Fmoc-L-2-碘苯丙氨酸 | 210282-32-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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: Fmoc-L-2-碘苯丙氨酸
• 中文别名: FMOC-L-2-碘苯丙氨酸；Fmoc-2-碘-l-苯丙氨酸
• 英文名称: Fmoc-(2-I)Phe-OH
• 英文别名: Fmoc-Phe(2-I)-OH；N-Fmoc-L-2-iodophenylalanine；Fmoc-2-iodo-l-phenylalanine；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-iodophenyl)propanoic acid
• CAS: 210282-32-9
• 化学式: C₂₄H₂₀INO₄
• 分子量: 513.332
• InChiKey: YMKDZEDXFIXGNK-QFIPXVFZSA-N

物化性质

• 沸点：
  672.3±55.0 °C(Predicted)
• 密度：
  1.577±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

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: Fmoc-2-iodo-l-phenylalanine
Synonyms: Fmoc-L-Phe(2-I)-OH

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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-2-iodo-l-phenylalanine
CAS number: 210282-32-9

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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: C24H20INO4
Molecular weight: 513.3

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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 Iodide.

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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-2-碘苯丙氨酸 在 N-甲基吗啉 、 hydroxylamine Wang resin 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 哌啶 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 (S)-2-amino-N-hydroxy-3-(2-iodophenyl)propanamide
  参考文献：
  名称：

  Design and Evaluation of Hydroxamate Derivatives as Metal-Mediated Inhibitors of a Protein Tyrosine Kinase

  摘要：

  Protein tyrosine kinases use two Mg2+ ions as cofactors in catalysis, one as the ATP-Mg complex (M1) and the other as an essential activator (M2). The M2-binding site has high affinity for transition metal cations such as cobalt and zinc. Taking advantage of this high affinity, we examined hydroxamates as metal-mediated inhibitors against C-terminal Src kinase (Csk), a protein tyrosine kinase. Of a small group of amino acid hydroxamates, tyrosine and phenylalanine hydroxamates inhibited Csk activity only in the presence of Co2+. Four classes of phenylalanine and tyrosine hydroxamate derivatives were synthesized and evaluated as metal-mediated inhibitors of Csk, leading to improved inhibition and a better understanding of the structure-activity relationships. This study suggests that hydroxamates may serve as a general scaffold for developing metal-mediated inhibitors against protein tyrosine kinases. To the best of our knowledge, this is the first report of designing metal-mediated inhibitors against a protein tyrosine kinase by targeting a metal binding site.

  DOI：

  10.1021/jm061058c

文献信息

• Oxidative couplings on tryptophan-based diketopiperazines leading to fused and bridged chemotypes
  作者：Lorena Mendive-Tapia、Arantxa Albornoz-Grados、Alexandra Bertran、Fernando Albericio、Rodolfo Lavilla

  DOI：10.1039/c7cc00555e

  日期：——

  Selective C–C and C–N oxidative couplings on tryptophan-based diketopiperazines allow the direct access to two novel scaffolds.

  在色氨酸基二酮哌嗪上进行选择性 C-C 和 C-N 氧化偶联，可直接获得两种新型支架。
• Constrained Cyclopeptides: Biaryl Formation through Pd-Catalyzed C−H Activation in Peptides-Structural Control of the Cyclization vs. Cyclodimerization Outcome
  作者：Lorena Mendive-Tapia、Alexandra Bertran、Jesús García、Gerardo Acosta、Fernando Albericio、Rodolfo Lavilla

  DOI：10.1002/chem.201601832

  日期：2016.9.5

  on the phenyl ring was subjected to Pd‐catalyzed CH activation reactions to give the corresponding aryl‐indole coupled products. Two types of adducts were generated: cyclomonomer and cyclodimeric peptides; no evidence of oligo‐ or polymerization products was detected. Contrary to standard peptide macrocyclizations, the factors controlling the fate of the reaction are the number of amino acids between

  对一系列在苯环上含有碘取代基的色氨酸-苯丙氨酸短肽进行Pd催化的CH活化反应，得到相应的芳基-吲哚偶联产物。生成了两种类型的加合物：环单体和环二聚体肽；环糊精和环糊精。没有发现低聚或聚合产物的证据。与标准肽大环化相反，控制反应命运的因素是芳香族残基之间的氨基酸数量和母体碘代衍生物的区域化学，而与浓度和环化模式无关。该方法是通用的，并且允许访问已经被充分表征的新颖的联芳基肽拓扑。
• PEPTIDE-COMPOUND CYCLIZATION METHOD
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20150080549A1

  公开（公告）日：2015-03-19

  An object of the present invention is to provide methods of discovering drugs effective for tough targets, which have conventionally been discovered only with difficulty. The present invention relates to novel methods for cyclizing peptide compounds, and novel peptide compounds and libraries comprising the same, to achieve the above object.

  本发明的目的是提供一种发现对于难以处理的靶点有效的药物的方法，这些药物通常很难被发现。本发明涉及新型的环化肽化合物的方法，以及包含这些化合物的新型肽库，以实现上述目的。
• Chemical space screening around Phe3 in opioid peptides: Modulating µ versus δ agonism by Suzuki-Miyaura cross-couplings
  作者：Tom Willemse、Emilie Eiselt、Karlijn Hollanders、Wim Schepens、Herman W.T. van Vlijmen、Nga N. Chung、Véronique Blais、Brain Holleran、Jean-Michel Longpré、Peter W. Schiller、Bert U.W. Maes、Philippe Sarret、Louis Gendron、Steven Ballet

  DOI：10.1016/j.bmcl.2018.05.015

  日期：2018.7

  In this study, affinities and activities of derivatized analogues of Dmt-dermorphin[1-4] (i.e. Dmt-D-Ala-Phe-GIyNH(2), Dmt = 2',6'-dimethyl-(S)-tyrosine) for the mu opioid receptor (MOP) and delta opioid receptor (DOP) were evaluated using radioligand binding studies, functional cell-based assays and isolated organ bath experiments. By means of solid-phase or solution-phase Suzuki-Miyaura cross-couplings, various substituted regioisomers of the phenylalanine moiety in position 3 of the sequence were prepared. An 18-membered library of opioid tetrapeptides was generated via screening of the chemical space around the Phe(3) side chain. These substitutions modulated bioactivity, receptor subtype selectivity and highly effective ligands with subnanomolar binding affinities, contributed to higher functional activities and potent analgesic actions. In search of selective peptidic ligands, we show here that the Suzuki-Miyaura reaction is a versatile and robust tool which could also be deployed elsewhere. (C) 2018 Elsevier Ltd. All rights reserved.
• Modulation of the Interaction between a Peptide Ligand and a G Protein-Coupled Receptor by Halogen Atoms
  作者：Mònica Rosa、Gianluigi Caltabiano、Katy Barreto-Valer、Verónica Gonzalez-Nunez、José C. Gómez-Tamayo、Ana Ardá、Jesús Jiménez-Barbero、Leonardo Pardo、Raquel E. Rodríguez、Gemma Arsequell、Gregorio Valencia

  DOI：10.1021/acsmedchemlett.5b00126

  日期：2015.8.13

  Systematic halogenation of two native opioid peptides has shown that halogen atoms can modulate peptide receptor interactions in different manners. First, halogens may produce a steric hindrance that reduces the binding of the peptide to the receptor. Second, chlorine, bromine, or iodine may improve peptide binding if their positive sigma-hole forms a halogen bond interaction with negatively charged atoms of the protein. Lastly, the negative electrostatic potential of fluorine can interact with positively charged atoms of the protein to improve peptide binding.