N-Fmoc-N’-丹磺酰基-L-赖氨酸 | 118584-90-0

• 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 - 萘
• 中文名称: N-Fmoc-N’-丹磺酰基-L-赖氨酸
• 中文别名: N-芴甲氧羰基-N'-丹磺酰基-L-赖氨酸
• 英文名称: Fmoc-Lys(dansyl)-OH
• 英文别名: (2S)-6-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid
• CAS: 118584-90-0
• 化学式: C₃₃H₃₅N₃O₆S
• 分子量: 601.723
• InChiKey: SLBNIPMLSUPCFW-LJAQVGFWSA-N

物化性质

• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  8

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-Lys(dansyl)-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-Lys(dansyl)-OH
CAS number: 118584-90-0

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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, refrigerated.
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: C33H35N3O6S
Molecular weight: 601.7

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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：

  2-chlorotrityl resin 、 t-叔丁氧羰基-氨基氧基乙酸N-羟基琥珀酰亚胺酯 、 N-Fmoc-N’-丹磺酰基-L-赖氨酸 、 [2-[2-(Fmoc-氨基)乙氧基]乙氧基]乙酸 在 哌啶 、 O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 1.03h， 以15%的产率得到
  参考文献：
  名称：

  Palladium-unleashed proteins: gentle aldehyde decaging for site-selective protein modification

  摘要：

  已开发出一种生物正交解笼策略，使用一当量钯来暴露蛋白质醛，实现位点选择性蛋白质标记。

  DOI：

  10.1039/c7cc07740h
• 作为产物：
  描述：

  丹酰氯 、 FMOC-赖氨酸 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以67%的产率得到N-Fmoc-N’-丹磺酰基-L-赖氨酸
  参考文献：
  名称：

  使用分选酶对蛋白质进行有效的 N 端标记

  摘要：

  “整理” N 端标记：转肽酶反应的可逆性使蛋白质 N 端标记具有挑战性。分选酶 A 的缩肽底物在连接过程中释放醇副产物，这些副产物是逆反应的不良亲核试剂。具有不受阻碍的 N 末端甘氨酸残基的蛋白质只需少量过量的标记试剂即可有效标记（见方案）。

  DOI：

  10.1002/anie.201204538

文献信息

• Synthesis of the Rheb and K-Ras4B GTPases
  作者：Yong-Xiang Chen、Sebastian Koch、Katharina Uhlenbrock、Katrin Weise、Debapratim Das、Lothar Gremer、Luc Brunsveld、Alfred Wittinghofer、Roland Winter、Gemma Triola、Herbert Waldmann

  DOI：10.1002/anie.201001884

  日期：2010.8.16

  Now available! Farnesylated and carboxymethylated Rheb (see picture) and K‐Ras4B GTPases were synthesized in useful amounts by a combination of expressed protein ligation and solid‐phase lipopeptide synthesis. The functionality of the proteins was proven by biochemical, biophysical, and cell‐based investigations.

  现在可用！法尼基化和羧甲基化的Rheb（见图）和K‐Ras4B GTPases通过表达的蛋白质连接和固相脂肽合成相结合，以有用的量合成。蛋白质的功能已通过生化，生物物理和基于细胞的研究证明。
• [EN] HIGH-THROUGHPUT METHOD TO RAPIDLY ADD CHEMICAL MOIETIES TO A SMALL MOLECULE LIBRARY<br/>[FR] PROCÉDÉ À HAUT RENDEMENT POUR AJOUTER RAPIDEMENT DES FRACTIONS CHIMIQUES À UNE BIBLIOTHÈQUE DE PETITES MOLÉCULES
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2022060459A1

  公开（公告）日：2022-03-24

  Organic compounds for target identification, drug discovery, chemical library production, high-throughput screening, fluorophore conjugation, chemiluminescent compound conjugation, creation of proximity induced modulators (e.g., protein degraders)/chimeric molecules, or a combination thereof are described. The compounds can contain small molecule moieties for identification of their potential targets; an isocyanate, photoactivatable groups; chemical moieties for enrichment and detection of target-small molecule moiety interactions; proximity induced modulator element; fluorophores; chemiluminescent groups; or combinations thereof.

  本文描述了用于目标识别、药物发现、化学库生产、高通量筛选、荧光物质偶联、化学发光物质偶联、接近诱导调节剂（例如，蛋白降解剂）/嵌合分子或其组合的有机化合物。这些化合物可以含有小分子基团，以识别它们的潜在靶点；异氰酸酯，光活化基团；化学基团，用于丰富和检测靶标-小分子基团相互作用；接近诱导调节剂元素；荧光物质；化学发光基团；或其组合。
• Structure−Activity Relationship Studies for the Peptide Portion of the Bladder Epithelial Cell Antiproliferative Factor from Interstitial Cystitis Patients
  作者：Piotr Kaczmarek、Susan K. Keay、Gillian M. Tocci、Kristopher R. Koch、Chen-Ou Zhang、Joseph J. Barchi、David Grkovic、Li Guo、Christopher J. Michejda

  DOI：10.1021/jm8002763

  日期：2008.10.9

  We performed comprehensive structure-activity relationship (SAR) studies on the peptide portion of antiproliferative factor (APF), a sialylated frizzled-8 related glycopeptide that inhibits normal bladder epithelia] and urothelial carcinoma cell proliferation. Glycopeptide derivatives were synthesized by solid-phase methods using standard Fmoc chemistry and purified by RP-HPLC; all intermediate and final products were verified by HPLC-MS and NMR analyses. Antiproliferative activity of each derivative was determined by inhibition of (3)H-thymidine incorporation in primary normal human bladder epithelial cells. Structural components of the peptide segment of APF that proved to be important for biological activity included the presence of at least eight of the nine N-terminal amino acids, a negative charge in the C-terminal amino acid, a free amino group at the N-terminus, maintenance of a specific amino acid sequence in the C-terminal tail, and trans conformation for the peptide bonds. These data provide critical guidelines for optimization of structure in design of APF analogues as potential therapeutic agents.
• Qualmann, Britta; Kessels, Michael Manfred; Musiol, Hans-Juergen, Angewandte Chemie, 1996, vol. 108, # 8, p. 970 - 973
  作者：Qualmann, Britta、Kessels, Michael Manfred、Musiol, Hans-Juergen、Sierralta, Walter Daniel、Jungblut, Peter Wilhelm、Moroder, Luis

  DOI：——

  日期：——
• New Peptide-Based Antimicrobials for Tackling Drug Resistance in Bacteria: Single-Cell Fluorescence Imaging
  作者：Jean-Marie Pagès、Slavka Kascàkovà、Laure Maigre、Anas Allam、Mickael Alimi、Jacqueline Chevalier、Erwan Galardon、Matthieu Réfrégiers、Isabelle Artaud

  DOI：10.1021/ml400073g

  日期：2013.6.13

  New peptide molecules with metal binding :abilities proved to he active against multidrug resistant clinical isolates. One of them, labeled with a dansylated lysine has been imaged inside single-multidrug resistant bacteria cells by deep ultraviolet fluorescence, showing a heterogeneous Subcellular localization. The fluorescence intensity is clearly related to the accumulation of the drug inside the bacteria, being dependent both on its concentration and on the incubation time with cells.