Fmoc-D-4-溴苯丙氨酸 | 198545-76-5

• 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-D-4-溴苯丙氨酸
• 中文别名: FMOC-D-4-溴苯丙氨酸；N-(9-芴甲氧羰基)-4-溴苯基-D-丙氨酸
• 英文名称: Fmoc-D-Phe(4-Br)-OH
• 英文别名: Fmoc-D-4-Bromophenylalanine；(2R)-3-(4-bromophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 198545-76-5
• 化学式: C₂₄H₂₀BrNO₄
• 分子量: 466.331
• InChiKey: TVBAVBWXRDHONF-JOCHJYFZSA-N

物化性质

• 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，则不会发生分解。

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
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  29223990
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封保存于0℃阴凉干燥处

SDS

Name:	(R)-N-FMOC-4-Bromophenylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	N-(9-Fluorenylmethoxycarbonyl)-4-Bromophenyl-D-Alanine
CAS:	198545-76-5

Section 1 - Chemical Product MSDS Name:(R)-N-FMOC-4-Bromophenylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:N-(9-Fluorenylmethoxycarbonyl)-4-Bromophenyl-D-Alanine

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
198545-76-5	(R)-N-FMOC-4-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# 198545-76-5: 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: Not available.
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# 198545-76-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-N-FMOC-4-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# 198545-76-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 198545-76-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 198545-76-5 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

制备方法与用途

Fmoc-D-Phe(4-Br)-OH是一种苯丙氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  Fmoc-D-4-溴苯丙氨酸 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.22h， 生成 cyclo(Asp(OtBu)-D-Phe(p-Br)-Lys(Boc)-Arg(Pbf)-Gly)
  参考文献：
  名称：

  在受控微波加热下高效固相合成环状RGD肽

  摘要：

  环状RGD肽是用于α有效拮抗剂v β 3整联蛋白受体。在这封信中，描述了环状RGD肽的微波辅助固相合成。在Fmoc-Arg（Pbf）-OH与高负荷H-Gly-Trt（2-Cl）树脂之间的偶联反应中，在常规HBTU活化下需要多次偶联反应才能完成。我们发现，在微波加热至50°C的情况下，使用新型偶联剂COMU甚至可以加速树脂内部的反应。该方法适用于线性五肽H-Asp（OtBu）-Xxx-Yyy-Arg（Pbf）-Gly-OH（Xxx = d-Phe（p -Br）或d-Tyr，Yyy = Lys（ Boc）或MeVal）。将这些肽环化，然后脱保护，得到所需的具有高纯度的环状RGD肽。

  DOI：

  10.1016/j.tetlet.2011.12.069

文献信息

• Substituted indoles and methods of their use
  申请人：Hu Baihua

  公开号：US20070043101A1

  公开（公告）日：2007-02-22

  The present invention relates generally to substituted indoles and methods of using them.

  本发明一般涉及替代吲哚化合物及其使用方法。
• 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。
• Synthesis of fluorescent d-amino acids with 4-acetamidobiphenyl and 4-N,N-dimethylamino-1,8-naphthalimido containing side chains
  作者：Jyotirmoy Maity、Dmytro Honcharenko、Roger Strömberg

  DOI：10.1016/j.tetlet.2015.06.059

  日期：2015.8

  report the synthesis and fluorescence properties of two aromatic d-amino acids. The key step for the synthesis of (R)-2-amino-3-(4′-acetamido-[1,1′-biphenyl]-4-yl)propanoic acid was a Suzuki cross-coupling reaction between the pinacol diester of N-acetylphenylboronic acid and Fmoc-d-p-bromo-phenylalanine. The second amino acid, (R)-2-amino-4-(4′-N,N-dimethylamino-1,8-naphthalimido)butanoic acid [(R)-2

  我们报告了两种芳族d-氨基酸的合成和荧光性质。合成（R）-2-氨基-3-（4'-乙酰氨基-[1,1'-联苯] -4-基）丙酸的关键步骤是松果酚的频哪醇二酯之间的Suzuki交叉偶联反应ñ -acetylphenylboronic酸和的Fmoc- d - p溴-苯丙氨酸。第二个氨基酸（（R）-2-氨基-4-（4'- N，N-二甲基氨基-1,8-萘二甲酰亚胺）丁酸[（R）-2-氨基-4-DMNA-丁酸]是由4-溴-1,8-萘酐分四个步骤合成的。氨基酸以易于通过使用Fmoc-策略通过固相肽合成掺入肽序列中的形式制备。联苯氨基酸的荧光性质的评估显示在384 nm处有最大发射（在295 nm处激发），而萘二甲酰亚胺基氨基酸在545 nm处有最大发射（在450 nm处激发）。
• Structure-Based Design of Melanocortin 4 Receptor Ligands Based on the SHU-9119-hMC4R Cocrystal Structure
  作者：Charlotte Martin、Luis E. Gimenez、Savannah Y. Williams、Yu Jing、Yiran Wu、Charlie Hollanders、Olivier Van der Poorten、Simon Gonzalez、Kevin Van holsbeeck、Santo Previti、Arthur Lamouroux、Suwen Zhao、Dirk Tourwé、Raymond C. Stevens、Roger D. Cone、Steven Ballet

  DOI：10.1021/acs.jmedchem.0c01620

  日期：2021.1.14

  cyclic peptides based on the recent crystal structure of MC4R in complex with the well-characterized antagonist SHU-9119 (Ac-Nle4-c[Asp5-His6-DNal(2′)7-Arg8-Trp9-Lys10]-NH2). These analogues were pharmacologically characterized in vitro, giving key insights into exploiting binding site subpockets to deliver more selective ligands. More specifically, the side chains of the Nle4, DNal(2′)7, and Trp9 residues

  黑皮质素受体 (MC1R-MC5R) 属于 A 类 G 蛋白偶联受体 (GPCR)，已知在正常和疾病状态下具有受体特异性作用。MC4R 的选择性特别令人感兴趣，因为它涉及各种代谢紊乱，包括肥胖、喂养调节和性功能障碍。为了进一步提高 MC4R（抗）激动剂肽配体的效力和选择性，我们基于 MC4R 最近的晶体结构与充分表征的拮抗剂SHU-9119 (Ac-Nle 4 - c[Asp 5 -His 6 -DNal(2′) 7 -Arg 8 -Trp 9 -Lys 10 ]-NH2 )。这些类似物在体外进行了药理学表征，为利用结合位点亚袋递送更具选择性的配体提供了关键见解。更具体地说，发现SHU-9119中 Nle 4、DNal(2') 7和 Trp 9残基的侧链，以及 Asp 5和 Lys 10侧链之间的酰胺键，代表了结构特征。 hMC4R/hMC3R 选择开关。
• NTS2-selective neurotensin mimetics with tetrahydrofuran amino acids
  作者：Nadja A. Simeth、Manuel Bause、Michael Dobmeier、Ralf C. Kling、Daniel Lachmann、Harald Hübner、Jürgen Einsiedel、Peter Gmeiner、Burkhard König

  DOI：10.1016/j.bmc.2016.10.039

  日期：2017.1

  important in the modulation of tonic pain sensitivity. We report the synthesis and properties of a small library of peptidic agonists based on the active neurotensin fragment NT(8–13). Two tetrahydrofuran amino acid derivatives were synthesized to replace Tyr11 in NT(8–13). Additionally, Arg8, Arg9, and Ile12 of the lead peptide were exchanged by Lys, Lys, and Gly, respectively. The new compounds showed

  NTS2神经降压素受体的刺激引起抗精神病作用，并导致非阿片类阿片类抗伤害感受的促进，这在调节补剂疼痛敏感性中很重要。我们报告了基于活性神经降压素片段NT（8-13）的小肽激动剂文库的合成和性质。合成了两个四氢呋喃氨基酸衍生物来取代NT（8-13）中的Tyr 11。另外，先导肽的Arg 8，Arg 9和Ile 12分别被Lys，Lys和Gly交换。新化合物显示出显着的NTS2结合亲和力，选择性是NTS1的1000倍。最高选择性（K i（NTS2）：29 nM，K对于肽类似物17 R反式观察到i（NTS1）：35,000 nM）。