Boc-rac-Lys(Z)-OH | 55878-47-2

• 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
• 英文名称: Boc-rac-Lys(Z)-OH
• 英文别名: Boc-Lys(Z)-OH；6-(((benzyloxy)carbonyl)amino)-2-((tert butoxycarbonyl)amino)-hexanoic acid；N₆-((benzyloxy)carbonyl)-N₂-(tert-butoxycarbonyl)lysine；(2S)-6-(Benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino) hexanoic acid；Nα-butyloxycarbonyl-Nε-benzyloxycarbonyl-Lysine；N-Cbz-N-Boc-lysine；Boc-Lys(Cbz)-OH；Boc-lysin(Z)；2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 55878-47-2；2389-45-9
• 化学式: C₁₉H₂₈N₂O₆
• mdl: MFCD01026148
• 分子量: 380.441
• InChiKey: BDHUTRNYBGWPBL-UHFFFAOYSA-N

物化性质

• 熔点：
  75.0 to 79.0 °C
• 沸点：
  587.0±50.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)
• 溶解度：
  在醋酸中几乎透明

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.526
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• TSCA：
  Yes
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  应密封于0℃以下干燥避光保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-D-Lys(Z)-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: Boc-D-Lys(Z)-OH
CAS number: 55878-47-2

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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, 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: C19H28N2O6
Molecular weight: 380.4

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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

制备方法与用途

制备N-Boc-N'-Cbz-L-赖氨酸的过程如下：向20℃下冷却的(2S)-6-氨基-2-(叔丁氧基羰基氨基)己酸（100.00g，406.01mmol，1.00当量）和NaHCO3（102.33g，1.22mol，3.00当量）的THF（1000mL）与水（1000mL）溶液中缓慢加入CbzOSu（101.19g，406.01mmol，1.00当量）。然后将反应混合物在30℃下搅拌16小时。完成后，用1N HCl调节pH至5-6，并用乙酸乙酯（EA）萃取三次（每次600mL），经Na2SO4干燥后浓缩，最终得到黄色油状的N-Boc-N'-Cbz-L-赖氨酸（142.00g，373.26mmol，91.9％收率）。

N-Boc-N'-Cbz-L-赖氨酸是一种N-末端保护的氨基酸，适用于固相肽合成（SPPS），能够提供带有保护赖氨酰侧链的肽。

反应信息

• 作为反应物：
  描述：

  Boc-rac-Lys(Z)-OH 生成 DL-赖氨酸
  参考文献：
  名称：

  HENKLEIN, P.;GEORGI, M.;LOTH, F.;DAUTZENBERG, H.

  摘要：

  DOI：
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 N-ε-benzyloxycarbonyl lysine 在 sodium hydroxide 、 potassium hydrogensulfate 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 Boc-rac-Lys(Z)-OH
  参考文献：
  名称：

  [EN] HETEROCYCLIC SCAFFOLDS USEFUL FOR PREPARATION OF COMBINATORIAL LIBRARIES, LIBRARIES AND METHODS OF PREPARATION THEREOF
  [FR] ECHAFAUDAGES HÉTÉROCYCLIQUES UTILES POUR LA PRÉPARATION DE BIBLIOTHÈQUES COMBINATOIRES, BIBLIOTHÈQUES ET LEURS PROCÉDÉS DE PRÉPARATION

  摘要：

  揭示了有用的杂环支架，例如用于组合库的固相有机合成以及其制备方法。还公开了包括组合库在内的库以及其制备方法。以下是示例支架（I）:

  公开号：

  WO2009037642A1

文献信息

• [EN] CONJUGATED ANTISENSE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS ANTISENS CONJUGUÉS ET LEUR UTILISATION
  申请人：ISIS PHARMACEUTICALS INC

  公开号：WO2014179620A1

  公开（公告）日：2014-11-06

  Provided herein are oligomeric compounds with conjugate groups. In certain embodiments, the oligomeric compounds are conjugated to N-Acetylgalactosamine.

  本文提供了具有共轭基团的寡聚化合物。在某些实施例中，这些寡聚化合物与N-乙酰半乳糖结合。
• [EN] TARGETED THERAPEUTIC NUCLEOSIDES AND THEIR USE<br/>[FR] NUCLÉOSIDES THÉRAPEUTIQUES CIBLÉES ET LEUR UTILISATION
  申请人：ISIS PHARMACEUTICALS INC

  公开号：WO2015042447A1

  公开（公告）日：2015-03-26

  Provided herein are compounds comprising one or more therapeutic nucleosides and one or more targeting groups. In certain embodiments, the compounds further comprise one or more oligonucleotides. In certain embodiments, a targeting group comprises one or more N-Acetylgalactosamine.

  本文提供的化合物包括一个或多个治疗性核苷和一个或多个靶向基团。在某些实施例中，这些化合物进一步包括一个或多个寡核苷酸。在某些实施例中，一个靶向基团包括一个或多个N-乙酰半乳糖胺。
• Light‐Driven Carbene Catalysis for the Synthesis of Aliphatic and α‐Amino Ketones
  作者：Anna V. Bay、Keegan P. Fitzpatrick、Gisela A. González‐Montiel、Abdikani Omar Farah、Paul Ha‐Yeon Cheong、Karl A. Scheidt

  DOI：10.1002/anie.202105354

  日期：2021.8.9

  Catalyst potential is harnessed in the visible-light driven generation of an acyl azolium radical species that undergoes selective coupling with various radical partners to afford diverse ketone products. This methodology is showcased in the direct late-stage functionalization of amino acids and pharmaceutical compounds, highlighting the utility of single-electron NHC operators.

  单电子N-杂环卡宾（NHC）催化最近因合成CC键而受到关注。在密度泛函理论和机理分析的指导下，我们报告了使用单电子 NHC 算子光驱动合成脂肪族酮和 α-氨基酮。计算和实验结果表明，关键自由基中间体的反应性依赖于底物，并且可以通过 NHC 的空间和电子参数进行调节。催化剂潜力被利用在可见光驱动的酰基唑鎓自由基物种的生成中，该自由基物种与各种自由基伙伴选择性偶联以提供多种酮产物。这种方法在氨基酸和药物化合物的直接后期功能化中得到了展示，突出了单电子 NHC 操作符的实用性。
• Modified aminoacids, pharmaceuticals containing these compounds and method for their production
  申请人：Dr. Karl Thomae GmbH

  公开号：US06344449B1

  公开（公告）日：2002-02-05

  The present invention relates to modified amino acids of general formula wherein A, Z, X, n, m, R, R2, R3, R4 and R11 are defined as in claims 1 to 5, their tautomers, their diastereomers, their enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, pharmaceutical compositions containing these compounds, the use thereof and processes for preparing them as well as their use for the production and purification of antibodies and as labelled compounds in RIA- and ELISA assays and as diagnostic or analytical aids in neurotransmitter research.

  本发明涉及一般式的改性氨基酸 其中 A、Z、X、n、m、R、R2、R3、R4和R11的定义如权利要求1至5中所述，它们的互变异构体、对映异构体、立体异构体、它们的混合物及其盐，特别是其与无机或有机酸或碱的生理上可接受的盐，含有这些化合物的药物组合物，其用途以及制备它们的过程，以及它们在抗体的生产和纯化中的用途以及在RIA和ELISA测定中作为标记化合物以及在神经递质研究中作为诊断或分析辅助工具的用途。
• [EN] PRODRUGS OF FENCAMFAMINE<br/>[FR] PROMÉDICAMENTS DE FENCAMFAMINE
  申请人：PRAXIS BIOSCIENCES LLC

  公开号：WO2017048720A1

  公开（公告）日：2017-03-23

  Disclosed herein are pharmaceutical compositions comprising fencamfamine or fencamfamine related prodrug derivatives for targeted therapeutic applications and methods of synthesizing the compositions.

  本文披露了包含芬卡麦非或芬卡麦非相关的前药衍生物的药物组合物，用于靶向治疗应用，并且披露了合成这些组合物的方法。