Cbz-L-鸟氨酸 | 2640-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Cbz-L-鸟氨酸
• 中文别名: (S)-5-氨基-2-(苄氧羰基氨基)戊酸；苄氧羰基-L-鸟氨酸
• 英文名称: Nα-benzyloxycarbonyl-L-ornithine
• 英文别名: Z-Orn-OH；N-alpha-benzyloxycarbonyl-L-ornithine；(S)-5-amino-2-(((benzyloxy)carbonyl)amino)pentanoic acid；(2S)-5-amino-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 2640-58-6
• 化学式: C₁₃H₁₈N₂O₄
• 分子量: 266.297
• InChiKey: ZYGRWJVRLNJIMR-NSHDSACASA-N

物化性质

• 熔点：
  209-210 °C(Solv: water (7732-18-5))
• 沸点：
  489.4±45.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于酸性水溶液（轻微）、甲醇（轻微）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存储于室温下。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-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: Z-Orn-OH
CAS number: 2640-58-6

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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: C13H18N2O4
Molecular weight: 266.3

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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：

  Cbz-L-鸟氨酸 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 192.0h， 生成 Nω-单甲基-L-精氨酸乙酸酯
  参考文献：
  名称：

  Multigram Synthesis of N^G-Methyl-(L)-Arginine and Its Analytical Characterization

  摘要：

  A multigram preparation and analytical characterization of N(G)-methyl-(L)-arginine (L-NMMA) 1, the most important inhibitor of the biosynthesis of Endothelium-Derived Relaxing Factor (EDRF), is reported.

  DOI：

  10.1080/00397919108020795
• 作为产物：
  描述：

  L-鸟氨酸 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Cbz-L-鸟氨酸
  参考文献：
  名称：

  Benzimidazole analogs ofl-tryptophan are substrates and inhibitors of tryptophan indole lyase fromEscherichia coli

  摘要：

  Tryptophan indole lyase (TIL), an enzyme found in Escherichia coli and related enterobacteria, produces indole from l‐tryptophan (l‐Trp). Indole is a signaling molecule in bacteria, affecting biofilm formation, pathogenicity and antibiotic resistance. β‐(Benzimidazol‐1‐yl)‐l‐alanine (BZI‐Ala), 2‐amino‐4‐(benzimidazol‐1‐yl)butyric acid (homo‐BZI‐Ala) and 2‐amino‐5‐(benzimidazol‐1‐yl)pentanoic acid (bishomo‐BZI‐Ala) were synthesized and tested as substrates and inhibitors of TIL. BZI‐Ala is a good substrate of TIL, with Km = 300 μm, kcat = 5.6 s−1 and kcat/Km = 1.9 × 104, similar to l‐Trp. BZI‐Ala is also a good substrate for H463F mutant TIL, which has very low activity with l‐Trp. In contrast, homo‐BZI‐Ala was found to be a potent competitive inhibitor of TIL, with a Ki of 13.4 μm. However, the higher homolog, bishomo‐BZI‐Ala, was inactive as an inhibitor of TIL at a concentration of 600 μm, and is thus a much weaker inhibitor. The reaction of TIL with BZI‐Ala was too fast to be observed in the stopped‐flow spectrophotometer, and shows an aldimine intermediate in the steady state. However, H463F TIL shows equilibrating mixtures of aldimine and quinonoid complexes in the steady state. The spectra of the reaction of TIL with homo‐BZI‐Ala show a rapidly formed intermediate absorbing at 340 nm, probably a gem‐diamine, that decays slowly to form a quinonoid complex absorbing at 494 nm. The potent binding of homo‐BZI‐Ala may be due to it being a ‘bi‐product’ analog of the indole‐α‐aminoacrylate complex. These results demonstrate that an amino acid substrate may be converted to a potent inhibitor of TIL simply by homologation, which may be useful in the design of other potent TIL inhibitors.

  DOI：

  10.1111/febs.12205

文献信息

• Design and synthesis of Fmoc-SPPS-ready iodoarene amino acid pre-catalysts and their reactivity in the catalytic oxytosylation of ketones
  作者：Timothy R. Lex、Maria I. Swasy、Soham Panda、Beau R. Brummel、Lauren N. Giambalvo、Kristopher G. Gross、Colin D. McMillen、Khadijatul Kobra、William T. Pennington、Daniel C. Whitehead

  DOI：10.1016/j.tetlet.2020.151723

  日期：2020.4

  synthesized and assessed as catalysts for the hypervalent iodine(III) mediated α-oxytosylation of ketones. The efficiency of each catalyst was determined by comparing the relative rates of catalysis in the direct α-oxytosylation of propiophenone. In addition, these catalysts can be easily converted to congeners that are suitable for Fmoc-solid phase peptide synthesis for facile incorporation into a chiral

  合成了一小套含氨基酸的碘-芳基酰胺，并将其评估为高碘（III）介导的酮的α-氧羰基化的催化剂。通过比较在苯乙酮的直接α-氧羰基化反应中的相对催化速率来确定每种催化剂的效率。另外，这些催化剂可以容易地转化成适合于Fmoc-固相肽合成的同类物，以便容易地掺入手性肽骨架中。这项工作促进了我们计划的更大目标，即开发用于高价碘化学的基于肽的对映选择性催化剂。
• [EN] MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES MACROCYCLIQUES À LARGE SPECTRE
  申请人：RQX PHARMACEUTICALS INC

  公开号：WO2018149419A1

  公开（公告）日：2018-08-23

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本文提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌类型1信号肽酶（SpsB）发挥作用，这是细菌中的一种必需蛋白质。还提供了使用所述化合物的药物组合物和治疗方法。
• Flies and flowers: taxonomic diversity of anthophiles and pollinators
  作者：B.M.H. Larson、P.G. Kevan、D.W. Inouye

  DOI：10.4039/ent133439-4

  日期：2001.8

  The Diptera are the second most important order among flower-visiting (anthophilous) and flower-pollinating insects worldwide. Their taxonomic diversity ranges from Nematocera to Brachycera, including most families within the suborders. Especially important are Syrphidae, Bombyliidae, and Muscoidea. Other families, especially of small flies, are less appreciated and often overlooked for their associations with flowers. We have compiled records of their flower visitations to show that they may be more prevalent than usually thought. Our knowledge of anthophilous Diptera needs to be enhanced by future research concerning (i) the significance of nocturnal Nematocera and acalypterate muscoids as pollinators, (ii) the extent to which the relatively ineffective pollen-carrying ability of some taxa can be compensated by the abundance of individuals, and (iii) the role of Diptera as pollinators of the first flowering plants (Angiospermae) by using phylogenetic and palaeontological evidence. Specializations in floral relationships involve the morphology of Diptera, especially of their mouthparts, nutritional requirements, and behaviour, as well as concomitant floral attributes. The South African flora has the most highly specialized relations with dipterous pollinators, but in arctic and alpine generalist fly–flower relations are important in pollination and fly nutrition.

  摘要双翅目昆虫是全世界访花（嗜蚁）昆虫和授粉昆虫中第二重要的目。双翅目昆虫在分类学上具有多样性，从线虫纲（Nematocera）到臂翅目（Brachycera），包括亚目中的大多数科。其中尤为重要的是蚜蝇科（Syrphidae）、蝇科（Bombyliidae）和麝科（Muscoidea）。其他科，尤其是小型苍蝇科，与花卉的关系较少受到重视，也经常被忽视。我们汇编了它们的访花记录，以显示它们可能比通常认为的更为普遍。我们对嗜粉双翅目昆虫的了解需要通过未来的研究来加强，这些研究涉及：（i）夜行蝇类（Nematocera）和螨类作为授粉者的重要性；（ii）某些类群相对较弱的花粉携带能力在多大程度上可以通过个体的丰富程度来弥补；以及（iii）通过使用系统发育和古生物学证据来研究双翅目昆虫作为最早开花植物（被子植物）授粉者的作用。花卉关系中的特化涉及双翅目昆虫的形态，尤其是其口器、营养需求和行为，以及相关的花卉属性。南非植物区系与双翅目传粉昆虫的关系最为专业化，但在北极和高山地区，普通苍蝇与花卉的关系在传粉和苍蝇营养方面也很重要。
• Verbesserte Synthese von tert.-Butyloxycarbonyl-aminosäuren durch pH-Stat-Reaktion
  作者：Eugen Schnabel

  DOI：10.1002/jlac.19677020123

  日期：1967.3.21

  teilgeschützten Derivate mit tert.-Butyloxy-carbonylazid führt bei kontrolliertem pH in guten Ausbeuten zu den tert.-Butyloxycarbonyl-Derivaten. Auch sterisch gehinderte Aminosäuren reagieren glatt. Durch die Wahl der pH-Werte lassen sich die günstigsten Bedingungen für eine rasche und weitgehende Umsetzung bequem ermitteln.

  游离氨基酸或其部分保护的衍生物与叔丁氧基羰基叠氮化物的反应在控制的pH值下可产生高收率的叔丁氧基羰基衍生物。甚至位阻氨基酸也能平稳反应。通过选择pH值，可以轻松确定快速，广泛实施的最有利条件。
• C-Glycoside Analogues ofN4-(2-Acetamido-2-deoxy-?-D-glucopyranosyl)-L-asparagine: Synthesis and conformational analysis of a cyclicC-glycopeptide
  作者：Matthias Hoffmann、Fred Burkhart、Gerhard Hessler、Horst Kessler

  DOI：10.1002/hlca.19960790602

  日期：1996.9.18

  propanoic acid (22) can be used in solid-phase peptide synthesis. The conformation of 24 was determined by NMR and molecular-dynamics (MD) techniques. Evidence is provided that the CGaa side chain interacts with the peptide backbone. The different C-glycosylated amino acids 15–21 were prepared by coupling 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-β-D-glycero-D-gulo-heptonic acid (4) with diamino-acid

  的合成Ç糖苷类似物15-22的ñ 4 - （2-乙酰氨基-2-脱氧- β-d-D-吡喃葡萄糖基）-L-天冬酰胺（ASN（Ñ 4的GlcNAc））具有相反的酰胺键为电子等排取代给出了N-糖苷键的结构。制备了肽环（-D-Pro-Phe-Ala-CGaa-Phe-Phe-）（CGaa = C-糖基化氨基酸；24），以证明3-[（3-acetamido-2,6-anhydro- 4,5,7-三-O-苄基-3-脱氧-β-D-甘油-D-邻庚基庚酰基）氨基] -2-[（9 H-氟-9-酰氧基羰基）氨基]丙酸（22）可以用于固相肽合成。的构象通过NMR和分子动力学（MD）技术确定24。提供的证据表明，CGaa侧链与肽主链相互作用。不同Ç -glycosylated氨基酸15-21被偶合制备3-乙酰氨基-2,6-脱水-4,5,7-三ö苄基-3-脱氧β-D-甘油基-D-庚-带有二氨基酸衍生物8-14的庚酸（4