Fmoc-L-3-溴苯丙氨酸 | 220497-48-3

• 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-3-溴苯丙氨酸
• 中文别名: (S)-N-FMOC-3-溴苯丙氨酸；N-(9-芴甲氧羰基)-3-溴苯基-L-丙氨酸；Fmoc-Phe(3-Br)-OH
• 英文名称: (9H-fluoren-9-yl)methyl (S)-(3-bromo)phenylalanine
• 英文别名: N-Fmoc-L-3-bromophenylalanine；Fmoc-3-Br-Phe；Fmoc-3-bromo-L-phenylalanine；(2S)-3-(3-bromophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 220497-48-3
• 化学式: C₂₄H₂₀BrNO₄
• 分子量: 466.331
• InChiKey: CALGTIKYXVBTAO-QFIPXVFZSA-N

物化性质

• 熔点：
  144.2 °C
• 沸点：
  660.8±55.0 °C(Predicted)
• 密度：
  1.4220 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

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

• 危险等级：
  IRRITANT
• 安全说明：
  S24/25
• 海关编码：
  29223900
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于0°C阴凉干燥处。

SDS

Name:	(S)-N-FMOC-3-Bromophenylalanine 95% (98% e.e.) Material Safety Data Sheet
Synonym:	N-(9-Fluorenylmethoxycarbonyl)-3-Bromophenyl-L-Alanine
CAS:	220497-48-3

Section 1 - Chemical Product MSDS Name:(S)-N-FMOC-3-Bromophenylalanine 95% (98% e.e.) Material Safety Data Sheet
Synonym:N-(9-Fluorenylmethoxycarbonyl)-3-Bromophenyl-L-Alanine

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
220497-48-3	(S)-N-FMOC-3-Bromophenylalanine	95%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 220497-48-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 144.2 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C24H20BrNO4
Molecular Weight: 466.32

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 220497-48-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-N-FMOC-3-Bromophenylalanine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 220497-48-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 220497-48-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 220497-48-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  Fmoc-L-3-溴苯丙氨酸 在 哌啶 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 (9H-fluoren-9-yl)methyl ((S)-1-(((S)-3-(3-bromophenyl)-1-(methylamino)-1-oxopropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  设计，合成，和化合物-15的衍生物作为用于β负变构调节剂的功能评估2 -肾上腺素能受体

  摘要：

  所述β 2 -肾上腺素能受体（β 2 AR），G蛋白偶联受体，是一个重要的治疗目标。我们最近描述CMPD-15，第一小分子负变构调节剂（NAM）为β 2 AR。本文中，我们详细报告了7种Cmpd-15衍生物的设计，合成和构效关系（SAR）。此外，我们提供一种在剂量-响应范例，它们的衍生物的效果的细节在调节激动剂诱导的β 2在放射性配体竞争结合试验中，AR活性（G蛋白介导的cAMP产生和β-arrestin募集到受体）以及正构激动剂的结合亲和力。我们的研究结果表明，一些修改，包括在除去甲酰胺基的第-formamido苯丙氨酸区域和溴在元-bromobenzyl甲基苯甲酰胺区域引起CMPD-15的功能活性显着降低。这些SAR结果提供了宝贵的见解NAM CMPD-15的作用机制以及为更有效和选择性调节剂的未来发展，为β的基础2基于CMPD-15的化学支架AR。

  DOI：

  10.1016/j.bmc.2018.03.023
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 L-3-溴苯丙氨酸 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 22.0h， 生成 Fmoc-L-3-溴苯丙氨酸
  参考文献：
  名称：

  设计，合成，和化合物-15的衍生物作为用于β负变构调节剂的功能评估2 -肾上腺素能受体

  摘要：

  所述β 2 -肾上腺素能受体（β 2 AR），G蛋白偶联受体，是一个重要的治疗目标。我们最近描述CMPD-15，第一小分子负变构调节剂（NAM）为β 2 AR。本文中，我们详细报告了7种Cmpd-15衍生物的设计，合成和构效关系（SAR）。此外，我们提供一种在剂量-响应范例，它们的衍生物的效果的细节在调节激动剂诱导的β 2在放射性配体竞争结合试验中，AR活性（G蛋白介导的cAMP产生和β-arrestin募集到受体）以及正构激动剂的结合亲和力。我们的研究结果表明，一些修改，包括在除去甲酰胺基的第-formamido苯丙氨酸区域和溴在元-bromobenzyl甲基苯甲酰胺区域引起CMPD-15的功能活性显着降低。这些SAR结果提供了宝贵的见解NAM CMPD-15的作用机制以及为更有效和选择性调节剂的未来发展，为β的基础2基于CMPD-15的化学支架AR。

  DOI：

  10.1016/j.bmc.2018.03.023

文献信息

• The Meta-Position of Phe4 in Leu-Enkephalin Regulates Potency, Selectivity, Functional Activity, and Signaling Bias at the Delta and Mu Opioid Receptors
  作者：Robert J. Cassell、Krishna K. Sharma、Hongyu Su、Benjamin R. Cummins、Haoyue Cui、Kendall L. Mores、Arryn T. Blaine、Ryan A. Altman、Richard M. van Rijn

  DOI：10.3390/molecules24244542

  日期：——

  As tool compounds to study cardiac ischemia, the endogenous δ-opioid receptors (δOR) agonist Leu5-enkephalin and the more metabolically stable synthetic peptide (d-Ala2, d-Leu5)-enkephalin are frequently employed. However, both peptides have similar pharmacological profiles that restrict detailed investigation of the cellular mechanism of the δOR’s protective role during ischemic events. Thus, a need remains for δOR peptides with improved selectivity and unique signaling properties for investigating the specific roles for δOR signaling in cardiac ischemia. To this end, we explored substitution at the Phe4 position of Leu5-enkephalin for its ability to modulate receptor function and selectivity. Peptides were assessed for their affinity to bind to δORs and µ-opioid receptors (µORs) and potency to inhibit cAMP signaling and to recruit β-arrestin 2. Additionally, peptide stability was measured in rat plasma. Substitution of the meta-position of Phe4 of Leu5-enkephalin provided high-affinity ligands with varying levels of selectivity and bias at both the δOR and µOR and improved peptide stability, while substitution with picoline derivatives produced lower-affinity ligands with G protein biases at both receptors. Overall, these favorable substitutions at the meta-position of Phe4 may be combined with other modifications to Leu5-enkephalin to deliver improved agonists with finely tuned potency, selectivity, bias and drug-like properties.

  作为研究心脏缺血的工具化合物，内源性δ-阿片受体（δOR）激动剂Leu5-恩啡啶和更具代谢稳定性的合成肽（d-Ala2，d-Leu5）-恩啡啶经常被使用。然而，这两种肽具有类似的药理特性，限制了对δOR在缺血事件中保护作用的细胞机制进行详细研究。因此，需要具有改进选择性和独特信号特性的δOR肽，以便研究心脏缺血中δOR信号的特定作用。为此，我们探索了Leu5-恩啡啶的Phe4位置的取代物对调节受体功能和选择性的能力。评估了肽对δOR和µ-阿片受体（µOR）的结合亲和力以及抑制cAMP信号和招募β-阻滞蛋白2的效力。此外，还测量了肽在大鼠血浆中的稳定性。通过在Leu5-恩啡啶的Phe4的间位进行取代，提供了具有不同选择性和偏向性水平的高亲和力配体，同时改善了肽的稳定性，而用吡啶衍生物进行取代则产生了在两种受体上具有G蛋白偏向性的亲和力较低的配体。总的来说，Phe4的间位的这些有利取代物可以与Leu5-恩啡啶的其他修饰结合，提供具有精心调节的效力、选择性、偏向性和药物样性质的改进激动剂。
• Stabilized minimal coiled-coil mimetics
  申请人：NEW YORK UNIVERSITY

  公开号：US10851133B2

  公开（公告）日：2020-12-01

  This invention relates to a macrostructure that includes an antiparallel coiled-coil structure shown below or a parallel coiled-coil structure shown below and described in the present application.

  本发明涉及一种宏观结构，它包括下图所示的反平行盘卷结构或下图所示的平行盘卷结构，并在本申请中进行了描述。
• Biaryl-Bridged Macrocyclic Peptides: Conformational Constraint via Carbogenic Fusion of Natural Amino Acid Side Chains
  作者：Falco-Magnus Meyer、James C. Collins、Brendan Borin、James Bradow、Spiros Liras、Chris Limberakis、Alan M. Mathiowetz、Laurence Philippe、David Price、Kun Song、Keith James

  DOI：10.1021/jo202105v

  日期：2012.4.6

  A general method for constraining peptide conformations via linkage of aromatic sidechains has been developed. Macrocydization of suitably functionalized tri-, tetra- and pentapeptides via Suzuki-Miyaura cross-coupling has been used to generate side chain to side chain, biaryl-bridged 14- to 21-membered macrocyclic peptides. Biaryl bridges possessing three different configurations, meta-meta, meta-ortho, and ortho-meta, were systematically explored through regiochemical variation of the aryl halide and aryl boronate coupling partners, allowing fine-tuning of the resultant macrocycle conformation. Suzuki-Miyaura macrocyclizations were successfully achieved both in solution and on solid phase for all three sizes of peptide. This approach constitutes a means of constraining peptide conformation via direct carbogenic fusion of side chains of naturally occurring amino acids such as phenylalanine and tyrosine, and so is complementary to strategies involving non-natural, for example, hydrocarbon, bridges.
• STABILIZED MINIMAL COILED-COIL MIMETICS
  申请人：New York University

  公开号：EP3303367A1

  公开（公告）日：2018-04-11
• NEMO COILED COIL MIMICS AND METHODS OF USING SAME
  申请人：NEW YORK UNIVERSITY

  公开号：US20200190155A1

  公开（公告）日：2020-06-18

  This invention relates to macrostructures (and pharmaceutical formulations containing them) that include a parallel coiled-coil structure, wherein the parallel coiled-coil comprises a first coil of Formula I and a second coil of Formula II: T 1 -f 0 -g 0 -a 1 -b 1 -c 1 -d 1 -e 1 -f 1 -g 1 -a 2 -b 2 -c 2 -d 2 -e 2 -f 2 -g 2 -a 3 -b 3 -c 3 -d 3 -e 3 -T 2 (I) T 3 -g′ 0 -a′ 1 -b′ 1 -c′ 1 -d′ 1 -e′ 1 -f′ 1 -g′ 1 -a′ 2 -b′ 2 -c′ 2 -d′ 2 -e′ 2 -f′ 2 -g′ 2 -a′ 3 -b′ 3 -c′ 3 -d′ 3 -e′ 3 -f′ 3 -T 4 (II), as described in the present application. Methods of using these macrostructures are also disclosed.