N’-叔丁氧羰基-N-芴甲氧羰基-N’-甲基-L-赖氨酸 | 951695-85-5

• 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 - 芴
• 中文名称: N’-叔丁氧羰基-N-芴甲氧羰基-N’-甲基-L-赖氨酸
• 中文别名: N'-叔丁氧羰基-N-芴甲氧羰基-N'-甲基-L-赖氨酸；Fmoc-Lys(Boc,Me)-OH
• 英文名称: N'-tert-butyloxycarbonyl-N-fluorenylmethoxycarbonyl-N'-methyl-L-lysine
• 英文别名: Ν_ε-tert-butoxycarbonyl-Ν_α-(9-fluorenylmethoxycarbonyl)-Ν_ε-methyllysine；Fmoc-Lys(Me,Boc)-OH；N^α-Fmoc-N^ε-(Boc, methyl)-L-lysine；N2-Fmoc-N6-Boc-N6-monomethylhexanoic acid；Fmoc-Lys(N^ε-Boc-N^ε-Me)-OH；N-ζ-mono-Me-Lys-OH；Fmoc-L-Lysine(Me,Boc)-OH；Fmoc-L-Lys(Me,Boc)-OH；Fmoc-Lys(Boc)(Me)-OH；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]hexanoic acid
• CAS: 951695-85-5
• 化学式: C₂₇H₃₄N₂O₆
• 分子量: 482.577
• InChiKey: JHMSFOFHTAYQLS-QHCPKHFHSA-N

物化性质

• 熔点：
  85-87℃
• 沸点：
  665.4±55.0 °C(Predicted)
• 密度：
  1.200
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  2
• 海关编码：
  2924 29 70
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-lys(me,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: Fmoc-lys(me,boc)-oh
CAS number: 951695-85-5

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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: C27H34N2O6
Molecular weight: 482.6

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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

简介

N'-叔丁氧羰基-N-芴甲氧羰基-N'-甲基-L-赖氨酸是一种氨基酸类衍生物，可用作医药中间体。

用途

N'-叔丁氧羰基-N-芴甲氧羰基-N'-甲基-L-赖氨酸用作医药中间体。

应用

N'-叔丁氧羰基-N-芴甲氧羰基-N'-甲基-L-赖氨酸不仅用作医药中间体，还可用作氨基酸保护单体。

反应信息

• 作为反应物：
  描述：

  N’-叔丁氧羰基-N-芴甲氧羰基-N’-甲基-L-赖氨酸 在 polymer bound piperazine 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以95%的产率得到N^ε-tert-butyl-oxycarbonyl-N^ε-methyl-L-lysine
  参考文献：
  名称：

  Genetically Encoding N^ϵ-Methyl-l-lysine in Recombinant Histones

  摘要：

  Lysine methylation is an important post-translational modification of histone proteins that defines epigenetic status and controls heterochromatin formation, X-chromosome inactivation, genome imprinting, DNA repair, and transcriptional regulation. Despite considerable efforts by chemical biologists to synthesize modified histones for use in deciphering the molecular role of methylation in these phenomena, no general method exists to synthesize proteins bearing quantitative site-specific methylation. Here we demonstrate a general method for the quantitative installation of N-epsilon-methyl-L-lysine at defined positions in recombinant histones and demonstrate the use of this method for investigating the methylation dependent binding of HP1 to full length histone H3 monomethylated on K9 (H3K9me1). This strategy will find wide application in defining the molecular mechanisms by which histone methylation orchestrates cellular phenomena.

  DOI：

  10.1021/ja906603s
• 作为产物：
  描述：

  N2-[芴甲氧羰基]-N6-(三苯甲基)-L-赖氨酸 在 盐酸 、 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 13.0h， 生成 N’-叔丁氧羰基-N-芴甲氧羰基-N’-甲基-L-赖氨酸
  参考文献：
  名称：

  一种Nε-叔丁氧羰基-Nα-芴甲氧羰基-Nε-甲基-赖氨酸的制备方法

  摘要：

  本发明公开了一种Nε‑叔丁氧羰基‑Nα‑芴甲氧羰基‑Nε‑甲基‑赖氨酸的制备方法。包括以下步骤：以Nα‑芴甲氧羰基‑赖氨酸盐酸盐为原料，在碱性条件下与卤化物(R‑X)进行烷基化应，烷基化产物在甲醛水溶液中进行还原氨化引入甲基，还原氨化产物在酸性条件下脱除R基团，接着在碱性条件下引入叔丁氧羰基(BOC)保护基，重结晶处理后得到产物。本发明合成路线简洁，反应条件温和，中间体简单洗涤浓缩后便可直接进行下一步反应。各步反应收率接近定量，总收率可达80％以上，终产品纯度超过98％，为Nε‑叔丁氧羰基‑Nα‑芴甲氧羰基‑Nε‑甲基‑赖氨酸的制备提供了一条安全高效的合成路线。

  公开号：

  CN108383757A

文献信息

• [EN] PEPTIDE MACROCYCLES AGAINST ACINETOBACTER BAUMANNII<br/>[FR] MACROCYCLES PEPTIDIQUES CONTRE ACINETOBACTER BAUMANNII
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017072062A1

  公开（公告）日：2017-05-04

  The present invention provides compounds of formula (I) wherein X1 to X8 and R1 to R8 are as described herein, as well as pharmaceutically acceptable salts thereof. Further the present invention is concerned with the manufacture of the compounds of formula (I), pharmaceutical compositions comprising them and their use as medicaments for the treatment of diseases and infections caused by Acinetobacter baumannii.

  本发明提供了式（I）的化合物，其中X1至X8和R1至R8如本文所述，以及其药学上可接受的盐。此外，本发明涉及制备式（I）的化合物，包括它们的药物组合物以及它们作为治疗由鲍曼不动杆菌引起的疾病和感染的药物的用途。
• [EN] SOMATOSTATIN RECEPTOR ANTAGONIST COMPOUNDS AND METHODS OF USING THE SAME<br/>[FR] COMPOSÉS ANTAGONISTES DU RÉCEPTEUR DE LA SOMATOSTATINE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：CDRD VENTURES INC

  公开号：WO2017136943A1

  公开（公告）日：2017-08-17

  The present invention is directed to somatostatin receptor antagonist compounds having the structure of Formula I, compositions comprising the same, and methods of using such compounds and compositions. The compounds may be useful in the prevention or treatment of hypoglycemia.

  本发明涉及具有式I结构的生长抑素受体拮抗剂化合物，包含该化合物的组合物，以及使用该化合物和组合物的方法。这些化合物可能有助于预防或治疗低血糖。
• Analysis of JmjC Demethylase-Catalyzed Demethylation Using Geometrically-Constrained Lysine Analogues
  作者：Gareth W. Langley、Anne Brinkø、Martin Münzel、Louise J. Walport、Christopher J. Schofield、Richard J. Hopkinson

  DOI：10.1021/acschembio.5b00738

  日期：2016.3.18

  Nε-amino group in JmjC KDM catalysis. Demethylation of a trans-C-4/C-5 dehydrolysine substrate analogue was observed with representative KDM4 subfamily members KDM4A, KDM4B and KDM4E, and KDM7B, which are predicted, based on crystallographic analyses, to bind the Nε-methylated lysine residue in different conformations during catalysis. This information may be useful in the design of JmjC KDM selective

  组蛋白的动态翻译后修饰在动物转录调控中发挥重要作用。的脱甲基化Ñ ε -甲基赖氨酸残基Ñ组蛋白H3的末端尾部由脱甲基酶催化的，其中最大的家族是经由的初始羟基化亚铁和2-酮戊二酸依赖性脱甲基酶（JmjC结构KDMS），其催化脱甲基化所述ñ甲基的基团。我们报告了使用通过适当保护的N-烯丙基甘氨酸的复分解反应制备的N-甲基化赖氨酸类似物的 JmjC KDM 底物的构象要求的研究。结果支持对带正电的N提出的要求JmjC KDM 催化中的ε-氨基。一个脱甲基化反式-C-4 / -5℃dehydrolysine底物类似物用代表KDM4亚家族成员KDM4A，KDM4B和KDM4E，和KDM7B，被预测，基于晶体的分析观察到的，以结合Ñ ε甲基化的赖氨酸残基中催化过程中的不同构象。此信息可能有助于设计 JmjC KDM 选择性抑制剂。
• 2,2′-Bipyridine and hydrazide containing peptides for cyclization and complex quaternary structural control
  作者：Erik T. Hernandez、P. Rogelio Escamilla、Sang-Yop Kwon、Jonathan Partridge、Matthew McVeigh、Sebastian Rivera、James F. Reuther、Eric V. Anslyn

  DOI：10.1039/c8nj00184g

  日期：——

  A synthetic peptide containing two Nε-methyl lysines (Ac-K(Nε-Me)GYTGYTGK(Nε-Me)D-OH) was alkylated with bipyridine (bipy) ligands substituted at the fifth (MP-5) and sixth (MP-6) positions, thereby creating Ac-K(Nε-Me, Nε-Bipy)GYTGYTGK(Nε-Me, Nε-Bipy)D-OH. Peptides with a bipyridine at the 6-position did not bind to Fe2+ and Zn2+. Peptides with a bipyridine at the 5-position bound these metals, and

  含有合成肽2 Ñ ε -甲基赖氨酸（AC-K（Ñ ε -Me）GYTGYTGK（Ñ ε -Me）d-OH）与联吡啶（联吡啶）烷基化的配体在第五取代的（MP-5 ）和第六（MP-6 ）的位置，由此产生的Ac-K（ñ ε -Me，ñ ε -Bipy）GYTGYTGK（ñ ε -Me，ñ ε -Bipy）d-OH。在6位带有联吡啶的肽不与Fe 2+和Zn 2+结合。在5位带有联吡啶的肽结合这些金属，并且在一当量的游离联吡啶衍生物存在的情况下折叠成大环。此外，游离联吡啶衍生物还可以包含衍生自形成的环化肽，从而形成复杂但受控的季肽结构。
• Is JmjC Oxygenase Catalysis Limited to Demethylation?
  作者：Richard J. Hopkinson、Louise J. Walport、Martin Münzel、Nathan R. Rose、Tristan J. Smart、Akane Kawamura、Timothy D. W. Claridge、Christopher J. Schofield

  DOI：10.1002/anie.201303282

  日期：2013.7.22

  Jobs on the side: Substrate selectivity studies indicate that members of the biomedically important JmjC demethylase family of histone Nε‐methyllysine demethylases are capable of catalyzing the de‐N‐alkylation of groups other than N‐methyl and can catalyze reactions that form stable hydroxylated products. The differences in binding preferences in this set of enzymes may be helpful in the design of

  上侧的作业：底物选择性的研究表明，生物医学重要JmjC结构的成员家族脱甲基酶的组蛋白的Ñ ε -methyllysine脱甲基酶是能够催化去的Ñ比其它基团的烷基化ñ -甲基和可催化反应，其形成稳定的羟基化产品。这组酶中结合偏好的差异可能有助于设计选择性抑制剂。