Z-L-丙氨酰胺 | 13139-27-0

• 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: Z-L-丙氨酰胺
• 中文别名: 苄氧羰基-L-丙氨酰胺
• 英文名称: L-α-N-Cbz-alaninamide
• 英文别名: (S)-benzyl (1-amino-1-oxopropan-2-yl)carbamate；Cbz-Ala-NH2；benzyl N-[(1S)-1-carbamoylethyl]carbamate；Cbz-L-Ala-NH₂；Cbz-L-alanine amide；Z-Ala-NH2；benzyl N-[(2S)-1-amino-1-oxopropan-2-yl]carbamate
• CAS: 13139-27-0
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: CTZZSWNVVFTJRN-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-Ala-NH2
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-Ala-NH2
CAS number: 13139-27-0

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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: C11H14N2O3
Molecular weight: 222.2

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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：

  Z-L-丙氨酰胺 在 CPase Y 作用下， 以 various solvent(s) 为溶剂， 反应 0.08h， 生成 苄氧羰基-L-丙氨酸
  参考文献：
  名称：

  羧肽酶Y的底物识别机制。

  摘要：

  为了阐明羧肽酶Y，Fmoc-（Glu）n Ala-OH（n = 1至6），Fmoc-（Glu）n Ala-NH2（1至5）和Fmoc-Lys（Glu）的底物识别机制合成了3Ala-NH2，并测量了这些底物的动力学参数。Fmoc肽的Km随肽长度从n = 1增加到n = 5而显着降低，而kcat仅有微小变化。Fmoc-（Glu）（5,6）Ala-OH的Km与先前描述的蛋白质底物的Km几乎相同（Nakase等，Bull。Chem。Soc。Jpn。，73，2587-2590）。这些结果表明该酶具有六个亚位点（S1'和S1-S5）。由Km计算的每个子位点亲和力揭示了子位点的性质，并且根据pH 6.5和5.0之间的子位点亲和力的差异，可以预测每个子位点中的残基。对于Fmoc肽酰胺底物，酰胺酶和羧酰胺肽酶活性的优先级取决于底物。肽的侧链与亚位点之间的相互作用很可能弥补了P1'-S1'相互作用的缺乏，因此

  DOI：

  10.1271/bbb.65.2465
• 作为产物：
  描述：

  N-苄氧羰基-L-丙氨酸 N-羟基琥珀酰亚胺酯 在 氨 作用下， 以 甲醇 为溶剂， 以89%的产率得到Z-L-丙氨酰胺
  参考文献：
  名称：

  功能化谷氨酰胺和天冬酰胺类肽的合成–范围和局限性

  摘要：

  N烷基化的甘氨酸低聚物（“类肽”）可以用作有效的拟肽系统。安装不同的功能组通常是一个挑战，并且会使产量和纯度降至最低。在这里，我们描述了以游离碱形式获得的不同含酰胺亚单体的合成，以及它们掺入类肽的过程。通过使用游离胺，可以改善在固体载体上的偶联结果，并制备了各种官能化的类肽。另外，在合成过程中观察到有趣的二聚化副反应，导致交联的类肽。

  DOI：

  10.1002/hlca.201200451

文献信息

• Convenient Preparation of Primary Amides via Activation of Carboxylic Acids with Ethyl Chloroformate and Triethylamine under Mild Conditions
  作者：Takuya Noguchi、Masahiro Sekine、Yuki Yokoo、Seunghee Jung、Nobuyuki Imai

  DOI：10.1246/cl.130096

  日期：2013.6.5

  Primary amides were easily prepared in 22–99% yields from the corresponding carboxylic acids 1 or 5 with NH4Cl via activation with ClCO2Et and Et3N. The enantiomers of the corresponding primary ami...

  通过用 ClCO2Et 和 Et3N 活化，用 NH4Cl 从相应的羧酸 1 或 5 中很容易以 22-99% 的产率制备伯酰胺。相应伯胺的对映体...
• [EN] CATHEPSIN CYSTEINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉASES À CYSTÉINE DE TYPE CATHEPSINES
  申请人：MERCK SHARP & DOHME

  公开号：WO2015054038A1

  公开（公告）日：2015-04-16

  This invention relates to a novel class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis.

  这项发明涉及一类新型化合物，它们是半胱氨酸蛋白酶抑制剂，包括但不限于对卡特普辛K、L、S和B的抑制剂。这些化合物可用于治疗需要抑制骨吸收的疾病，如骨质疏松症。
• [EN] P2X3, RECEPTOR ANTAGONISTS FOR TREATMENT OF PAIN<br/>[FR] ANTAGONISTES DU RÉCEPTEUR P2X3 POUR LE TRAITEMENT DE LA DOULEUR
  申请人：MERCK SHARP & DOHME

  公开号：WO2010111058A1

  公开（公告）日：2010-09-30

  The subject invention relates to novel P2X3 receptor antagonists that play a critical role in treating disease states associated with pain, in particular peripheral pain, inflammatory pain, or tissue injury pain that can be treated using a P2X3 receptor subunit modulator.

  该发明涉及新型P2X3受体拮抗剂，其在治疗与疼痛相关的疾病状态中发挥关键作用，特别是可以使用P2X3受体亚单位调节剂来治疗的外周疼痛、炎症性疼痛或组织损伤疼痛。
• A Fast Procedure for the Preparation of Amides/Peptides from Carboxylic Acids and Azides via Two Redox Reactions: Application to the Synthesis of Methionine Enkephalin
  作者：Sunil K. Ghosh、Rekha Verma、Usha Ghosh、Vasant R. Mamdapur

  DOI：10.1246/bcsj.69.1705

  日期：1996.6

  A one-pot self regulated approach for the synthesis of amides/peptides based on two reduction–oxidation (redox) reactions has been described. The primary and secondary amides/peptides are made by using azidotrimethylsilane and alkyl azides/α-azido acid derivatives respectively as the direct source of amine components. Benzeneselenol, generated in the reaction medium during carboxyl activation, has

  已经描述了基于两个还原-氧化（氧化还原）反应的用于合成酰胺/肽的一锅自调节方法。一级和二级酰胺/肽分别使用叠氮三甲基硅烷和烷基叠氮化物/α-叠氮酸衍生物作为胺组分的直接来源制备。已发现在羧基活化过程中在反应介质中产生的苯甲酚是用于将叠氮化物转化为伯胺的有效还原剂。该方法已应用于甲硫氨酸脑啡肽的合成。
• A new approach to peptide synthesis
  作者：Christopher J. Moody、Elizabeth Swann、Christopher J. Moody、Leigh Ferris、David Haigh

  DOI：10.1039/a706658i

  日期：——

  A new approach to the synthesis of dipeptides is described based on the formation of the NHCHR1CONH–CHR2CO bond by carbenoid N–H insertion, rather than the formation of the peptide bond itself.

  基于卡宾氮–氢插入形成NHCHR1CONH–CHR2CO键，而非肽键本身形成的新方法，被描述用于二肽的合成。