穿透结核病变的能力尚不清楚。然而，内源性背景干扰阻碍了我们直接分析组织中的INH。化学衍生化已成功用于通过基质辅助激光解吸电离（MALDI）成像质谱法（IMS）直接从组织样本中测量异烟肼。在组织切片装载之前，MALDI靶点预先处理了反肉桂醛（CA）。组织中存在的异烟肼被有效地衍生化，并通过MS/MS测量INH-CA产物。MALDI靶点的预涂层允许组织直接解冻装载和衍生化，从而简化了制备过程。一系列来自感染结核病/接受INH治疗的动物的组织进行了时间过程系列检测，MALDI MS/MS的响应与通过高效液相色谱（HPLC）-MS/MS确定的组织中INH含量有很好的相关性。
• Localization of the O-Glycosylated Sites in Peptides by Fixed-Charge Derivatization with a Phosphonium Group
  作者：Xavier Czeszak、Willy Morelle、Guy Ricart、Daniel Tétaert、Jérôme Lemoine

  DOI：10.1021/ac049767q

  日期：2004.8.1

  The present study demonstrates that matrix-assisted laser desorption ionization/postsource decay (MALDI/PSD) analysis of the molecular cation of glycopeptides derivatized at their amino terminus with a phosphonium group cleaves peptide backbone without removing the glycan. The predictable a-type fragment ions retain the glycan moiety, enabling unambiguous localization of O-glycans on the peptide chain. In contrast, collision-activated dissociation tandem mass spectrometry analysis carried out on the doubly charged protonated phosphonium cation results in the predominant loss of the sugar moiety from the peptide. This result supports the previously proposed charge-induced fragmentation mechanism of the sugar−peptide bond. MALDI/PSD analysis of glycopeptides converted to their acetyl phosphonium derivatives is an effective alternative to electron capture dissociation, as illustrated by the positioning of up to three GalNac residues along the full tandem repeat peptide sequence derived from the MUC 5AC mucin.

  本研究表明，对氨基末端带有鏻基团的糖肽的分子阳离子进行基质辅助激光解吸电离/源后衰变 (MALDI/PSD) 分析，可以在不去除聚糖的情况下裂解肽主链。可预测的 a 型碎片离子保留了聚糖部分，从而能够明确定位 O-聚糖在肽链上。相反，对带双电荷的质子化鏻阳离子进行的碰撞激活解离串联质谱分析导致肽中糖部分的主要损失。这一结果支持了先前提出的糖肽键电荷诱导断裂机制。对转化为乙酰基鏻衍生物的糖肽进行 MALDI/PSD 分析是电子捕获解离的有效替代方法，如沿源自 MUC 5AC 粘蛋白的完整串联重复肽序列定位最多三个 GalNac 残基所示。
• Photodissociation of Charge Tagged Peptides
  作者：Yi He、Ramakrishnan Parthasarathi、Krishnan Raghavachari、James P. Reilly

  DOI：10.1007/s13361-012-0379-x

  日期：2012.7.1

  Tris(2,4,6-trimethoxyphenyl) phosphonium acetyl (TMPP-Ac) was previously introduced to improve the mass spectrometric sequence analysis of peptides by fixing a permanent charge at the N-termini. However, peptides containing arginine residues did not fragment efficiently after TMPP-Ac modification. In this work, we combine charge derivatization with photodissociation. The fragmentation of TMPP-derivatized peptides is greatly improved and a series of N-terminal fragments is generated with complete sequence information. Arginine has a special effect on the fragmentation of the TMPP tagged peptides when it is the N-terminal peptide residue. Theoretical and experimental results suggest that this is due to hydrogen transfer from the charged N-terminus to the hydrogen-deficient peptide sequence.

  三(2,4,6-三甲氧基苯基)乙酰鏻（TMPP-Ac）以前是通过在 N 端固定永久电荷来改进肽的质谱序列分析的。然而，含有精氨酸残基的肽在经过 TMPP-Ac 修饰后并不能有效地破碎。在这项工作中，我们将电荷衍生与光解离相结合。经 TMPP 衍生化的肽的破碎效果大大提高，并产生了一系列具有完整序列信息的 N 端片段。当精氨酸是 N 端肽残基时，它对 TMPP 标记肽的碎裂有特殊的影响。理论和实验结果表明，这是由于氢从带电的 N 端转移到缺氢的肽序列所致。
• Improving de Novo Sequencing of Peptides Using a Charged Tag and C-Terminal Digestion
  作者：Weibin Chen、Peter J. Lee、Henry Shion、Nicholas Ellor、John C. Gebler

  DOI：10.1021/ac061670b

  日期：2007.2.1

  An improved method for peptide de novo sequencing by MALDI mass spectrometry is presented. The method couples a charge derivatization reaction with C-terminal digestion to modify tryptic peptides. The charge derivatization attaches a fixed charge group onto the N-termini of peptides, and the enzymatic digestion after the derivatization step removes C-terminal basic amino acid residues such as arginine and lysine. The fragmentation of the modified peptide(s) under low-energy CID conditions (MALDI Q-TOF mass spectrometer) yields a simplified yet complete ion series of the peptide sequence. The validity of the method is demonstrated by the results from several model protein digests, where peptide sequences were correctly deduced either manually or through an automated sequencing program.

  本文介绍了一种通过 MALDI 质谱进行肽从头测序的改进方法。该方法将电荷衍生反应与 C 端消化结合起来，对胰蛋白酶肽进行修饰。电荷衍生将一个固定的电荷基团附着在肽的 N 端，衍生步骤后的酶解去除 C 端基本氨基酸残基，如精氨酸和赖氨酸。在低能 CID 条件下（MALDI Q-TOF 质谱仪）对修饰肽进行碎裂，可得到简化但完整的肽序列离子系列。几种蛋白质消化模型的结果证明了该方法的有效性，无论是手动还是通过自动测序程序，都能正确推断出肽序列。