N-叔丁氧羰基-S-叔丁基-L-半胱氨酸 | 56976-06-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 半胱氨酸类衍生物
• 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-叔丁氧羰基-S-叔丁基-L-半胱氨酸
• 中文别名: 叔丁氧羰-S-叔丁基-L-半胱氨酸
• 英文名称: Boc-Cys(t-Bu)-OH
• 英文别名: Boc-L-Cys(t-Bu)-OH；Boc-Cys(tBu)-OH；(2R)-3-tert-butylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 56976-06-8
• 化学式: C₁₂H₂₃NO₄S
• mdl: MFCD00076918
• 分子量: 277.385
• InChiKey: OGARKMDCQCLMCS-QMMMGPOBSA-N

物化性质

• 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)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  Store at 0°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-Cys(tbu)-OH
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-Cys(tbu)-OH
CAS number: 56976-06-8

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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: C12H23NO4S
Molecular weight: 277.4

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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, sulfur 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

Boc-Cys(tBu)-OH 是一种半胱氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-S-叔丁基-L-半胱氨酸 在 三氟甲磺酸三甲基硅酯 、 二苯硫醚 作用下， 以 三氟乙酸 为溶剂， 反应 0.5h， 以97.1%的产率得到L-半胱氨酸
  参考文献：
  名称：

  肽的研究。CLII。用于肽合成的硬酸脱保护程序。

  摘要：

  考察了使用三甲基硅烷三氟甲磺酸酯作为肽脱保护试剂的效果，并探讨了软碱的作用。基于硬酸原理，提出了一种新的脱保护程序。

  DOI：

  10.1248/cpb.35.3447
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 D-S-叔丁基半胱氨酸 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 生成 N-叔丁氧羰基-S-叔丁基-L-半胱氨酸
  参考文献：
  名称：

  Cysteine-based fluorescence “turn-on” sensors for Cu²⁺ and Ag⁺

  摘要：

  半胱氨酸被转化为荧光开关传感器，用于检测Cu⁺²和Ag⁺。通过光谱学、显微镜、热量计和计算方法对金属离子结合进行了详细研究。

  DOI：

  10.1039/c4ra10936h

文献信息

• Rapid and column-free syntheses of acyl fluorides and peptides using <i>ex situ</i> generated thionyl fluoride
  作者：Cayo Lee、Brodie J. Thomson、Glenn M. Sammis

  DOI：10.1039/d1sc05316g

  日期：——

  Thionyl fluoride (SOF2) was first isolated in 1896, but there have been less than 10 subsequent reports of its use as a reagent for organic synthesis. This is partly due to a lack of facile, lab-scale methods for its generation. Herein we report a novel protocol for the ex situ generation of SOF2 and subsequent demonstration of its ability to access both aliphatic and aromatic acyl fluorides in 55–98%

  亚硫酰氟 (SOF 2 ) 于 1896 年首次分离出来，但随后关于其用作有机合成试剂的报道不到 10 例。这部分是由于缺乏简便的、实验室规模的方法来生成它。在这里，我们报告了一种用于异地生成 SOF 2的新协议随后证明了它在温和条件和短反应时间下以 55-98% 的分离产率获得脂肪族和芳香族酰氟的能力。我们进一步证明了它在氨基酸偶联方面的能力，采用一锅无柱策略，以 65-97% 的分离产率提供相应的二肽，且差向异构化最少甚至没有。广泛的范围允许广泛的保护基团以及天然和非天然氨基酸。最后，我们证明了这种新方法可用于连续液相肽合成 (LPPS)，以 14-88% 的收率提供三肽、四肽、五肽和十肽，而无需柱层析。我们还证明了这种新方法适用于固相肽合成 (SPPS)，以 80-98% 的产率提供二肽和五肽。
• Substrate-Directed Lewis-Acid Catalysis for Peptide Synthesis
  作者：Wataru Muramatsu、Tomohiro Hattori、Hisashi Yamamoto

  DOI：10.1021/jacs.9b03850

  日期：2019.8.7

  A Lewis-acid-catalyzed method for the substrate-directed formation of peptide bonds has been developed, and this powerful approach is utilized for the new "remote" activation of carboxyl groups under solvent-free conditions. The presented method has the following advantages: 1) the high-yielding peptide synthesis uses a tantalum catalyst for any amino acids; 2) the reaction proceeds without any racemization;

  一种路易斯酸催化的底物定向形成肽键的方法已经被开发出来，这种强大的方法被用于在无溶剂条件下对羧基进行新的“远程”活化。该方法具有以下优点：1）高产肽合成对任何氨基酸均使用钽催化剂；2) 反应进行时没有任何外消旋化；3）采用钛催化剂的新型底物导向化学连接适用于会聚肽合成。这些优势克服了经典肽合成中一些未解决的问题。
• Chemical Synthesis of Glycoproteins with the Specific Installation of Gradient-Enriched¹⁵N-Labeled Amino Acids for Getting Insights into Glycoprotein Behavior
  作者：Nguyen Minh Hien、Masayuki Izumi、Hajime Sato、Ryo Okamoto、Yasuhiro Kajihara

  DOI：10.1002/chem.201606049

  日期：2017.5.11

  the attachment of an oligosaccharide of either a bi‐antennary complex‐type or a high‐mannose‐type did not disturb protein conformation. However, T1 values suggested that the oligosaccharide influenced dynamics at the local conformation. Temperature‐varied circular dichroism (CD) spectra and T1 values clearly indicated that oligosaccharides appeared to inhibit protein fluctuation or, in other words

  阐明寡糖对糖蛋白特性（例如局部构象变化，稳定性和动力学）的影响仍然具有挑战性。本文提出了一种新的部分15 N标记方法，用于合成糖蛋白的酰胺主链。使用固相肽合成（SPPS）和天然化学连接（NCL），在蛋白质主链的特定位置插入了13个15 N标记的氨基酸，同时有意地改变了15 N原子的富集度。根据1 H- 15的强度，这种想法甚至可以区分相同类型的氨基酸N HSQC信号与经典的同核TOCSY和NOESY方法相结合，因此可以理解合成的同质糖蛋白的局部构象动态。结果表明，双天线复合型或高甘露糖型寡糖的附着均不会干扰蛋白质构象。然而，T 1值表明寡糖影响局部构象的动力学。温变圆二色性（CD）光谱和T 1值清楚地表明，寡糖似乎抑制了蛋白质的波动，或者换句话说，稳定了蛋白质的结构。对寡糖行为的这种了解表明，它对糖蛋白与其受体之间的结合亲和力有进一步的影响。
• Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method
  申请人：——

  公开号：US20020019411A1

  公开（公告）日：2002-02-14

  Dipeptidyl peptidase IV (DP 4) inhibiting compounds are provided having the formula 1 where x is 0 or 1 and y is 0 or 1 (provided that x=1 when y=0 and x=0 when y=1); n is 0 or 1; X is H or CN; and wherein R 1 , R 2 , R 3 and R 4 are as described herein. A method is also provided for treating diabetes and related diseases, especially Type II diabetes, and other diseases as set out herein, employing such DP 4 inhibitor or a combination of such DP 4 inhibitor and one or more of another antidiabetic agent such as metformin, glyburide, troglitazone, pioglitazone, rosiglitazone and/or insulin and/or one or more of a hypolipidemic agent and/or anti-obesity agent and/or other therapeutic agent.

  提供了具有公式1的抑制二肽基肽酶IV（DP 4）的化合物，其中x为0或1，y为0或1（前提是当y=0时，x=1，当y=1时，x=0）；n为0或1；X为H或CN；其中R1、R2、R3和R4如本文所述。还提供了一种治疗糖尿病和相关疾病，特别是II型糖尿病以及本文中列出的其他疾病的方法，使用这种DP 4抑制剂或这种DP 4抑制剂与另一种或多种抗糖尿病药物（如二甲双胍、格列本脲、曲格列酮、吡格列酮、罗格列酮和/或胰岛素）的组合，以及一种或多种降脂药物和/或抗肥胖药物和/或其他治疗药物。
• Compounds and Methods for Inhibiting the Interaction of BCL Proteins with Binding Partners
  申请人：CASTRO C. Alfredo

  公开号：US20080114167A1

  公开（公告）日：2008-05-15

  The invention relates to isoxazolidine containing compounds that bind to bcl proteins and inhibit Bcl function. The compounds may be used for treating and modulating disorders associated with hyperproliferation, such as cancer.

  该发明涉及含有结合到Bcl蛋白并抑制Bcl功能的异氧杂环丙氨酸化合物。这些化合物可用于治疗和调节与过度增殖相关的疾病，如癌症。