Fmoc-β-氰基-1-丙氨酸 | 127273-06-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-β-氰基-1-丙氨酸
• 英文名称: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-cyanopropanoic acid
• 英文别名: (2S)-3-cyano-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 127273-06-7
• 化学式: C₁₉H₁₆N₂O₄
• 分子量: 336.347
• InChiKey: FJSOTHAUCCEZLI-KRWDZBQOSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  617.1±55.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-beta-cyano-l-alanine
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-beta-cyano-l-alanine
CAS number: 127273-06-7

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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: C19H16N2O4
Molecular weight: 336.3

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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-β-氰基-1-丙氨酸 在 N-甲基吗啉 、 ammonium hydroxide 、 叠氮基三甲基硅烷 、 二正丁基氧化锡 、 N,N-二异丙基乙胺 、 三氟乙酸酐 、 氯甲酸异丁酯 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 (S)-(9H-fluoren-9-yl)methyl 1-cyano-2-(1H-tetrazol-5-yl)ethylcarbamate
  参考文献：
  名称：

  Caspase inhibitors

  摘要：

  公式I:X-W的化合物或药学上可接受的盐或酯，其中X是一种选择性卡他蛋白酶结构，W具有如下结构：—NH—CH(Y)(Z)，其中Y是一种能够与卡他蛋白酶形成可逆共价键的结构；Z选自羧基或羧酸类似物。

  公开号：

  US09365612B2
• 作为产物：
  描述：

  Fmoc-L-天冬酰胺 在 吡啶 、 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 Fmoc-β-氰基-1-丙氨酸
  参考文献：
  名称：

  使用Fmoc化学合成氨基酸的四唑类似物：分离游离氨基的四唑并将其掺入肽中

  摘要：

  从开始氨基酸的四唑类似物的有效合成Ñ α报道-Fmoc氨基酸在三步骤的协议。除去Fmoc基团后，以良好的产率和优异的纯度获得了游离的氨基四唑。还描述了合成的天冬氨酸和谷氨酸类似物，其中5-四唑基部分从Fmoc-Asn和Fmoc-Gln开始插入β/γ羧基，并将这些四唑掺入肽中。

  DOI：

  10.1016/j.tetlet.2007.07.129

文献信息

• Synthesis of tetrazole analogues of amino acids using Fmoc chemistry: isolation of amino free tetrazoles and their incorporation into peptides
  作者：Vommina V. Sureshbabu、Rao Venkataramanarao、Shankar A. Naik、G. Chennakrishnareddy

  DOI：10.1016/j.tetlet.2007.07.129

  日期：2007.9

  An efficient synthesis of tetrazole analogues of amino acids starting from Nα-Fmoc amino acid in a three-step protocol is reported. The free amino tetrazoles were obtained in good yields and with excellent purity after removal of the Fmoc group. The synthesis of analogues of aspartic and glutamic acids in which the 5-tetrazolyl moiety is inserted at the β/γ carboxyl group starting from Fmoc-Asn and

  从开始氨基酸的四唑类似物的有效合成Ñ α报道-Fmoc氨基酸在三步骤的协议。除去Fmoc基团后，以良好的产率和优异的纯度获得了游离的氨基四唑。还描述了合成的天冬氨酸和谷氨酸类似物，其中5-四唑基部分从Fmoc-Asn和Fmoc-Gln开始插入β/γ羧基，并将这些四唑掺入肽中。
• [EN] GLP RECEPTOR AGONISTS<br/>[FR] AGONISTES DU RÉCEPTEUR GLP
  申请人：HEPTARES THERAPEUTICS LTD

  公开号：WO2021186166A1

  公开（公告）日：2021-09-23

  The disclosures herein relate to novel compounds of formula (1 ): and salts thereof, wherein Q, W, X, Y, Z, AA1, AA2, AA3, AA4, AA5, AA6, AA7, AA8, AA9, LysR, R1, R2 and n are defined herein, and their use in treating, preventing, ameliorating, controlling or reducing the risk of disorders associated with Glucagon-like peptide (GLP) receptors.

  本公开涉及式(1)的新化合物及其盐，其中Q、W、X、Y、Z、AA1、AA2、AA3、AA4、AA5、AA6、AA7、AA8、AA9、LysR、R1、R2和n在此处有定义，并其在治疗、预防、改善、控制或减少与胰高血糖素样肽（GLP）受体相关的疾病风险方面的用途。
• A Highly Potent and Selective Caspase 1 Inhibitor that Utilizes a Key 3-Cyanopropanoic Acid Moiety
  作者：Matthew B. Boxer、Amy M. Quinn、Min Shen、Ajit Jadhav、William Leister、Anton Simeonov、Douglas S. Auld、Craig J. Thomas

  DOI：10.1002/cmdc.200900531

  日期：2010.5.3

  propionic acid moiety as an electrophile for covalent attack by the active‐site cysteine residue of caspase 1. The syntheses of several cyanopropanate‐containing small molecules based on the optimized peptidic scaffold of prodrug VX‐765 were accomplished. These compounds were found to be potent inhibitors of caspase 1 (IC50 values ≤1 nM). Examination of these novel small molecules against a caspase panel

  在此，我们研究了含腈丙酸部分作为亲电子试剂被 caspase 1 活性位点半胱氨酸残基共价攻击的潜力。基于前药 VX- 的优化肽支架，合成了几种含氰基丙酸酯的小分子。已完成 765 项。这些化合物被发现是 caspase 1 的有效抑制剂（IC 50值≤1 n M ）。针对 caspase 组对这些新型小分子的检查表明，与其他 caspase 同工酶相比，它们对 caspase 1 抑制具有令人印象深刻的选择性。水解稳定性和选定的 ADME 特性的评估强调了这些药物作为研究各种环境下 caspase 1 下调（包括体内分析）的潜在有用工具。
• Chemical Synthesis and Cell-Free Expression of Thiazoline Ring-Bridged Cyclic Peptides and Their Properties on Biomembrane Permeability
  作者：Takashi Tamura、Masaaki Inoue、Yuji Yoshimitsu、Ichihiko Hashimoto、Noriyuki Ohashi、Kyosuke Tsumura、Koo Suzuki、Takayoshi Watanabe、Takahiro Hohsaka

  DOI：10.1246/bcsj.20210409

  日期：2022.2.15

  versatility of a novel type of cyclic peptide having a thiazoline ring structure in the main chain were investigated. The thiazoline ring-bridged cyclic peptides were chemically synthesized by the intramolecular cyclization of linear peptides composed of N-terminal Cys and a non-natural amino acid having a cyano group on the side chain. The thiazoline ring-bridged cyclic peptides had higher model membrane

  表现出生物膜渗透性的环肽为开发肽药物提供了一个有用的平台。在此，研究了在主链中具有噻唑啉环结构的新型环肽的反应特性和通用性。噻唑啉环桥环肽是通过由N端Cys和侧链具有氰基的非天然氨基酸组成的线性肽分子内环化而化学合成的。噻唑啉环桥环肽的模型膜通透性高于具有相似氨基酸序列的酰胺和硫醚桥环肽。通过比较溶液结构，检查了导致更高膜渗透性的因素。此外，本肽环化应用于无细胞翻译系统。成功实现了具有氰化非天然氨基酸的肽的表达和随后的自发环化。
• [EN] ORAL GLP RECEPTOR AGONISTS<br/>[FR] AGONISTES DU RÉCEPTEUR DE GLP ORAUX
  申请人：HEPTARES THERAPEUTICS LTD

  公开号：WO2021186169A1

  公开（公告）日：2021-09-23

  The disclosures herein relate to novel compounds of formula (1a) or formula (1b): and salts thereof, wherein S, T, W, Z, AA1, AA2, AA3, AA4, AA5, AA6, AA7, AA8, AA9, AA10, AA11, AA12, AA13, AA14, AA15, A16, AA17, AA18, AA19, AA20, AA21, AA22, Sa, Ta, Wa, Xa, Ya, Za, AA1a, AA2a, AA3a, AA4a, AA 5a, AA 6a,AA 7a,AA8a,AA 9a,AA 10a,AA11a,AA 12a,AA13aAA 14a,AA15a,AA 16a, R, R1 and R2 are defined herein, and their use in treating, preventing, ameliorating, controlling or reducing the risk of disorders associated with Glucagon-like peptide (GLP) receptors.

  本文所披露的是公式（1a）或公式（1b）的新化合物及其盐，其中S，T，W，Z，AA1，AA2，AA3，AA4，AA5，AA6，AA7，AA8，AA9，AA10，AA11，AA12，AA13，AA14，AA15，A16，AA17，AA18，AA19，AA20，AA21，AA22，Sa，Ta，Wa，Xa，Ya，Za，AA1a，AA2a，AA3a，AA4a，AA5a，AA6a，AA7a，AA8a，AA9a，AA10a，AA11a，AA12a，AA13a，AA14a，AA15a，AA16a，R，R1和R2在此定义，并用于治疗、预防、改善、控制或降低与胰高血糖素样肽（GLP）受体相关的疾病的风险。