Fmoc-(R)-2-氨基-3-苄氧基丙酸 | 122889-11-6

• 物质功能分类: 生物化工 - 生化试剂 - 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-(R)-2-氨基-3-苄氧基丙酸
• 中文别名: FMOC-O-苄基-D-丝氨酸
• 英文名称: N-[(9H-fluoren-9-yl)methoxycarbonyl]-O-(benzyl)-D-serine
• 英文别名: Fmoc-D-Ser(Bzl)-OH；N-[(9H-fluoren-9-yl)methoxycarbonyl]-O-benzyl-D-serine；[(9-fluorenyl)methoxycarbonyl]-O-benzyl-D-serine；FMOC-(OBzl)DSer-OH；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylmethoxypropanoic acid
• CAS: 122889-11-6
• 化学式: C₂₅H₂₃NO₅
• 分子量: 417.461
• InChiKey: DYBDGLCDMLNEMJ-HSZRJFAPSA-N

物化性质

• 沸点：
  642.4±55.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  应存放在2-8℃的环境中，保持干燥并密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-d-ser(bzl)-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-ser(bzl)-oh
CAS number: 122889-11-6

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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: C25H23NO5
Molecular weight: 417.5

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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

N-(9H-芴-9-基甲氧基羰基)-O-(苯基甲基)-D-丝氨酸是一种丝氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  Fmoc-(R)-2-氨基-3-苄氧基丙酸 在 哌啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  JTE-013 衍生物的设计、合成和评价作为新型强效 S1PR2 拮抗剂以恢复结直肠癌对 5-氟尿嘧啶的敏感性

  摘要：

  靶向鞘氨醇-1-磷酸受体 2 (S1PR2) 已被证明是逆转 5-氟尿嘧啶 (5-FU) 耐药性的一种有前途的策略。在这里，我们报告发现新型 JTE-013 衍生化合物37 小时作为一种更有效的 S1PR2 拮抗剂来逆转 SW620/5-FU 和 HCT116 DPD细胞中的 5-FU 抗性，而不是 JTE-013 和先前报道的化合物5。化合物37h可有效结合S1PR2并降低其表达，从而导致JMJD3和二氢嘧啶脱氢酶（DPD）的表达降低，同时还增加H3K27me3的水平以减少5-FU的降解，从而增加其在SW620 /中的细胞内浓度5-FU、HCT116 DPD和 L02 细胞。此外，复合37 h显示出对其他 S1PR 和正常结肠细胞系 NCM460 的良好选择性。蛋白质印迹分析证明化合物37 h可以消除 FBAL 刺激的 S1PR2 对 DPD 表达的上调。重要的是，化合物37 h还显示出良好的代谢稳定性，半衰期

  DOI：

  10.1016/j.bioorg.2022.106318

文献信息

• Total Synthesis of Pagoamide A
  作者：Fusong Wu、Jie Yu、Jiawei Meng、Yian Guo、Tao Ye

  DOI：10.3390/molecules26144224

  日期：——

  The first total synthesis of the thiazole-containing cyclic depsipeptide pagoamide A, is detailed. The longest linear sequence of the liquid-phase synthesis comprises 9 long linear steps from simple known starting materials, which led to the unambiguous structural confirmation of pagoamide A.

  详细介绍了含噻唑环缩肽 pagoamide A 的首次全合成。液相合成的最长线性序列包括来自简单已知起始材料的 9 个长线性步骤，这导致了 pagoamide A 的明确结构确认。
• Peptide‐Chain Elongation Using Unprotected Amino Acids in a Micro‐Flow Reactor
  作者：Shinichiro Fuse、Koshiro Masuda、Yuma Otake、Hiroyuki Nakamura

  DOI：10.1002/chem.201903531

  日期：2019.11.27

  Conventional peptide synthesis requires a deprotection step after each amidation step, which decreases synthetic efficiency. Therefore, peptide synthesis using unprotected amino acids is considered an ideal approach. Here, we report peptide chain elongation using unprotected amino acids via a mixed carbonic anhydride. Micro-flow technology enabled rapid mixing of an organic layer containing a protected

  常规的肽合成在每个酰胺化步骤之后都需要脱保护步骤，这降低了合成效率。因此，使用未保护的氨基酸合成肽被认为是一种理想的方法。在这里，我们报告使用未保护的氨基酸通过混合碳酸酐的肽链延长。微流技术使含有受保护的氨基酸或二肽的有机层与含有未保护的氨基酸或二肽的水层快速混合，从而加速了所需的酰胺化反应，该方法成功地抑制了不良的消旋/表观异构化（≤0.4％）。以高到高的产率获得了各种二肽，三肽和四肽。这是有关肽链延长的第一篇报道，该报道使用廉价，非爆炸性的，
• Selective Substrates and Activity-Based Probes for Imaging of the Human Constitutive 20S Proteasome in Cells and Blood Samples
  作者：Wioletta Rut、Marcin Poręba、Paulina Kasperkiewicz、Scott J. Snipas、Marcin Drąg

  DOI：10.1021/acs.jmedchem.8b00026

  日期：2018.6.28

  the HyCoSuL approach, we designed and synthesized novel and selective fluorogenic substrates for each of these three constitutive 20S proteasome activities and applied them to assess inhibition of proteasome subunits by MG-132 and a clinically used inhibitor bortezomib. Our results confirm the utility of designed substrates in biochemical assays. Furthermore, selective peptide sequences obtained in this

  蛋白酶体是维持蛋白质稳态的关键酶复合物。蛋白酶体功能紊乱导致包括癌症，自身免疫和神经退行性疾病在内的病理。因此，蛋白酶体构成药物开发的极好的分子靶标。在这里，我们使用HyCoSuL方法为这三个20S组成型蛋白酶体活性中的每一个设计和合成了新颖的选择性荧光底物，并将它们应用于评估MG-132和临床使用的硼替佐米对蛋白酶体亚基的抑制作用。我们的结果证实了设计的底物在生化分析中的实用性。此外，以此方式获得的选择性肽序列用于构建荧光团标记的基于活性的探针，然后用于同时检测HEK-293F细胞和红细胞裂解液中的每个20S组成型蛋白酶体亚基。总体而言，我们描述了一种简单而快速的方法，可用于测量全血样本中20S组成型蛋白酶体的活性，该方法可以早期诊断与异常上调的蛋白酶体活性有关的病理状态。
• [EN] COMPOSITIONS AND METHODS FOR TREATING NEURODEGENERATIVE DISEASES<br/>[FR] COMPOSITIONS ET MÉTHODES POUR TRAITER DES MALADIES NEURODÉGÉNÉRATIVES
  申请人：AZEVAN PHARMACEUTICALS INC

  公开号：WO2015148962A1

  公开（公告）日：2015-10-01

  Compounds, and compositions, methods, and uses thereof, are described herein for treating neurodegenerative diseases and disorders. In particular, vasopressin receptor modulators, and compositions, methods and uses thereof, are described herein for treating neuropsychiatric aspects of neurodegenerative diseases such as Huntingtons Disease, Parkinson's Disease, and Alzheimers Disease.

  本文描述了用于治疗神经退行性疾病和紊乱的化合物、组合物、方法和用途。具体地，本文描述了用于治疗神经退行性疾病如亨廷顿病、帕金森病和阿尔茨海默病的抗利尿激素受体调节剂，以及其组合物、方法和用途。
• Rapid and Mild Synthesis of Amino Acid <i>N</i> -Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor
  作者：Yuma Otake、Hiroyuki Nakamura、Shinichiro Fuse

  DOI：10.1002/anie.201803549

  日期：2018.8.27

  Polymerization of N‐carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is key to the efficient synthesis of polypeptides. The only practical method that can be used to synthesize NCAs requires harsh acidic conditions that make acid‐labile substrates unusable and results in an undesired ring opening of NCAs. Basic‐to‐acidic flash switching

  N的聚合‐羧酸酐（NCA）是用于制备多肽的主要过程。各种纯净NCA的合成是有效合成多肽的关键。唯一可用于合成NCA的实用方法要求苛刻的酸性条件，使酸不稳定的底物无法使用，并导致NCA出现不希望的开环。在微流反应器中使用从碱性到酸性的闪蒸切换和随后的闪蒸稀释技术来演示NCA的合成。它既快速（0.1 s）又温和（20°C），并且包括含有酸不稳定官能团的底物。从基本到酸性的闪光切换既可以加速所需的NCA形成，又可以避免NCA出现不希望的开环。快速稀释排除了酸不稳定官能团的不希望的分解。