O-苯基-N-叔丁基羰基-L-酪氨酸 | 16677-29-5

• 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: O-苯基-N-叔丁基羰基-L-酪氨酸
• 中文别名: Z-O-苄基-L-酪氨酸；苄氧羰基-O-苄基-L-酪氨酸；N-苄氧羰基-O-苄基-L-酪氨酸
• 英文名称: N-benzyloxycarbonyl-O-benzyl-L-tyrosine
• 英文别名: Cbz-Tyr(Bn)-OH；N-Cbz-O-benzyl-L-tyrosine；Z-Tyr(Bn)OH；(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(benzyloxy)phenyl)propanoic acid；Nα-Benzyloxycarbonyl-O-benzyl-L-tyrosine；Z-Tyr(Bzl)-OH；(2S)-2-(phenylmethoxycarbonylamino)-3-(4-phenylmethoxyphenyl)propanoic acid
• CAS: 16677-29-5
• 化学式: C₂₄H₂₃NO₅
• mdl: MFCD00037819
• 分子量: 405.45
• InChiKey: IPAODWFPTVIUSZ-QFIPXVFZSA-N

物化性质

• 沸点：
  624.4±55.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Z-Tyr(Bzl)-OH
CAS-No. : 16677-29-5
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
Synonyms : Z-O-benzyl-L-tyrosine
Formula : C24H23NO5
Molecular Weight : 405,44 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.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.
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: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 102 - 112 °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 bases, Strong acids, 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
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

Z-Tyr(Bzl)-OH 是一种酪氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  O-苯基-N-叔丁基羰基-L-酪氨酸 在 茴香硫醚 、 N,N'-二环己基碳二亚胺 作用下， 以 三氟乙酸 为溶剂， 反应 4.0h， 生成 蛋氨酸-脑啡呔
  参考文献：
  名称：

  使用硫代苯甲醚-三氟乙酸通过“推-拉”机制有效去除N-苄氧基羰基，以合成Met-脑啡肽为例

  摘要：

  该Ñ -苄氧羰基可在温和条件下平稳地切割，用苯硫基甲烷-三氟乙酸，其可以脱保护ö -benzyltyrosine而不形成ø -到- Ç重排产物; 该去嵌段方法已成功地用于合成Met-脑啡肽。

  DOI：

  10.1039/c39800000101
• 作为产物：
  描述：

  N-benzyloxycarbonyl-O-benzyl-L-tyrosine benzyl ester 在 palladium on activated charcoal 、 乙二胺 三乙烯二胺 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 24.0h， 以72%的产率得到O-苯基-N-叔丁基羰基-L-酪氨酸
  参考文献：
  名称：

  Pd/C(en)-Catalyzed Chemoselective Hydrogenation with Retention of the N-Cbz Protective Group and its Scope and Limitations

  摘要：

  A chemoselective method for the hydrogenation of acetylene, olefin, azide, nitro and benzyl ester functionalities with retention of the aliphatic N-Cbz group was established. The chemoselectivity was accomplished by using a combination of 5% Pd/C-ethylenediamine [5% Pd/C(en)] and THF (or 1,4-dioxane) as a solvent, and the scope and limitations of this methodology were investigated. These results reinforce the utility of N-Cbz protective groups in synthetic chemistry, especially in peptide synthesis (C) 2000 Elsevier Science Ltd. All lights reserved.

  DOI：

  10.1016/s0040-4020(00)00771-7

文献信息

• Hydrodehalogenation of Alkyl Iodides with Base-Mediated Hydrogenation and Catalytic Transfer Hydrogenation: Application to the Asymmetric Synthesis of N-Protected α-Methylamines
  作者：Pijus K. Mandal、J. Sanderson Birtwistle、John S. McMurray

  DOI：10.1021/jo500911v

  日期：2014.9.5

  We report a very mild synthesis of N-protected α-methylamines from the corresponding amino acids. Carboxyl groups of amino acids are reduced to iodomethyl groups via hydroxymethyl intermediates. Reductive deiodination to methyl groups is achieved by hydrogenation or catalytic transfer hydrogenation under alkaline conditions. Basic hydrodehalogenation is selective for the iodomethyl group over hydrogenolysis-labile

  我们报告了从相应的氨基酸非常温和地合成 N-保护的 α-甲胺。氨基酸的羧基通过羟甲基中间体被还原为碘甲基。在碱性条件下通过氢化或催化转移氢化实现甲基的还原脱碘。碱性加氢脱卤对碘甲基的选择性高于氢解不稳定的保护基团，例如苄氧羰基、苄酯、苄醚和 9-芴氧基甲基，因此几乎可以将任何受保护的氨基酸转化为相应的 N-保护的 α-甲胺。
• Design and Synthesis of Peptides Passing through the Blood-Brain Barrier
  作者：Tateaki Wakamiya、Makoto Kamata、Shoichi Kusumoto、Hiroyuki Kobayashi、Yoshimichi Sai、Ikumi Tamai、Akira Tsuji

  DOI：10.1246/bcsj.71.699

  日期：1998.3

  The blood-brain barrier (BBB) is a highly selective membranous barrier regulating the transport of substances in blood into the brain parenchyma. At present, delivery of biologically active peptides or peptide drugs into the brain is quite an important subject from the standpoint of chemotherapy for brain diseases. H–MeTyr–Arg–MeArg–d-Leu–NH(CH2)8NH2 termed 001-C8 was first synthesized to elucidate the structural specificity of peptides for passing through the BBB. The Nα-methylamino acid and d-amino acid residues were appropriately situated in this peptide to protect against the digestion by peptidase. Furthermore, a number of basic peptides were prepared as 001-C8 analogs for studying the relationship between structure and BBB permeability of peptides.

  血脑屏障（BBB）是一种高度选择性的膜屏障，调控血液中的物质向脑实质内的转运。目前，从脑部疾病化学治疗的角度出发，如何将生物活性肽或肽类药物递送入脑是一个相当重要的课题。首先合成了名为001-C8的H-MeTyr-Arg-MeArg-d-Leu-NH(CH2)8NH2，以阐明肽穿越BBB所需的结构特异性。在此肽中，Nα-甲基氨基酸和d-氨基酸残基适当地分布，以防止被肽酶降解。此外，还制备了一批001-C8类似物，即多种碱性肽，用于研究肽的结构与其BBB通透性之间的关系。
• Benzotriazole-Mediated Synthesis of Aza-peptides: En Route to an Aza-Leuenkephalin Analogue
  作者：Nader E. Abo-Dya、Suvendu Biswas、Akash Basak、Ilker Avan、Khalid A. Alamry、Alan R. Katritzky

  DOI：10.1021/jo302251e

  日期：2013.4.19

  with an ester bond 26b, and a hybrid azatripeptide with an ester bond 28. A new protocol for the synthesis of N-Pg-azatripeptides 33a,b and 35a,b, each containing a natural amino acid at the N-terminus, avoids the low coupling rates of the aza-amino acid residue and enables the solution-phase synthesis of an azaphenylalanine analogue of Leu-enkephalin 40.

  新颖ñ - （Ñ -Pg-azadipeptidoyl）苯并三唑20A - ë与α氨基酸有效耦合21A - ë，二肽22A - Ç，氨基羟乙酸23A，depsidipeptide 23B，和α羟基β苯基丙酸27屈服，分别，三氮杂肽24a – g，氮杂三肽25a，b，具有氧酰胺键的杂合氮杂三肽26a，具有酯键的杂合氮杂四肽26b杂化的带有酯键的氮杂三肽28。用于合成N -Pg-氮杂三肽33a，b和35a，b的新方案，每个肽在N-末端均包含天然氨基酸，避免了氮杂氨基酸残基的低偶联率并使溶液相成为可能。亮脑啡肽40的氮杂苯丙氨酸类似物的合成。
• Oxyazapeptides: Synthesis, Structure Determination, and Conformational Analysis
  作者：Suvendu Biswas、Nader E. Abo-Dya、Alexander Oliferenko、Amir Khiabani、Peter J. Steel、Khalid A. Alamry、Alan R. Katritzky

  DOI：10.1021/jo401234g

  日期：2013.9.6

  we report the synthesis, X-ray structure determination, and conformational analysis of a novel class of heteroatom-modified peptidomimetics, which we shall call “oxyazapeptides”. Substituting the typical native N-Cα bond with an O-Nα bond creates a completely new, previously unknown family of peptidomimetics, which are hydrolytically stable and display very interesting conformational behavior. Force

  在本文中，我们报告了一类新型的杂原子修饰的拟肽模拟物的合成，X射线结构测定和构象分析，我们将其称为“氧杂肽”。代典型的原生NC α与债券α债券创建一个全新的，以前未知的家族肽，它们是水解稳定和显示非常有趣的构象的行为。力场计算表明，屏障围绕ON旋转α在oxyazapeptides键比NN周围低五倍α氮杂肽中的键。此外，X射线支持的构象分析表明，氧杂氮杂部分可以有效诱导β转角，这可以使新发现的氧杂氮杂肽支架成为药物发现和生物制剂设计的有用工具。
• [EN] MACROCYCLIZATION OF PEPTIDOMIMETICS<br/>[FR] MACROCYCLISATION DE PEPTIDOMIMÉTIQUES
  申请人：UNIV WARWICK

  公开号：WO2019186174A1

  公开（公告）日：2019-10-03

  The invention provides an improved method of macrocyclization of peptidomimetics, as measured by isolated yields and product distribution, which comprises substitution of one or more of the backbone amide C=O bonds with a turn-inducing motif. The method is general with enhancements seen across a range of ring sizes (e.g. tri-, tetra-, penta- and hexapeptides). Specifically, the invention provides a peptidomimetic macrocycle comprising a carbonyl bioisosteric turn-inducing element having the structure: (I) wherein X is a heteroatom; and wherein R1 to R6 are each independently selected from alkyl, aryl, heteroaryl and H.

  该发明提供了一种改进的肽类类似物的大环化方法，通过孤立产量和产物分布来衡量，其中包括用诱导转向基团替代一个或多个骨架酰胺C=O键。该方法是通用的，在一系列环大小（例如三肽、四肽、五肽和六肽）中均可见到增强效果。具体而言，该发明提供了一种包含具有结构的羰基生物等同体诱导转向元素的肽类类似物大环：（I）其中X是杂原子；其中R1至R6分别独立地选自烷基、芳基、杂芳基和氢。