(+)-(1S,3R)-N-FMOC-3-环亮氨酸 | 220497-66-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - FMOC-氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (+)-(1S,3R)-N-FMOC-3-环亮氨酸
• 中文别名: (1S,3R)-N-FMOC-3-氨基环戊烷甲酸；(1S,3R)-3-[[(9H-芴-9-基甲氧基)羰基]氨基]-环戊基羧酸；(+)-(1S,3r)-n-Fmoc-3-氨基环戊烷羧酸
• 英文名称: (1S,3R)-3-(9-fluorenylmethoxycarbonylamino)cyclopentanecarboxylic acid
• 英文别名: (1S,3R)-3-amino-N-(9H-fluoren-9-yl)methyloxycarbonylcyclopentanecarboxylic acid；D-Fmoc-γ-Acp-OH；N-Fmoc-1-aminocyclopentane-3-carboxylic acid；N-FMOC-3-aminocyclopentane-1-carboxylic acid；(1S,3R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)cyclopentanecarboxylic acid；(1S,3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)cyclopentane-1-carboxylic acid
• CAS: 220497-66-5
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: BHDMUBZVWRSQOT-UONOGXRCSA-N

物化性质

• 熔点：
  164.7 °C
• 沸点：
  485.2°C (rough estimate)
• 密度：
  1.32±0.1 g/cm3 (20 ºC 760 Torr)
• 稳定性/保质期：
  <p>遵照规定使用和储存，则不会分解。</p>

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 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：
  29223900
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	(1R 3S)-N-FMOC-1-Aminocyclopentane-3-Carboxylic Acid 95% (98% E.E.) Material Safety Data Sheet
Synonym:
CAS:	220497-66-5

Section 1 - Chemical Product MSDS Name:(1R 3S)-N-FMOC-1-Aminocyclopentane-3-Carboxylic Acid 95% (98% E.E.) Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
220497-66-5	(1R,3S)-N-FMOC-1-Aminocyclopentane-3-C	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 cool, dry place. Store in a tightly closed container.

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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# 220497-66-5: 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: 164.7 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: C21H21NO4
Molecular Weight: 351.41

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
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# 220497-66-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1R,3S)-N-FMOC-1-Aminocyclopentane-3-Carboxylic 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# 220497-66-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 220497-66-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 220497-66-5 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

反应信息

• 作为反应物：
  描述：

  (+)-(1S,3R)-N-FMOC-3-环亮氨酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 二乙胺 、 三乙胺 、 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 2.0h， 生成 (1S,3R)-3-acetamido-N-methyl-N-(4-phenylphenyl)cyclopentane-1-carboxamide
  参考文献：
  名称：

  Discovery of BI 99179, a potent and selective inhibitor of type I fatty acid synthase with central exposure

  摘要：

  Based on a high-throughput screen, cyclopentanecarboxanilides were identified as a new chemotype of non-covalent inhibitors of type I fatty acid synthase (FAS). Starting from initial hits we aimed at generating a tool compound suitable for the in vivo validation of FAS as a therapeutic target. Optimisation yielded BI 99179 which is characterised by high potency, remarkably high selectivity and significant exposure (both peripheral and central) upon oral administration in rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.083
• 作为产物：
  描述：

  (1S,3R)-3-氨基环戊羧酸 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以38%的产率得到(+)-(1S,3R)-N-FMOC-3-环亮氨酸
  参考文献：
  名称：

  将氨基环戊烷羧酸接枝到RGD三肽序列上会产生低纳摩尔浓度的alphaVbeta3 / alphaVbeta5整联蛋白双结合剂。

  摘要：

  以手性非外消旋形式制备了11个γ-氨基环戊烷羧酸（Acpca）平台，包括四个二羟基代表分子（19-22），三个羟基类似物（34-36）和四个脱氧衍生物（30-33）。然后通过混合固相/溶液方案将这些简单的单元嫁接到Arg-Gly-Asp（RGD）三肽构架上，从而提供11种环-[-Arg-Gly-Asp-Acpca-]型大环类似物的集合体-11。评价各个化合物对αVbeta3和αVbeta5整联蛋白受体的结合亲和力。与参考化合物EMD121974和ST1646相比，类似物10表现出非常有趣的活性谱（IC50 / alphaVbeta3 = 1.5 nM； IC50 / alphaVbeta5 = 0.59 nM）。密切相关的同类物6、8 和9也被证明是出色的双重粘合剂，其活性水平在低纳摩尔范围内。确定了三维（3D）NMR溶液结构，并在选定的类似物上与参照化合物EMD121974进行了整合素α

  DOI：

  10.1021/jm050698x

文献信息

• Nickel Catalysis via S_H2 Homolytic Substitution: The Double Decarboxylative Cross-Coupling of Aliphatic Acids
  作者：Artem V. Tsymbal、Lorenzo Delarue Bizzini、David W. C. MacMillan

  DOI：10.1021/jacs.2c08989

  日期：2022.11.23

  generation, radical sorting via selective binding to a Ni(II) center, and bimolecular homolytic substitution (SH2) at a high-valent nickel–alkyl complex. This catalytic manifold enables the hitherto elusive cross-coupling of diverse aliphatic carboxylic acids to generate valuable C(sp3)–C(sp3)-products. Notably, the powerful SH2 mechanism provides general access to sterically encumbered quaternary carbon

  交叉偶联平台传统上是围绕一系列闭壳步骤构建的，例如氧化加成、金属转移和还原消除。在此，我们描述了一种双光/镍催化歧管，它通过互补序列进行交叉偶联，涉及自由基生成、通过选择性结合到 Ni(II) 中心的自由基分选以及高催化下的双分子均解取代 (S H 2)。 -价镍-烷基络合物。这种催化歧管能够实现迄今为止难以捉摸的不同脂肪族羧酸的交叉偶联，生成有价值的 C(sp 3 )–C(sp 3 )-产物。值得注意的是，强大的 S H 2 机制提供了对空间阻碍的季碳中心的普遍访问，解决了片段偶联化学中长期存在的挑战。
• Peptides having antiangiogenic activity
  申请人：——

  公开号：US20030045477A1

  公开（公告）日：2003-03-06

  Compounds having the formula A 0 -A 1 -A 2 -A 3 -A 4 -A 5 -A 6 -A 7 -A 8 -A 9 -A 10 , which are useful for treating conditions that arise from or are exacerbated by angiogenesis are described. Also disclosed are pharmaceutical compositions comprising these compounds, methods of treatment using these compounds, and methods of inhibiting angiogenesis.

  具有以下式子的化合物 A 0 -A 1 -A 2 -A 3 -A 4 -A 5 -A 6 -A 7 -A 8 -A 9 -A 10 , 描述了可用于治疗血管生成引起或加剧的病症的化合物。还公开了包含这些化合物的药物组合物、使用这些化合物的治疗方法以及抑制血管生成的方法。
• α,γ-Peptide Nanotube Templating of One-Dimensional Parallel Fullerene Arrangements
  作者：César Reiriz、Roberto J. Brea、Rocío Arranz、José L. Carrascosa、Alejandra Garibotti、Brendan Manning、José M. Valpuesta、Ramón Eritja、Luis Castedo、Juan R. Granja

  DOI：10.1021/ja904548q

  日期：2009.8.19

  The formation and full characterization of single self-assembling alpha,gamma-peptide nanotubes (alpha,gamma-SPNs) is described. The introduction of C-60 into cyclic peptides allows the preparation of supramotecular 1D fullerene arrangements induced by peptide nanotube formation under appropriate conditions.
• Discovery of BI 99179, a potent and selective inhibitor of type I fatty acid synthase with central exposure
  作者：Jörg T. Kley、Jürgen Mack、Bradford Hamilton、Stefan Scheuerer、Norbert Redemann

  DOI：10.1016/j.bmcl.2011.07.083

  日期：2011.8

  Based on a high-throughput screen, cyclopentanecarboxanilides were identified as a new chemotype of non-covalent inhibitors of type I fatty acid synthase (FAS). Starting from initial hits we aimed at generating a tool compound suitable for the in vivo validation of FAS as a therapeutic target. Optimisation yielded BI 99179 which is characterised by high potency, remarkably high selectivity and significant exposure (both peripheral and central) upon oral administration in rats. (C) 2011 Elsevier Ltd. All rights reserved.
• Grafting Aminocyclopentane Carboxylic Acids onto the RGD Tripeptide Sequence Generates Low Nanomolar α_Vβ₃/α_Vβ₅ Integrin Dual Binders
  作者：Giovanni Casiraghi、Gloria Rassu、Luciana Auzzas、Paola Burreddu、Enrico Gaetani、Lucia Battistini、Franca Zanardi、Claudio Curti、Giuseppe Nicastro、Laura Belvisi、Ilaria Motto、Massimo Castorina、Giuseppe Giannini、Claudio Pisano

  DOI：10.1021/jm050698x

  日期：2005.12.1

  the low nanomolar range. The three-dimensional (3D) NMR solution structures were determined, and docking studies to X-ray crystal structure of the extracellular segment of integrin alphaVbeta3 in complex with the reference compound EMD121974 were performed on selected analogues to elucidate the interplay between structure and function in these systems and to evidence the subtle bases for receptorial recognition

  以手性非外消旋形式制备了11个γ-氨基环戊烷羧酸（Acpca）平台，包括四个二羟基代表分子（19-22），三个羟基类似物（34-36）和四个脱氧衍生物（30-33）。然后通过混合固相/溶液方案将这些简单的单元嫁接到Arg-Gly-Asp（RGD）三肽构架上，从而提供11种环-[-Arg-Gly-Asp-Acpca-]型大环类似物的集合体-11。评价各个化合物对αVbeta3和αVbeta5整联蛋白受体的结合亲和力。与参考化合物EMD121974和ST1646相比，类似物10表现出非常有趣的活性谱（IC50 / alphaVbeta3 = 1.5 nM； IC50 / alphaVbeta5 = 0.59 nM）。密切相关的同类物6、8 和9也被证明是出色的双重粘合剂，其活性水平在低纳摩尔范围内。确定了三维（3D）NMR溶液结构，并在选定的类似物上与参照化合物EMD121974进行了整合素α