FMOC-N-L-BETA-二苯基丙氨酸 | 201484-50-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: FMOC-N-L-BETA-二苯基丙氨酸
• 中文别名: 芴甲氧羰基-Β-二苯基-L-苯丙氨酸；N-FMOC-3,3-联苯基-L-丙氨酸；Fmoc-L-3,3-二苯基丙氨酸；N-芴甲氧羰基-L-3,3-二苯基丙氨酸
• 英文名称: Fmoc-3,3-diphenyl-L-alanine
• 英文别名: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3,3-diphenylpropanoic acid；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3,3-diphenylpropanoic acid
• CAS: 201484-50-6
• 化学式: C₃₀H₂₅NO₄
• mdl: MFCD00672337
• 分子量: 463.533
• InChiKey: PENQOTJCVODUQU-NDEPHWFRSA-N

物化性质

• 熔点：
  125-129 °C(lit.)
• 比旋光度：
  -12 º (c=1 in chloroform)
• 沸点：
  676.5±55.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)
• 闪点：
  63 °C
• 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)：
  6.1
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险等级：
  9
• 危险品标志：
  N,Xi
• 安全说明：
  S60,S61
• 危险类别码：
  R50/53
• WGK Germany：
  3
• 危险品运输编号：
  UN 3077 9/PG 3
• 危险性防范说明：
  P273
• 危险性描述：
  H302,H412
• 储存条件：
  密封保存，储存在阴凉干燥的仓库中。冷藏时温度应保持在2-8°C。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: Fmoc-β-phenyl-Phe-OH
Product name
CAS-No. : 201484-50-6
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
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute aquatic toxicity (Category 1)
Chronic aquatic toxicity (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H410 Very toxic to aquatic life with long lasting effects.
Precautionary statement(s)
P273 Avoid release to the environment.
P501 Dispose of contents/ container to an approved waste disposal plant.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in
the aquatic environment.
S-phrase(s)
S60 This material and its container must be disposed of as hazardous waste.
S61 Avoid release to the environment. Refer to special instructions/ Safety
data sheets.
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Fmoc-3,3-diphenyl-L-alanine
Fmoc-β,β-diphenyl-Ala-OH
N-(9-Fluorenylmethoxycarbonyl)-β-phenyl-L-phenylalanine
Formula : C30H25NO4
Molecular Weight : 463,52 g/mol
Component Concentration
Fmoc-β-phenyl-Phe-OH
CAS-No. 201484-50-6 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
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. Consult a physician.
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. Ensure adequate ventilation. Evacuate
personnel to safe areas.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. 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
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
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.
Immersion protection
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: > 480 min
Material tested:Dermatril® ( Z677272, Size M)
Splash protection
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: > 30 min
Material tested:Dermatril® ( Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone] test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an Industrial Hygienist familiar with the specific situation of anticipated use by our
customers. It should not be construed as offering an approval for any specific use scenario.
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 Melting point/range: 125 - 129 °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- log Pow: 4,637
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
Very toxic to aquatic life.

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 3077 IMDG: 3077 IATA: 3077
UN proper shipping name
ADR/RID: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Fmoc-β-phenyl-Phe-OH)
ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Fmoc-β-phenyl-Phe-OH)
IMDG:
Environmentally hazardous substance, solid, n.o.s. (Fmoc-β-phenyl-Phe-OH)
IATA:
Transport hazard class(es)
ADR/RID: 9 IMDG: 9 IATA: 9
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: yes IMDG Marine pollutant: yes IATA: yes
Special precautions for user
Further information
EHS-Mark required (ADR 2.2.9.1.10, IMDG code 2.10.3) for single packagings and combination
packagings containing inner packagings with Dangerous Goods > 5L for liquids or > 5kg for solids.

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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

(S)-2-((9H-芴-9-基)甲氧基羰基氨基)-3,3-二苯基丙酸是一种苯丙氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  Fmoc-Pbf-L-精氨酸 、 FMOC-N-L-BETA-二苯基丙氨酸 在 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 C₁₂₁H₁₅₃N₁₉O₂₀S₄
  参考文献：
  名称：

  小两亲性肽：对多种耐药细菌的活性和对膜分解特性的结构洞察

  摘要：

  我们报告了一系列两亲膜活性肽的合成和抗菌活性，这些肽部分由各种非遗传编码的疏水性氨基酸组成。先导环肽，8C和9C，对耐药革兰氏阳性菌（最低抑菌浓度 (MIC) = 1.5–6.2 μg/mL）和革兰氏阴性菌（MIC = 12.5–25 μg/mL）显示出广谱活性。细胞毒性研究表明，与哺乳动物细胞相比，肽对细菌的主要致死作用。一项血浆稳定性研究表明，在孵育 24 小时后，与线性对应物相比，铅环肽的稳定性大约高出 2 倍。钙黄绿素染料渗漏实验揭示了环肽的膜溶解作用。肽与磷脂双层相互作用的核磁共振光谱和分子动力学模拟研究为解释具有原子细节的肽的膜分解作用提供了坚实的结构基础。

  DOI：

  10.1021/acs.jmedchem.1c01782

文献信息

• Development of a fluorescent cardiomyocyte specific binding probe
  作者：Lara Pes、Young Kim、Ching-Hsuan Tung

  DOI：10.1016/j.bmc.2016.02.042

  日期：2016.4

  optimizing the affinity and the specificity towards cardiac myocytes and to better understand structure–activity relationship, a library of MTP derivatives was designed. Exploiting a fluorescent tag, the selectivity of the MTP analogs to myocardium over skeletal and stomach muscle tissues was assayed by fluorescence imaging. Among the tested sequences, the peptide probe Bip2, H-Lys(FITC)-Arg-Arg-Arg

  心肌细胞是心脏的主要成分。它们的功能失调或损坏可能导致严重的心血管疾病，在世界范围内夺走了无数生命。能够识别心肌细胞的分子在诊断和治疗中将具有重要价值。最近，一种称为肌细胞靶向肽（MTP）的新型肽具有非天然氨基酸联苯丙氨酸（Bip）的三个残基，对心肌细胞显示出良好的亲和力。结论其对心脏组织的选择性归因于Bip结合心肌肌钙蛋白I的能力。为了优化对心肌细胞的亲和力和特异性，并更好地了解结构-活性关系，设计了MTP衍生物库。利用荧光标签，通过荧光成像测定MTP类似物对骨骼肌和胃肌组织的心肌的选择性。在测试的序列中，肽探针Bip2，H-Lys（FITC）-Arg-Arg-Arg-Arg-Arg-Arg-Arg-Gly-Ser-Gly-Ser-Bip-Bip-NH2，显示出对心肌细胞的最佳选择性。
• Reversible Folding of a β-Hairpin Peptide by a Metal-Chelating Amino Acid
  作者：Jan Reutzel、Timm M. Diogo、Armin Geyer

  DOI：10.1002/chem.201700698

  日期：2017.6.22

  metal‐chelating properties of DOPA (3,4‐dihydroxy phenylalanine) but without its unwanted redox activity. The Fmoc‐protected amino acid Fmoc‐l‐Hop(tBu)‐OH (11) was synthesized from glycine phosphonate followed by enzymatic hydrolysis of the methyl ester yielding the Hop l‐isomer in 96 % ee. The amino acid 11 is used in automated peptide synthesis for the assembly of a 14mer β‐hairpin peptide with the sequence

  5-（1-羟基-吡啶-2-2 （1 H）-基）-1-丙氨酸（Hop）是具有N-羟基-1,2-吡啶酮官能化的α-氨基酸，具有所需的DOPA金属螯合性能（ 3,4-二羟基苯丙氨酸），但没有不需要的氧化还原活性。该Fmoc-保护的氨基酸的Fmoc-升-Hop（吨丁基）-OH（11）从甘氨酸膦酸盐，随后的甲酯得到的合的酶水解来合成升在96％异构体ee值。氨基酸11在自动化肽合成用于14merβ发夹肽的装配与序列[DSB 1，14 1 H-CH XETGKHGHKLVC‐OH（X = W，l‐ Hop）。而10π电子含有的吲哚侧链升-Trp在肽14只完成一个疏水簇的形成，并且在90％的折叠的结果，折叠部分被显著降低为6的π电子大约30％升-Hop侧链在肽16中。由于Ga（16）3三聚体的形成，Ga 3+的金属螯合将16的折叠重构到60％以上。16的螯合过程通过NMR光谱监测，随后Ga 3+的释放 竞
• Construction of Cyclophane-Braced Peptide Macrocycles via Palladium-Catalyzed Picolinamide-Directed Intramolecular C(sp²)–H Arylation
  作者：Boyang Han、Bo Li、Liping Qi、Peng Yang、Gang He、Gong Chen

  DOI：10.1021/acs.orglett.0c02422

  日期：2020.9.4

  A versatile method for the construction of C(sp2)-linked cyclophane peptide macrocycles via Pd-catalyzed picolinamide-directed intramolecular arylation of aryl and alkenyl C–H bonds of amino acid side chains with aryl iodides is developed. This method provides simple and efficient access to a variety of cyclophane-braced structures from readily accessible linear peptide precursors.

  开发了一种通过 Pd 催化的吡啶酰胺导向的氨基酸侧链的芳基和烯基 C-H 键与芳基碘进行分子内芳基化来构建 C(sp 2 ) 连接的环芳肽大环的通用方法。这种方法提供了从容易获得的线性肽前体中获得各种环芳支撑结构的简单有效的途径。
• Peptide Deformylase Inhibitors as Antibacterial Agents: Identification of VRC3375, a Proline-3-Alkylsuccinyl Hydroxamate Derivative, by Using an Integrated Combinatorial and Medicinal Chemistry Approach
  作者：D. Chen、C. Hackbarth、Z. J. Ni、C. Wu、W. Wang、R. Jain、Y. He、K. Bracken、B. Weidmann、D. V. Patel、J. Trias、R. J. White、Z. Yuan

  DOI：10.1128/aac.48.1.250-261.2004

  日期：2004.1

  Peptide deformylase (PDF), a metallohydrolase essential for bacterial growth, is an attractive target for use in the discovery of novel antibiotics. Focused chelator-based chemical libraries were constructed and screened for inhibition of enzymatic activity, inhibition ofStaphylococcus aureusgrowth, and cytotoxicity. Positive compounds were selected based on the results of all three assays. VRC3375 [N-hydroxy-3-R-butyl-3-(2-S-(tert-butoxycarbonyl)-pyrrolidin-1-ylcarbonyl)propionamide] was identified as having the most favorable properties through an integrated combinatorial and medicinal chemistry effort. This compound is a potent PDF inhibitor with aK_iof 0.24 nM against theEscherichia coliNi²⁺enzyme, possesses activity against gram-positive and gram-negative bacterial pathogens, and has a low cytotoxicity. Mechanistic experiments demonstrate that the compound inhibits bacterial growth through PDF inhibition. Pharmacokinetic studies of this drug in mice indicate that VRC3375 is orally bioavailable and rapidly distributed among various tissues. VRC3375 has in vivo activity againstS. aureusin a murine septicemia model, with 50% effective doses of 32, 17, and 21 mg/kg of body weight after dosing by intravenous (i.v.), subcutaneous (s.c.), and oral (p.o.) administration, respectively. In murine single-dose toxicity studies, no adverse effects were observed after dosing with more than 400 mg of VRC3375 per kg by i.v., p.o., or s.c. administration. The in vivo efficacy and low toxicity of VRC3375 suggest the potential for developing this class of compounds to be used in future antibacterial drugs.

  摘要肽变形酶（PDF）是细菌生长所必需的一种金属水解酶，是发现新型抗生素的一个有吸引力的目标。我们构建了基于螯合剂的化学库，并对其酶活性抑制、金黄色葡萄球菌生长抑制和细胞毒性进行了筛选。根据所有三项检测的结果筛选出阳性化合物。VRC3375 [N-羟基-3-R-丁基-3-(2-S-(叔丁氧羰基)-吡咯烷-1-基羰基)丙酰胺] 通过组合化学和药物化学的综合努力被鉴定为具有最有利的特性。该化合物是一种强效的 PDF 抑制剂，对大肠杆菌 Ni2+ 酶的 Kio 值为 0.24 nM，对革兰氏阳性和革兰氏阴性细菌病原体均有活性，而且细胞毒性低。机理实验证明，该化合物通过 PDF 抑制作用抑制细菌生长。该药物在小鼠体内的药代动力学研究表明，VRC3375 具有口服生物利用度，并能迅速分布于各种组织。在小鼠败血症模型中，VRC3375 对金黄色葡萄球菌具有体内活性，静脉注射、皮下注射和口服给药的 50%有效剂量分别为 32、17 和 21 毫克/千克体重。在小鼠单剂量毒性研究中，通过静脉注射、皮下注射或口服给药，每公斤剂量超过 400 毫克 VRC3375 后，未观察到任何不良反应。VRC3375 的体内疗效和低毒性表明，这类化合物具有开发潜力，可用于未来的抗菌药物中。
• χ-Conopeptide Pharmacophore Development: Toward a Novel Class of Norepinephrine Transporter Inhibitor (Xen2174) for Pain
  作者：Andreas Brust、Elka Palant、Daniel E. Croker、Barbara Colless、Roger Drinkwater、Brad Patterson、Christina I. Schroeder、David Wilson、Carsten K. Nielsen、Maree T. Smith、Dianne Alewood、Paul F. Alewood、Richard J. Lewis

  DOI：10.1021/jm9003413

  日期：2009.11.26

  Norepinephrine (NE) amplifies the strength of descending pain inhibition, giving inhibitors of spinal NET clinical utility in the management of pain. χ-MrIA isolated from the venom of a predatory marine snail noncompetitively inhibits NET and reverses allodynia in rat models of neuropathic pain. An analogue of χ-MrIA has been found to be a suitable drug candidate. On the basis of the NMR solution structure

  去甲肾上腺素（NE）增强了向下疼痛抑制的强度，使脊髓NET抑制剂在疼痛控制中具有临床应用价值。从掠食性海洋蜗牛毒液中分离得到的χ-MrIA非竞争性抑制NET并逆转神经性疼痛大鼠模型的异常性疼痛。已经发现χ-MrIA的类似物是合适的候选药物。基于该相关肽，Xen2174（3）的NMR溶液结构以及类似物的构效关系，提出了3与NET的变构结合的药效团模型。如图所示3NET主要通过第一个环中的氨基酸与NET相互作用，形成紧密的反向旋转，以允许与NET高亲和力相互作用的方向呈现氨基酸Tyr7，Lys8和Leu9。第二环与转运蛋白内的大疏水口袋相互作用。基于药效基团的类似物证明了支持所提出模型的活性。基于改善的化学稳定性和广泛的治疗指数，选择了3种药物进行进一步开发，目前处于II期临床试验中。