N-苄氧羰基-O-叔丁基-L-酪氨酸二环己胺盐 | 16879-90-6

• 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: N-苄氧羰基-O-叔丁基-L-酪氨酸二环己胺盐
• 中文别名: Z-O-O-叔丁基-L-酪氨酸二环己胺盐
• 英文名称: N-Z-O-tert-butyl-L-tyrosine dicyclohexylammonium salt
• 英文别名: Z-L-Tyr(Bu^t)-OH*DCHA；N-α-benzyloxycarbamoyl-O-t-butyl-L-tyrosine dicyclohexylammonium salt；Cbz-Tyr(tBu)-OH DCHA salt；Z-Tyr(OtBu)-OH*DCHA；(S)-Cbz-tyrosine t-butyl ether DCHA salt；Cbz-Tyr(tBu)-OH*DCHA；Z-Tyr(tBu)-OH*DCHA；Z-O-tert.butyl-L-tyrosine dicyclohexylamine salt；dicyclohexylazanium;(2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 16879-90-6
• 化学式: C₁₂H₂₃N*C₂₁H₂₅NO₅
• mdl: MFCD00038245
• 分子量: 552.755
• InChiKey: FDNJRKLIHBJXIR-FERBBOLQSA-N

物化性质

• 熔点：
  158-161 °C
• 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)：
  4.14
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.575
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-Tyr(tbu)-oh dcha
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: Z-Tyr(tbu)-oh dcha
CAS number: 16879-90-6

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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.
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.C12H23N
Molecular weight: 552.8

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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

反应信息

• 作为反应物：
  描述：

  N-苄氧羰基-O-叔丁基-L-酪氨酸二环己胺盐 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 生成 O-叔丁基-L-酪氨酸
  参考文献：
  名称：

  Jost,K., Collection of Czechoslovak Chemical Communications, 1971, vol. 36, p. 218 - 233

  摘要：

  DOI：

文献信息

• Synthesis and Properties of the retro-Analogue of Myelopeptide MP-2
  作者：L. A. Fonina、M. V. Ovchinnikov、S. A. Gur’yanov、S. V. Sychev、R. G. Belevskaya、E. M. Treshchalina

  DOI：10.1007/s11171-005-0029-1

  日期：2005.5

  The bone marrow myelopeptide MP-2 (Leu-Val-Val-Tyr-Pro-Trp), exhibiting antitumor activity, and its retro-analogue (Trp-Pro-Tyr-Val-Val-Leu) were synthesized, and their properties were studied. The in vitro and in vivo activities of retro-MP-2 were comparable with those of MP-2. Both peptides equally restored the functional activity of T-lymphocytes inhibited by toxins released by HL-60 cells and inhibited by 70–82% the growth of various types of transplantable solid tumors: Ca-755 adenocarcinoma of the mammary gland, Lewis adenocarcinoma of the lung, and S180 sarcoma. The positions and intensities of the Cotton effects in CD spectra of the MP-2 peptide and its retro-analogue in various solvents are almost indistinguishable. The positions of extrema and integral intensities of the amide I and amide A bands in IR spectra of both peptides were practically identical.

  合成了具有抗肿瘤活性的骨髓髓肽 MP-2 (Leu-Val-Val-Tyr-Pro-Trp) 及其逆向类似物 (Trp-Pro-Tyr-Val-Val-Leu)，其特性为研究过。 Retro-MP-2的体外和体内活性与MP-2相当。两种肽均能恢复受 HL-60 细胞释放毒素抑制的 T 淋巴细胞的功能活性，并抑制各种类型可移植实体瘤生长 70-82%：乳腺 Ca-755 腺癌、Lewis 腺癌肺和 S180 肉瘤。 MP-2 肽及其逆类似物在各种溶剂中的 CD 光谱中 Cotton 效应的位置和强度几乎无法区分。两种肽的红外光谱中酰胺 I 和酰胺 A 带的极值位置和积分强度几乎相同。
• MC-1. A “designer” surfactant engineered for peptide synthesis in water at room temperature
  作者：Margery Cortes-Clerget、Summer E. Spink、Gregory P. Gallagher、Laurent Chaisemartin、Edith Filaire、Jean-Yves Berthon、Bruce H. Lipshutz

  DOI：10.1039/c9gc01050e

  日期：——

  Aqueous micellar catalysis has previously been shown to be an enabling technology for green peptide synthesis. Nonetheless, in response to limitations associated with use of selected amino acids in peptide constructions, a new surfactant has been designed, inspired by the commonplace use of the environmentally egregious dipolar aprotic solvent DMSO. A new amphiphile, MC-1, introduces a highly polar

  胶束水催化作用先前已被证明是绿色肽合成的一项可行技术。然而，响应于在肽结构中使用选定氨基酸的局限性，在环境上令人讨厌的偶极非质子溶剂DMSO的普遍使用的启发下，已经设计了一种新的表面活性剂。新的两亲物MC-1将高极性砜组分引入表面活性剂的非极性区域，从而引入其衍生的纳米胶束的内芯。这不仅导致解决了溶解性问题，而且导致了高收率，易于处理反应混合物以及消除了助溶剂。革兰氏反应也在本文中描述。
• Pattern-Based Detection of Different Proteins Using an Array of Fluorescent Protein Surface Receptors
  作者：Laura Baldini、Andrew J. Wilson、Jason Hong、Andrew D. Hamilton

  DOI：10.1021/ja039562j

  日期：2004.5.1

  A small library of porphyrin derivatives whose fluorescence emission changes on binding to protein surfaces has been developed as a protein "fingerprinting" array. When incubated with different proteins, the array yields a characteristic response, specific for every protein analyte. At the same time, this design allows for the rapid screening of the porphyrin library for the identification of high

  一个小的卟啉衍生物库，其荧光发射在与蛋白质表面结合时发生变化，已被开发为蛋白质“指纹”阵列。当与不同的蛋白质一起孵育时，该阵列会产生对每种蛋白质分析物特异的特征响应。同时，这种设计允许快速筛选卟啉库，以识别高亲和力蛋白质表面配体。
• Substituted 2-Imino-5-arylidenethiazolidin-4-one Inhibitors of Bacterial Type III Secretion
  作者：Toni Kline、Heather B. Felise、Kathleen C. Barry、Stona R. Jackson、Hai V. Nguyen、Samuel I. Miller

  DOI：10.1021/jm8004515

  日期：2008.11.27

  factors that help establish and maintain infection. Disruption of such secretion systems is a potentially effective therapeutic strategy. We developed a high-throughput screen and identified a tris-aryl substituted 2-imino-5-arylidenethiazolidin-4-one, compound 1, as an inhibitor of the type III secretion system. Expansion of this chemotype enabled us to define the essential pharmacophore for type III

  多种致病性革兰氏阴性细菌利用分泌系统输出各种有助于建立和维持感染的蛋白质毒素和毒力因子。破坏这种分泌系统是一种潜在的有效治疗策略。我们开发了一个高通量的筛选器，并确定了三化合物被化合物1取代的三芳基取代的2-亚氨基5-芳基内酯-硫唑烷4-1，它是III型分泌系统的抑制剂。这种化学型的扩展使我们能够定义该结构类别用于抑制III型分泌的基本药效基团。合成多样性集帮助我们将N-3鉴定为最允许的基因座，并导致设计了一组具有改善的活性和理化性质的新型N-3-二肽修饰的同类物。现在，我们报告这些化合物的合成，
• Synthetic studies on enkephalin analogs. II. Enhanced analgesic activity of H-Tyr-D-Ala-Gly-Phe-NHNH-CO-CH2CH3 following N-methylation of Tyr and Phe.
  作者：SUSUMU SHINAGAWA、MASAHIKO FUJINO、HARUMITSU ISHII、KIYOHISA KAWAI

  DOI：10.1248/cpb.29.3639

  日期：——

  In order to study the effect of N-methylation of a potent enkephalin analog, H-Tyr-D-Ala-Gly-Phe-NHNH-CO-CH2CH3, on analgesic activity, six new analogs were synthesized in which one or more of amino acid residues and the acyl-hydrazide constituting the tetrapeptide acyl-hydrazide were N-methylated. N-Methylation of both Tyr at position 1 and Phe at position 4 of the analog led to a derivative which was twice as potent as morphine. On the other hand, N-methylation of D-Ala at position 2, Gly at position 3 or NHNH-CO-CH2CH3 at position 5 markedly decreased the analgesic potency. Five analogs with a modified tyrosine residue at position 1 of the tetrapeptide acyl-hydrazide were also synthesized in order to assess the role of the N-terminal Tyr residue in the biological activity.

  为了研究强效脑啡肽类似物 H-Tyr-D-Ala-Gly-Phe-NHNH-CO-CH2CH3的 N-甲基化对镇痛活性的影响，我们合成了六种新的类似物，其中一个或多个氨基酸残基和构成四肽酰肼的酰基被 N-甲基化。将类似物中位于 1 号位置的 Tyr 和位于 4 号位置的 Phe N-甲基化后，得到的衍生物的药效是吗啡的两倍。另一方面，第 2 位 D-Ala、第 3 位 Gly 或第 5 位 NHNH-CO-CH2CH3 的 N-甲基化会明显降低镇痛效力。为了评估 N 端 Tyr 残基在生物活性中的作用，我们还合成了五种在四肽酰肼的第 1 位修饰了酪氨酸残基的类似物。