Nε-Boc-Nα-Cbz-L-赖氨酸二环己基铵盐 | 2212-76-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 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: Nε-Boc-Nα-Cbz-L-赖氨酸二环己基铵盐
• 中文别名: Z-6-叔丁氧羰酰赖氨酸·二环己基胺盐；N-Cbz-N’-Boc-L-赖氨酸二环己胺盐；Z-6-叔丁氧羰酰赖氨酸· 二环己基胺盐；N-苄氧羰基-N'-叔丁氧羰基-L-赖氨酸二环己胺盐；芴甲氧羰基-叔丁氧羰基-L-赖氨酸二环己基铵盐；Z-赖氨酸(Boc)-二环己胺盐
• 英文名称: N-Benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt
• 英文别名: N^α-Benzyloxycarbonyl-N^ε-t-butoxycarbonyl-L-lysine dicyclohexylamine salt；N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt；N^α-Z-N^ε-Boc-L-lysine dicyclohexylamine salt；N²-(benzyloxycarbonyl)-N⁶-<(tert-butoxy)carbonyl>lysin-dicyclohexylamin；N2-[(benzyloxy)carbonyl]-N6-(tert-butoxycarbonyl)-L-lysine, compound with dicyclohexylamine (1:1)；N^α-Carbobenzoxy-N^ε-tert.-butyloxycarbonyl-L-lysin；Z-Lys(Boc)-OH dicyclohexylamine salt；Z-Lys(Boc)-OH*HN(C6H11)2；Z-Lys(Boc)-OH.DCHA；N-cyclohexylcyclohexanamine;(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 2212-76-2
• 化学式: C₁₂H₂₃N*C₁₉H₂₈N₂O₆
• mdl: MFCD00038269
• 分子量: 561.762
• InChiKey: VTDLJMATIHSOTR-RSAXXLAASA-N

物化性质

• 熔点：
  154-156 °C
• 比旋光度：
  8.2 º (C=1% IN ETOH)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.709
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-Lys(boc)-oh dcha
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-Lys(boc)-oh dcha
CAS number: 2212-76-2

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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.
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: C19H28N2O6.C12H23N
Molecular weight: 561.8

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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：

  Nε-Boc-Nα-Cbz-L-赖氨酸二环己基铵盐 在 potassium hydrogensulfate 、 palladium on activated charcoal 、 氢气 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 di-tert-butyl ((5S,5'S)-(hexane-1,6-diylbis(azanediyl))bis(5-oleamido-6-oxohexane-6,1-diyl))dicarbamate
  参考文献：
  名称：

  赖氨酸基双子表面活性剂及其脂质复合物的结构-传递关系。

  摘要：

  报告了（R（1）（CO）-Lys（H）-NH）2（CH2）n型双子表面活性剂的合成和性能。对于间隔长度为n = 6的疏水性酰基尾巴，其长度有所变化（R（1）= C8，C10，C12，C14，C16和C18），而对于R（1）= C18，不饱和度。对于R（1）（CO）=油酰基（C18：1 Z），间隔区长度（n = 2-8）和赖氨酸结构单元的立体化学是变化的；还制备了具有单个油酰基尾部和头部基团的“半双子座”衍生物。在存在和不存在辅助脂质DOPE的情况下，通过用β-半乳糖苷酶转染HeLa细胞，研究了双子表面活性剂在细胞膜上转移多核苷酸的潜力。迄今为止，油酰已被证明是具有这种生物学活性的最佳疏水性尾基，而赖氨酸立体化学的作用不太明显。仅在不存在辅助脂质的情况下才能观察到最佳间隔区长度（n = 6）的效果。活性最高的表面活性剂，即具有油酰基链且n = 6的表面活性剂，形成尺寸在60-350 nm范围

  DOI：

  10.1039/c4sm00881b
• 作为产物：
  描述：

  Nε-Boc-Nα-Cbz-L-赖氨酸 、 二环己胺 以 醋酸异丙酯 为溶剂， 生成 Nε-Boc-Nα-Cbz-L-赖氨酸二环己基铵盐
  参考文献：
  名称：

  WO2008/14811

  摘要：

  公开号：

文献信息

• Transesterifications with 1,8-Diazabicyclo[5.4.0]undec-7-ene/Lithium Bromide (DBU/LiBr) - Also Applicable to Cleavage of Peptides from Resins inMerrifleld Syntheses
  作者：Dieter Scebach、Adrian Thaler、Denis Blaser、Soo Y. Ko

  DOI：10.1002/hlca.19910740520

  日期：1991.8.7

  amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and LiBr (preferably 0,5 and 5 equiv., resp.) turns out to be a highly efficient catalyst (at 0–25°) for saponifications (in THF/H2O) and transesterifications (in ROH). The scope and limitations of the method are determined using ca. two dozens of different ester/alcohol combinations (Schemes 2 and 3). The investigation is focused on peptides as substrates

  base碱的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）和LiBr（最好分别为0.5和5当量）的混合物被证明是一种高效催化剂（0时） –25°）用于皂化（在THF / H 2 O中）和酯交换（在ROH中）。该方法的范围和局限性由ca确定。两种不同的酯/醇组合（方案2和3）。研究集中在肽作为底物上。在精心控制的条件下，N -Boc-和N不会发生准分子反应-Z-保护的肽酯，当是甲基，乙基，异丙基或烯丙基酯的产物时，如含多达六个氨基酸的肽所示，C端带有Ala，Len MeLeu，Asp（OEt）或Tyr （方案3以及表1和2）。Bom-Leu-Ala-Gly-Val-OR和Boc-Leu-Ala-Gly-Phe-OR（R = H，Me）从PAM和Wang树脂中水解和酯基转移（R = H，Me）（0–25°下1–8 h ，通过这种方法可以在不致使C端立体异构中心发生差向异构的情况下，获
• Herstellung von Analoga von Polyamin-Spinnentoxinen
  作者：Herbert Benz、Manfred Hesse

  DOI：10.1002/hlca.19940770408

  日期：1994.6.29

  Synthesis of Polyamine Analoga of Spider Toxins

  蜘蛛毒素多胺类似物的合成
• Synthesis and In Vitro Neuroprotective Activity of Glycine Analogs of Gk-2 Dimeric Dipeptide Mimetic of Nerve Growth Factor 4th Loop
  作者：N. M. Sazonova、A. V. Tarasyuk、Yu. N. Firsova、A. A. Zvyagintsev、A. G. Rebeko、P. I. Antipov、S. V. Nikolaev、T. A. Antipova、T. A. Gudasheva

  DOI：10.1007/s11094-020-02168-0

  日期：2020.5

  (-Asp94-Glu95-Lys96-Gln97-) of the NGF 4th loop and preserved the central dipeptide fragment (-Glu95-Lys96-). The Asp94 residue was replaced by its monosuccinyl bioisostere. The dimeric structure of NGF was reproduced using a bivalent hexamethylenediamine spacer. The structure—activity (neuroprotective) relationship for GK-2 was studied in the present work using a glycine scan, i.e., successive replacement of the

  神经生长因子 (NGF) 的二聚二肽模拟物，双-（N-单琥珀酰-L-谷氨酰-L-赖氨酸）六亚甲基二酰胺（GK-2），先前在 VV Zakusov 州立药理学研究所开发，可激活特定的 TrkA 受体，并在体外 (10–5 – 10–9 M) 和体内 (0.1 – 10 mg/kg ip 和 po) 表现出神经保护活性。GK-2 是基于 NGF 第 4 环的 β-转角 (-Asp94-Glu95-Lys96-Gln97-) 设计的，并保留了中心二肽片段 (-Glu95-Lys96-)。Asp94 残基被其单琥珀酰生物电子等排体取代。使用二价六亚甲基二胺间隔物复制 NGF 的二聚体结构。在目前的工作中使用甘氨酸扫描研究了 GK-2 的结构 - 活性（神经保护）关系，即肽侧基连续替换为 H。双-(N-乙酰基-L-谷氨酰-L-赖氨酸) (GK-2Ac)、双-(N-单琥珀酰甘氨酰-L-赖氨酸) (GK
• Syntheses of Peptides Related to the<i>N</i>-Terminal Structure of Corticotropin. IV. The Synthesis of the Amino Acid Sequences, Lys-Pro-Val-Gly and Lys-Pro-Val-Gly-Lys
  作者：Hideo Otsuka、Ken Inouye、Yoshiko Jono

  DOI：10.1246/bcsj.37.1471

  日期：1964.10

  The amino acid sequence Lys-Pro-Val-Gly-Lys, which corresponds to positions 11 to 15 of the corticotropin molecule, has been synthesized in the form of a crystalline derivative, Nα-carbobenzoxy-Ne-t-butyloxycarbonyl-L- lysyi-L-prolyl-L-valyl-glycyl-Ne-t-butyloxycarbonyl-L-lysine methyl ester, from which the crystalline hydrazide has then been obtained. The syn-thesis of the Lys-Pro-Val-Gly sequence

  氨基酸序列 Lys-Pro-Val-Gly-Lys 对应于促肾上腺皮质激素分子的 11 至 15 位，已以结晶衍生物 Nα-羧基苯甲氧基-Ne-叔丁氧羰基-L-赖氨酸的形式合成-L-脯氨酰-L-缬氨酰-甘氨酰-Ne-叔丁氧羰基-L-赖氨酸甲酯，然后从中获得结晶酰肼。还描述了与促肾上腺皮质激素的 11 至 14 位对应的 Lys-Pro-Val-Gly 序列的合成。
• Searching for improved mimetic peptides inhibitors preventing conformational transition of amyloid-β42 monomer
  作者：János Gera、Titanilla Szögi、Zsolt Bozsó、Livia Fülöp、Exequiel E. Barrera、Ana M. Rodriguez、Luciana Méndez、Carina M.L. Delpiccolo、Ernesto G. Mata、Federica Cioffi、Kerensa Broersen、Gabor Paragi、Ricardo D. Enriz

  DOI：10.1016/j.bioorg.2018.08.018

  日期：2018.12

  A series of novel mimetic peptides were designed, synthesised and biologically evaluated as inhibitors of A beta(42) aggregation. One of the synthesised peptidic compounds, termed compound 7 modulated A beta(42) aggregation as demonstrated by thioflavin T fluorescence, acting also as an inhibitor of the cytotoxicity exerted by A beta(42) aggregates. The early stage interaction between compound 7 and the A beta(42) monomer was investigated by replica exchange molecular dynamics (REMD) simulations and docking studies. Our theoretical results revealed that compound 7 can elongate the helical conformation state of an early stage A beta(42) monomer and it helps preventing the formation of beta-sheet structures by interacting with key residues in the central hydrophobic cluster (CHC). This strategy where early "on-pathway" events are monitored by small molecules will help the development of new therapeutic strategies for Alzheimer's disease.