N-Fmoc-N'-三苯甲基-L-组氨酸五氟苯基酯 | 109434-24-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 组氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: N-Fmoc-N'-三苯甲基-L-组氨酸五氟苯基酯
• 中文别名: N-Fmoc-N’-三苯甲基-L-组氨酸五氟苯基酯
• 英文名称: Fmoc-His(Trt)-OPfp
• 英文别名: (2,3,4,5,6-pentafluorophenyl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1-tritylimidazol-4-yl)propanoate
• CAS: 109434-24-4
• 化学式: C₄₆H₃₂F₅N₃O₄
• 分子量: 785.77
• InChiKey: BEYCFWPYIFVBLO-QNGWXLTQSA-N

物化性质

• 熔点：
  97～100℃
• 沸点：
  857.8±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 稳定性/保质期：

  在常温常压下稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  58
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Fmoc-His(Trt)-OPfp
CAS-No. : 109434-24-4
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.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: Nα-Fmoc-N(im)-trityl-L-histidine pentafluorophenyl ester
Synonyms
Formula : C46H32F5N3O4
Molecular Weight : 785,76 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), Hydrogen fluoride
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.Normal measures for preventive fire
protection.
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
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
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.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
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: crystalline
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

反应信息

• 作为反应物：
  描述：

  N-Fmoc-N'-三苯甲基-L-组氨酸五氟苯基酯 在 sodium acetate 、 sodium glyoxylate 、 copper(II) sulfate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.17h， 生成 3-(imidazo-4-yl)-2-oxopropanoyl-Leu-Phe-Leu-Gly
  参考文献：
  名称：

  α-酮羰基肽：合成肽等排体中反应性树脂结合中间体的一般方法，用于在固体载体上筛选蛋白酶抑制剂

  摘要：

  α-酮羰基肽是通过金属离子催化的转氨作用从固体支持物上的肽前体生成的。反应在 2 小时内完成，乙醛酸盐作为亲电子试剂，铜 (II) 离子作为催化剂，在 pH 5.5-6.0 的醋酸水溶液缓冲液中。各种天然存在的 α-氨基酸底物产生了一组不同的差异功能化酮。高度反应性的末端酮羰基易于发生羟醛型二聚反应，并且可以分别通过肟形成、还原为醇或还原胺化而转化为稳定的部分。α-酮羰基肽在 C-亲核试剂的亲核加成中是有效的，例如膦酰基内酯和烯丙基硅烷。

  DOI：

  10.1021/ja003690f

文献信息

• Peptidotriazoles on Solid Phase:  [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
  作者：Christian W. Tornøe、Caspar Christensen、Morten Meldal

  DOI：10.1021/jo011148j

  日期：2002.5.1

  The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]-triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely

  叠氮化物与炔烃的环加成反应是合成1H- [1,2,3]-三唑的最重要合成途径之一。在这里报道了一种新型的区域特异性铜（I）催化的末端炔烃在固相上与叠氮化物的1,3-偶极环加成反应。伯，仲和叔烷基叠氮化物，芳基叠氮化物和叠氮糖已成功用于铜（I）催化的环加成反应中，在肽主链或侧链上产生了不同的1,4-取代的[1,2,3]-三唑。反应条件与极性载体上的固相肽合成完全相容。铜（I）催化反应温和有效（大多数情况下> 95％的转化率和纯度），此外，2-叠氮基-2-甲基丙酸的X射线结构得到了解析，以得到有关1， 3-偶极子进入反应。
• Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptide thioesters
  作者：Hironobu Hojo、Hajime Kobayashi、Risa Ubagai、Yuya Asahina、Yuko Nakahara、Hidekazu Katayama、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1039/c1ob05831b

  日期：——

  The synthesis of Fmoc-aminoacyl-N-ethyl-S-triphenylmethylcysteine, an N- to S-acyl migratory device for the preparation of peptide thioesters by Fmoc-SPPS (solid-phase peptide synthesis) is described. Condensation of Fmoc-aminoacyl pentafluorophenyl ester and N-ethyl-S-triphenylmethylcysteine was efficiently performed in the presence of HOOBt (3-hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine) in DMF. A small amount of diastereomer yielded during the reaction was easily separated by HPLC purification and the highly pure devices were obtained for most of the proteinogenic amino acids.

  描述了Fmoc-氨酰-N-乙基-S-三苯基甲基半胱氨酸的合成，这是一种用于通过Fmoc-SPPS（固相肽合成）制备肽硫酯的N至S-酰基迁移装置。在DMF中，在HOOBt（3-羟基-3,4-二氢-4-氧代-1,2,3-苯并三氮唑）的存在下，Fmoc-氨酰五氟苯基酯与N-乙基-S-三苯基甲基半胱氨酸的缩合反应有效进行。在反应过程中产生的小量非对映体可以通过HPLC纯化轻松分离，绝大多数蛋白源氨基酸获得了高纯度的迁移装置。
• Solid-state¹⁷O NMR in Biological Solids: Efficient¹⁷O Labeling of Amino Acids and Peptides
  作者：Kazuhiko Yamada、Toshio Yamazaki、Miwako Asanuma、Hiroshi Hirota、Naoki Yamamoto、Yasuhiro Kajihara

  DOI：10.1246/cl.2007.192

  日期：2007.1

  A highly effective labeling method for 17O-enriched amino acids and peptides at moderate experimental conditions (Japanese Patent 2006-8666) has been presented, which has enabled us to readily carry out solid-state 17O NMR experiments in almost all amino acids and peptides.

  已经提出了一种在温和实验条件下对富含 17O 的氨基酸和肽进行高效标记的方法（日本专利 2006-8666），这使得我们能够轻松地对几乎所有氨基酸和肽进行固态 17O NMR 实验。
• A Novel Synthetic Method for Bepotastine, a Histamine H1 Receptor Antagonist
  作者：Tae Hee Ha、Kwee-Hyun Suh、Gwan Sun Lee

  DOI：10.5012/bkcs.2013.34.2.549

  日期：2013.2.20

  (+)-(S)-4-(4-((4-chlorophenyl)(pyrid-2-yl)methoxy]piperidin-1-yl)butanoic acid, bepotastine (1) is described. The key resolution of (R/S)-bepotastine l-menthyl ester (3) is achived via diastereomeric salt crystallization using N-benzyloxycarbonyl-L-aspartic acid (NCbzLAA) as the resolving agent to provide (S)-bepotastine l-menthyl ester (S)-3. Hydrolysis of (S)-bepotastine l-menthyl ester (S)-3 afforded

  对映体纯 (+)-(S)-4-(4-((4-氯苯基)(吡啶-2-基)甲氧基]哌啶-1-基)丁酸贝他斯汀 (1) 的一种有效且替代的合成方法是(R/S)-贝他斯汀 l-薄荷酯 (3) 的关键拆分是通过使用 N-苄氧基羰基-L-天冬氨酸 (NCbzLAA) 作为拆分剂的非对映体盐结晶来提供 (S)-贝他斯汀 l -薄荷酯 (S)-3. (S)-贝他斯汀 l-薄荷酯 (S)-3 的水解得到所需的贝他斯汀 (1)，具有良好的收率和对映体纯度 (> 99%)。最后，苯磺酸贝他斯汀 (4)贝他斯汀钙(1)分别与苯磺酸和钙盐成盐得到贝他斯汀钙(5)，并优化反应条件，使其适合工业化规模生产。