N-芴甲氧羰基-L-2-氨基丁酸 | 135112-27-5

• 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: N-芴甲氧羰基-L-2-氨基丁酸
• 中文别名: (S)-2-(FMOC-氨基)丁酸；芴甲氧羰酰基Α氨基丁酸；L-2-(芴甲氧羰基氨基)丁酸；Fmoc-L-2-氨基丁酸；FMOC-L-2-氨基丁酸
• 英文名称: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid
• 英文别名: Fmoc-Abu-OH；Fmoc-Abu；Fmoc-L-Abu-OH；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid；Fmoc-L-α-Abu-OH；Fmoc-2-Abu-OH
• CAS: 135112-27-5
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: XQIRYUNKLVPVRR-KRWDZBQOSA-N

物化性质

• 熔点：
  161-163°C
• 沸点：
  550.7±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

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
• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2924 29 70
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-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-Abu-OH
CAS number: 135112-27-5

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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

制备方法与用途

Fmoc-Abu-OH是丙氨酸的衍生物[1]。

反应信息

• 作为反应物：
  描述：

  N-芴甲氧羰基-L-2-氨基丁酸 在 吡啶 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到9H-fluoren-9-ylmethyl [(2S)-1-fluoro-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  改进的微管溶素的全合成以及对癌细胞具有高效细胞毒性的新型微管溶素的设计、合成和生物学评价，作为抗体-药物偶联物的潜在有效载荷

  摘要：

  V (Tb45) 和 U (Tb46) 和 pretubulysin D (PTb-D43) 等天然微管溶素的改进、简化的全合成，以及它们在合成设计的微管溶素类似物（Tb44、PTb-D42、PTb-D47-PTb）中的应用-D49 和 Tb50-Tb120)，进行了描述。合成化合物对某些癌细胞系的细胞毒性评估揭示了许多具有特殊效力的新型类似物[例如，Tb111：IC50 = 40 pM 对 MES SA（子宫肉瘤）细胞系；针对 HEK 293T（人胚胎肾癌）细胞系的 IC50 = 6 pM；和 IC50 = 1.54 nM，对 MES SA DX（具有明显多重耐药性的 MES SA）细胞系]。这些研究产生了一组有价值的构效关系，为进一步的分子设计、合成和生物学评价研究提供指导。

  DOI：

  10.1021/jacs.7b12692
• 作为产物：
  描述：

  L-2-氨基丁酸 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 生成 N-芴甲氧羰基-L-2-氨基丁酸
  参考文献：
  名称：

  真菌双加氧酶AsqJ是混杂的且是双峰的：喹诺酮类与喹唑啉酮类的底物定向形成

  摘要：

  先前的研究表明，Fe II /α-酮戊二酸依赖性双加氧酶AsqJ诱导构巢曲霉在viridicatin生物合成中的骨架重排，从苯并[1,4]二氮杂-2,5-二酮底物生成喹诺酮骨架。我们报告说，仅通过改变苯并二氮杂二酮底物中的取代基，AsqJ即可催化另外的，完全不同的反应。通过底物筛选，功能探针的应用和计算分析来建立这种新机制。AsqJ消费税H 2由合适的苯并[1,4]二氮杂-2-5,5-二酮底物的杂环结构生成CO，生成喹唑啉酮。这种新颖的AsqJ催化途径由复杂底物中的单个取代基控制。AsqJ的这种独特的底物定向反应性可实现喹诺酮或喹唑啉酮的靶向生物催化生成，喹诺酮或喹唑啉酮是两种具有特殊生物医学相关性的生物碱框架。

  DOI：

  10.1002/anie.202017086

文献信息

• [EN] EPHA4 CYCLIC PEPTIDE ANTAGONISTS AND METHODS OF USE THEREOF<br/>[FR] ANTAGONISTES PEPTIDIQUES CYCLIQUES DE L'EPHA4 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：IRON HORSE THERAPEUTICS INC

  公开号：WO2019213620A1

  公开（公告）日：2019-11-07

  Disclosed herein are compounds and methods of use thereof for the modulation of EphA4 receptor activity. In an aspect, is provided a method of treating or preventing a disease or disorder mediated by EphA4, comprising administering to a subject in need thereof a therapeutically effective amount of a compound as described herein, including certain embodiments, or the structural Formula (I), (l-A), (II), (III), (IV), (IV-1), (V), (Vl-A), (Vl-B), (VII-1), (VII-2), (VIII-1), or (VIII-2), or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof; or a pharmaceutically acceptable salt, solvate, or hydrate thereof.

  本文揭示了化合物及其使用方法，用于调节EphA4受体活性。在一个方面，提供了一种治疗或预防由EphA4介导的疾病或紊乱的方法，包括向需要的受试者施用本文描述的化合物的治疗有效量，包括某些实施例，或结构式(I)，(l-A)，(II)，(III)，(IV)，(IV-1)，(V)，(Vl-A)，(Vl-B)，(VII-1)，(VII-2)，(VIII-1)，或(VIII-2)，或其对映体，对映体混合物，两个或更多对映异构体混合物，或其同位素变体；或其药学上可接受的盐，溶剂合物或水合物。
• [EN] MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES MACROCYCLIQUES À LARGE SPECTRE
  申请人：RQX PHARMACEUTICALS INC

  公开号：WO2018149419A1

  公开（公告）日：2018-08-23

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本文提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌类型1信号肽酶（SpsB）发挥作用，这是细菌中的一种必需蛋白质。还提供了使用所述化合物的药物组合物和治疗方法。
• On-Resin Native Chemical Ligation for Cyclic Peptide Synthesis¹^,²
  作者：Judit Tulla-Puche、George Barany

  DOI：10.1021/jo049839d

  日期：2004.6.1

  selective Pd(0)-promoted cleavage of the C-terminal allyl ester; (vi) coupling of the C-terminal residue, i.e., H-Phe-SBzl, preactivated as a thioester; (vii) selective removal of the Nα-Trt and S-Xan protecting groups under very mild acid conditions; (viii) on-resin cyclization by native chemical ligation in an aqueous milieu; and (ix) final acidolytic cleavage of the cyclic peptide from the resin. The strategy

  一种新的半胱氨酸衍生物，Ñ α三苯甲基小号- （9 ħ -呫吨-9-基） -升-半胱氨酸[TRT-半胱氨酸（克桑）-OH]已引入用于肽合成的，专门为应用到一个新的战略用于制备环肽。进行以下步骤以合成环状模型肽环（Cys-Thr-Abu-Gly-Gly-Ala-Arg-Pro-Asp-Phe）：（i）Fmoc-Asp-OAl通过其侧链锚定将β-羧基作为对烷氧基苄基酯游离到固体载体上；（ii）通过标准Fmoc / t逐步提高肽链的延伸率Bu固相化学；（iii）除去N-末端的Fmoc基团；（iv）Trt-Cys（Xan）-OH的偶联；（v）C末端烯丙基酯的选择性Pd（0）促进的裂解；（vi）预活化为硫酯的C-末端残基，即H-Phe-SBzl的偶联；（ⅶ）选择性移除的Ñ α -Trt和小号-Xan保护基团非常温和的酸性条件下; （viii）在水性环境中通过天然化学连接在树脂上进行环化；（ix）从树
• Microwave-assisted solution phase peptide synthesis in neat water
  作者：Amit Mahindra、Karthik Nooney、Shrikant Uraon、Krishna K. Sharma、Rahul Jain

  DOI：10.1039/c3ra43040e

  日期：——

  An environmentally benign protocol for solution phase peptide synthesis has been developed in neat water using TBTU/HOBt/DIEA as a coupling combination under microwave irradiation. Key features of this procedure are the replacement of commonly used toxic organic solvents like DMF and NMP, the use of lower amounts of reactants, compatibility with both N-α-Boc- and N-α-Fmoc-protected amino acids and all commonly used side-chain protective groups, short reaction time, and racemization-free synthesis in high yield and purity.

  在微波辐射下，使用TBTU/HOBt/DIEA作为耦合组合，在纯水中开发了一种环境友好的溶液相多肽合成方法。该方法的关键特点包括替代常见的毒性有机溶剂如DMF和NMP，使用更少的反应物，与N-α-Boc保护和N-α-Fmoc保护的氨基酸以及所有常用侧链保护基团兼容，反应时间短，且在高效和高纯度下实现无消旋合成。
• Rational Design and Synthesis of Modified Teixobactin Analogues: In Vitro Antibacterial Activity against <i>Staphylococcus aureus</i> , <i>Propionibacterium acnes</i> and <i>Pseudomonas aeruginosa</i>
  作者：Vivian Ng、Sarah A. Kuehne、Weng C. Chan

  DOI：10.1002/chem.201801423

  日期：2018.6.26

  Extensive antimicrobial susceptibility assessment against a panel of clinically relevant Staphylococcus aureus and Propionibacterium acnes strains led to the identification of the new lead compound, [Arg(Me)10,Nle11]teixobactin, with an excellent bactericidal activity (minimum inhibitory concentration (MIC)=2–4 μg mL−1). Significantly, the antimicrobial activity of several of the teixobactin analogues against

  Teixobactin是最近发现的一种与细菌脂质II和脂质III结合的二肽肽，为设计新的抗菌剂提供了有希望的分子支架。在这里，我们描述了系统修饰的teixobactin类似物的合成和抗菌评估。Ile 11残基被脂肪族等聚体取代，修饰残基10的胍基基团，以及向大环引入刚性化残基（即脱氢氨基酸），产生了有用的结构活性信息。针对一组临床相关的金黄色葡萄球菌和痤疮丙酸杆菌菌株进行了广泛的药敏评估，从而鉴定出了新的先导化合物[Arg（Me）10，Nle 11 ] teixobactin，具有优异的杀菌活性（最低抑菌浓度（MIC）= 2-4μgmL -1）。值得注意的是，当与亚MIC浓度的外膜破坏性抗生素大肠菌素结合使用时，“ teixobactin类似物”对致病性革兰氏阴性铜绿假单胞菌的抗微生物活性被“恢复”。[Tfn 10，Nle 11 ] teixobactin（32μgmL -1）-colistin（2μgmL