Nα-芴甲氧羰基-Nγ-烯丙氧羰基-L-2,4-二氨基丁酸 | 204316-32-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Nα-芴甲氧羰基-Nγ-烯丙氧羰基-L-2,4-二氨基丁酸
• 中文别名: Fmoc-4-烯丙氧基羰基-L-2,4-氨基丁酸；2-芴甲氧羰基氨基-4-[[(烯丙氧基)羰基]氨基-L-丁酸；N-芴甲氧羰基-N'-[(烯丙氧基)羰基]-L-2,4-二氨基丁酸；2-Fmoc-氨基-4-[[(烯丙氧基)羰基]氨基-L-丁酸
• 英文名称: Fmoc-Dab(Alloc)-OH
• 英文别名: Fmoc-L-Dab(Alloc)-OH；Nα-Fmoc-Nγ-alloc-L-2,4-diaminobutyric acid；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(prop-2-enoxycarbonylamino)butanoic acid
• CAS: 204316-32-5
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: YIVBOSPUFNDYMF-FQEVSTJZSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  676.7±55.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 海关编码：
  29242990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保存方法：在2至-8°C之间存储。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Fmoc-Dab(Alloc)-OH
CAS-No. : 204316-32-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: Nα-Fmoc-Nγ-Alloc-L-2,4-diaminobutyric acid
Synonyms
Nγ-Alloc-Nα-Fmoc-L-2,4-diaminobutyric acid
Formula : C23H24N2O6
Molecular Weight : 424,45 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Store under inert gas.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：储存温度为2-8°C

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  NAlpha-芴甲氧羰基-Nγ-羰-L-2,4-氨基丁酸	(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid	125238-99-5	C24H28N2O6	440.496
  Fmoc-L-2,4-二氨基丁酸	Fmoc-Dab-OH	161420-87-7	C19H20N2O4	340.379
  ——	(S)-(3-fluoren-9-ylmethoxycarbonyl)-4-[2-(allyloxycarbonylamino)ethyl]-5-oxazolidinone	918428-73-6	C24H24N2O6	436.464
  ——	Nα-Fmoc-Glu-5-oxazolidinone	159530-17-3	C21H19NO6	381.385
  ——	9H-9-fluorenylmethyl (4S)-4-(3-azido-2-oxopropyl)-5-oxo-1,3-oxazolone-3-carboxylate	918428-66-7	C21H18N4O5	406.398

反应信息

• 作为反应物：
  描述：

  、 Nα-芴甲氧羰基-Nγ-烯丙氧羰基-L-2,4-二氨基丁酸 在 N-羟基-7-氮杂苯并三氮唑 、 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5-b] pyridinium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design and Synthesis of FAJANU: a de Novo C₂ Symmetric Cyclopeptide Family

  摘要：

  A novel cyclic peptide has been designed from several potent marine cytotoxic peptides, including IB-01212, luzopeptin, triostin, and thiocoraline. The FAJANU scaffold maintains C-2 symmetry, cyclic structure, and the construction of aromatic and aliphatic character at the N- and C-terminal extremes. A first six-member family was previously synthesized and evaluated biologically. Several analogues presented greater activity than IB-01212. Furthermore, on the basis of the most active candidate, we have performed a more exhaustive synthetic and structural analysis: (i) structure-activity relationship provided clues about the key elements in the framework, (ii) NMR assignment confirmed C-2, symmetry, and (iii) confocal images revealed its penetration and cellular localization.

  DOI：

  10.1021/jm800047b
• 作为产物：
  描述：

  N^α-Fmoc-Glu-5-oxazolidinone 在 N-甲基吗啉 、 lithium hydroxide 、 sodium azide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.75h， 生成 Nα-芴甲氧羰基-Nγ-烯丙氧羰基-L-2,4-二氨基丁酸
  参考文献：
  名称：

  Practical and Efficient Synthesis of Orthogonally Protected α‐2,3‐Diaminopropionic Acid (2,3‐Dap), 2,4‐Diaminobutanoic Acid (2,4‐Dab), and their N‐Methylated Derivatives

  摘要：

  DOI：

  10.1080/00397910600772827

文献信息

• [EN] BETA-HAIRPIN PEPTIDOMIMETICS<br/>[FR] PEPTIDOMIMÉTIQUES EN ÉPINGLE À CHEVEUX BÊTA
  申请人：POLYPHOR AG

  公开号：WO2016150576A1

  公开（公告）日：2016-09-29

  Beta-hairpin peptidomimetics of the general formula (I), and pharmaceutically acceptable salts thereof, with P, T, Q., and optionally L being elements as defined in the description and the claims, have Gram-negative antimicrobial activity to e.g. inhibit the growth or to kill microorganisms such as Klebsiellapneumoniae and/or Acinetobacter baumannii and/or Escherichia coli and/or Pseudomonas aeruginosa. They ca n be used as medicaments to treat or prevent infections or as disinfectants for foodstuffs, cosmetics, medicaments or other nutrient-containing materials. These peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  Beta-发夹仿生肽的一般公式（I），及其药学上可接受的盐，其中P、T、Q.，以及可选的L作为描述和权利要求中定义的元素，具有抗革兰氏阴性微生物活性，例如抑制生长或杀灭肺炎克雷伯菌、包括鲍曼不动杆菌、大肠杆菌和铜绿假单胞菌等微生物。它们可用作药物治疗或预防感染，或用作食品、化妆品、药物或其他含营养物质的材料的消毒剂。这些仿生肽可以通过基于混合固相和溶液相合成策略的过程制造。
• Identification of the Natural Product Rotihibin A as a TOR Kinase Signaling Inhibitor by Unbiased Transcriptional Profiling
  作者：Vivek Halder、Julian Oeljeklaus、Geronimo Heilmann、Jan H. Krahn、Yanlin Liu、Yan Xiong、Markus Schlicht、Jasmin Schillinger、Barbara Kracher、Michael Ehrmann、Erich Kombrink、Farnusch Kaschani、Markus Kaiser

  DOI：10.1002/chem.201802647

  日期：2018.8.27

  a rapid, label‐free, and compound economic evaluation of a natural product′s bioactivity profile in a complex multicellular organism. To this end, we established a chemical synthesis of Rotihibin A as well as that of structural analogues, followed by transcriptional profiling‐guided identification and validation of Rotihibin A as a TOR signaling inhibitor (TOR=target of rapamycin). These findings illustrate

  具有生物活性的天然产物是开发用于生物学研究的化学工具的重要起点。为了阐明其生物活性特征，通常使用具有简洁复杂性的生物系统（例如细胞培养系统），而仅在较复杂的多细胞系统中进行无偏研究的情况很少。在这里，我们用天然产物Rotihibin A和植物研究模型系统拟南芥（Arabidopsis thaliana）进行了演示。无偏见的转录谱分析可以对复杂的多细胞生物中的天然产物的生物活性进行快速，无标记的复合经济评估。为此，我们建立了Rotihibin A和结构类似物的化学合成方法，然后进行转录谱分析指导鉴定和验证Rotihibin A作为TOR信号抑制剂（TOR =雷帕霉素的靶标）。这些发现表明，转录谱分析和天然产物研究的组合方法可能代表一种简化了天然产物化学工具开发的技术简单方法，即使对于生物复杂的多细胞生物系统也是如此。
• [EN] GELATINASE INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS DES GÉLATINASES ET LEUR UTILISATION
  申请人：IPROTEOS S L

  公开号：WO2017085034A1

  公开（公告）日：2017-05-26

  New gelatinase inhibitors, processes for their preparation, pharmaceutical compositions comprising them, and their use in therapy and/or prophylaxis of conditions wherein inhibition of gelatinases is useful such as epilepsy, schizophrenia, Alzheimer disease, autism (in particular associated to fragile X syndrome), mental retardation, mood disorders such as bipolar disorders, depression, vascular diseases such as ischemic stroke and atherosclerosis, inflammatory diseases such as multiple sclerosis, rheumatoid arthritis and inflammatory bowel disease, drug addiction, neuropathic pain, lung diseases such as asthma and chronic obstructive pulmonary disease, cancer and sepsis.

  新明胶酶抑制剂，其制备方法，包括它们的药物组合物，以及它们在治疗和/或预防明胶酶抑制对疾病有用的情况下的用途，如癫痫、精神分裂症、阿尔茨海默病、自闭症（尤其是与脆性X综合症相关）、智力障碍、情绪障碍如躁郁症、抑郁症、血管疾病如缺血性中风和动脉粥样硬化、炎症性疾病如多发性硬化、类风湿关节炎和炎症性肠病、药物成瘾、神经病性疼痛、肺部疾病如哮喘和慢性阻塞性肺病、癌症和败血症。
• [EN] COMPOUNDS AND THERAPEUTIC USES THEREOF<br/>[FR] COMPOSÉS ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：CENTAURI THERAPEUTICS LTD

  公开号：WO2018203087A1

  公开（公告）日：2018-11-08

  The invention relates to novel compounds with the ability to link an immune response to a pathogen, to the use of said compounds in a disease or disorder mediated and/or caused by an infective agent, to compositions containing said compounds, processes for their preparation and to novel intermediates used in said process.

  本发明涉及具有将免疫应答与病原体连接起来的新化合物，以及在由感染性因子介导和/或引起的疾病或紊乱中使用该类化合物，包含该类化合物的组合物，其制备方法以及在该方法中使用的新中间体。
• [EN] PEPTIDE ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES PEPTIDIQUES
  申请人：UNIV QUEENSLAND

  公开号：WO2019084628A1

  公开（公告）日：2019-05-09

  There is provided a range of novel compounds. These novel compounds may demonstrate a broad spectrum antibacterial and antifungal activity. These compounds may be active against the emerging polymyxin resistant bacteria. These compounds may also be useful when used in conjunction with other pharmaceutically active agents.

  提供了一系列新化合物。这些新化合物可能表现出广谱抗菌和抗真菌活性。这些化合物可能对新出现的多粘菌素耐药细菌具有活性。这些化合物在与其他药用活性剂一起使用时也可能很有用。