(2S)-2,5-双[(叔丁氧羰基)氨基]戊酸 | 57133-29-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2S)-2,5-双[(叔丁氧羰基)氨基]戊酸
• 英文名称: (S)-2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid
• 英文别名: Boc-Orn(Boc)-OH；(2S)-2,5-bis({[(tert-butoxy)carbonyl]amino})pentanoic acid；Boc-L-Orn(Boc)-OH；N_α,N_δ-bis(tert-butoxycarbonyl)-L-ornithine；2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid；(2S)-2,5-bis[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• CAS: 57133-29-6
• 化学式: C₁₅H₂₈N₂O₆
• mdl: MFCD00151882
• 分子量: 332.397
• InChiKey: RJOJSMIZZYHNQG-JTQLQIEISA-N

物化性质

• 沸点：
  504.1±45.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,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: Boc-Orn(Boc)-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: Boc-Orn(Boc)-OH
CAS number: 57133-29-6

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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.
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: C15H28N2O6
Molecular weight: 332.4

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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：

  (2S)-2,5-双[(叔丁氧羰基)氨基]戊酸 在 氯甲酸乙酯 、 三乙胺 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 di-tert-butyl (5-hydroxypentane-1,4-diyl)(S)-dicarbamate
  参考文献：
  名称：

  使用酶级联反应合成受保护的3-氨基哌啶和3-氨基氮杂环庚烷衍生物。

  摘要：

  利用半乳糖氧化酶和亚胺还原酶的变体的多酶级联反应成功地将N -Cbz保护的L-鸟氨酸和L-赖氨醇成功转化为L -3- N -Cbz-氨基哌啶和L -3- N -Cbz-氨基氮杂环庚烷分别获得高达54％的分离产率。将反应简化为一锅法可防止关键的不稳定中间体发生潜在的外消旋作用，并产生具有高对映体纯度的产品。

  DOI：

  10.1039/d0cc02976a
• 作为产物：
  描述：

  L-鸟氨酸 、 二碳酸二叔丁酯 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 生成 (2S)-2,5-双[(叔丁氧羰基)氨基]戊酸
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Methyl Glycyrrhetinate Esterified with Amino Acids

  摘要：

  甘草酸甲酯使用不同的氨基酸在 A 环的 C3 位进行酯化。结果表明，在第 2 位和第 4 位含有两个氨基的四碳原子无支链短链是该系列中活性最强的化合物（对脂肪肉瘤 Lipo 细胞的 IC50 = 0:8 M）。吖啶橙/溴化乙锭试验、胰蓝试验和 DNA 梯度实验均表明，这些化合物可引发细胞凋亡。

  DOI：

  10.5560/znb.2012-0107

文献信息

• Phase-transfer reagents as C-terminal protecting groups; facile incorporation of free amino acids or peptides into peptide sequences
  作者：Shui-Tein Chen、Kung-Tsung Wang

  DOI：10.1039/c39900001045

  日期：——

  Phase-transfer reagents (basic, neutral, and acidic) can effect temporary protection of carboxy groups by salt formation in C-terminal free amino acids or peptides during peptide synthesis; the use of acidic or neutral phase-transfer reagents as the C-terminal protecting group will not affect the nucleophilicity of the amino group of the salts thus prepared in an organic solvent.

  相转移试剂（碱性，中性和酸性）可通过在肽合成过程中在C端游离氨基酸或肽中形成盐来暂时保护羧基。使用酸性或中性相转移试剂作为C-末端保护基不会影响在有机溶剂中如此制得的盐的氨基的亲核性。
• PRODRUGS OF FUSED-BICYCLIC C5aR ANTAGONISTS
  申请人：CHEMOCENTRYX, INC.

  公开号：US20190300526A1

  公开（公告）日：2019-10-03

  The present disclosure provides, inter alia, Compounds of Formulae IA, IB, IC, IIA, IIB and IIC or pharmaceutically acceptable salts thereof that are modulators of the C5a receptor. Also provided are pharmaceutical compositions and methods of use including the treatment of diseases or disorders involving pathologic activation from C5a and non-pharmaceutical applications.

  本公开提供了化合物IA、IB、IC、IIA、IIB和IIC的结构，或其在药学上可接受的盐，这些化合物是C5a受体的调节剂。还提供了包括治疗涉及C5a病理性激活的疾病或疾病的药物组合物和使用方法，以及非药物应用。
• Non-Amide-Based Combinatorial Libraries Derived fromN-Boc-Iminodiacetic Acid: Solution-Phase Synthesis of Piperazinone Libraries with Activity Against LEF-1/β-Catenin-Mediated Transcription
  作者：Dale L. Boger、Joel Goldberg、Shigeki Satoh、Yves Ambroise、Steven B. Cohen、Peter K. Vogt

  DOI：10.1002/1522-2675(20000809)83:8<1825::aid-hlca1825>3.0.co;2-4

  日期：2000.8.9

  methodology was applied to the synthesis of a diverse 150-member library with substituents in three positions of the piperazinone core. Screening results from a luciferase reporter assay indicate that a number of library members are novel repressors of LEF-1/β-catenin-mediated transcription, and may be effective agents against colorectal tumors. Two secondary libraries (100 members each) designed from

  详细介绍了从 N-Boc-亚氨基二乙酸开始仅需四个步骤即可快速、平行合成高度官能化哌嗪酮的溶液相方法。这些努力代表了组合文库的溶液相合成从 N-Boc-亚氨基二乙酸扩展到基于非酰胺的文库，其中使用简单的液-液萃取来纯化所有反应产物。该方法被应用于合成一个多样化的 150 成员库，在哌嗪酮核心的三个位置具有取代基。荧光素酶报告基因检测的筛选结果表明，许多文库成员是 LEF-1/β-连环蛋白介导的转录的新阻遏物，可能是对抗结肠直肠肿瘤的有效药物。合成和筛选了从这些先导结构设计的两个二级库（每个 100 个成员），提供额外的活性剂并深入了解该系列中的关键结构-活性关系。这些化合物仅代表第二类小分子，其抑制含有 LEF-1 响应元件的报告基因的转录，第一类不基于 DNA 小沟结合剂。
• COMPOUND HAVING READ-THROUGH ACTIVITY
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US20140364642A1

  公开（公告）日：2014-12-11

  [Problem] Provision of a novel compound having read-through activity and a drug for the treatment of nonsense mutation-type disease containing this compound. [Solution] A compound represented by the following general formula (1): and a pharmaceutical composition containing this compound.

  一种具有读穿活性的新化合物以及包含该化合物的用于治疗无义突变型疾病的药物。 一种由以下一般式（1）表示的化合物： 以及含有该化合物的药物组合物。
• Synthesis and in vitro biological evaluation of novel derivatives of Flexicaulin A condensation with amino acid trifluoroacetate
  作者：Yu Ke、Tian-Xing Hu、Jun-Feng Huo、Jun-Ke Yan、Jin-Yi Wang、Rui-Hua Yang、Hang Xie、Ying Liu、Ni Wang、Zi-Jun Zheng、Ya-Xin Sun、Cong Wang、Juan Du、Hong-Min Liu

  DOI：10.1016/j.ejmech.2019.111645

  日期：2019.11

  anticancer drugs, two series of novel derivatives of Flexicaulin A (FA), an ent-kaurene diterpene, condensation with amino acid trifluoroacetate were synthesized, and their anti-proliferative activity against four human cancer cell lines (TE-1, MCF-7, A549 and MGC-803) were evaluated. Compared with FA, the anticancer activity and solubility of most derivatives were significantly improved. Among them

  由于我们的研究集中在抗癌药物上，因此合成了Flexicaulin A（FA）的两个系列新衍生物，对映体-月桂烯二萜，与三氟乙酸氨基酸缩合，以及它们对四种人类癌细胞系（TE-1）的抗增殖活性。 ，MCF-7，A549和MGC-803）进行了评估。与FA相比，大多数衍生物的抗癌活性和溶解度均得到显着提高。其中，化合物6d的活性最高，其对食道癌细胞（TE-1）的IC50值高达0.75μM。随后的细胞机制研究表明，化合物6d可以抑制癌细胞的增殖，细胞集落的形成并增加TE-1细胞上ROS​​的水平。此外，6d可能上调SAPK / JNK途径相关蛋白（p-ASK1，p-MKK4和p-JNK）和促凋亡蛋白（Bak，Bad和Noxa）显着增加Bax与Bcl-2的比例并激活Cleaved Caspase-3 / 9 / PARP。这些结果表明化合物6d通过ROS / JNK / Bcl-2途径诱导细胞凋亡，并具有作为抗增殖剂的有希望的潜力。