Z-n-me-l-2-氨基己酸 | 225386-32-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Z-n-me-l-2-氨基己酸
• 中文别名: Cbz-N-甲基-L-正亮氨酸
• 英文名称: (2S)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid
• 英文别名: N-benzyloxycarbonyl-N-methyl-L-norleucine；N-Cbz-L-norleucine；Z-N-ME-L-2-Aminohexanoic acid；(2S)-2-[methyl(phenylmethoxycarbonyl)amino]hexanoic acid
• CAS: 225386-32-3
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: ZRIGUBDEWMLBRB-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-N-Me-l-2-aminohexanoic acid
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-N-Me-l-2-aminohexanoic acid
CAS number: 225386-32-3

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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: C15H21NO4
Molecular weight: 279.3

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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

反应信息

• 作为反应物：
  描述：

  Z-n-me-l-2-氨基己酸 在 palladium on activated charcoal 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 20.0~25.0 ℃ 、206.85 kPa 条件下， 反应 5.0h， 生成 N-methyl-L-norleucyl-L-norleucine methylamide
  参考文献：
  名称：

  三肽基肽酶II的抑制剂。2.产生第一个使胆囊收缩素8失活的肽酶的新型先导抑制剂：肽酶抑制剂设计的策略。

  摘要：

  失活胆囊收缩素8（CCK-8）的肽酶是一种丝氨酸肽酶，已证明是三肽基肽酶II的膜结合同工型（EC 3.4.14.10）。它在Met-Gly键处裂解神经递质CCK-8硫酸盐，得到Asp-Tyr（SO（3）H）-Met-OH + Gly-Trp-Met-Asp-Phe-NH（2）。为了寻找该肽酶的可逆抑制剂，使用基于人工底物Ala-Ala-Phe-酰胺基甲基香豆素水解的荧光分析法来表征酶促结合亚位点。对具有各种烷基或芳基侧链的一系列二肽和三肽进行了研究，以确定可结合的体积并探讨疏水相互作用的可能性。根据这项初步研究，三肽Ile-Pro-Ile-OH（K（i）= 1 microM）和Ala-Pro-Ala-OH（K（i）= 3 microM）和二肽酰胺Val-Nvl-NHBu（K（ i）= 3 microM）作为线索出现。这些结构的比较导致Val-Pro-NHBu（K（i）= 0.57 micr

  DOI：

  10.1021/jm990226g
• 作为产物：
  描述：

  N-苄氧羰基-L-己氨酸 在 camphor-10-sulfonic acid 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 Z-n-me-l-2-氨基己酸
  参考文献：
  名称：

  1,3-恶唑烷酮-5-酮和1,3-恶唑烷酮-6-酮由二十种常见的α-氨基酸合成N-甲基β-氨基酸的有效方法

  摘要：

  应用N-甲基β-氨基酸通常是潜在合成具有生物活性的修饰的肽和其他寡聚体的应用。先前的工作强调了1，3-恶唑烷-5-酮的还原裂解以合成N-甲基α-氨基酸。从α-氨基酸开始，使用两种方法来制备相应的N-甲基β-氨基酸。首先，α -氨基酸转化为Ñ甲基α -氨基酸由所谓的“-1,3-恶唑-5-酮的策略”，将它们再由同系阿恩特-艾斯特方法，得到Ñ-protected Ñ -甲基β -氨基酸选自20种常见衍生α -氨基酸。这些化合物的制备产率为23–57％（相对于N-甲基α-氨基酸）。在第二种方法中，可以通过Arndt–Eistert方法将12个N保护的α-氨基酸直接同源，然后将所得的β-氨基酸以30–45％的产率转化为1,3-恶二嗪-6-酮。 。最后，还原裂解以41–63％的收率提供了所需的N-甲基β-氨基酸。

  DOI：

  10.1002/hlca.200690235

文献信息

• A Mild Multistep Conversion of N-Protected α-Amino Acids into N-Protected β3-Amino Acids Utilizing the Nef Reaction
  作者：Andrew Hughes、Brad Sleebs、Nghi Nguyen

  DOI：10.1055/s-0032-1318344

  日期：——

  Current methods of homologation of alpha-amino acids to beta-amino acids have limitations. To overcome these shortfalls the Nef reaction has been utilized in the multistep synthesis of beta(3)-amino acids from alpha-amino acids. In this approach, N-protected amino aldehydes, easily accessed from alpha-amino acids, were transformed into the N-protected.gamma-amino nitroalkanes. The Nef reaction was then used to smoothly convert the nitroalkanes into the corresponding N-protected beta(3)-amino acids without notable racemization.
• Effective Methods for the Synthesis ofN-Methylβ-Amino Acids from All Twenty Commonα-Amino Acids Using 1,3-Oxazolidin-5-ones and 1,3-Oxazinan-6-ones
  作者：Andrew B. Hughes、Brad E. Sleebs

  DOI：10.1002/hlca.200690235

  日期：2006.11

  N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to

  应用N-甲基β-氨基酸通常是潜在合成具有生物活性的修饰的肽和其他寡聚体的应用。先前的工作强调了1，3-恶唑烷-5-酮的还原裂解以合成N-甲基α-氨基酸。从α-氨基酸开始，使用两种方法来制备相应的N-甲基β-氨基酸。首先，α -氨基酸转化为Ñ甲基α -氨基酸由所谓的“-1,3-恶唑-5-酮的策略”，将它们再由同系阿恩特-艾斯特方法，得到Ñ-protected Ñ -甲基β -氨基酸选自20种常见衍生α -氨基酸。这些化合物的制备产率为23–57％（相对于N-甲基α-氨基酸）。在第二种方法中，可以通过Arndt–Eistert方法将12个N保护的α-氨基酸直接同源，然后将所得的β-氨基酸以30–45％的产率转化为1,3-恶二嗪-6-酮。 。最后，还原裂解以41–63％的收率提供了所需的N-甲基β-氨基酸。
• Inhibitors of Tripeptidyl Peptidase II. 2. Generation of the First Novel Lead Inhibitor of Cholecystokinin-8-Inactivating Peptidase:  A Strategy for the Design of Peptidase Inhibitors
  作者：C. Robin Ganellin、Paul B. Bishop、Ramesh B. Bambal、Suzanne M. T. Chan、James K. Law、Benoit Marabout、Pratibha Mehta Luthra、Andrew N. J. Moore、Olivier Peschard、Pierre Bourgeat、Christiane Rose、Froylan Vargas、Jean-Charles Schwartz

  DOI：10.1021/jm990226g

  日期：2000.2.1

  fluorimetric assay based on the hydrolysis of the artificial substrate Ala-Ala-Phe-amidomethylcoumarin. A series of di- and tripeptides having various alkyl or aryl side chains was studied to determine the accessible volume for binding and to probe the potential for hydrophobic interactions. From this initial study the tripeptides Ile-Pro-Ile-OH (K(i) = 1 microM) and Ala-Pro-Ala-OH (K(i) = 3 microM) and dipeptide

  失活胆囊收缩素8（CCK-8）的肽酶是一种丝氨酸肽酶，已证明是三肽基肽酶II的膜结合同工型（EC 3.4.14.10）。它在Met-Gly键处裂解神经递质CCK-8硫酸盐，得到Asp-Tyr（SO（3）H）-Met-OH + Gly-Trp-Met-Asp-Phe-NH（2）。为了寻找该肽酶的可逆抑制剂，使用基于人工底物Ala-Ala-Phe-酰胺基甲基香豆素水解的荧光分析法来表征酶促结合亚位点。对具有各种烷基或芳基侧链的一系列二肽和三肽进行了研究，以确定可结合的体积并探讨疏水相互作用的可能性。根据这项初步研究，三肽Ile-Pro-Ile-OH（K（i）= 1 microM）和Ala-Pro-Ala-OH（K（i）= 3 microM）和二肽酰胺Val-Nvl-NHBu（K（ i）= 3 microM）作为线索出现。这些结构的比较导致Val-Pro-NHBu（K（i）= 0.57 micr