S-2-(苄氧羰基氨基)-6-(叔丁氧羰基氨基)己酸甲酯 | 2389-49-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: S-2-(苄氧羰基氨基)-6-(叔丁氧羰基氨基)己酸甲酯
• 英文名称: (S)-methyl 2-(benzyloxycarbonylamino)-6-(tert-butoxycarbonylamino)hexanoate
• 英文别名: Z-Lys(Boc)-OMe；methyl (2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 2389-49-3
• 化学式: C₂₀H₃₀N₂O₆
• 分子量: 394.468
• InChiKey: ZJWQKFBUQSKZOS-INIZCTEOSA-N

物化性质

• 熔点：
  62.5-63.5 °C
• 沸点：
  544.7±50.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-Lys(Boc)-OMe
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)-OMe
CAS number: 2389-49-3

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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, 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: C20H30N2O6
Molecular weight: 394.5

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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：

  S-2-(苄氧羰基氨基)-6-(叔丁氧羰基氨基)己酸甲酯 生成 (S)-methyl 6-amino-2-(benzyloxycarbonylamino)hexanoate
  参考文献：
  名称：

  Ç的糖苷类似物ñ 4 - （2-乙酰氨基-2-脱氧- β-d-D-吡喃葡萄糖基）-L-天冬酰胺的合成和循环的构象分析Ç -glycopeptide †

  摘要：

  的合成Ç糖苷类似物15-22的ñ 4 - （2-乙酰氨基-2-脱氧- β-d-D-吡喃葡萄糖基）-L-天冬酰胺（ASN（Ñ 4的GlcNAc））具有相反的酰胺键为电子等排取代给出了N-糖苷键的结构。制备了肽环（-D-Pro-Phe-Ala-CGaa-Phe-Phe-）（CGaa = C-糖基化氨基酸；24），以证明3-[（3-acetamido-2,6-anhydro- 4,5,7-三-O-苄基-3-脱氧-β-D-甘油-D-邻庚基庚酰基）氨基] -2-[（9 H-氟-9-酰氧基羰基）氨基]丙酸（22）可以用于固相肽合成。的构象通过NMR和分子动力学（MD）技术确定24。提供的证据表明，CGaa侧链与肽主链相互作用。不同Ç -glycosylated氨基酸15-21被偶合制备3-乙酰氨基-2,6-脱水-4,5,7-三ö苄基-3-脱氧β-D-甘油基-D-庚-带有二氨基酸衍生物8-14的庚酸（4

  DOI：

  10.1002/hlca.19960790602
• 作为产物：
  描述：

  N^α-benzyloxycarbonyl-N^ε-(3-methyl-2-butenyl)oxycarbonyl-L-lysine methyl ester 在 碘 、 三乙胺 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 S-2-(苄氧羰基氨基)-6-(叔丁氧羰基氨基)己酸甲酯
  参考文献：
  名称：

  Prenyl carbamates: preparation and deprotection

  摘要：

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.028
• 作为试剂：
  描述：

  Nε-Boc-Nα-Cbz-L-赖氨酸 、 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate 、 三乙胺 在 盐酸 、 水 、 碳酸氢钠 、 Sodium sulfate-III 、 silica gel 、 ethyl acetate heptane 、 S-2-(苄氧羰基氨基)-6-(叔丁氧羰基氨基)己酸甲酯 作用下， 以 methanol-dichloromethane 为溶剂， 反应 2.0h， 生成 S-2-(苄氧羰基氨基)-6-(叔丁氧羰基氨基)己酸甲酯
  参考文献：
  名称：

  THROMBIN INHIBITORS

  摘要：

  本发明涉及公式为：A-B-C-Lys-D的非缓慢结合凝血酶抑制剂，其中A为H，2-羟基-3-环己基-丙酰基，R1，R1-O-CO-，R1-SO2-，-(CHR2)nCOOR3或N-保护基，其中R1选自-(1-6C)烷基-COOH，(1-12C)烯基，(6-14C)芳基，(7-15C)芳基烷基和(8-16C)芳基烯基，该基团可以被(1-6C)烷基，(2-12C)烷氧基，羟基或卤素取代；R2为H或具有与R1相同的含义，R3选自H，(112C)烷基，(2-12C)烯基，(6-14C)芳基，(7-15C)芳基烷基和(8-16C)芳基烯基，其中芳基基团可以被(1-6C)烷基，(2-12C)烷氧基，羟基或卤素取代；n是1到3的整数；B是键，L-Asp或其衍生物，Leu，norLeu，-n(benzyl)-CH2-CO-，-N(2-茚烷)-CH2-CO-，D-1Piq，D-Tiq，Atc或具有疏水芳香侧链的D-氨基酸；C是Azt，Pro，Pec，norLeu(cyclo)Gly，其中一种氨基酸的化学式为-N[(3-8C)环烷基]-CH-CO-或-N(benzyl)-CH2-CO-，D选自COOH，四唑，噁唑，噻唑和苯并噻唑，或A和C具有上述含义，B为D-(3-8C)环烷基丙氨酸，D为四唑，噁唑，噻唑或苯并噻唑；或其前药；或其药学上可接受的盐；但不包括化合物Me-D-Phe-Pro-Lys-COOH。这些化合物可用作抗血栓剂。

  公开号：

  US20010007764A1

文献信息

• Amphiphilic dendronized homopolymers
  作者：Wen Li、AFang Zhang

  DOI：10.1007/s11426-010-4136-3

  日期：2010.12

  A series of second generation of amphiphilic dendronized homopolymers are efficiently synthesized, and their thermoresponsiveness in aqueous solutions and secondary structures in methanol solutions are described. These polymers are constructed in each repeat unit with various generations of hydrophobic 4-aminoproline and hydrophilic oligoethylene glycol (OEG)-based dendrons, and their over-all hydrophilicity is tuned by varying these dendron generations. Polymers with or without the first generation of proline dendron show good water solubility at room temperature, but exhibit typical thermoresponsive behaviors at elevated temperatures as characterized by turbidity measurements using UV-vis spectroscopy, while the polymer with the secondary generation of proline dendron is not soluble in water. All polymers show ordered secondary structures as evidenced by the optical rotation and circular dichroism experiments. Finally, assembly of these amphiphilic homopolymers into porous films via breath figure (BF) technique is described, and polymer structures are found to show significant influence on the morphology of porous film.

  一系列第二代两亲性树枝化均聚物的合成效率很高，并且描述了它们在水溶液中的热响应性和甲醇溶液中的二级结构。这些聚合物在每个重复单元中构建了不同代数的疏水性4-氨基脯氨酸和亲水性聚氧乙烯甘油（OEG）基树枝状物，并通过改变这些树枝状物的代数来调节它们的整体亲水性。含有或不含第一代脯氨酸树枝状物的聚合物在室温下表现出良好的水溶性，但在升温时表现出典型的热响应行为，这是通过紫外-可见光谱法测定浊度来表征的，而含有第二代脯氨酸树枝状物的聚合物在水中不溶。所有聚合物都显示出有序的二级结构，光学旋转和圆二色实验证明了这一点。最后，描述了这些两亲性均聚物通过呼吸图案（BF）技术组装成多孔膜，并且发现聚合物结构对多孔膜的形态有显著影响。
• Cobalt (III) Complexes as Novel Matrix Metalloproteinase-9 Inhibitors
  作者：Ji-Youn Lee

  DOI：10.5012/bkcs.2012.33.8.2762

  日期：2012.8.20

  chromatographic data suggested that the complexes bind to a histidine residue by axial ligand substitution. When an appropriate targeting group is attached, the cobalt(III) complexes can selectively inhibit the histidinecontaining enzymes such as thermolysin, human α-thrombin, and carbonic anhydrase. Since histidine is the most commonly found residue in the active sites of zinc enzymes and zinc-binding proteins

  基质金属蛋白酶 (MMPs) 是锌结合内肽酶家族，在胚胎生长、血管生成、关节炎、皮肤溃疡、肝纤维化和肿瘤转移等各种生理过程和疾病中发挥重要作用。由于它们对多种疾病的影响，MMPs 被认为是有趣的药物靶点。大多数 MMP 抑制剂是有机小分子，含有用于锌结合基团的异羟肟酸酯官能团。该异羟肟酸酯基团以双齿方式与锌 (II) 中心结合，并产生扭曲的三角双锥几何形状。尽管异羟肟酸酯基团是报道的最有效的锌结合部分，但它在临床试验中显示出两个主要限制：低生物利用度和缺乏特异性。由于异羟肟酸酯基团易于快速代谢并且对各种过渡金属具有高结合亲和力，因此已经做出了许多努力来开发新的锌结合基团，包括反向异羟肟酸酯、磷酸盐和吡啶酮。然而，这些新开发的抑制剂的体外活性不如异羟肟酸盐衍生物高。以前曾报道过，金合欢钴 (III) 复合物可以与蛋白质和模型肽的组氨酸残基相互作用。钴 (III) 配合物以随机方式结合活性位点
• New leupeptin analogs: synthesis and inhibition data
  作者：Rose M. McConnell、George E. Barnes、Charles F. Hoyng、J. Martin Gunn

  DOI：10.1021/jm00163a014

  日期：1990.1

  and plasmin activity. Of the three enzymes tested, (benzyloxycarbonyl)-L-leucyl-L-leucyl-L-ornithinal (2i) showed significant inhibition of kallikrein activity only. Modifications made in the composition and sequence of the P2 and P3 amino acids also resulted in variations in the inhibitory activity of the analogues. In general, plasmin showed a strong preference for inhibitors which contain an L-phenylalanyl-L-leucyl

  介绍了几种含有C末端精氨酸，赖氨酸或鸟氨酸单位的亮肽素的三肽类似物的合成。测试了合成类似物作为胰蛋白酶，纤溶酶和激肽释放酶的抑制剂。（苯甲氧基羰基）-L-亮氨酰-L-亮氨酰-L-精氨酸（2a）作为胰蛋白酶和纤溶酶活性的抑制剂的功效明显低于Leupeptin。（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-赖氨酸（2e）和（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-鸟氨酸（2i）显示出与（苄氧羰基）-L-亮氨酰-L不同的抑制特性。 L-亮氨酰-L-精氨酸（2a）。尽管（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-精氨酸（2a）对所有三种酶均显示中等抑制作用，但（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-赖氨酸（2e）效果不佳胰蛋白酶和纤溶酶活性的抑制剂。在测试的三种酶中，（苄氧羰基）-L-亮氨酰-L-亮氨酰-L-鸟氨酸（2i）仅显示出激肽释放酶活性的显着抑制。对P2和P3氨基酸的组成和序列进行的修饰也导致
• Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates
  作者：Sateeshkumar Kumbhakonam、Kasipandi Vellaisamy、Soumya Saroj、Nalini Venkatesan、Karunagaran D.、Muraleedharan Kannoth Manheri

  DOI：10.1039/c7nj03999a

  日期：——

  A modular strategy that gives access to a library of peptide–Pt conjugates and their anticancer potential is presented.

  提供一种模块化策略，可以访问肽-Pt共轭物及其抗癌潜力的库。
• Concise Modular Synthesis and NMR Structural Determination of Gallium Mycobactin T
  作者：Kiat Hwa Chan、John T. Groves

  DOI：10.1021/acs.joc.1c01966

  日期：2021.11.5

  A modular synthesis of mycobactin T and its N-acetyl analogue is reported in a route that facilitates permutation of the lipid tails. A key feature is the generation of N(α)-Cbz-N(ε)-benzyloxy-N(ε)-Boc-lysine (A4) with methyl(trifluoromethyl)dioxirane in 59% yield. Selective hydroxamate N-acylation was achieved with acyl fluorides, enabling installation of lipids tails in the final step. O-Benzyl-dehydrocobactin

  在促进脂质尾部排列的途径中报道了分枝杆菌素 T 及其N-乙酰类似物的模块化合成。一个关键特征是 N(α)-Cbz-N(ε)-苄氧基-N(ε)-Boc-赖氨酸 ( A4 ) 与甲基（三氟甲基）二环氧乙烷的生成率为 59%。使用酰氟实现选择性异羟肟酸N-酰化，从而能够在最后一步中安装脂质尾部。O -Benzyl-dehydrocobactin T ( B4 ) 通过修改已知的五步序列制备，总产率为 49%。2-羟基苯基-4-羧基恶唑啉 ( C3 ) 由 2-羟基苯甲酸和l-丝氨酸甲酯分三步，总收率为55%。A4和B4与 EDCI的酯偶联以 73% 的产率提供MbI-1。用 Pd/BaSO 4和 50 psi 的 H 2催化氢化同时进行烯烃还原和脱苄基化，以 96% 的收率得到MbI-2。片段C3被转化为酰氟C4，其与MbI-2偶联以 51% 的产率得到MbI-3。最后，用 HCl/EtOAc 去除