N6-叔丁氧羰基-D-赖氨酸 | 31202-69-4

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N6-叔丁氧羰基-D-赖氨酸
• 中文别名: N-ε-BOC-D-赖氨酸；N^e-Boc-D-赖氨酸
• 英文名称: H-D-Lys(Boc)-OH
• 英文别名: N_ε-(tert-butoxycarbonyl)-D-lysine；(R)-2-Amino-6-((tert-butoxycarbonyl)amino)hexanoic acid；(2R)-2-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 31202-69-4
• 化学式: C₁₁H₂₂N₂O₄
• mdl: MFCD00076958
• 分子量: 246.307
• InChiKey: VVQIIIAZJXTLRE-MRVPVSSYSA-N

物化性质

• 沸点：
  412.9±40.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储于室温下。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-D-Lys(boc)-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: H-D-Lys(boc)-oh
CAS number: 31202-69-4

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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: C11H22N2O4
Molecular weight: 246.3

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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：

  N6-叔丁氧羰基-D-赖氨酸 在 1H-咪唑-1-磺酰叠氮 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 18.0h， 以89%的产率得到(R)-2-azido-6-((tert-butoxycarbonyl)amino)hexanoic acid
  参考文献：
  名称：

  阳离子联芳基1,2,3-三唑基拟肽两亲物：合成，抗菌作用评估和初步作用机理研究

  摘要：

  合成的小分子抗菌肽模拟物因其破坏膜的能力和降低的细菌耐药性而代表了有希望的一类潜在的抗生素。基于先前建立的铅联芳基肽模拟物和已知药效基团，设计和合成了43种单和双阳离子联芳基1,2,3-三唑基肽模拟物的文库。可靠，便捷和模块化的合成途径可有效合成多个独特的支架，这些支架经过发散衍生作用可提供两亲性化合物。体外测试显示对多种病原菌具有增强的抗菌功效，这些病原菌包括具有甲氧西林，万古霉素，达托霉素或多药耐药性的细菌分离株。初步的时间杀灭动力学和膜破坏试验表明，拟肽模拟物可能具有膜活性机制。发现疏水性和阳离子电荷之间的最佳平衡对于降低细胞毒性/溶血作用（即膜选择性）和增强革兰氏阴性活性至关重要。阳离子联芳两亲物81被鉴定为有效的广谱拟肽，对革兰氏阳性（耐甲氧西林的金黄色葡萄球菌-MIC = 2μg/ mL）和革兰氏阴性（大肠杆菌）具有活性 -MIC = 4μg/ mL）致病菌。

  DOI：

  10.1016/j.ejmech.2019.02.013
• 作为产物：
  描述：

  N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-D-赖氨酸 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 生成 N6-叔丁氧羰基-D-赖氨酸
  参考文献：
  名称：

  通过立体α-氨基酸桥微调订书肽的性质

  摘要：

  α-氨基酸被用作构建 IL-17A 结合肽 (HAP) 侧链装订类似物库的桥梁，并评估了订书钉手性 (L/D) 对肽特性的影响。虽然所有 AA 衍生的肽基主食都会显着提高 HAP 的酶促稳定性，但与D -氨基酸桥相比，基于L -AA 的主食在增加修饰肽的螺旋性和结合亲和力方面产生更显着的影响。

  DOI：

  10.1002/chem.202203624

文献信息

• Novel β- and γ-Amino Acid-Derived Inhibitors of Prostate-Specific Membrane Antigen
  作者：Kyul Kim、Hongmok Kwon、Cyril Barinka、Lucia Motlova、SangJin Nam、Doyoung Choi、Hyunsoo Ha、Hwanhee Nam、Sang-Hyun Son、Il Minn、Martin G. Pomper、Xing Yang、Zsofia Kutil、Youngjoo Byun

  DOI：10.1021/acs.jmedchem.9b02022

  日期：2020.3.26

  clinical phase are based on the Lys-Urea-Glu motif, in which Lys and Glu are α-(L)-amino acids. In this study, we aimed to determine the effect of β- and γ-amino acids in the S1 pocket on the binding affinity for PSMA. We synthesized and evaluated β- and γ-amino acid analogs with (S)- or (R)-configuration with keeping α-(L)-Glu as the S1'-binding pharmacophore. Structure-activity relationship studies identified

  前列腺特异性膜抗原（PSMA）是前列腺癌进展和转移的早期诊断的极佳生物标志物。在临床阶段，最有希望的PSMA靶向药物是基于Lys-尿素-Glu基序，其中Lys和Glu是α-（L）-氨基酸。在这项研究中，我们旨在确定S1口袋中β-和γ-氨基酸对PSMA结合亲和力的影响。我们合成并评估了具有（S）-或（R）-构型的β-和γ-氨基酸类似物，并保持α-（L）-Glu作为S1'结合药效基团。结构活性关系研究确定，化合物13c（具有（R）-构型的β-氨基酸类似物）表现出最有效的PSMA抑制活性，IC50值为3.97 nM。
• [EN] KETONE INHIBITORS OF LYSINE GINGIPAIN<br/>[FR] INHIBITEURS CÉTONE DE LYSINE GINGIPAÏNE
  申请人：CORTEXYME INC

  公开号：WO2018053353A1

  公开（公告）日：2018-03-22

  The present invention provides compounds according to Formula (I) as described herein, and their use for inhibiting the lysine gingipain protease (Kgp) from the bacterium Porphyromonas gingivalis. Also described are gingipain activity probe compounds and methods for assaying gingipain activity are also described, as well as methods for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease.

  本发明提供了如下式（I）所述的化合物，以及它们用于抑制牙龈假单胞菌（Porphyromonas gingivalis）的赖氨酸基因底物蛋白酶（Kgp）的用途。还描述了牙龈蛋白酶活性探针化合物和测定牙龈蛋白酶活性的方法，以及用于治疗与牙龈假单胞菌感染相关的疾病的方法，包括阿尔茨海默病等脑部疾病。
• CYCLODEXTRIN PROTEIN DRUG CONJUGATES
  申请人：Regeneron Pharmaceuticals, Inc.

  公开号：US20180333504A1

  公开（公告）日：2018-11-22

  Provided herein are compounds, compositions, conjugates and methods for the treatment of diseases, and/or conditions such as, but not limited to, proliferative diseases. In certain embodiments, compounds, compositions, and conjugates are provided, which include cyclodextrin-based linker-payloads and protein conjugates thereof, and/or in combination with other agents. By administering these compounds, compositions, and conjugates as described herein to specific target cells, side-effects due to non-specific binding phenomena, for example, to non-target cells are reduced.

  本文提供了用于治疗疾病和/或病况，如但不限于增生性疾病的化合物、组合物、共轭物和方法。在某些实施例中，提供了包括基于环糊精的连接剂-药物载体和蛋白质共轭物的化合物、组合物和共轭物，以及/或与其他药剂结合使用。通过将本文描述的这些化合物、组合物和共轭物投与特定靶细胞，可以减少由于非特异性结合现象（例如对非靶细胞的结合）而产生的副作用。
• Submonomeric Strategy with Minimal Protection for the Synthesis of C(2)-Modified Peptide Nucleic Acids
  作者：Stefano Volpi、Andrea Rozzi、Nicola Rivi、Martina Neri、Wolfgang Knoll、Roberto Corradini

  DOI：10.1021/acs.orglett.0c04116

  日期：2021.2.5

  A novel synthesis of C(2)-modified peptide nucleic acids (PNAs) is proposed, using a submonomeric strategy with minimally protected building blocks, which allowed a reduction in the required synthetic steps. N(3)-unprotected, d-Lys- and d-Arg-based backbones were used to obtain positively charged PNAs with high optical purity, as inferred from chiral GC measurements. “Chiral-box” PNAs targeting the

  提出了一种新的 C(2) 修饰肽核酸 (PNA) 合成方法，采用具有最低限度保护的构建模块的亚单体策略，从而减少了所需的合成步骤。根据手性 GC 测量推断，N(3)-未保护的、基于d -Lys- 和d -Arg 的主链用于获得具有高光学纯度的带正电荷的 PNA。使用这种方法生产了针对KRAS基因G12D 点突变的“手性盒”PNA ，与未修饰的 PNA 相比，突变型 DNA 链与野生型 DNA 链的序列选择性有所提高。
• Selective Targeting of the TPX2 Site of Importin-α Using Fragment-Based Ligand Design
  作者：Rhian S. Holvey、Eugene Valkov、David Neal、Murray Stewart、Chris Abell

  DOI：10.1002/cmdc.201500014

  日期：2015.7

  partners bind. Most nuclear transport cargoes use the major site, whereas TPX2 binds principally to the minor site. Fragment‐based approaches were used to identify small molecules that bind importin‐α, and crystallographic studies identified a lead series that was observed to bind specifically to the minor site, representing the first ligands specific for this site. Structure‐guided synthesis informed the

  蛋白质-蛋白质相互作用是困难的治疗靶点，在不破坏其他重要相互作用的情况下抑制病理相关相互作用提出了额外的挑战。在此，我们报告了潜在的抗癌靶点 TPX2-importin-α 相互作用如何实现这一目标。Importin-α 是一种核转运蛋白，可调节纺锤体组装蛋白 TPX2。它有两个结合位点——主要和次要——与合作伙伴结合。大多数核运输货物使用主要站点，而 TPX2 主要绑定到次要站点。基于片段的方法被用于识别结合 importin-α 的小分子，晶体学研究确定了一个铅系列，观察到该铅系列与次要位点特异性结合，代表了该位点特异性的第一个配体。结构指导的合成为这些片段的精细化提供了信息，以探索次要位点和主要位点之间配体选择性的来源。这些配体是开发这种蛋白质-蛋白质相互作用抑制剂的起点。