BOC-D-硝基精氨酸 | 50913-12-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 精氨酸类衍生物
• 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: BOC-D-硝基精氨酸
• 中文别名: Nalpha-Boc-Nomega-硝基-D-精氨酸；N’-硝基-N-叔丁氧羰基-D-精氨酸；N'-硝基-N-叔丁氧羰基-D-精氨酸；NALPHA-BOC-NOMEGA-硝基-D-精氨酸
• 英文名称: Boc-D-Arg(NO2)-OH
• 英文别名: (R)-N^α-Boc-N^G-nitroarginine；(2R)-2-(tert-butoxycarbonylamino)-5-[(N-nitrocarbamimidoyl)amino]pentanoic acid；Boc-Arg(NO₂)-OH；Boc-(R)-Arg(NO₂)-OH；2-(R)-tert-butoxycarbonylamino-5-nitroguanidino-pentanoic acid；(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(Z)-N'-nitrocarbamimidoyl]amino]pentanoic acid
• CAS: 50913-12-7
• 化学式: C₁₁H₂₁N₅O₆
• mdl: MFCD00038091
• 分子量: 319.318
• InChiKey: OZSSOVRIEPAIMP-SSDOTTSWSA-N

物化性质

• 熔点：
  113-126°C (dec.)
• 密度：
  1.40±0.1 g/cm3(Predicted)
• 溶解度：
  碱性溶液（微溶），DMSO（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.727
• 拓扑面积：
  176
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 包装等级：
  III
• 危险类别：
  4.1
• 危险性防范说明：
  P261,P210,P264,P280,P370+P378,P302+P352+P312
• 危险品运输编号：
  1325
• 危险性描述：
  H302+H312+H332,H315,H319,H228
• 储存条件：
  -15°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-D-Arg(NO2)-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-D-Arg(NO2)-OH
CAS number: 50913-12-7

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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: C11H21N5O6
Molecular weight: 319.3

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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：

  BOC-D-硝基精氨酸 在 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 戊酰胺,2-氨基-N-[(4-羟基苯基)甲基]-5-[[亚氨基(硝基氨基)甲基]氨基]-,(R)-
  参考文献：
  名称：

  Structure–activity relationships of neuropeptide Y Y1 receptor antagonists related to BIBP 3226

  摘要：

  Analogues of BIBP 3226, (R)-N-alpha-diphenylacetyl-N-(4-hydroxybenzyl)argininamide, were synthesized and investigated for Y-1 antagonism (Ca2+-assay, HEL cells) and binding on Y-1, Y-2 and Y-5 receptors. Replacing the benzylamino by a tetrahydrobenzazepinyl group preserves most of the Y-1 activity. Combination with a N-G-phenylpropyl arginine and a N-alpha-p-biphenyly-lacetyl moiety shifted the NPY receptor selectivity towards Y-5 (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00292-4

文献信息

• Peptide Mechanosynthesis by Direct Coupling of <i>N</i> ‐Protected α‐Amino Acids with Amino Esters
  作者：Vincent Porte、Marion Thioloy、Titouan Pigoux、Thomas‐Xavier Métro、Jean Martinez、Frédéric Lamaty

  DOI：10.1002/ejoc.201600617

  日期：2016.7

  In view of developing alternatives to classical peptide synthesis strategies that suffer from low efficacy and negative environmental impact, the reactivity of N-protected α-amino acids, amino esters, and N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide was studied under liquid-assisted grinding (LAG) conditions. The optimal reaction conditions enabled the intensive and environmentally benign mechanosynthesis

  鉴于开发效率低且对环境产生负面影响的经典肽合成策略的替代方案，研究了 N-保护的 α-氨基酸、氨基酯和 N-乙基-N'-(3-二甲氨基丙基)碳二亚胺的反应性在液体辅助研磨 (LAG) 条件下。最佳反应条件能够实现多种二肽的密集且环境友好的机械合成，这些二肽可以生产至数克规模。揭示了液体添加剂的性质对反应过程的关键影响。结合无溶剂叔丁氧羰基脱保护步骤，这种方法被应用于三肽和四肽的合成，从而为合成更长的肽开辟了道路。
• Studies on analgesic oligopeptides. V. Structure-activity relationship of tripeptide alkylamides, Tyr-D-Arg-Phe-X.
  作者：KENJI SUZUKI、HIROKI FUJITA、YUSUKE SASAKI、MIKI SHIRATORI、SHINOBU SAKURADA、KENSUKE KISARA

  DOI：10.1248/cpb.36.4834

  日期：——

  Twenty-one analogs based on the structure Tyr-D-Arg-Phe-X (X=OH, alkyl ester, alkylamide or amino acid having a different carbon chain) were synthesized by the solution method and their analgesic activities were tested after subcutaneous (s. c.) administration in mice. Most tripeptide alkylamides showed no analgesia at a dose of 10 mg/kg, s. c. However, some tripeptide alkylamides having the hydroxyl group on the alkyl moiety showed greater activity than morphine. Introduction of the carboxyl group on the alkyl moiety also led to tetrapeptide analogs with potent analgesia, e. g., the compound with X=β-alanine is 33 times more potent than morphine on a molar basis. These results suggest that proper carbon chain lengths and the presence of an oxygen atom at the fourth position are important for high analgesic activity in the series of D-Arg2-dermorphin analogs.

  通过溶液法合成了基于结构Tyr-D-Arg-Phe-X（X=OH，烷基酯，烷基酰胺或具有不同碳链的氨基酸）的21种类似物，并在小鼠皮下（s.c.）给药后测试了它们的镇痛活性。大多数三肽烷基酰胺在10 mg/kg，s.c.剂量下没有镇痛作用。然而，一些在烷基部分具有羟基的三肽烷基酰胺显示出比吗啡更大的活性。在烷基部分引入羧基也导致具有强效镇痛作用的四肽类似物，例如，X=β-丙氨酸的化合物在摩尔基础上比吗啡强33倍。这些结果表明，适当的碳链长度和在第四位存在氧原子对于D-Arg2-dermorphin类似物系列中的高镇痛活性是重要的。
• Amino Acids and Peptides. XXIII. Leu-Enkephalin Analogs Containing a Fluorinated Amino Acid at Position 2, 4 or 5.
  作者：Mitsuko MAEDA、Koichi KAWASAKI、Takeo TAGUCHI、Yoshiro KOBAYASHI、Yoshihiro YAMAMOTO、Kazuhiro SHIMOKAWA、Masakatsu TAKAHASHI、Kaoru NAKAO、Hiroshi KANETO

  DOI：10.1248/cpb.42.1658

  日期：——

  Fluorinated analogs of Leu-enkephalin were synthesized by the solution method and the solid-phase method. The synthetic peptides were examined for opioid activities on mouse vas deferens and guinea pig ileum. Among the synthetic peptides, [D-Ala2, Leu(F3)(2R, 4S)5]enkephalin and [D-Ala2, Leu(F3)(2S, 4R)5]enkephalin exhibited potent opioid activity, and [Leu(F3)(2S, 4R)5]enkephalin exhibited high δ-receptor selectivity.

  氟化的Leu-内啡肽类似物通过溶液法和固相法合成。合成的肽在小鼠输精管和豚鼠回肠中进行了阿片活性测试。在合成的肽中，[D-Ala2, Leu(F3)(2R, 4S)5]内啡肽和[D-Ala2, Leu(F3)(2S, 4R)5]内啡肽表现出强效的阿片活性，而[Leu(F3)(2S, 4R)5]内啡肽则表现出较高的δ-受体选择性。
• Tailored Peptide Phenyl Esters Block ClpXP Proteolysis by an Unusual Breakdown into a Heptamer–Hexamer Assembly
  作者：Markus Lakemeyer、Eva Bertosin、Friederike Möller、Dóra Balogh、Ralf Strasser、Hendrik Dietz、Stephan A. Sieber

  DOI：10.1002/anie.201901056

  日期：2019.5.20

  binding of probes arrested ClpXP in an unprecedented heptamer–hexamer assembly, in which the two heptameric ClpP rings are dissociated from each other. At the same time, the affinity between ClpX and ClpP increased, leading to inhibition of both enzymes. This conformational arrest is beneficial for the consolidated shutdown of ClpXP, as well as for the study of the oligomeric state during its catalytic

  蛋白水解复合物ClpXP是细菌稳态和发病机理的基础。由于其构象的灵活性，有效的ClpXP抑制剂的开发具有挑战性，迫切需要新的工具来解密其复杂的调控。在这里，我们提出了基于氨基酸的苯基酯作为分子探针，以研究金黄色葡萄球菌的ClpXP复合物的活性和低聚。系统地筛选（R）和（S）氨基酸导致化合物显示出有效的抑制作用，并刺激ClpXP介导的蛋白水解作用。探针的亚化学计量结合使ClpXP停滞在前所未有的七聚体-六聚体组装中，其中两个七聚体ClpP环彼此解离。同时，ClpX和ClpP之间的亲和力增加，导致两种酶的抑制作用。这种构象停滞对于ClpXP的合并关闭以及在其催化循环期间研究低聚状态是有益的。
• IMMUNOSTIMULATING AGENT
  申请人：AJINOMOTO CO., INC.

  公开号：US20180311342A1

  公开（公告）日：2018-11-01

  The present invention aims to provide an immunostimulating agent superior in an immunostimulatory effect, particularly a compound useful as a vaccine adjuvant, a pharmaceutical composition containing the compound, a vaccine containing the compound and an antigen. An immunostimulating agent containing at least one kind of a compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a salt thereof.

  本发明旨在提供一种免疫刺激剂，其在免疫刺激效果方面优越，特别是作为疫苗佐剂有用的化合物，包含该化合物的药物组合物，含有该化合物和抗原的疫苗。一种免疫刺激剂，包含至少一种由以下式（I）表示的化合物中的一种： 其中每个符号如本说明书中所定义，或其盐。