Boc-D-丙氨酸-OSu | 34404-33-6

• 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: Boc-D-丙氨酸-OSu
• 中文别名: BOC-D-丙氨酸N-羟基琥珀酰亚胺酯；N-[(叔丁氧基)羰基]-D-丙氨酸2,5-二氧代-1-吡咯烷基酯；N-[(叔丁氧基)羰基]-D-丙氨酸 2,5-二氧代-1-吡咯烷基酯
• 英文名称: N-tertiarybutoxycarbonyl-D-alanine N-hydroxysuccinimide ester
• 英文别名: (R)-2,5-dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)propanoate；2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-D-alaninate；Boc-D-alanine-O-succinimide；Boc-D-Ala-ONSu；Boc-D-Ala-OSu；Boc-Ala-ONSu；(2,5-dioxopyrrolidin-1-yl) (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 34404-33-6
• 化学式: C₁₂H₁₈N₂O₆
• 分子量: 286.285
• InChiKey: COMUWNFVTWKSDT-SSDOTTSWSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2925190090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-D-Ala-OSu
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-Ala-OSu
CAS number: 34404-33-6

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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: C12H18N2O6
Molecular weight: 286.3

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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.

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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-D-Ala-OSu是丙氨酸的一种衍生物[1]。

反应信息

• 作为反应物：
  描述：

  Boc-D-丙氨酸-OSu 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-D-Ala-Val-Orn(Z)-Leu-Pro-ONSu
  参考文献：
  名称：

  肽的β-转角的研究。七、在β-转角部分具有L-Pro-L-Asn或L-Pro-D-Ala序列的短杆菌肽S类似物的合成和抗生素活性

  摘要：

  合成短杆菌肽 S (GS) 的两种类似物 [L-Pro4,4', L-Asn5,5']-GS (10a) 和 [L-Pro4,4', D-Ala5,5']-GS研究用不同类型的 β-转角替代 GS 的 β-转角部分的可能性，以保持生物活性。对于10a的合成，采用活性酯法在C端用L-Pro环化线性十肽，考察了三种方法，得到了满意的结果。两种类似物均未显示抗生素活性，表明 GS 的 β-转角部分不能被 L-Pro-L-Asn 或 L-Pro-D-Ala 序列取代而不影响其活性。类似物及其 2,4-二硝基苯基衍生物的 CD 和 ORD 光谱分别显示出比 GS 及其衍生物更弱的棉花效应。因此，类似物被认为不具有 GS 样 β-折叠构象。

  DOI：

  10.1246/bcsj.56.3329
• 作为产物：
  描述：

  BOC-D-丙氨酸 、 丁二酰亚胺 生成 Boc-D-丙氨酸-OSu
  参考文献：
  名称：

  JUDD, AMRIT K.;LAWSON, JOHN A.;OLSEN, CRIS M.;TOLL, LAWRENCE R.;POLGAR, W+, INT. J. PEPTIDE AND PROTEIN RES., 30,(1987) N 3, 299-317

  摘要：

  DOI：

文献信息

• Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome
  作者：Andrey G. Tereshchenkov、Malgorzata Dobosz-Bartoszek、Ilya A. Osterman、James Marks、Vasilina A. Sergeeva、Pavel Kasatsky、Ekaterina S. Komarova、Andrey N. Stavrianidi、Igor A. Rodin、Andrey L. Konevega、Petr V. Sergiev、Natalia V. Sumbatyan、Alexander S. Mankin、Alexey A. Bogdanov、Yury S. Polikanov

  DOI：10.1016/j.jmb.2018.01.016

  日期：2018.3

  bacterial ribosome and inhibits peptide bond formation. As an approach for modifying and potentially improving properties of this inhibitor, we explored ribosome binding and inhibitory activity of a number of amino acid analogs of CHL. The L-histidyl analog binds to the ribosome with the affinity exceeding that of CHL by 10 fold. Several of the newly synthesized analogs were able to inhibit protein synthesis

  抗生素氯霉素（CHL）以中等亲和力结合在细菌核糖体的肽基转移酶中心，并抑制肽键的形成。作为修饰和潜在改善该抑制剂性质的方法，我们探索了核糖体结合和许多CHL氨基酸类似物的抑制活性。L-组氨酸类似物以超过CHL十倍的亲和力与核糖体结合。一些新合成的类似物能够抑制蛋白质合成，并表现出不同于CHL的作用方式。然而，半合成CHL类似物的抑制特性与其亲和力不相关，并且一般而言，与原始抗生素相比，CHL的氨基酸类似物是不太有效的翻译抑制剂。与三个半合成类似物复合的嗜热栖热菌70S核糖体显示，CHL衍生物在肽基转移酶中心结合，在那里被测化合物的氨酰基部分与rRNA建立了特异相互作用。尽管仍然是效率低下的翻译抑制剂，但合成的化合物仍代表着有前途的化学支架，其靶向核糖体的肽基转移酶中心，并可能适合进一步研究。
• [EN] STABILITY-MODULATING LINKERS FOR USE WITH ANTIBODY DRUG CONJUGATES<br/>[FR] LIEURS MODULANT LA STABILITÉ DESTINÉS À ÊTRE UTILISÉS AVEC DES CONJUGUÉS ANTICORPS-MÉDICAMENT
  申请人：PFIZER

  公开号：WO2016030791A1

  公开（公告）日：2016-03-03

  The present invention provides stability-modulated antibody-drug conjugates, stability-modulating linker components used to make these stability-modulated antibody-drug conjugates, therapeutic methods using stability-modulated antibody-drug conjugates, and methods of making stability modulating linkers and stability-modulated antibody-drug conjugates.

  本发明提供了稳定性调节的抗体药物偶联物，用于制造这些稳定性调节的抗体药物偶联物的稳定性调节连接器组分，使用稳定性调节的抗体药物偶联物的治疗方法，以及制造稳定性调节连接器和稳定性调节的抗体药物偶联物的方法。
• Prevention of diketopiperazine formation in peptide synthesis by a simultaneous deprotection–coupling procedure: entrapment of reactive nucleophilic species by in situ acylation
  作者：Richard E. Shute、Daniel H. Rich

  DOI：10.1039/c39870001155

  日期：——

  acetic acid results, almost quantitavely, in the formation of diketopiperazines, whereas in the presence of Boc- or 2-(trimethylsilyl)ethoxycarbonyl protected amino acid pentafluorophenyl or N-hydroxysuccinimidyl active esters, protected tripeptides are formed; a simultaneous deprotection/acylation methodology with potential utility for peptide synthesis thus results.

  在乙酸存在下Z-氨基酸-D -Pro-OMe二肽的氢解几乎定量地导致了二酮哌嗪的形成，而在Boc-或2-（三甲基甲硅烷基）乙氧基羰基保护的氨基酸五氟苯基或N的存在下-羟基琥珀酰亚胺基活性酯，形成受保护的三肽；因此产生了同时脱保护/酰化方法，其具有潜在的肽合成用途。
• Exploiting Ligand Conformation in Selective Inhibition of Non-Ribosomal Peptide Synthetase Amino Acid Adenylation with Designed Macrocyclic Small Molecules
  作者：Justin S. Cisar、Julian A. Ferreras、Rajesh K. Soni、Luis E. N. Quadri、Derek S. Tan

  DOI：10.1021/ja0721521

  日期：2007.6.1

  or three-carbon linker between Cβ of the amino acid moiety and C8 of the adenine ring and a sulfamate in place of the phosphate group. These compounds are potent inhibitors of the cysteine adenylation domain activity of the yersiniabactin siderophore synthetase HMWP2 and, unlike the corresponding linear aminoacyl-AMP analogs, do not inhibit protein translation in vitro. Selective small molecule inhibitors

  已开发出大环氨酰基-AMP 类似物，通过模拟晶体结构中观察到的 cisoid 配体结合构象，选择性地抑制非核糖体肽合成酶氨基酸腺苷酸化结构域。相比之下，这些大环化合物不抑制氨酰-tRNA 合成酶，它们在机制上密切相关，但以不同的转体构象结合它们的配体。大环在氨基酸部分的 Cβ 和腺嘌呤环的 C8 之间包含一个两碳或三碳连接器，以及一个氨基磺酸盐代替磷酸基团。这些化合物是耶尔森菌素铁载体合成酶 HMWP2 的半胱氨酸腺苷酸化结构域活性的有效抑制剂，并且与相应的线性氨酰基-AMP 类似物不同，它们不抑制体外蛋白质翻译。
• Synthesis and Antiviral Activity of 5′-O-(Substituted) Sulfamoyl Pyrimidine Nucleosides
  作者：Julia Castro-Pichel、M. Teresa García-López、Federico G. de Las Heras、Rosario Herranz、Concepción Pérez、Pilar Vilas

  DOI：10.1002/ardp.19893220104

  日期：——

  l]‐2′,3′‐O‐isopropylidenecytidine (7) was prepared by reaction of 2,3′‐O‐isopropylidene‐4‐N‐[(dimethylamino)methylene] cytidine with N‐isopropylsulfamoyl chloride. Acidic hydrolysis of 7 provided 8 which, upon acetylation, gave the corresponding 2′,3′‐di‐O‐acetyl derivative 9. Compounds 7–9 show antiviral effect. Structure‐activity relationships are discussed.

  5'-O-[N-（氨基酰基或异丁酰基）氨磺酰基]尿苷 4a-e、5a-e 和 5'-O-[N-（异丙基）氨磺酰基]胞苷 7-9 已合成并针对单纯疱疹病毒进行了测试类型 2. 2', 3'-O-isopropidene-5'-O-氨磺酰尿苷与 Boc-Gly、Boc-L-Ala、Boc-D-Ala 和 Boc-L-Phe 的 N-羟基琥珀酰亚胺酯的缩合，得到 4a-d，在酸性条件下脱保护得到 5a-d。2', 3'-二-O-乙酰基-5'-O-氨磺酰尿苷与异丁酸的N-羟基琥珀酰亚胺酯类似缩合得到4e，脱酰后得到5e。5'-O-[N-(异丙基)氨磺酰基]-2', 3'-O-异亚丙基(7)由2,3'-O-异亚丙基-4-N-[(二甲氨基)亚甲基]反应制备胞苷与 N-异丙基氨磺酰氯。7 的酸水解得到 8，乙酰化后得到相应的 2'，3′-二-O-乙酰基衍生物 9. 化合物7-9具有抗病毒作用。讨论了结构-活性关系。