丁氧羰基-酪氨酸-苄氧基酯 | 19391-35-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酪氨酸类衍生物
• 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: 丁氧羰基-酪氨酸-苄氧基酯
• 英文名称: N-tert-butoxycarbonyl-L-tyrosine benzyl ester
• 英文别名: Boc-Tyr-OBn；benzyl (2S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate；(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate；benzyl (2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 19391-35-6
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: HZDNRJRGRZEVCM-SFHVURJKSA-N

物化性质

• 熔点：
  126.0 to 130.0 °C
• 沸点：
  543.8±50.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储温度应保持在0-5°C之间。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-Tyr-OBzl
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Boc-Tyr-OBzl
CAS number: 19391-35-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C21H25NO5
Molecular weight: 371.4

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

苄基(叔丁氧羰基)-L-酪氨酸是一种酪氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  丁氧羰基-酪氨酸-苄氧基酯 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (S)-2-tert-Butoxycarbonylamino-3-(4-ethoxycarbonylmethoxy-phenyl)-propionic acid
  参考文献：
  名称：

  Identification of a monoacid-Based, cell permeable, selective inhibitor of protein tyrosine phosphatase 1B

  摘要：

  Monoacid-based PTP1B inhibitors with improved physiochemical properties have been investigated. A (2-hydroxy-phenoxy) acetic acid-based phosphotyrosyl mimetic has been linked with an optimized second arylphosphate binding site ligand to produce compound 20 with low micromolar potency against PTP1B, good selectivity over TCPTP (20-fold) and high cell permeability in the Caco-2 system.

  DOI：

  10.1016/j.bmcl.2003.08.064
• 作为产物：
  描述：

  L-酪氨酸 在 碳酸氢钠 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 丁氧羰基-酪氨酸-苄氧基酯
  参考文献：
  名称：

  由含修饰酪氨酸的肽光化学形成醌甲基化物†

  摘要：

  我们已经证明，可以在肽结构中引入甲基苯醌（QM）前体，并用作肽修饰的光开关单元。在曼尼希反应中由受保护的酪氨酸制备QM前体1，并进一步用作肽合成的基础。此外，可以通过曼尼希反应将含有酪氨酸的肽转化成可光活化的QM前体，该反应可以提供单取代的衍生物2或双取代的衍生物3。通过在CH 3中的制备性辐射研究了修饰的酪氨酸1和二肽2和3的光化学反应性发生光脱氨基和光甲烷分解的OH。在肽结合QM前体经历photomethanolysis与量子效率Φ - [R = 0.1-0.2，其中所述肽主链，不影响其光化学反应性。从二肽形成QMS通过激光闪光光解检测（λ最大≈400纳米，τ= 100 μs–20 ms），并研究了它们与亲核试剂的反应性。因此，源自酪氨酸的QM前体可以是肽骨架的一部分，在电子激发后可以转化为QM，从而导致肽与不同试剂的反应。该原理证明显示了光化学引发肽修饰和与其他分子相互作用的能力，可

  DOI：

  10.1039/c6ob02191c

文献信息

• Peptide Synthesis in Aqueous Solution. V. Properties and Reactivities of (<i>p</i>-Hydroxyphenyl)benzylmethylsulfonium Salts for Direct Benzyl Esterification of<i>N</i>-Acylpeptides
  作者：Takashi Nakata、Masaru Nakatani、Masatoshi Takahashi、Jiro Okai、Yoshiaki Kawaoka、Katsushige Kouge、Hideo Okai

  DOI：10.1246/bcsj.69.1099

  日期：1996.4

  Some (p-hydroxyphenyl)benzylmethylsulfonium salts were prepared. These compounds generated a benzyl cation and converted not only N-acylamino acids but also N-acylpeptides into their corresponding benzyl esters without causing the racemization.

  制备了一些（对羟基苯基）苄基甲基硫盐。这些化合物生成了苄基阳离子，并且不仅将N-酰基氨基酸，还将N-酰基肽转化为其相应的苄基酯，而没有引起消旋化。
• Non-Covalent Binding of Tripeptides-Containing Tryptophan to Polynucleotides and Photochemical Deamination of Modified Tyrosine to Quinone Methide Leading to Covalent Attachment
  作者：Antonija Erben、Igor Sviben、Branka Mihaljević、Ivo Piantanida、Nikola Basarić

  DOI：10.3390/molecules26144315

  日期：——

  describing the highest reactivity of QMs with the GC reach regions of polynucleotides. Our investigations show a proof of principle that QM precursor can be imbedded into a peptide and used as a photochemical switch to enable alkylation of polynucleotides, enabling further applications in chemistry and biology.

  合成了一系列三肽TrpTrpPhe ( 1 )、TrpTrpTyr( 2 )和TrpTrpTyr[CH 2 N(CH 3 ) 2 ] ( 3 )，并研究了它们的光物理性质和与多核苷酸的非共价结合。荧光色氨酸残基（水性溶剂中的量子产率 Φ F = 0.03–0.06），允许对 DNA 和 RNA 的非共价结合进行荧光测定研究。此外，发现2×HCl和3×HCl对所有研究的双链 (ds)-多核苷酸具有高且相似的亲和力（log K a= 6.0–6.8）。然而，荧光光谱响应强烈依赖于碱基对组成：含 GC 的多核苷酸有效地淬灭 Trp 发射，与诱导双信号响应的 AT 或 AU 多核苷酸不同。即，添加过量超过研究肽的 AT(U) 多核苷酸诱导淬灭（归因于多核苷酸凹槽中的聚集），而当 DNA/RNA 超过肽时，观察到 Trp 的荧光增加。热变性和圆二色性 (CD) 实验支持肽结合在多核苷酸的凹槽内。光生醌甲基化物
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR STABILIZING TRANSTHYRETIN AND INHIBITING TRANSTHYRETIN MISFOLDING<br/>[FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS DE STABILISATION DE LA TRANSTHYRÉTINE ET D'INHIBITION DU MAUVAIS REPLIEMENT DE LA TRANSTHYRÉTINE
  申请人：PROTEGO BIOPHARMA INC

  公开号：WO2021154842A1

  公开（公告）日：2021-08-05

  Provided herein are compounds having activity against TTR related conditions, and pharmaceutically accepted salts and solvates thereof. Also provided are methods of using the compounds for inhibiting and preventing TTR aggregation and/or amyloid formation in the peripheral nerves, kidney, cardiac tissue, eye and CNS, and of treating a subject with peripheral TTR amyloidosis.

  本文件提供了对TTR相关疾病具有活性的化合物，以及可被药物接受的盐和溶剂化物。还提供了使用这些化合物来抑制和预防外周神经、肾脏、心肌组织、眼睛和中枢神经系统的TTR聚集和/或淀粉样蛋白形成的方法，以及治疗患有外周TTR淀粉样变性的主体的方法。
• Synthesis of the C-Terminal Macrocycle of Asperipin-2a
  作者：Sadegh Shabani、Jonathan M. White、Craig A. Hutton

  DOI：10.1021/acs.orglett.9b00488

  日期：2019.3.15

  A synthetic approach to the C-terminal macrocycle of asperipin-2a is presented. Two epimers were prepared, possessing R- and S-configurations at the β-position of Tyr3. Comparison of NMR data of the natural product with these isomers and X-ray crystallographic data for one macrocycle support assignment of the 2S,3S-configuration of Tyr3. Key steps in the synthesis include a stereoselective benzylic

  提出了一种合成方法，用于Caspase-2a的C末端大环。制备了两个差向异构体，它们在Tyr 3的β位置具有R和S构型。这些异构体和X射线晶体学数据为2的一个大环支持分配的天然产物的NMR数据的比较小号，3小号-酪氨酸的结构3。合成中的关键步骤包括酪氨酸残基的立体选择性苄基氧化和随后生成的氮丙啶的路易斯酸催化的开环。
• Pd/C-Catalyzed Chemoselective Hydrogenation in the Presence of a Phenolic MPM Protective Group Using Pyridine as a Catalyst Poison.
  作者：Hironao Sajiki、Kosaku Hirota

  DOI：10.1248/cpb.51.320

  日期：——

  Employment of a Pd/C–pyridine combination as a catalyst is a very useful method for the selective removal (hydrogenolysis) of phenolic O-benzyl, N-Cbz and benzyl ester protective groups and for the selective hydrogenation of nitro and olefin functions of phenol derivatives protected with the MPM group. These discriminatory results are apparently attributable to the effect of pyridine. The MPM group could be extensively applied to chemoselective hydrogenation as a protective group for phenolic hydroxyl functions.

  使用Pd/C-吡啶组合作为催化剂是一种非常有用的方法，用于选择性地去除（氢解）酚类化合物的O-苄基、N-Cbz和苄基酯保护基团，以及选择性地氢化带有MPM保护基团的酚类衍生物中的硝基和烯烃功能团。这些差异性结果显然归因于吡啶的作用。MPM基团可广泛应用于作为酚羟基功能团的选择性氢化保护基。