Fmoc-L-beta-高脯氨酸 | 193693-60-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-L-beta-高脯氨酸
• 中文别名: FMOC-L-Β-高脯氨酸；N-Fmoc-L-β-高脯氨酸；Fmoc-L-β3-高脯氨酸；FMOC-L-Β3-高脯氨酸；2-[(2S)-(1-芴甲氧羰基)吡咯烷-2-基]乙酸；N-FMOC-L-Β-高脯氨酸
• 英文名称: Fmoc-β³-HPro-OH
• 英文别名: Fmoc-β-HPro；Fmoc-homoPro-OH；Fmoc-L-beta-homoproline；2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidin-2-yl]acetic acid
• CAS: 193693-60-6
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: ZNIGOUDZWCDFFC-AWEZNQCLSA-N

物化性质

• 熔点：
  175-177 °C
• 沸点：
  562.1±23.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29339900
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-l-beta-homoproline
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-l-beta-homoproline
CAS number: 193693-60-6

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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: C21H21NO4
Molecular weight: 351.4

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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

用途

Fmoc-L-β-高脯氨酸是氨基酸的一种衍生物，主要用于医药合成及实验研究。

反应信息

• 作为反应物：
  描述：

  Fmoc-L-beta-高脯氨酸 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (9H-fluoren-9-yl)methyl (S)-2-(formamidomethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis of β-lactam peptidomimetics through Ugi MCR: first application of chiral Nβ-Fmoc amino alkyl isonitriles in MCRs

  摘要：

  Chiral N-beta-Fmoc amino alkyl isonitriles were employed in Ugi multi component reactions (Ugi 4C-3CR) to obtain functionalized beta-lactam peptidomimetics with L-aspartic acid alpha-methyl ester/peptide ester and organic aldehydes. The reactions were carried out in MeOH. Thirteen Ugi products have been prepared in good to moderate yields with good diastereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.090
• 作为产物：
  描述：

  在 silver(I) acetate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 生成 Fmoc-L-beta-高脯氨酸
  参考文献：
  名称：

  通过直接同源法合成N -{[（9 H-氟9-基）甲氧基]羰基}保护的（Fmoc）β-氨基酸（=均α-氨基酸）

  摘要：

  Arndt-Eistert方案的成功应用始于可商购的N -{[（9 H-氟-9-基）甲氧基]羰基}保护的（Fmoc）α-氨基酸，产生对映体纯的N -Fmoc保护的β报道了仅两步且高收率的β-氨基酸。

  DOI：

  10.1002/hlca.19980810107

文献信息

• Permeation through Phospholipid Bilayers, Skin-Cell Penetration, Plasma Stability, and CD Spectra of<i>α</i>- and<i>β</i>-Oligoproline Derivatives
  作者：Beata Kolesinska、Dominika J. Podwysocka、Magnus A. Rueping、Dieter Seebach、Faustin Kamena、Peter Walde、Markus Sauer、Barbara Windschiegl、Mira Meyer-Ács、Marc Vor der Brüggen、Sebastian Giehring

  DOI：10.1002/cbdv.201200393

  日期：2013.1

  translocation rates of cell-penetrating peptides (CPPs) across lipid bilayers. Cell penetration is observed with mouse (3T3) and human foreskin fibroblasts (HFF; Figs. 5 and 6-8, resp.). The stabilities of oligoprolines in heparin-stabilized human plasma increase with decreasing chain lengths (Figs. 9-11). Time- and solvent-dependent CD spectra of most of the oligoprolines (Figs. 13 and 14) show changes that

  在对氨基酸脯氨酸在生命化学中所起的特殊作用进行了调查之后，讨论了含聚阳离子脯氨酸的肽的细胞穿透特性，以及Giralt小组（J.Am. Soc。2002，124，8876），据此，荧光素标记的十四碳脯氨酸被大鼠肾细胞（NRK-49F）缓慢吸收。在这里，我们描述了我们先前提到的（Chem。Biodiversity 2004，1，1111）六-β（3）-Pro衍生物穿透成纤维细胞的观察结果的细节，并且我们提出了对寡聚L-和oligo-D-α-脯氨酸，以及不带有和带有荧光标记的oligo-β（2）h-和oligo-β（3）h-脯氨酸（1-8;图1）。用nanoFAST生物芯片技术检测到无蛋白质磷脂双层的渗透（图2-4）。首次将这种方法用于定量测定跨脂质双层的细胞穿透肽（CPP）的转运速率。用小鼠（3T3）和人包皮成纤维细胞（HFF；图5和6-8，分别）观察到细胞渗透。肝素稳定的人血浆中寡脯氨酸的稳
• Chiral <i>N</i>-Fmoc-β-Amino Alkyl Isonitriles Derived from Amino Acids: First Synthesis and Application in 1-Substituted Tetrazole Synthesis
  作者：Vommina V. Sureshbabu、N. Narendra、G. Nagendra

  DOI：10.1021/jo801527d

  日期：2009.1.2

  A novel class of optically active N-Fmoc-protected amino isonitriles has been described for the first time. Conversion of the carboxyl group of Fmoc-β-amino acids into an isocyano group has resulted in a new class of N-urethane-protected amino isonitriles. All the isonitriles have been isolated as stable solids, purified, and completely characterized. A synthetic application of the obtained isonitriles

  首次描述了一类新型的具有光学活性的N -Fmoc保护的氨基异腈。Fmoc-β-氨基酸的羧基转化为异氰基导致了新型的N-氨基甲酸酯保护的氨基异腈。所有的异腈均已分离为稳定的固体，经过纯化并进行了完全鉴定。通过与三甲基甲硅烷基叠氮化物通过2 + 3环加成反应合成氨基酸的1-取代的四唑类似物，也证明了所获得的异腈的合成应用。
• Cyanogen Bromide as Dehydrosulfurizing Agent for the Synthesis of Nβ-Fmoc-Amino Alkyl Isonitriles from Nβ-Fmoc-Amino Alkyl Thioformamides
  作者：V. Sureshbabu、T. Vishwanatha、H. Hemantha

  DOI：10.1055/s-0029-1219583

  日期：2010.4

  Synthetically useful NI²-Fmoc amino alkyl isonitriles are prepared conveniently from NI²-Fmoc amino alkyl thioformamides via a cyanogen bromide mediated dehydrosulfurization. The reaction is fast, clean, and yields are good. © Georg Thieme Verlag Stuttgart - New York.

  合成有用的NI 2 -Fmoc氨基烷基异腈可以方便地从NI 2 -Fmoc氨基烷基硫代甲酰胺通过溴化氰介导的脱硫脱硫来制备。反应快速、清洁、收率良好。© Georg Thieme Verlag 斯图加特 - 纽约。
• Discovery of TP0597850: A Selective, Chemically Stable, and Slow Tight-Binding Matrix Metalloproteinase-2 Inhibitor with a Phenylbenzamide–Pentapeptide Hybrid Scaffold
  作者：Tomoki Takeuchi、Yusaku Nomura、Tomoko Tamita、Rie Nishikawa、Hiroyuki Kakinuma、Naoki Kojima、Kosuke Hitaka、Yunoshin Tamura、Masafumi Kamitani、Masashi Mima、Akiko Nozoe、Masato Hayashi

  DOI：10.1021/acs.jmedchem.2c01698

  日期：2023.1.12

  discovery of a novel MMP2-selective inhibitor with high chemical stability and slow tight-binding features. Based on the degradation mechanism of our small-molecule–peptide hybrid 1, the tripeptide linker 5-aminopentanoic acid [Ape(5)]–Glu–Asp} of 1 was replaced by a shorter linker (γ-D-Glu). Phenylbenzamide was suitable for the new generation of MMP2 inhibitors as an S1′ pocket-binding group. The

  基质金属蛋白酶 2 (MMP2) 是一种锌依赖性内肽酶，是癌症和纤维化等多种疾病的有希望的靶点。在此，我们报告了一种新型 MMP2 选择性抑制剂的发现，该抑制剂具有高化学稳定性和缓慢的紧密结合特性。基于我们的小分子-肽杂化物1的降解机制，1的三肽接头 5-氨基戊酸 [Ape(5)]–Glu–Asp}被更短的接头 (γ-D-Glu) 取代。苯基苯甲酰胺适合作为新一代 MMP2 抑制剂的 S1' 口袋结合基团。(4 S )-氨基脯氨酸的引入显着提高了化学稳定性，同时由于其与 Glu130 的相互作用而保持了高亚型选择性。TP0597850 ( 18) 在广泛的 pH 值范围内表现出高稳定性以及有效的 MMP2 抑制 ( K i = 0.034 nM) 和使用抑制常数确定的 ≥ 2000 倍选择性。动力学分析表明它具有缓慢的紧密结合性质和较长的 MMP2 解离半衰期 ( t 1/2 = 265
• ＭＭＰ２阻害作用を有するポリペプチドを有効成分として含有する医薬
  申请人：大正製薬株式会社

  公开号：JP2022173143A

  公开（公告）日：2022-11-17

  【課題】ＭＭＰ２を阻害する作用を有する、新規な化合物を有効成分として含有する医薬の提供。【解決手段】下記式［Ｉ’］で表される置換されているポリペプチド又はその製薬学的に許容される塩を有効成分として含有する医薬。 JPEG 2022173143000375.jpg 19 150 【選択図】なし

  【问题】提供一种含有具有抑制MMP2作用的新化合物作为有效成分的药物。 【解决方案】提供以下式[I']所表示的置换多肽或其制药学上允许的盐作为有效成分的药物。