N2-[芴甲氧羰基]-N5-[亚氨基(硝基氨基)甲基]-D-鸟氨酸 | 160347-94-4

• 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 - 苯类化合物 - 芴
• 中文名称: N2-[芴甲氧羰基]-N5-[亚氨基(硝基氨基)甲基]-D-鸟氨酸
• 中文别名: FMOC-硝基-D-精氨酸
• 英文名称: Fmoc-D-Arg(NO2)-OH
• 英文别名: (2R)-5-[[amino(nitramido)methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
• CAS: 160347-94-4
• 化学式: C₂₁H₂₃N₅O₆
• 分子量: 441.444
• InChiKey: RXMHIKWOZKQXCJ-GOSISDBHSA-N

物化性质

• 熔点：
  148 °C
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 危险等级：
  IRRITANT
• 包装等级：
  II
• 危险类别：
  4.1
• 危险性防范说明：
  P280,P210,P240,P264,P270,P301+P310,P330,P370+P378,P403+P233,P405,P501
• 危险品运输编号：
  1325
• 危险性描述：
  H228,H302,H317,H319,H341,H351
• 储存条件：
  存储温度：0-5°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-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: Fmoc-D-Arg(NO2)-OH
CAS number: 160347-94-4

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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: C21H23N5O6
Molecular weight: 441.4

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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：

  N2-[芴甲氧羰基]-N5-[亚氨基(硝基氨基)甲基]-D-鸟氨酸 在 2,4,6-三甲基吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of arginine-containing hydroxamate dipeptidomimetics

  摘要：

  The syntheses of arginine-containing hydroxamates using various peptide coupling methods are described. Fmoc-Arg(NO2)-Cl prepared at low temperature did not undergo intramolecular delta-lactam formation and effectively provided desired hydroxamates (8 and 10) in good yields. Fmoc and N-nitro protecting groups can be easily removed. Therefore, this report provides a facile synthesis of arginine-containing peptidomimetic compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.190
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 N'-硝基-D-精氨酸 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 15.0h， 以73%的产率得到N2-[芴甲氧羰基]-N5-[亚氨基(硝基氨基)甲基]-D-鸟氨酸
  参考文献：
  名称：

  Callipeltin B的固相全合成及结构证明

  摘要：

  细胞毒性、环状七肽、天然产物 callipeltin B 在固相载体上合成，总产率为 15%。三种合成异构体的 1H NMR 谱与 callipeltin B 的 1H NMR 谱的比较证实其苏氨酸残基的构型重新分配为 d-别苏氨酸，并将其 β-甲氧基酪氨酸残基的构型分配为 (2R,3R)。

  DOI：

  10.1021/ja0666250

文献信息

• 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。
• <i>N</i>^ω-Nitroarginine-Containing Dipeptide Amides. Potent and Highly Selective Inhibitors of Neuronal Nitric Oxide Synthase
  作者：Hui Huang、Pavel Martasek、Linda J. Roman、Bettie Sue Siler Masters、Richard B. Silverman

  DOI：10.1021/jm990111c

  日期：1999.8.1

  Selective inhibition of the isoforms of nitric oxide synthase (NOS) could be therapeutically useful in the treatment of certain disease states arising from the overproduction of nitric oxide (NO). Recently, we reported the dipeptide methyl ester, D-Phe-D-Arg(NO)()2-OMe (19), as a modest inhibitor of nNOS (K(i) = 2 microM), but with selectivity over iNOS as high as 1800-fold (Silverman, R. B.; Huang

  选择性抑制一氧化氮合酶（NOS）的同工型在治疗某些因一氧化氮（NO）过量生产而引起的疾病中可能有用。最近，我们报道了二肽甲酯D-Phe-D-Arg（NO）（）2-OMe（19）作为nNOS的适度抑制剂（K（i）= 2 microM），但对iNOS的选择性为高达1800倍（Silverman，RB; Huang，H .; Marletta，MA; Martasek，PJ Med.Chem。1997，40，2813-2817）。这里合成了包含硝基精氨酸和Phe以外的氨基酸的152种二肽酰胺的文库，并筛选了其活性。含有碱性胺侧链（20-24）的二肽酰胺可实现对nNOS优于eNOS和iNOS的出色抑制力和选择性。这表明在酶活性位点可能发生静电（或氢键）相互作用。在这些化合物中，最有效的nNOS抑制剂是L-Arg（NO）（）2-L-Dbu-NH（2）（23）（K（i）= 130 nM），它对eNOS的选择性也最高（>
• Solid-Phase Total Synthesis and Structure Proof of Callipeltin B
  作者：Ravi Krishnamoorthy、Leslie D. Vazquez-Serrano、Jeffrey A. Turk、Jennifer A. Kowalski、Alan G. Benson、Nneka T. Breaux、Mark A. Lipton

  DOI：10.1021/ja0666250

  日期：2006.12.1

  The cytotoxic, cyclic heptadepsipeptide, natural product callipeltin B was synthesized on a solid-phase support in 15% overall yield. Comparison of the 1H NMR spectra of three synthetic isomers with those of callipeltin B confirmed the configurational reassignment of its threonine residues as d-allothreonine and the assignment of the configuration of its beta-methoxytyrosine residue as (2R,3R).

  细胞毒性、环状七肽、天然产物 callipeltin B 在固相载体上合成，总产率为 15%。三种合成异构体的 1H NMR 谱与 callipeltin B 的 1H NMR 谱的比较证实其苏氨酸残基的构型重新分配为 d-别苏氨酸，并将其 β-甲氧基酪氨酸残基的构型分配为 (2R,3R)。
• Synthesis of arginine-containing hydroxamate dipeptidomimetics
  作者：Jiwon Seo、Richard B. Silverman

  DOI：10.1016/j.tetlet.2006.03.190

  日期：2006.6

  The syntheses of arginine-containing hydroxamates using various peptide coupling methods are described. Fmoc-Arg(NO2)-Cl prepared at low temperature did not undergo intramolecular delta-lactam formation and effectively provided desired hydroxamates (8 and 10) in good yields. Fmoc and N-nitro protecting groups can be easily removed. Therefore, this report provides a facile synthesis of arginine-containing peptidomimetic compounds. (c) 2006 Elsevier Ltd. All rights reserved.