Fmoc-D-烯丙基甘氨酸 | 170642-28-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-D-烯丙基甘氨酸
• 中文别名: (R)-2-(芴甲氧羰基-氨基)-4-戊烯酸；N-芴甲氧羰基-D-烯丙基甘氨酸；2-烯丙基-N-FMOC-D-氨基乙酸；2-烯丙基-N-Fmoc-D-氨基乙酸；(R)-N-Fmoc-烯丙基甘氨酸
• 英文名称: (R)-2-(9-fluorenylmethoxycarbonyl)amino-4-pentenoic acid
• 英文别名: N-Fmoc D-allylglicine；Fmoc-D-allylglycine；(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-4-enoic acid；Fmoc-(D)-Agl-OH；Fmoc-D-allylglicine-OH；N-Fmoc-D-allylglycine；Fmoc-D-Gly(All)-OH；Fmoc-AllylGly-OH；Fmoc-D Alg-OH；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pent-4-enoic acid
• CAS: 170642-28-1
• 化学式: C₂₀H₁₉NO₄
• mdl: MFCD01311776
• 分子量: 337.375
• InChiKey: YVBLQCANYSFEBN-GOSISDBHSA-N

物化性质

• 熔点：
  134 °C
• 沸点：
  473.68°C (rough estimate)
• 密度：
  1.2486 (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)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  29242990
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放在0°C以下的阴凉干燥处。

SDS

Name:	(R)-N-FMOC-Allylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	(R)-N-(9-Fluorenylmethoxycarbonyl)-2-Amino-4-Pentenoic Acid
CAS:	170642-28-1

Section 1 - Chemical Product MSDS Name:(R)-N-FMOC-Allylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:(R)-N-(9-Fluorenylmethoxycarbonyl)-2-Amino-4-Pentenoic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
170642-28-1	(R)-N-FMOC-Allylglycine	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:
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# 170642-28-1: 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: 134 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: C20H19NO4
Molecular Weight: 337.37

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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# 170642-28-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-N-FMOC-Allylglycine - 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# 170642-28-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 170642-28-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 170642-28-1 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-Gly(烯丙基)-OH是甘氨酸（HY-Y0966）的一种衍生物。

反应信息

• 作为反应物：
  描述：

  Fmoc-D-烯丙基甘氨酸 在 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 D-2-(9H-fluorenyl-9-methoxycarbonylamino)-4-oxo-butyric acid
  参考文献：
  名称：

  固相支持物上双环β-转二肽的新颖设计和[3.3.0]-双环（[2,3]）-亮脑啡肽类似物的合成。

  摘要：

  [结构：参见文本]外部双环β-转二肽模拟物提供了一种出色的设计方法，可以提供具有不同主链构象的丰富手性结构。我们在这里报告了一种收敛组合合成方法的新颖设计，通过一系列[3.3.0]-双环（[2,3]）-Leu-脑啡肽类似物的固相合成来说明。优化反应并通过2D NMR光谱确定差向异构构型。生物学分析表明，这些类似物相对于微阿片受体对δ具有更强的δ结合亲和力和生物活性，这可能与这些类似物在我们的建模研究中优选的不同构象有关。

  DOI：

  10.1021/ol0488183
• 作为产物：
  描述：

  D-烯丙基甘氨酸 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 生成 Fmoc-D-烯丙基甘氨酸
  参考文献：
  名称：

  固相支持物上双环β-转二肽的新颖设计和[3.3.0]-双环（[2,3]）-亮脑啡肽类似物的合成。

  摘要：

  [结构：参见文本]外部双环β-转二肽模拟物提供了一种出色的设计方法，可以提供具有不同主链构象的丰富手性结构。我们在这里报告了一种收敛组合合成方法的新颖设计，通过一系列[3.3.0]-双环（[2,3]）-Leu-脑啡肽类似物的固相合成来说明。优化反应并通过2D NMR光谱确定差向异构构型。生物学分析表明，这些类似物相对于微阿片受体对δ具有更强的δ结合亲和力和生物活性，这可能与这些类似物在我们的建模研究中优选的不同构象有关。

  DOI：

  10.1021/ol0488183

文献信息

• Highly Practical Methodology for the Synthesis of <scp>d</scp>- and <scp>l</scp>-α-Amino Acids, <i>N</i>-Protected α-Amino Acids, and <i>N</i>-Methyl-α-amino Acids
  作者：Andrew G. Myers、James L. Gleason、Taeyoung Yoon、Daniel W. Kung

  DOI：10.1021/ja9624073

  日期：1997.1.1

  step the asymmetric alkylation of pseudoephedrine glycinamide (1) or pseudoephedrine sarcosinamide (2). Practical procedures for the synthesis of 1 and 2 from pseudoephedrine and glycine methyl ester or sarcosine methyl ester, respectively, are presented. Optimum protocols for the enolization and subsequent alkylation of 1 and 2 are described. Alkylation reactions of 1 and 2 are found to be quite efficient

  提供了一种非常实用的合成 d-和 l-α-氨基酸、N-保护的 α-氨基酸和 N-甲基-α-氨基酸的方法的完整细节，其中使用伪麻黄碱甘氨酰胺的不对称烷基化作为关键步骤(1) 或伪麻黄碱肌酰胺 (2)。介绍了分别从伪麻黄碱和甘氨酸甲酯或肌氨酸甲酯合成 1 和 2 的实用程序。描述了 1 和 2 的烯醇化和随后的烷基化的最佳方案。发现 1 和 2 的烷基化反应对于范围广泛的卤代烷底物非常有效，并且产物以高非对映选择性形成。通过在水或水-二恶烷混合物中加热，这些烷基化反应的产物可以有效地水解并且几乎没有外消旋化。该协议为制备高对映体纯度的无盐 α-氨基酸提供了一种非常实用的方法。或者，烷基化产物...
• Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 1
  作者：John B. Bremner、Paul A. Keller、Stephen G. Pyne、Timothy P. Boyle、Zinka Brkic、Dorothy M. David、Mark Robertson、Kittiya Somphol、Dean Baylis、Jonathan A. Coates、John Deadman、Darshini Jeevarajah、David I. Rhodes

  DOI：10.1016/j.bmc.2010.02.033

  日期：2010.4

  An efficient synthesis of 29 new binaphthyl-based neutral, and mono- and di-cationic, peptoids is described. Some of these compounds had antibacterial activities with MIC values of 1.9–3.9 μg/mL against Staphylococcus aureus. One peptoid had a MIC value of 6 μg/mL against a methicillin-resistant strain of S. aureus (MRSA) and a MIC value of 2 μg/mL against vancomycin-resistant strains of enterococci

  描述了29种新的基于双萘基的中性，单和双阳离子类肽的有效合成。其中一些化合物对金黄色葡萄球菌具有抗菌活性，MIC值为1.9–3.9μg/ mL 。一种类肽对耐金霉素的金黄色葡萄球菌（MRSA）的MIC值为6μg/ mL，对耐万古霉素的肠球菌（VRE）的MIC值为2μg/ mL。
• A conformationally fixed analog of the peptide mimic Grb2–SH2 domain: synthesis and evaluation against the A431 cancer cell
  作者：Takayuki Iwata、Katsunori Tanaka、Tsuyoshi Tahara、Satoshi Nozaki、Hirotaka Onoe、Yasuyoshi Watanabe、Koichi Fukase

  DOI：10.1039/c3mb25462c

  日期：——

  A small peptide mimic of the Grb2-SH2 domain, which was previously prepared through the template-assisted click approach and exhibited selective A431 tumor growth inhibition both in vitro and in vivo, was further elaborated on to enhance the interaction with target phosphorylated proteins. A conformationally fixed analog was efficiently synthesized by solid-supported ring-closing metathesis and Cu(I)/His-mediated self-activating Huisgen [3+2] cycloadditon as the key steps, and exhibited a 10-fold enhanced affinity to a phosphorylated peptide, a truncated peptide analog of the Grb2–SH2-interacting phosphoproteins. A stronger interaction with the target phosphorylated proteins gave this cyclic analog cytotoxic activity in A431 cells.

  一个小肽模拟物，代表Grb2-SH2结构域，先前通过模板辅助的点击化学方法制备，并在体外和体内显示出对A431肿瘤的选择性生长抑制，进一步进行了改进以增强其与目标磷酸化蛋白的相互作用。通过固态支撑的环闭交叉反应和Cu(I)/His介导的自激活Huisgen [3+2]环加成作为关键步骤，高效合成了一个构象固定的类似物，其对一个磷酸化肽（Grb2-SH2相互作用磷蛋白的截短肽类比物）的亲和力提高了10倍。与目标磷酸化蛋白的更强相互作用使得该环状类似物在A431细胞中具有细胞毒活性。
• Highly Efficient Solid-Phase Oxidative Cleavage of Olefins by OsO₄−NaIO₄ in the Intramolecular <i>N</i>-Acyliminium Pictet−Spengler Reaction
  作者：Thomas E. Nielsen、Morten Meldal

  DOI：10.1021/ol050870r

  日期：2005.6.1

  solid-supported peptide olefins were converted quantitatively to aldehydes via the OsO(4)-NaIO(4)-mediated oxidative cleavage reaction. Addition of DABCO was essential to efficiently suppress the formation of hydroxymethyl ketone side products. The generated aldehydes were used in intramolecular N-acyliminium Pictet-Spengler reactions to produce highly pure pyrroloisoquinoline derivatives. The methodology

  [反应：见正文]在本研究中，固体支持的肽烯烃通过OsO（4）-NaIO（4）介导的氧化裂解反应定量转化为醛。DABCO的添加对于有效抑制羟甲基酮副产物的形成是必不可少的。生成的醛用于分子内N-酰亚胺Pictet-Spengler反应中，以生成高纯度的吡咯并异喹啉衍生物。该方法已扩展到烯丙基甘氨酸衍生物，以使吡咯并异喹啉支架能够掺入肽中。
• Design, Structural Optimization, and Characterization of the First Selective Macrocyclic Neurotensin Receptor Type 2 Non-opioid Analgesic
  作者：Magali Chartier、Michael Desgagné、Marc Sousbie、Jérôme Côté、Jean-Michel Longpré、Eric Marsault、Philippe Sarret

  DOI：10.1021/acs.jmedchem.0c01726

  日期：2021.2.25

  Neurotensin (NT) receptor type 2 (NTS2) represents an attractive target for the development of new NT-based analgesics. Here, we report the synthesis and functional in vivo characterization of the first constrained NTS2-selective macrocyclic NT analog. While most chemical optimization studies rely on the NT(8-13) fragment, we focused on NT(7-12) as a scaffold to design NTS2-selective macrocyclic peptides

  神经降压素 (NT) 受体 2 型 (NTS2) 是开发新型 NT 镇痛药的一个有吸引力的靶点。在这里，我们报告了第一个受限 NTS2 选择性大环 NT 类似物的合成和体内功能表征。虽然大多数化学优化研究依赖于 NT(8-13) 片段，但我们重点关注 NT(7-12) 作为支架来设计 NTS2 选择性大环肽。用 Leu 替换 Ile 12 ，用烯丙基甘氨酸残基替换 Pro 7 /Pro 10，然后通过闭环复分解进行环化，得到大环4 ，它对 NTS2 (50 nM) 表现出良好的亲和力，对 NTS1 (>100 μM) 具有高选择性，与 NT(8-13) 相比，稳定性有所提高。大鼠体内分析表明，大环化合物4在三种不同的啮齿动物疼痛模型中产生有效的镇痛作用，而不会引起与 NTS1 激活相关的不良影响。我们进一步提供了其非阿片类镇痛活性的证据，因此强调了 NTS2 选择性类似物在治疗急性和慢性疼痛方面的强大治疗潜力。