缬氨酰-苯丙氨酸 | 3918-92-1

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 缬氨酰-苯丙氨酸
• 英文名称: L-valyl L-phenylalanine
• 英文别名: Val-Phe-OH；L-valyl-L-phenylalanine；valylphenylalanine；(S)-Val-(S)-Phe；H-Val-Phe-OH；L-val-L-phe；(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-phenylpropanoic acid
• CAS: 3918-92-1
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: GJNDXQBALKCYSZ-RYUDHWBXSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Val-Phe
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 3918-92-1
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
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C14H20N2O3
Molecular Weight : 264,32 g/mol
CAS-No. : 3918-92-1
No components need to be disclosed according to the applicable regulations.

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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 vapours, mist or gas.
For personal protection see section 8.
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.
For precautions see section 2.2.
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: -20 °C
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
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) Evapouration 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) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
no data available
Germ cell mutagenicity
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
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Further information
Copyright 2014 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

生物活性 - L-Valyl-L-phenylalanine (Valylphenylalanine; H-VAL-PHE-OH) 是一种报道具有生物兼容性的聚合物。

靶点

Human Endogenous Metabolite

体外研究

由氨基酸组成的疏水侧链二肽酯类化合物，可能用于耗竭细胞毒性T淋巴细胞或自然杀伤细胞。

反应信息

• 作为反应物：
  描述：

  缬氨酰-苯丙氨酸 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 20.0~25.0 ℃ 、206.85 kPa 条件下， 反应 3.0h， 生成 H-甘氨酰-缬氨酰-苯丙氨酸
  参考文献：
  名称：

  三肽基肽酶II的抑制剂。2.产生第一个使胆囊收缩素8失活的肽酶的新型先导抑制剂：肽酶抑制剂设计的策略。

  摘要：

  失活胆囊收缩素8（CCK-8）的肽酶是一种丝氨酸肽酶，已证明是三肽基肽酶II的膜结合同工型（EC 3.4.14.10）。它在Met-Gly键处裂解神经递质CCK-8硫酸盐，得到Asp-Tyr（SO（3）H）-Met-OH + Gly-Trp-Met-Asp-Phe-NH（2）。为了寻找该肽酶的可逆抑制剂，使用基于人工底物Ala-Ala-Phe-酰胺基甲基香豆素水解的荧光分析法来表征酶促结合亚位点。对具有各种烷基或芳基侧链的一系列二肽和三肽进行了研究，以确定可结合的体积并探讨疏水相互作用的可能性。根据这项初步研究，三肽Ile-Pro-Ile-OH（K（i）= 1 microM）和Ala-Pro-Ala-OH（K（i）= 3 microM）和二肽酰胺Val-Nvl-NHBu（K（ i）= 3 microM）作为线索出现。这些结构的比较导致Val-Pro-NHBu（K（i）= 0.57 micr

  DOI：

  10.1021/jm990226g
• 作为产物：
  描述：

  CBZ-L-缬氨酸 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， -15.0~20.0 ℃ 、620.54 kPa 条件下， 反应 24.33h， 生成 缬氨酰-苯丙氨酸
  参考文献：
  名称：

  氨基酸和小肽催化的直接不对称分子间羟醛反应。

  摘要：

  在自然界中，至少有十九种不同的无环氨基酸可作为具有不同功能的多肽和蛋白质的组成部分。在这里我们报告，α-氨基酸，β-氨基酸和含有伯胺官能团的手性胺催化具有高对映选择性的直接不对称分子间羟醛反应。此外，氨基酸可以组合成高度模块化的天然和不寻常的小肽，它们还可以催化具有高立体选择性的直接不对称分子间羟醛反应，从而为相应的羟醛产物提供高达99％的ee。因此，简单的氨基酸和小肽可以催化不对称的醛缩反应，其立体选择性与数十亿年进化的天然酶的立体选择性相匹配。少量水会加速氨基酸和小肽催化的不对称羟醛反应，并增加其立体选择性。值得注意的是，小肽和氨基酸四唑能够催化具有高对映选择性的直接不对称醛醇缩合反应，而母体氨基酸则形成了几乎外消旋的产物。这些结果表明，氨基酸的益生元低聚为肽可能与糖的同手性的演化有关。还讨论了反应的机理和立体化学。小肽和氨基酸四唑可以催化具有高对映选择性的直接不对称醛醇缩合反应，而相

  DOI：

  10.1002/chem.200501639
• 作为试剂：
  描述：

  2,2-二甲基-1,3-二恶烷-5-酮 、 对硝基苯甲醛 在 缬氨酰-苯丙氨酸 作用下， 以 甲醇 为溶剂， 生成 (S)-4-((S)-hydroxy(4-nitrophenyl)methyl)-2,2-dimethyl-1,3-dioxan-5-one 、 4-(hydroxy(4-nitrophenyl)methyl)-2,2-dimethyl-1,3-dioxan-5-one
  参考文献：
  名称：

  The small peptide-catalyzed direct asymmetric aldol reaction in water

  摘要：

  N 末端带有伯胺的简单模块化二肽和三肽可催化未修饰的酮和醛之间的水性不对称羟醛反应，为相应的 β-羟基酮提供在水中高达 86% ee 和在水介质中高达 99% ee 的 β-羟基酮。

  DOI：

  10.1039/b515880j

文献信息

• Small peptides as modular catalysts for the direct asymmetric aldol reaction: ancient peptides with aldolase enzyme activity
  作者：Weibiao Zou、Ismail Ibrahem、Pawel Dziedzic、Henrik Sundén、Armando Córdova

  DOI：10.1039/b509920j

  日期：——

  Simple peptides and their analogues having a primary amino group as the catalytic residue mediate the direct asymmetric intermolecular aldol reaction with high stereoselectivity and furnish the corresponding aldol products with up to 99% ee; this intrinsic ability of highly modular peptides may explain the initial molecular evolution of aldolase enzymes.

  具有作为催化残基的主氨基的简单肽及其类似物，能以高立体选择性促进直接的不对称分子间醛醇反应，并生成最高达99% 对映体过量值的相应醛醇产物；这种高度模块化肽的内在能力可能解释了醛缩酶酶的初始分子进化过程。
• Redox-triggered changes in the self-assembly of a ferrocene–peptide conjugate
  作者：Bimalendu Adhikari、Heinz-Bernhard Kraatz

  DOI：10.1039/c3cc49268k

  日期：——

  Redox and ultrasound directed self-assembly of a ferrocene–peptide conjugate was studied, showing redox-controlled reorganization between gel nanofibers and spherical micelles.

  氧化还原和超声波引导的ferrocene-肽共轭物的自组装进行了研究，显示了在凝胶纳米纤维和球形胶束之间的氧化还原控制的重组。
• Synthesis and NMR elucidation of pentacycloundecane-derived hydroxy acid peptides as potential anti-HIV-1 agents
  作者：Rajshekhar Karpoormath、Fernando Albericio、Thavendran Govender、Glenn E. M. Maguire、Hendrik G. Kruger

  DOI：10.1007/s11224-012-0164-2

  日期：2013.10

  The synthesis and NMR elucidation of eight novel peptides incorporating the pentacycloundecane (PCU)-derived hydroxy acid are reported. The PCU cage amino acids were synthesized as racemates and the incorporation of the PCU-derived hydroxy acid with natural (S)-amino acids produced inseparable diastereomeric peptides. A series of overlapping signals from the cage and that of the peptide side chain

  报道了八种新型肽的合成和核磁共振分析，其中包含五环十一烷 (PCU) 衍生的羟基酸。PCU 笼氨基酸被合成为外消旋物，并且 PCU 衍生的羟基酸与天然 (S)-氨基酸的结合产生不可分离的非对映体肽。在 1H- 和 13C-NMR 光谱中观察到来自笼子和肽侧链的一系列重叠信号，使其阐明复杂化。二维核磁共振技术被证明是克服这些困难的非常有用的工具。这些化合物是潜在的 HIV 蛋白酶抑制剂。
• Organic functionalization of ultradispersed nanodiamond: synthesis and applications
  作者：Wen-Wei Zheng、Yi-Han Hsieh、Yu-Chung Chiu、Sian-Jhu Cai、Chia-Liang Cheng、Chinpiao Chen

  DOI：10.1039/b904302k

  日期：——

  This work describes the chemical modification of ultradispersed nanodiamond results in the enrichment of the surface hydroxyl groups as by FT-IR, TGA, RGA-MS and XRD measurements. These hydroxyl groups can be conveniently functionalized with long chain alcohols (oxyhexanol) for easy manipulation of different functional groups. The surface loading of the oxyhexanol groups were found to be 0.13 mmol/g of nanodiamond. The functionalities on the surface of the modified nanodiamond afford a new solid phase for the synthesis of peptides to facilitate the covalent attachment of drug molecules. The conjugation of chiral ligands with a nanodiamond yields a new enantioselective heterogeneous catalyst that exhibits moderate to good enantioselectivity in the asymmetric aldol reaction.

  这项工作描述了超分散纳米金刚石的化学修饰，结果表明表面羟基的富集，通过傅里叶变换红外光谱（FT-IR）、热重分析（TGA）、气体放大质谱（RGA-MS）和X射线衍射（XRD）测量。这些羟基可以便利地与长链醇（氧己醇）功能化，以便于不同功能团的操作。氧己醇在纳米金刚石表面的负载量为0.13 mmol/g。改性纳米金刚石表面的功能团为合成肽提供了一种新的固相，以促进药物分子的共价结合。手性配体与纳米金刚石的结合产生了一种新的不对称选择性杂化催化剂，在不对称醛醇反应中表现出中等至良好的不对称选择性。
• Synthesis and structural characterization of a series of ternary copper(II)-L-dipeptide-neocuproine complexes. Study of their cytotoxicity against cancer cells including MDA-MB-231, triple negative breast cancer cells
  作者：Natalia Alvarez、Diana Viña、Celisnolia M. Leite、Luis F.S. Mendes、Alzir A. Batista、Javier Ellena、Antonio J. Costa-Filho、Gianella Facchin

  DOI：10.1016/j.jinorgbio.2019.110930

  日期：2020.2

  This work presents the synthesis and characterization of eight copper complexes [Cu(L-dipeptide)(neo)]·nH2O (neo = neocuproine) and their cytotoxic activities against tumor cell lines. The crystalline structure of [Cu(gly-val)(neo)]·3H2O, [Cu(gly-leu)(neo)]·H2O, [Cu(ala-gly)(neo)]·4H2O, [Cu(val-phe)(neo)]·4.5H2O and [Cu(phe-phe)(neo)]·3H2O were determined by single crystal X-ray diffraction. In all

  这项工作介绍了八种铜配合物[Cu（L-二肽）（neo）]·n （neo = neocuproine）的合成和表征，以及它们对肿瘤细胞系的细胞毒活性。[Cu（gly-val）（neo）]·3 ，[Cu（gly-leu）（neo）]·H2O，[Cu（ala-gly）（neo）]·4 ，[Cu（val通过单晶X射线衍射测定-（phe）（neo）]·4.5H 2 O和[Cu（phe-phe）（neo）]·3H 2O。在所有这些中，Cu（II）在方形锥体环境中是五配位的。固态观察到的配位保留在水溶液中的主要物质中，如电子顺磁共振和紫外可见光谱所表明的。通过圆二色性实验确定，该复合物对分离的DNA具有亲和力。此外，生物学实验表明，所有复合物均具有针对细胞系的高细胞毒活性：MDA-MB-231，MCF-7（人类转移性乳腺癌），首批三阴性，MCF-10A（人类正常乳腺细胞），A549（人类）肺

表征谱图