N-[(9H-芴-9-基甲氧基)羰基]-3-硝基-L-苯丙氨酸 | 206060-42-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 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: N-[(9H-芴-9-基甲氧基)羰基]-3-硝基-L-苯丙氨酸
• 中文别名: Fmoc-L-3-硝基基苯丙氨酸；Fmoc-3-硝基-L-苯丙氨酸；9-芴甲氧羰基-L-3-硝基苯丙氨酸；Fmoc-L-3-硝基苯丙氨酸；FMOC-L-3-硝基苯丙氨酸
• 英文名称: Fmoc-(3-nitro)Phe-OH
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(3-nitrophenyl)propanoic acid
• CAS: 206060-42-6
• 化学式: C₂₄H₂₀N₂O₆
• 分子量: 432.433
• InChiKey: UDIZJKKIJYRJIN-QFIPXVFZSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  546.11°C (rough estimate)
• 密度：
  1.3445 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 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：
  121
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2924299090
• 危险类别：
  IRRITANT
• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

SDS

Name:	(S)-N-FMOC-3-Amino-3-(3-Nitrophenyl)Propanoic Acid 95% (98% E.E.) Material Safety Data Sheet
Synonym:	(S)-N-(9-Fluorenylmethoxycarbonyl)-3-Amino-(3-Nitrophenyl)Propionic Acid; (S)-N-FMOC-beta-(3-Nitrophenyl)-beta-Alanine
CAS:	206060-42-6

Section 1 - Chemical Product MSDS Name:(S)-N-FMOC-3-Amino-3-(3-Nitrophenyl)Propanoic Acid 95% (98% E.E.) Material Safety Data Sheet
Synonym:(S)-N-(9-Fluorenylmethoxycarbonyl)-3-Amino-(3-Nitrophenyl)Propionic Acid; (S)-N-FMOC-beta-(3-Nitrophenyl)-beta-Alanine

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
206060-42-6	(S)-N-FMOC-3-Amino-3-(3-Nitrophenyl)Pr	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# 206060-42-6: 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: 140 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C24H20N2O6
Molecular Weight: 432.44

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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.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 206060-42-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-N-FMOC-3-Amino-3-(3-Nitrophenyl)Propanoic Acid. - 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# 206060-42-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 206060-42-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 206060-42-6 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：

  N-[(9H-芴-9-基甲氧基)羰基]-3-硝基-L-苯丙氨酸 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  N-α-(2-羧基)苯甲酰基-N5-(2-氟-1-亚氨基乙基)-l-鸟氨酸酰胺(oF-脒)和N-α-(2-羧基)苯甲酰基-N5-( 2-氯-1-亚氨基乙基)-l-鸟氨酸酰胺（o-Cl-脒）作为第二代蛋白质精氨酸脱亚胺酶 (PAD) 抑制剂

  摘要：

  蛋白质精氨酸脱亚胺酶 (PAD) 活性在许多人类疾病中上调，包括类风湿性关节炎、溃疡性结肠炎和癌症。这些酶在人类中有五种（PADs 1-4 和 6），调节基因转录、细胞分化和先天免疫反应。在我们成功生成 F- 和 Cl-脒（它们不可逆地抑制所有 PAD）的基础上，进行了结构-活性关系以开发具有更高效力和选择性的第二代化合物。将羧酸盐与主链酰胺邻位结合导致鉴定了N -α-(2-羧基)苯甲酰基-N 5 -(2-氟-1-亚氨基乙基) -l-鸟氨酸酰胺 ( o - F-脒) 和N-α-(2-羧基)苯甲酰基-N 5 -(2-氯-1-亚氨基乙基)- l -鸟氨酸酰胺 ( o -Cl-脒)，作为 PAD 灭活剂，具有改进的效力（高达 65 倍）和选择性（高达 25 倍）。相对于 F- 和 Cl- 脒，这些化合物还显示出增强的纤维素效力。因此，这些化合物将成为 PAD 功能的通用化学探针。

  DOI：

  10.1021/jm2008985
• 作为产物：
  描述：

  Rink amide resin 、 Fmoc-对硝基-L-苯丙氨酸 在 三乙胺 、 S-(1-oxido-2-pyridyl)-thio-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 N-[(9H-芴-9-基甲氧基)羰基]-3-硝基-L-苯丙氨酸
  参考文献：
  名称：

  N-α-(2-羧基)苯甲酰基-N5-(2-氟-1-亚氨基乙基)-l-鸟氨酸酰胺(oF-脒)和N-α-(2-羧基)苯甲酰基-N5-( 2-氯-1-亚氨基乙基)-l-鸟氨酸酰胺（o-Cl-脒）作为第二代蛋白质精氨酸脱亚胺酶 (PAD) 抑制剂

  摘要：

  蛋白质精氨酸脱亚胺酶 (PAD) 活性在许多人类疾病中上调，包括类风湿性关节炎、溃疡性结肠炎和癌症。这些酶在人类中有五种（PADs 1-4 和 6），调节基因转录、细胞分化和先天免疫反应。在我们成功生成 F- 和 Cl-脒（它们不可逆地抑制所有 PAD）的基础上，进行了结构-活性关系以开发具有更高效力和选择性的第二代化合物。将羧酸盐与主链酰胺邻位结合导致鉴定了N -α-(2-羧基)苯甲酰基-N 5 -(2-氟-1-亚氨基乙基) -l-鸟氨酸酰胺 ( o - F-脒) 和N-α-(2-羧基)苯甲酰基-N 5 -(2-氯-1-亚氨基乙基)- l -鸟氨酸酰胺 ( o -Cl-脒)，作为 PAD 灭活剂，具有改进的效力（高达 65 倍）和选择性（高达 25 倍）。相对于 F- 和 Cl- 脒，这些化合物还显示出增强的纤维素效力。因此，这些化合物将成为 PAD 功能的通用化学探针。

  DOI：

  10.1021/jm2008985

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。
• A biocompatible stapling reaction for <i>in situ</i> generation of constrained peptides
  作者：Richard Morewood、Christoph Nitsche

  DOI：10.1039/d0sc05125j

  日期：——

  during solid-phase synthesis or following isolation of the linear peptide. The stapling reaction is orthogonal to natural amino acid side chains and completes in aqueous solution at physiological pH, enabling its direct use in biochemical assays. We performed a small screening campaign of short peptides targeting the Zika virus protease NS2B-NS3, allowing the direct comparison of linear with in situ

  受约束的肽是有前途的下一代疗法。肽钉是一种特别有吸引力的技术，可以产生具有改进的生物活性和代谢稳定性的受限大环化合物。我们介绍了一种基于试剂 2,6-二氰基吡啶和假半胱氨酸氨基酸的生物相容性双组分装订方法。装订可以在固相合成期间直接在树脂上进行，也可以在分离线性肽之后进行。装订反应与天然氨基酸侧链正交，并在生理 pH 值的水溶液中完成，使其能够直接用于生化分析。我们对针对寨卡病毒蛋白酶 NS2B-NS3 的短肽进行了小型筛选活动，从而可以直接比较线性与原位订书肽。钉合筛选命中显示出比其线性类似物强 28 倍以上的抑制作用，表明成功鉴定了受限肽抑制剂。
• The Development of <i>N-α</i>-(2-Carboxyl)benzoyl-<i>N</i>⁵-(2-fluoro-1-iminoethyl)-<scp>l</scp>-ornithine Amide (<i>o</i>-F-amidine) and <i>N-α</i>-(2-Carboxyl)benzoyl-<i>N</i>⁵-(2-chloro-1-iminoethyl)-<scp>l</scp>-ornithine Amide (<i>o</i>-Cl-amidine) As Second Generation Protein Arginine Deiminase (PAD) Inhibitors
  作者：Corey P. Causey、Justin E. Jones、Jessica L. Slack、Daisuke Kamei、Larry E. Jones、Venkataraman Subramanian、Bryan Knuckley、Pedram Ebrahimi、Alexander A. Chumanevich、Yuan Luo、Hiroshi Hashimoto、Mamoru Sato、Lorne J. Hofseth、Paul R. Thompson

  DOI：10.1021/jm2008985

  日期：2011.10.13

  relationship was performed to develop second generation compounds with improved potency and selectivity. Incorporation of a carboxylate ortho to the backbone amide resulted in the identification of N-α-(2-carboxyl)benzoyl-N5-(2-fluoro-1-iminoethyl)-l-ornithine amide (o-F-amidine) and N-α-(2-carboxyl)benzoyl-N5-(2-chloro-1-iminoethyl)-l-ornithine amide (o-Cl-amidine), as PAD inactivators with improved potency

  蛋白质精氨酸脱亚胺酶 (PAD) 活性在许多人类疾病中上调，包括类风湿性关节炎、溃疡性结肠炎和癌症。这些酶在人类中有五种（PADs 1-4 和 6），调节基因转录、细胞分化和先天免疫反应。在我们成功生成 F- 和 Cl-脒（它们不可逆地抑制所有 PAD）的基础上，进行了结构-活性关系以开发具有更高效力和选择性的第二代化合物。将羧酸盐与主链酰胺邻位结合导致鉴定了N -α-(2-羧基)苯甲酰基-N 5 -(2-氟-1-亚氨基乙基) -l-鸟氨酸酰胺 ( o - F-脒) 和N-α-(2-羧基)苯甲酰基-N 5 -(2-氯-1-亚氨基乙基)- l -鸟氨酸酰胺 ( o -Cl-脒)，作为 PAD 灭活剂，具有改进的效力（高达 65 倍）和选择性（高达 25 倍）。相对于 F- 和 Cl- 脒，这些化合物还显示出增强的纤维素效力。因此，这些化合物将成为 PAD 功能的通用化学探针。