叔丁氧羰基-丙氨酰-丙氨酸 | 27317-69-7

• 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: 叔丁氧羰基-丙氨酰-丙氨酸
• 中文别名: Boc-L-丙氨酰-L-丙氨酸
• 英文名称: N-tert-butoxycarbonyl-L-alanyl-L-alanine
• 英文别名: Boc-Ala-Ala-OH；(S)-2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoic acid；(tert-butoxycarbonyl)-L-alanyl-L-alanine；Boc-Ala-Ala；N-Boc-L-Ala-L-Ala-OH；N-tert-butyloxycarbonyl-L-alanyl-L-alanine；Boc-L-Ala-L-Ala-OH；N-Boc-Ala-Ala-OH；(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoic acid
• CAS: 27317-69-7
• 化学式: C₁₁H₂₀N₂O₅
• 分子量: 260.29
• InChiKey: BZNDDHWTEVCBAD-BQBZGAKWSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  483.5±30.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  105
• 氢给体数：
  3
• 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：
  H315,H319,H335
• 储存条件：
  存放于惰性气体中，并避免接触湿气（特别是吸湿性物质）。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-Ala-Ala-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-Ala-Ala-OH
CAS number: 27317-69-7

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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: C11H20N2O5
Molecular weight: 260.3

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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-Ala-Ala OH(NSC 334362)是一种丙氨酸衍生物，常用于制备抗菌剂。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	N-(tert-butoxycarbonyl)-L-alanyl-L-alanine benzyl ester	18670-98-9	C18H26N2O5	350.415
  L-丙氨酰-L-丙氨酸	Ala-Ala	1948-31-8	C6H12N2O3	160.173

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Boc-Ala-Ala-Ala-OH	27317-70-0	C14H25N3O6	331.369
  ——	Nα-tert-butoxycarbonyl-L-alanyl-L-alanyl-L-alanine methyl ester	19963-33-8	C15H27N3O6	345.396
  ——	Boc-Ala-Ala-NH2	41036-24-2	C11H21N3O4	259.305
  ——	N'-(3'-hydroxypropyl)-2-((S)-(2-(S)-(N-tert-butyloxycarbonyl)aminopropanoyl)aminopropanoyl)propanamide	1243118-38-8	C14H27N3O5	317.385
  ——	N-(tert-Butoxycarbonyl)-L-alanyl-N-prop-2-yn-1-yl-L-alaninamide	828927-37-3	C14H23N3O4	297.354
  ——	N'-(3'-bromopropyl)-2-((S)-(2-(S)-(N-tert-butyloxycarbonyl)aminopropanoyl)aminopropanoyl)propanamide	1243118-17-3	C14H26BrN3O4	380.282
  ——	N-hydroxy-N-tert-butoxycarbonyl-alanylalanine methyl ester	——	C12H22N2O6	290.316
  ——	N-(tert-butoxycarbonyl)-L-alanyl-L-alanine benzyl ester	18670-98-9	C18H26N2O5	350.415
  ——	N-{[(Prop-2-yn-1-yl)oxy]carbonyl}-L-alanyl-N-prop-2-yn-1-yl-L-alaninamide	828927-35-1	C13H17N3O4	279.296
  ——	Boc-L-Ala-L-Ala-L-Ala-OBzl	18671-06-2	C21H31N3O6	421.494

反应信息

• 作为反应物：
  描述：

  叔丁氧羰基-丙氨酰-丙氨酸 在 三己基(四癸基)膦 双(三氟甲基磺酰)氨 、 三氟乙酸 作用下， 反应 0.17h， 以94%的产率得到L-丙氨酰-L-丙氨酸
  参考文献：
  名称：

  Rapid, effective deprotection of tert-butoxycarbonyl (Boc) amino acids and peptides at high temperatures using a thermally stable ionic liquid

  摘要：

  描述了一种在磷铵离子液体中进行氨基酸和肽的高温Boc去保护的方法。

  DOI：

  10.1039/c5ra21279k
• 作为产物：
  描述：

  (2R)-2-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-sulfanylpropanoyl]amino]-3-sulfanylpropanoic acid 在 三(2-羰基乙基)磷盐酸盐 、 叔丁基硫醇 、 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride 作用下， 以 水 为溶剂， 反应 2.0h， 生成 叔丁氧羰基-丙氨酰-丙氨酸
  参考文献：
  名称：

  通过 β-硫内酯介导的天然化学连接来偶联空间要求高的肽†

  摘要：

  空间要求高的肽基位点（例如涉及 Val-Val 和 Val-Pro 连接的肽基位点）已被证明对于依赖外源硫醇添加剂的传统 NCL 方法极具挑战性。在此，我们报告了一种高效的 β-硫内酯介导的无添加剂 NCL 方案，该方案能够以良好的产量建立这些连接。快速 NCL 后进行原位脱硫。还研究了 β-硫内酯和常规硫酯之间对 NCL 的反应速率，并排除了直接氨解作为可能的途径。最后，使用所开发的方法制备了有效的细胞毒性环肽 axinastatin 1。

  DOI：

  10.1039/c7sc04744d
• 作为试剂：
  描述：

  单水氢氧化锂 、 甲醇 、 Boc-Ala-Ala-OMe 、 柠檬酸 在 乙酸乙酯 、 Sodium sulfate-III 、 叔丁氧羰基-丙氨酰-丙氨酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 叔丁氧羰基-丙氨酰-丙氨酸
  参考文献：
  名称：

  TEMPLATES FOR NUCLEATION AND PROPAGATION OF PEPTIDE SECONDARY STRUCTURE

  摘要：

  本文提供具有I式化合物及其药学上可接受的盐，其中变量在此处描述。还披露了制备I式化合物的方法。

  公开号：

  US20100228004A1

文献信息

• PRODRUGS OF FUSED-BICYCLIC C5aR ANTAGONISTS
  申请人：CHEMOCENTRYX, INC.

  公开号：US20190300526A1

  公开（公告）日：2019-10-03

  The present disclosure provides, inter alia, Compounds of Formulae IA, IB, IC, IIA, IIB and IIC or pharmaceutically acceptable salts thereof that are modulators of the C5a receptor. Also provided are pharmaceutical compositions and methods of use including the treatment of diseases or disorders involving pathologic activation from C5a and non-pharmaceutical applications.

  本公开提供了化合物IA、IB、IC、IIA、IIB和IIC的结构，或其在药学上可接受的盐，这些化合物是C5a受体的调节剂。还提供了包括治疗涉及C5a病理性激活的疾病或疾病的药物组合物和使用方法，以及非药物应用。
• Photoinduced Decarboxylative Radical Addition Reactions for Late Stage Functionalization of Peptide Substrates
  作者：Patricia Fernandez‐Rodriguez、Fabien Legros、Thomas Maier、Angelika Weber、María Méndez、Volker Derdau、Gerhard Hessler、Michael Kurz、Ana Villar‐Garea、Sven Ruf

  DOI：10.1002/ejoc.202001178

  日期：2021.2.5

  In our contribution we showcase an application of photochemistry for Late Stage Functionalization (LSF) of amino acids and small peptides in an industrial medicinal chemistry environment. The radical intermediates generated under photochemical conditions from the C‐terminal carboxylates undergo rapid 1,4‐conjugate additions to a variety of Michael acceptors. The studied methodology is applicable to

  在我们的贡献中，我们展示了在工业药物化学环境中光化学在氨基酸和小肽的后期功能化（LSF）中的应用。在光化学条件下，由C末端羧酸盐生成的自由基中间体会快速与各种Michael受体进行1,4-共轭加成。研究的方法学适用于已建立的药物和药物前体的功能化。
• Facile and Mild Synthesis of Linear and Cyclic Peptides via Thioesters
  作者：Paola Agrigento、Fernando Albericio、Sylvie Chamoin、Isabelle Dacquignies、Halil Koc、Martin Eberle

  DOI：10.1021/ol501669n

  日期：2014.8.1

  Thioester-mediated peptide bond formation has recently garnered a lot of attention, most notably in its relevance to condensation of large peptide fragments. Herein, a simple and general ligation method for the preparation of linear and cyclic peptides, starting from peptide thioester, mainly p-chlorophenyl, precursors is reported. The inherent advantages of this method are the low epimerization, reduced

  硫酯介导的肽键形成近来引起了很多关注，尤其是与大肽片段缩合有关。在本文中，报道了一种简单且通用的制备线性和环状肽的方法，该方法从肽硫酯，主要是对氯苯基前体开始。该方法的固有优点是低差向异构化，减少的二聚化，使用温和的反应条件以及消除了多余的偶联剂。
• [EN] 1,2,4-TRIAZOLYLAMINOARYL (HETEROARYL) SULFONAMIDE DERIVATIVES<br/>[FR] DERIVES DE 1,2,4-TRIAZOLYLAMINOARYL(HETEROARYL)SULFONAMIDE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006042215A1

  公开（公告）日：2006-04-20

  1,2,4 Triazolylaminoaryl(heteroaryl)sulfonamide derivatives of formula (I), pharmaceutically acceptable salts thereof, processes for the manufacture of 1,2,4 triazolylaminoaryl(heteroaryl) sulfonamide derivatives and pharmaceutical compositions containing 1,2,4 triazolylaminoaryl (heteroaryl)sulfonamide derivatives are disclosed: Formula (I) The 1,2,4 triazolylaminoaryl(heteroaryl)sulfonamide derivatives of formula (I) possess cell cycle inhibitory activity and are accordingly useful for their anti cell proliferation (such as anti cancer) activity.

  1,2,4-三唑基氨基芳基（杂芳基）磺酰胺衍生物的公式（I）、药用可接受的盐、1,2,4-三唑基氨基芳基（杂芳基）磺酰胺衍生物的制造工艺以及包含1,2,4-三唑基氨基芳基（杂芳基）磺酰胺衍生物的药物组合物被披露：公式（I）的1,2,4-三唑基氨基芳基（杂芳基）磺酰胺衍生物具有细胞周期抑制活性，因此可用于其抗细胞增殖（如抗癌）活性。
• Oxidation of Peptides by Methyl(trifluoromethyl)dioxirane:  The Protecting Group Matters
  作者：Maria Rosaria Rella、Paul G. Williard

  DOI：10.1021/jo061910n

  日期：2007.1.1

  Representative Boc-protected and acetyl-protected peptide methyl esters bearing alkyl side chains undergo effective oxidation using methyl(trifluoromethyl)dioxirane (1b) under mild conditions. We observe a protecting group dependency in the chemoselectivity displayed by the dioxirane 1b. N-Hydroxylation occurs in the case of the Boc-protected peptides, and side chain hydroxylation takes place in the

  带有烷基侧链的代表性Boc保护和乙酰保护肽甲基酯在温和的条件下使用甲基（三氟甲基）二环氧乙烷（1b）进行了有效的氧化。我们观察到由二环氧乙烷1b显示的化学选择性中的保护基依赖性。在Boc保护的肽中会发生N-羟基氧化，在乙酰保护的肽中会发生侧链羟基化。两者都是有吸引力的转化，因为它们产生了用作有价值的合成子的衍生肽。