Fmoc-D-2-氨基丁酸 | 170642-27-0

• 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: Fmoc-D-2-氨基丁酸
• 中文别名: N-芴甲氧羰基-D-2-氨基丁酸
• 英文名称: Fmoc-D-Abu-OH
• 英文别名: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• CAS: 170642-27-0
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: XQIRYUNKLVPVRR-QGZVFWFLSA-N

物化性质

• 沸点：
  550.7±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 溶解度：
  溶于水或1%醋酸

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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
• 海关编码：
  29214990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储于室温下。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-D-Abu-OH
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Fmoc-D-Abu-OH
CAS number: 170642-27-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C19H19NO4
Molecular weight: 325.4

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  Fmoc-D-2-氨基丁酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (9H-fluoren-9-yl)methyl (R)-(1-chloro-1-oxobutan-2-yl)carbamate
  参考文献：
  名称：

  [EN] ESTROGEN RECEPTOR MODULATORS
  [FR] MODULATEURS DU RÉCEPTEUR DES ŒSTROGÈNES

  摘要：

  化合物的化学式（I）是雌激素受体α调节剂，其中化学式（I）中的变量在披露中有描述。这些化合物以及其药学上可接受的盐和组合物对于治疗依赖雌激素受体α和/或由雌激素受体α介导的疾病或症状是有用的，包括由细胞过度增殖所特征化的疾病，如乳腺癌。

  公开号：

  WO2017172957A1
• 作为产物：
  描述：

  在 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 以83%的产率得到Fmoc-D-2-氨基丁酸
  参考文献：
  名称：

  合成 d-和l-α-氨基酸、N-保护的 α-氨基酸和 N-甲基-α-氨基酸的高度实用方法

  摘要：

  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...

  DOI：

  10.1021/ja9624073

文献信息

• Structure-guided engineering of<i>meso</i>-diaminopimelate dehydrogenase for enantioselective reductive amination of sterically bulky 2-keto acids
  作者：Xinkuan Cheng、Xi Chen、Jinhui Feng、Qiaqing Wu、Dunming Zhu

  DOI：10.1039/c8cy01426d

  日期：——

  (DAPDH) and mutant enzymes are an excellent choice of biocatalysts for the conversion of 2-keto acids to the corresponding D-amino acids. However, their application in the enantioselective reductive amination of bulky 2-keto acids, such as phenylglyoxylic acid, 2-oxo-4-phenylbutyric acid, and indole-3-pyruvic acid, is still challenging. In this study, the structure-guided site-saturation mutagenesis of a

  内消旋-二氨基庚二酸酯脱氢酶（DAPDH）和突变酶是将2-酮酸转化为相应的D-氨基酸的生物催化剂的绝佳选择。然而，它们在庞大的2-酮酸如苯乙醛酸，2-氧代-4-苯基丁酸和吲哚-3-丙酮酸的对映选择性还原胺化中的应用仍然具有挑战性。在这项研究中，嗜热共生菌DAPDH（StDAPDH）的结构指导的位点饱和诱变产生了一个双位点突变体W121L / H227I，该突变体显示出对包括这些空间庞大底物在内的各种2-酮酸的酶活性有了显着提高。几D-氨基酸以光学纯的形式制备。底物分子对接至野生型和突变型W121L / H227I酶的活性位点中显示，突变型酶的底物结合腔已重塑以适应这些庞大的底物，从而导致更高的酶活性。这些结果为进一步整形底物结合袋和操纵底物与结合位点之间的相互作用以接近高活性的D-氨基酸脱氢酶以制备具有合成挑战性的D-氨基酸奠定了基础。
• NON-NUCLEOSIDE ANTI-HEPACIVIRUS AGENTS AND USES THEREOF
  申请人：Boyd A. Vincent

  公开号：US20070021434A1

  公开（公告）日：2007-01-25

  The present dislcosure provides amide-based, non-nucleoside compounds having antiviral activity against Hepacivirus, such as hepatitis C virus (HCV), methods and intermediates for synthesizing such compounds, and methods of using the compounds in a variety of contexts, including in the treatment and prevention of viral infections. The present dislcosure also provides methods for identifying amide-based, non-nucleoside compounds having antiviral activity.

  本公开提供了基于酰胺的非核苷类化合物，具有抗Hepacivirus活性，例如丙型肝炎病毒（HCV），合成这类化合物的方法和中间体，以及在各种情境中使用这些化合物的方法，包括在治疗和预防病毒感染中的应用。本公开还提供了识别具有抗病毒活性的基于酰胺的非核苷类化合物的方法。
• COMPOSITIONS AND METHODS FOR TREATING HYPERPROLIFERATIVE DISEASE
  申请人：Cameron Dale Russell

  公开号：US20080171783A1

  公开（公告）日：2008-07-17

  The present disclosure provides amide-based, non-nucleoside compounds having an inhibitory activity against endogenous polymerases, such as polymerase alpha and polymerase gamma. This disclosure further provides uses of treating hyperproliferative diseases or disorders, such as benign or malignant neoplasms, and more specifically cancers that are sensitive to inhibition of polymerase alpha and polymerase gamma.

  本公开提供了基于酰胺的非核苷类化合物，具有对内源聚合酶（如聚合酶α和聚合酶γ）的抑制活性。本公开进一步提供了用于治疗过度增殖性疾病或疾病的用途，例如良性或恶性肿瘤，更具体地是对聚合酶α和聚合酶γ抑制敏感的癌症。
• Design and synthesis of 3,3′-biscoumarin-based c-Met inhibitors
  作者：Jimin Xu、Jing Ai、Sheng Liu、Xia Peng、Linqian Yu、Meiyu Geng、Fajun Nan

  DOI：10.1039/c4ob00364k

  日期：——

  A library of biscoumarin-based c-Met inhibitors was synthesized, based on optimization of 3,3′-biscoumarin hit 3, which was identified as a non-ATP competitive inhibitor of c-Met from a diverse library of coumarin derivatives. Among these compounds, 38 and 40 not only showed potent enzyme activities with IC50 values of 107 nM and 30 nM, respectively, but also inhibited c-Met phosphorylation in BaF3/TPR-Met

  基于3,3'-biscoumarin hit 3的优化，合成了基于双香豆素的c-Met抑制剂库，该库从多种香豆素衍生物库中被鉴定为c-Met的非ATP竞争性抑制剂。在这些化合物中，38和40不仅显示出强大的酶活性，IC 50值分别为107 nM和30 nM，而且还抑制了BaF3 / TPR-Met和EBC-1细胞中的c-Met磷酸化。
• Rational Design and Identification of a Non-Peptidic Aggregation Inhibitor of Amyloid-β Based on a Pharmacophore Motif Obtained from<i>cyclo</i>[-Lys-Leu-Val-Phe-Phe-]
  作者：Tadamasa Arai、Takushi Araya、Daisuke Sasaki、Atsuhiko Taniguchi、Takeshi Sato、Youhei Sohma、Motomu Kanai

  DOI：10.1002/anie.201405109

  日期：2014.7.28

  straightforward therapeutic strategy for curing amyloid diseases. Small‐molecule aggregation inhibitors of Alzheimer’s amyloid‐β (Aβ) are extremely scarce, however, and are mainly restricted to dye‐ and polyphenol‐type compounds that lack drug‐likeness. Based on the structure‐activity relationship of cyclic Aβ16–20 (cyclo‐[KLVFF]), we identified unique pharmacophore motifs comprising side‐chains of Leu2, Val3

  抑制病原性蛋白质聚集可能是治愈淀粉样蛋白疾病的重要且直接的治疗策略。但是，阿尔茨海默氏淀粉样β（Aβ）的小分子聚集抑制剂非常稀少，并且主要限于缺乏药物样的染料和多酚类化合物。基于环状Aβ16-20（环-[KLVFF]）的结构-活性关系，我们鉴定出了独特的药效基序，包括Leu 2，Val 3，Phe 4和Phe 5的侧链。残基不涉及主链酰胺键来抑制Aβ聚集。这一发现使我们能够设计具有有效活性的非肽类，小分子聚集抑制剂。基于合理的分子设计，这些分子是第一个成功的成功的非肽类，小分子淀粉样蛋白抑制剂。