Fmoc-L-2-氟苯丙氨酸 | 205526-26-7

• 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-氟苯丙氨酸
• 中文别名: FMOC-L-2-氟苯丙氨酸；N-(9-芴甲氧羰酰基)-L-2-氟苯丙氨酸
• 英文名称: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(2-fluorophenyl)propanoic acid
• 英文别名: Fmoc-L-Phe(2-F)-OH；Fmoc-(2-F)Phe-OH；Fmoc-Phe(2-F)-OH；Fmoc-2-F-Phe；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-fluorophenyl)propanoic acid
• CAS: 205526-26-7
• 化学式: C₂₄H₂₀FNO₄
• mdl: MFCD00672552
• 分子量: 405.426
• InChiKey: ARHOAMSIDCQWEW-QFIPXVFZSA-N

物化性质

• 熔点：
  113.4 °C
• 比旋光度：
  -44 º (c=1,DMF)
• 沸点：
  620.3±55.0 °C(Predicted)
• 密度：
  1.2642 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 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：
  储存条件：2~8℃，干燥处，密封保存。

SDS

Name:	(S)-N-FMOC-2-Fluorophenylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	N-(9-Fluorenylmethoxycarbonyl)-2-Fluorophenyl-L-Alanine
CAS:	205526-26-7

Section 1 - Chemical Product MSDS Name:(S)-N-FMOC-2-Fluorophenylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:N-(9-Fluorenylmethoxycarbonyl)-2-Fluorophenyl-L-Alanine

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
205526-26-7	(S)-N-FMOC-2-Fluorophenylalanine	95%	unlisted

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

---

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.

---

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.

---

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.

---

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.

---

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.

---

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# 205526-26-7: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 113.4 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: C24H20FNO4
Molecular Weight: 405.42

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 205526-26-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-N-FMOC-2-Fluorophenylalanine - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Not regulated as a hazardous material.

---

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# 205526-26-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 205526-26-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 205526-26-7 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Fmoc-Phe(2-F)-OH是一种苯丙氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  Fmoc-L-2-氟苯丙氨酸 在 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.5h， 生成 H2N-ahx-hArg-Pro-Phe(2-F)-Asp-VS
  参考文献：
  名称：

  选择性底物和基于活动的探针，用于细胞和血样中人类组成型20S蛋白酶体的成像

  摘要：

  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。

  DOI：

  10.1021/acs.jmedchem.8b00026
• 作为试剂：
  描述：

  4-甲氧基苯乙烯 、 tert-butyldiphenylpyridin-2-ylsilane 在 palladium(II) trifluoroacetate 、 caesium carbonate 、 silver(l) oxide 、 Fmoc-L-2-氟苯丙氨酸 作用下， 以 四氢呋喃 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 48.5h， 以36%的产率得到(S,E)-2-(tert-butyl(2-(4-methoxystyryl)phenyl)(phenyl)silyl)pyridine
  参考文献：
  名称：

  一种硅立体中心手性化合物及其合成方法

  摘要：

  本发明本发明涉及化学合成技术领域，为解决目前硅立体中心手性硅烷合成方法中存在诸如底物适用性差、化学选择性和立体选择性不高的问题，本发明提出了一种硅立体中心手性化合物及其合成方法，以烷基二芳基氮杂芳环硅烷化合物为原料，与烯烃反应合成高对映选择性的硅立体中心手性硅烷，条件温和、反应物廉价、制备方法简便。

  公开号：

  CN108558927B

文献信息

• [EN] N-SUBSTITUTED SECOND GENERATION DERIVATIVES OF ANTIFUNGAL ANTIBIOTIC AMPHOTERICIN B AND METHODS OF THEIR PREPARATION AND APPLICATION<br/>[FR] DÉRIVÉS DE SECONDE GÉNÉRATION N-SUBSTITUÉS DE L'AMPHOTÉRICINE B ANTIBIOTIQUE ANTIFONGIQUE ET LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：BLIRT S A

  公开号：WO2013186384A1

  公开（公告）日：2013-12-19

  The invention provides semisynthetic N-substituted derivatives of the antifungal antibiotic Amphotericin B and water soluble salts and complexes, pharmaceutical compositions and plant and building treatment products comprising the derivatives and their use as antifungal antibiotics.

  这项发明提供了抗真菌抗生素Amphotericin B的半合成N-取代衍生物以及水溶性盐和络合物，包括这些衍生物的药物组合物、植物和建筑处理产品，以及它们作为抗真菌抗生素的用途。
• Discovery of a Human Neuromedin U Receptor 1-Selective Hexapeptide Agonist with Enhanced Serum Stability
  作者：Kentaro Takayama、Kenji Mori、Akiko Tanaka、Erina Nomura、Yuko Sohma、Miwa Mori、Akihiro Taguchi、Atsuhiko Taniguchi、Toshiyasu Sakane、Akira Yamamoto、Naoto Minamino、Mikiya Miyazato、Kenji Kangawa、Yoshio Hayashi

  DOI：10.1021/acs.jmedchem.7b00694

  日期：2017.6.22

  Neuromedin U (NMU) activates two NMU receptors (NMUR1 and NMUR2) and is a useful antiobesity drug lead. We report discovery of a hexapeptide agonist, 2-thienylacetyl-Trp1-Phe(4-F)2-Arg3-Pro4-Arg5-Asn6-NH2 (4). However, the NMUR1 selectivity and serum stability of this agonist were unsatisfactory. Through a structure–activity relationship study focused on residue 2 of agonist 4, serum stability, and

  Neuromedin U（NMU）激活两个NMU受体（NMUR1和NMUR2），是一种有用的抗肥胖药。我们报告发现六肽激动剂，2-噻吩基乙酰基-Trp 1 -Phe（4-F）2 -Arg 3 -Pro 4 -Arg 5 -Asn 6 -NH 2（4）。但是，该激动剂的NMUR1选择性和血清稳定性不能令人满意。通过针对激动剂4的残基2 ，血清稳定性和药代动力学特性的结构-活性关系研究，我们在这里报告了抑制小鼠体重增加的新型NMUR1选择性六肽激动剂7b的发现。
• TOXIN AND METHOD FOR PREPARING INTERMEDIATE THEREOF
  申请人：Jiangsu Hengrui Medicine Co., Ltd.

  公开号：US20190055223A1

  公开（公告）日：2019-02-21

  The present invention relates to a new toxin and a method for preparing an intermediate thereof. In particular, the present invention relates to a new toxin and a method for preparating intermediates of Formula (III) and Formula (IV) thereof, and a preparation method for synthesizing what is shown in general formula (I). The method comprises subjecting a chiral compound shown in general formula (III) to a series of protecting group additions, protecting group removal and amidation so as to obtain a compound as shown in general formula (I). The present method has the advantages of mild reaction conditions, simple operation, high optical purity and high synthetic yield, and thus is suitable for large-scale production.

  本发明涉及一种新毒素及其中间体的制备方法。特别地，本发明涉及一种新毒素及其公式（III）和公式（IV）的中间体的制备方法，以及合成一般公式（I）所示的化合物的制备方法。该方法包括将一般公式（III）所示的手性化合物经过一系列保护基添加、保护基去除和酰胺化反应，以获得一般公式（I）所示的化合物。本方法具有反应条件温和、操作简单、光学纯度高和合成收率高的优点，因此适合大规模生产。
• Phenylalanine derivatives as herbicides
  申请人：Menges Markus

  公开号：US20050215435A1

  公开（公告）日：2005-09-29

  Phenylalanine derivatives of the formula I where the radicals are as defined in the description, and the use of these compounds as herbicides and/or for regulating plant growth is described.

  描述了公式I的苯丙氨酸衍生物，其中基团如描述中所定义，并且描述了这些化合物作为除草剂和/或用于调节植物生长的用途。
• Cyclic tetrapeptide compound and use thereof
  申请人：Satoh Shigeki

  公开号：US20060229236A1

  公开（公告）日：2006-10-12

  A cyclic tetrapeptide compound of the formula (I): wherein R 1 is hydrogen; R 2 is lower alkyl, aryl, optionally substituted ar(lower)alkyl, heterocyclic(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, lower alkylcarbamoyl(lower)alkyl or arylcarbamoyl(lower)alkyl; R 3 and R 4 are each independently hydrogen, lower alkyl, optionally substituted ar(lower)alkyl, optionally substituted heterocyclic(lower)alkyl or cyclo(lower)alkyl(lower)alkyl, or R 3 and R 4 are linked together to form lower alkylene or condensed ring, or one of R 3 and R 4 is linked to the adjacent nitrogen atom to form a ring; R 5 is lower alkylene or lower alkenylene, Y is [wherein R Y1 is hydrogen, halogen or optionally protected hydroxy, R Y2 is hydrogen, halogen, lower alkyl or phenyl, and R Y3 is hydrogen or lower alkyl]; R 8 is hydrogen or lower alkyl; and n is an integer of 1 or 2, or a salt thereof.

  公式（I）的环状四肽化合物：其中R1为氢；R2为低碳基、芳基、可选取代的芳基（较低）烷基、杂环（较低）烷基、环（较低）烷基（较低）烷基、低碳基氨基（较低）烷基或芳基氨基（较低）烷基；R3和R4各自独立地为氢、低碳基、可选取代的芳基（较低）烷基、可选取代的杂环（较低）烷基或环（较低）烷基（较低）烷基，或者R3和R4结合形成低碳基亚烷基或缩合环，或者R3和R4中的一个与相邻的氮原子结合形成环；R5为低碳基亚烷基或低碳基烯烃基，Y为[其中RY1为氢、卤素或可选保护的羟基，RY2为氢、卤素、低碳基或苯基，RY3为氢或低碳基]；R8为氢或低碳基；n为1或2的整数，或其盐。