(S)-2-((叔丁氧基羰基)氨基)-3-疏基丙酸 | 149270-12-2

• 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: (S)-2-((叔丁氧基羰基)氨基)-3-疏基丙酸
• 中文别名: Boc-D-半胱氨酸；BOC-D-半胱氨酸
• 英文名称: Boc-D-Cys-OH
• 英文别名: (S)-2-((tert-Butoxycarbonyl)amino)-3-mercaptopropanoic acid；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-sulfanylpropanoic acid
• CAS: 149270-12-2
• 化学式: C₈H₁₅NO₄S
• 分子量: 221.277
• InChiKey: ATVFTGTXIUDKIZ-RXMQYKEDSA-N

物化性质

• 沸点：
  361.4±37.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  76.6
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2930909090
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P260,P264,P270,P273,P280,P301+P312+P330,P304+P312,P305+P351+P338,P314,P337+P313,P391,P501
• 危险品运输编号：
  3077
• 危险性描述：
  H302,H319,H332,H372,H400

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-d-cys-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-d-cys-oh
CAS number: 149270-12-2

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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: C8H15NO4S
Molecular weight: 221.3

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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

反应信息

• 作为反应物：
  描述：

  (S)-2-((叔丁氧基羰基)氨基)-3-疏基丙酸 在 氢氧化钾 、 ammonium chloride 、 四丁基碘化铵 、 碳酸氢钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (3S)-3-[[叔丁氧羰基]氨基]-3,4-二氢-4-氧代-1,5-苯并硫氮杂卓-5(2H)-乙酸乙酯
  参考文献：
  名称：

  AN IMPROVED SYNTHESIS OF (S)- OR (R)-N-BcE-PROTECTED 1,5-BENZOTHIAZEPINE DERIVATIVES

  摘要：

  DOI：

  10.1080/00304940209458076
• 作为产物：
  描述：

  di-N,N-(tert-butyloxycarbonyl)-D-cystine 生成 (S)-2-((叔丁氧基羰基)氨基)-3-疏基丙酸
  参考文献：
  名称：

  EUERBY, MELVIN;PARTRIDGE, LYNDA Z.;GIBBONS, WILLIAM A., J. CHROMATOGR., 483,(1989) C. 239-252

  摘要：

  DOI：

文献信息

• Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base
  作者：Tanmay Chatterjee、Brindaban C. Ranu

  DOI：10.1039/c3ra41996g

  日期：——

  An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields.

  在没有任何催化剂、共氧化剂、溶剂或碱的情况下，通过球磨中性氧化铝（研磨辅助剂），实现了硫醇到二硫化物的有效有氧化学选择性氧化。多种功能化的二芳基、二杂芳基和二烷基二硫化物以高产率获得。
• Photoredox Mediated Nickel Catalyzed Cross-Coupling of Thiols With Aryl and Heteroaryl Iodides via Thiyl Radicals
  作者：Martins S. Oderinde、Mathieu Frenette、Daniel W. Robbins、Brian Aquila、Jeffrey W. Johannes

  DOI：10.1021/jacs.5b11244

  日期：2016.2.17

  Ni-catalyzed cross-couplings of aryl, benzyl, and alkyl thiols with aryl and heteroaryl iodides were accomplished in the presence of an Ir-photoredox catalyst. Highly chemoselective C-S cross-coupling was achieved versus competitive C-O and C-N cross-couplings. This C-S cross-coupling method exhibits remarkable functional group tolerance, and the reactions can be carried out in the presence of molecular

  Ni催化的芳基、苄基和烷基硫醇与芳基和杂芳基碘化物的交叉偶联是在Ir-光氧化还原催化剂存在下完成的。与竞争性 CO 和 CN 交叉偶联相比，实现了高度化学选择性的 CS 交叉偶联。这种CS交叉偶联方法表现出显着的官能团耐受性，反应可以在分子氧存在下进行。机理研究表明，该反应是通过瞬态 Ni(I) 物种和硫基自由基进行的。与涉及碳中心自由基的镍催化交叉偶联反应不同，对照实验和光谱研究表明，这种 CS 交叉偶联反应不涉及 Ni(0) 物种。
• Synthesis and biological evaluation of N-mercaptoacylcysteine derivatives as leukotriene A4 hydrolase inhibitors
  作者：Hiroshi Enomoto、Yuko Morikawa、Yurika Miyake、Fumio Tsuji、Maki Mizuchi、Hiroshi Suhara、Ken-ichi Fujimura、Masato Horiuchi、Masakazu Ban

  DOI：10.1016/j.bmcl.2008.11.042

  日期：2009.1

  We studied synthetic modifications of N-mercaptoacylamino acid derivatives to develop a new class of leukotriene A4 (LTA4) hydrolase inhibitors. S-(4-Dimethylamino)benzyl-l-cysteine derivative 2a (SA6541) showed inhibitory activity against LTA4 hydrolase (IC50, 270 nM) and selectivity over other metallopeptidases except angiotensin-converting enzyme (ACE, IC50, 520 nM). Modification at the para-substituent

  我们研究了N-巯基酰基氨基酸衍生物的合成修饰，以开发一类新的白三烯A 4（LTA 4）水解酶抑制剂。小号- （4-二甲基氨基）苄基-升-半胱氨酸衍生物2A（SA6541）显示针对LTA抑制活性4水解酶（IC 50，270 nm）的和选择性优于其它金属肽除了血管紧张素转换酶（ACE，IC 50，520 nm）的。化合物2a苯环的对位取代基上的修饰改进了LTA 4水解酶抑制活性以及对ACE的选择性。最后，我们获得了作为有效的和选择性的LTA 4水解酶抑制剂的S-（4-环己基）苯并-1-半胱氨酸衍生物11l和16i。
• Synthesis of modified pyrimidine bases and positive impact of chemically reactive substituents on their in vitro antiproliferative activity
  作者：Steffi Noll、Marijeta Kralj、Lidija Šuman、Holger Stephan、Ivo Piantanida

  DOI：10.1016/j.ejmech.2008.06.002

  日期：2009.3

  The antiproliferative activity screening on human tumor cell lines of a series of modified uracil and cytosine bases as well as some corresponding acyclonucleosides, and comparison of structure–activity relationship revealed the importance of chemical reactivity of the substituent attached to the C5-position of uracil for the activity of studied compounds. Namely, the results obtained for the most

  一系列修饰的尿嘧啶和胞嘧啶碱基以及一些相应的无环核苷在人肿瘤细胞系中的抗增殖活性筛选，以及结构-活性关系的比较表明，尿嘧啶C5位上取代基的化学反应活性对于研究化合物的活性。即，对于活性最高的化合物5-（氯乙酰氨基）尿嘧啶（2）及其无环糖类似物18所获得的结果表明，反应性取代基与胸苷酸合酶机制内若干可能的靶标之间形成了共价键（半胱氨酸残基，酶的基本部分，N，N-亚甲基四氢叶酸或其反应性亚胺形式）是最可能的作用方式。另外，新型的C 5-取代的尿嘧啶衍生物6（5- [双-（2-对-甲氧基苄基硫乙基）胺]乙酰氨基尿嘧啶）通过未知的机制对HeLa和MiaPaCa-2细胞系表现出高的抗增殖活性。
• Importance of Binding Site Hydration and Flexibility Revealed When Optimizing a Macrocyclic Inhibitor of the Keap1–Nrf2 Protein–Protein Interaction
  作者：Fabio Begnini、Stefan Geschwindner、Patrik Johansson、Lisa Wissler、Richard J. Lewis、Emma Danelius、Andreas Luttens、Pierre Matricon、Jens Carlsson、Stijn Lenders、Beate König、Anna Friedel、Peter Sjö、Stefan Schiesser、Jan Kihlberg

  DOI：10.1021/acs.jmedchem.1c01975

  日期：2022.2.24

  Upregulation of the transcription factor Nrf2 by inhibition of the interaction with its negative regulator Keap1 constitutes an opportunity for the treatment of disease caused by oxidative stress. We report a structurally unique series of nanomolar Keap1 inhibitors obtained from a natural product-derived macrocyclic lead. Initial exploration of the structure-activity relationship of the lead, followed

  通过抑制与其负调节因子 Keap1 的相互作用来上调转录因子 Nrf2 构成了治疗由氧化应激引起的疾病的机会。我们报告了从天然产物衍生的大环铅中获得的一系列结构独特的纳摩尔级 Keap1 抑制剂。对先导化合物的构效关系进行初步探索，然后进行结构导向优化，使抑制效力提高了 100 倍。纳摩尔抑制剂的大环核心定位三个药效团单元，用于与 Keap1 的关键残基（包括 R415、R483 和 Y572）进行有效相互作用。配体优化导致配位水分子从 Keap1 结合位点移位，并显着改变热力学曲线。此外，R415 和 R483 的微小重组伴随着配体之间亲和力的重大差异。因此，本研究表明在设计高亲和力配体时考虑 Keap1 结合位点的水合作用和灵活性的重要性。