Fmoc-O-三苯甲基-L-丝氨酸 | 111061-56-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丝氨酸类衍生物
• 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: Fmoc-O-三苯甲基-L-丝氨酸
• 中文别名: N-(9-芴甲氧羰酰基)-O-三苯甲基-L-丝氨酸；芴甲氧羰酰基-O-三苯甲基丝氨酸
• 英文名称: Fmoc-Ser(Trt)-OH
• 英文别名: Fmoc-L-Ser(Trt)-OH；FmocSer(OTrt)OH；N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-trityl-L-serine；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-trityloxypropanoic acid
• CAS: 111061-56-4
• 化学式: C₃₇H₃₁NO₅
• mdl: MFCD00153364
• 分子量: 569.657
• InChiKey: UCARTONYOJORBQ-UMSFTDKQSA-N

物化性质

• 熔点：
  200-210 °C (dec.)
• 比旋光度：
  8 º (c=1%, DMF)
• 沸点：
  750.4±60.0 °C(Predicted)
• 密度：
  1.256±0.06 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：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.135
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  29242990
• 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：
  存于2至8℃阴凉干燥处密封保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Fmoc-Ser(Trt)-OH
CAS-No. : 111061-56-4
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
Synonyms : Fmoc-O-trityl-L-serine
Formula : C37H31NO5
Molecular Weight : 569,65 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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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. Moisture sensitive.
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: beige
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 200 - 210 °C
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.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

Fmoc-Ser(Trt)-OH是一种丝氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  Fmoc-O-三苯甲基-L-丝氨酸 在 二乙胺 、 sodium hydroxide 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 O-三苯甲基-丝氨酸
  参考文献：
  名称：

  Oxazole and thiazole combinatorial libraries

  摘要：

  这项发明提供了一种合成多肽集合的新方法，允许生成无限数量的抗生素化合物。更具体地，该方法利用含有噻唑和/或噁唑的合成杂环氨基酸作为固相组合合成的构建单元，以产生天然和非天然的抗生素化合物。

  公开号：

  US20060161007A1
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 O-三苯甲基-丝氨酸 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以77%的产率得到Fmoc-O-三苯甲基-L-丝氨酸
  参考文献：
  名称：

  Barlos, Kleomenis; Mamos, Petros; Papaioannou, Dionysios, Liebigs Annalen der Chemie, 1987, p. 1025 - 1030

  摘要：

  DOI：

文献信息

• N‐Methylated Peptide Synthesis via Generation of an Acyl N‐Methylimidazolium Cation Accelerated by a Brønsted Acid
  作者：Yuma Otake、Yusuke Shibata、Yoshihiro Hayashi、Susumu Kawauchi、Hiroyuki Nakamura、Shinichiro Fuse

  DOI：10.1002/anie.202002106

  日期：2020.7.27

  formation remains a critical aspect of N‐methylated peptide synthesis. In this study, we synthesized a variety of dipeptides in high yields, without severe racemization, from equivalent amounts of amino acids. Highly reactive N‐methylimidazolium cation species were generated in situ to accelerate the amidation. The key to success was the addition of a strong Brønsted acid. The developed amidation enabled

  牢固的酰胺键形成的发展仍然是N-甲基化肽合成的关键方面。在这项研究中，我们从等量的氨基酸中高收率合成了各种二肽，而没有严重的消旋作用。高反应性的N-甲基咪唑鎓阳离子原位生成以加速酰胺化反应。成功的关键是加入强力的布朗斯台德酸。与常规酰胺化的结果相比，开发的酰胺化使得能够在较短的时间内以较高的产率合成大体积的肽。另外，可以通过使用微流反应器或常规烧瓶来进行酰胺化。天然存在的大体积N-甲基化肽，蝶酰胺I-IV的首次全合成。根据实验结果和理论计算，
• 항노화 펩타이드와 베타글루칸을 함유하는 피부 개선 및 보습 화장료 조성물
  申请人：Cellicon Lab Inc. (주)셀아이콘랩(120120391559) Corp. No ▼ 160111-0326408BRN ▼314-86-37832

  公开号：KR20180047207A

  公开（公告）日：2018-05-10

  본 발명은 항노화 펩타이드와 베타글루칸을 함유하는 피부 재생 및 보습 화장료 조성물에 관한 것이다. 본 발명에 따른 항노화 펩타이드와 베타글루칸을 함유하는 피부 재생 및 보습 화장료 조성물은 콜라겐 합성촉진 펩타이드, 베타-1,3/1,6-글루칸, 코퍼트리펩타이드-1 및 아세틸 헥사펩타이드-3(Acetyl Hexapeptide-3)을 유효성분으로 포함한다. 상기한 구성에 의해 본 발명은 콜라겐 합성 능력이 우수한 콜라겐 합성촉진 펩타이드를 최적의 배합비로 혼합하여 화장료 조성물을 제조함으로써 콜라겐 합성을 촉진하여 현저한 피부 재생 및 보습 효과를 발휘할 수 있고, 피부 내의 콜라겐 합성을 촉진함과 동시에 콜라겐의 분해를 저지하는 성분들을 함께 함유함으로써, 각 성분들의 상승작용에 의해 우수한 노화방지 효과를 발휘할 수 있다.

  本发明涉及含有抗衰老肽和β-葡聚糖的皮肤再生和保湿化妆品配方。根据本发明，含有抗衰老肽和β-葡聚糖的皮肤再生和保湿化妆品包括胶原合成促进肽，β-1,3/1,6-葡聚糖，胶原三肽-1和乙酰六肽-3（Acetyl Hexapeptide-3）作为有效成分。通过上述组合，本发明通过将具有优异胶原合成能力的胶原合成促进肽以最佳配比混合制造化妆品，从而促进胶原合成，展现显著的皮肤再生和保湿效果，并通过促进皮肤内胶原合成的同时含有阻止胶原分解的成分，通过各成分的协同作用展现出优秀的抗衰老效果。
• A Lanthanide(III) Triflate Mediated Macrolactonization/Solid-Phase Synthesis Approach for Depsipeptide Synthesis
  作者：Jordan D. Goodreid、Eduardo da Silveira dos Santos、Robert A. Batey

  DOI：10.1021/acs.orglett.5b00781

  日期：2015.5.1

  The effect of dysprosium(III) triflate on macrolactonization reactions to form depsipeptides using MNBA (Shiina’s reagent) is reported. Improved yields were obtained for the formation of 16-membered depsipeptides using lanthanide triflate additives. The use of a macrocyclization strategy permits the use of a semiautomated solid-phase synthesis approach for the rapid synthesis of analogues of the antibacterial

  报道了使用MNBA（Shiina's试剂）的三氟甲磺酸dy对大环内酯化反应形成二肽的影响。使用镧系元素三氟甲磺酸盐添加剂形成16元depsipeptide，可提高产率。大环化策略的使用允许使用半自动化的固相合成方法，以仅在两个物理操作中快速合成抗菌A54556酰基肽肽的类似物，仅需在环化后纯化最终产物。
• Synthesis of paenipeptin C′ analogues employing solution-phase CLipPA chemistry
  作者：Juliana T. W. Tong、Iman Kavianinia、Scott A. Ferguson、Gregory M. Cook、Paul W. R. Harris、Margaret A. Brimble

  DOI：10.1039/d0ob00950d

  日期：——

  We herein report the synthesis of analogues of the antimicrobial lipopeptide, paenipeptin C′, by installing varying lipid moieties using thiol–ene CLipPA (Cysteine Lipidation on a Peptide or Amino Acid) chemistry. Biological evaluation against both Gram-negative and Gram-positive strains indicated that several analogues possessed potent broad-spectrum antimicrobial activity.

  我们在此报告了通过使用硫醇-烯类CLipPA（肽或氨基酸上的半胱氨酸脂质化）化学方法安装不同的脂质部分，合成抗菌脂肽，paenipeptin C'的类似物的方法。对革兰氏阴性和革兰氏阳性菌株的生物学评估表明，几种类似物具有有效的广谱抗菌活性。
• Enzyme-cleavable linkers for peptide and glycopeptide synthesis
  作者：Beatrice A. Maltman、Mallesham Bejugam、Sabine L. Flitsch

  DOI：10.1039/b506154g

  日期：——

  Hydroxymethylphenoxy linkers that are commonly used in solid phase peptide synthesis are surprisingly susceptible to efficient cleavage by the protease chymotrypsin with a broad range of amino acid residues being tolerated at the scissile bond; this enzyme-cleavable linker system has been applied to peptide and glycopeptide synthesis.

  在固相肽合成中常用的羟甲基苯氧基连接剂出人意料地容易被胰凝乳蛋白酶有效切割，且在切断键上可容忍广泛的氨基酸残基；这种酶可切割的连接剂系统已应用于肽和糖肽的合成。