丁氧羰基-D-鸟氨酸-OH | 159877-12-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 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: 丁氧羰基-D-鸟氨酸-OH
• 中文别名: BOC-D-鸟氨酸
• 英文名称: (R)-5-amino-2-((tert-butoxycarbonyl)amino)pentanoic acid
• 英文别名: (α)N-1,1-dimethylethoxycarbonyl-L-ornithine；Boc-D-Orn-OH；L-ornithine；Nα-Boc-L-Orn-OH；N2-Boc-D-ornithine；Boc-D-Ornithine；(2R)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• CAS: 159877-12-0
• 化学式: C₁₀H₂₀N₂O₄
• 分子量: 232.28
• InChiKey: AMPVNPYPOOQUJF-SSDOTTSWSA-N

物化性质

• 沸点：
  398.9±37.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090
• 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: Boc-D-Orn-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-Orn-OH
CAS number: 159877-12-0

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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: C10H20N2O4
Molecular weight: 232.3

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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：

  丁氧羰基-D-鸟氨酸-OH 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 生成 (R)-2-(3-(叔丁氧基羰基氨基)-2-氧代哌啶-1-基)乙酸
  参考文献：
  名称：

  新型，选择性和口服可生物利用的凝血酶抑制剂的设计，合成和进化：掺有P3-P4内酰胺磺酰胺基团的P1-精氨酸衍生物。

  摘要：

  DOI：

  10.1021/jm960572n
• 作为产物：
  描述：

  N-叔丁氧羰基-N'-苄氧羰基-D-鸟氨酸 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到丁氧羰基-D-鸟氨酸-OH
  参考文献：
  名称：

  新型，选择性和口服可生物利用的凝血酶抑制剂的设计，合成和进化：掺有P3-P4内酰胺磺酰胺基团的P1-精氨酸衍生物。

  摘要：

  DOI：

  10.1021/jm960572n

文献信息

• 2-nitroaryl and 2-cyanoaryl compounds as regulators of nitric oxide
  申请人：Abbott Laboratories

  公开号：US05362747A1

  公开（公告）日：1994-11-08

  2-Nitroaryl or 2-cyanoaryl compounds of the formula ##STR1## pharmaceutical compositions thereof, intermediates useful in the preparation of these compounds, and methods for treating disorders of vascular smooth muscles or diseases of the cartilage, macrophages, neurons, platelets, bronchial smooth muscles, optic muscles and gastrointestinal smooth muscles, in addition to sickle cell anemia, diabetes, synovitis, chondroarthritis and osteoarthritis by employing these compounds.

  2-硝基芳基或2-氰基芳基化合物的化学式为##STR1##，其药物组合物，用于制备这些化合物的中间体，以及利用这些化合物治疗血管平滑肌障碍或软骨、巨噬细胞、神经元、血小板、支气管平滑肌、视肌和胃肠平滑肌疾病的方法，此外还包括镰刀细胞贫血、糖尿病、滑膜炎、软骨关节炎和骨关节炎。
• [EN] PYRIMIDINE COMPOUNDS FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS À BASE DE PYRIMIDINE UTILISABLES À DES FINS DE TRAITEMENT DU CANCER
  申请人：UNIV NORTH CAROLINA

  公开号：WO2014085225A1

  公开（公告）日：2014-06-05

  Compounds of Formula I or II: are described, along with pharmaceutical compositions containing the same and methods of using such compounds for the treatment of cancer.

  化合物的化学式I或II：已经描述，以及含有这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法。
• [EN] DIPHENYLAZETIDINONE DERIVATES POSSESSING CHOLESTEROL ABSORPTION INHIBITORY ACTIVITY<br/>[FR] DERIVES DIPHENYLAZETIDINONE A ACTIVITE INHIBITRICE DE L'ABSORPTION DU CHOLESTEROL
  申请人：ASTRAZENECA AB

  公开号：WO2005061452A1

  公开（公告）日：2005-07-07

  Compounds of formula (I) (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.

  化合物的结构式（其中变量基团如定义所示）及其药学上可接受的盐、溶剂合物、该类盐的溶剂合物和它们的前药，以及它们作为治疗高脂血症的胆固醇吸收抑制剂的用途被描述。还描述了它们的制备方法和含有它们的药物组合物。
• Total Synthesis of the Ramoplanin A2 and Ramoplanose Aglycon
  作者：Wanlong Jiang、Jutta Wanner、Richard J. Lee、Pierre-Yves Bounaud、Dale L. Boger

  DOI：10.1021/ja020237q

  日期：2002.5.1

  subunits composed of residues 3−9 (heptapeptide 15), pentadepsipeptide 26, and pentapeptide 34 (residues 10−14) were prepared, sequentially coupled, and cyclized to provide the 49-membered depsipeptide core of the aglycon. Key to the preparation of the pentadepsipeptide 26 incorporating the backbone ester was the asymmetric synthesis of an orthogonally protected l-threo-β-hydroxyasparagine and the development

  公开了ramoplanin A2和ramoplanose苷元的会聚全合成。制备由残基 3-9（七肽 15）、五肽 26 和五肽 34（残基 10-14）组成的三个关键亚基，依次偶联并环化以提供苷元的 49 元缩酚肽核心。制备包含主链酯的五肽 26 的关键是正交保护的 l-苏式-β-羟基天冬酰胺的不对称合成，以及为其受阻醇（EDCI、DMAP、0 ℃）。选择偶联位点以最大限度地提高合成的收敛性，包括三个亚基的收敛性，以防止羧酸盐活化的苯基甘氨酸衍生残基的晚期外消旋化，并为 49 元环闭合争取无环大环化底物的 β-折叠预组织。因此，所选 Phe9-d-Orn10 位点的大环化可能受益于...
• Heme-Coordinating Inhibitors of Neuronal Nitric Oxide Synthase. Iron−Thioether Coordination Is Stabilized by Hydrophobic Contacts without Increased Inhibitor Potency
  作者：Jeffrey D. Martell、Huiying Li、Tzanko Doukov、Pavel Martásek、Linda J. Roman、Michael Soltis、Thomas L. Poulos、Richard B. Silverman

  DOI：10.1021/ja908544f

  日期：2010.1.20

  between heme iron and native methionine ligands, but thioether-based heme-coordinating (type II) inhibitors are uncommon due to the difficulty in stabilizing the Fe-S bond. Here, a thioether-based inhibitor (3) of neuronal nitric oxide synthase (nNOS) was designed, and its binding was characterized by spectrophotometry and crystallography. A crystal structure of inhibitor 3 coordinated to heme iron was obtained

  血红素-硫醚配体相互作用通常发生在血红素铁和天然蛋氨酸配体之间，但由于难以稳定 Fe-S 键，基于硫醚的血红素配位（II 型）抑制剂并不常见。在这里，设计了一种基于硫醚的神经元一氧化氮合酶（nNOS）抑制剂（3），并通过分光光度法和晶体学对其结合进行了表征。获得了与血红素铁配位的抑制剂3的晶体结构，据我们所知，这代表了与任何血红素酶复合的硫醚抑制剂的第一个晶体结构。还评估了一系列相关的潜在抑制剂 (4-8)。化合物 4-8 均被发现是铁 nNOS 的 I 型（非血红素配位）抑制剂，但发现 4 和 6-8 在血红素还原为亚铁态时转变为 II 型，反映了硫醚的更高亲和力亚铁血红素比铁血红素。与人们普遍认为的相反，发现硫醚-血红素连接不会增加抑制剂的效力，这说明了硫醚-铁血红素连接的内在弱点。硫醚硫上烷基的细微变化引起了结合构象的剧烈变化，表明疏水接触在稳定硫醚-血红素配位中起着至关重要的作用。