N-芴甲氧羰基-S-甲基-L-半胱氨酸 | 138021-87-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 半胱氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-芴甲氧羰基-S-甲基-L-半胱氨酸
• 中文别名: FMOC-S-甲基-L-半胱氨酸
• 英文名称: Fmoc-Cys(Me)-OH
• 英文别名: Fmoc-S-methylcysteine–OH；Fmoc-S-Methyl-L-Cysteine；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylsulfanylpropanoic acid
• CAS: 138021-87-1
• 化学式: C₁₉H₁₉NO₄S
• 分子量: 357.43
• InChiKey: SKNJDZVHMNQAGO-KRWDZBQOSA-N

物化性质

• 沸点：
  594.5±50.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2930909090
• 危险类别：
  IRRITANT
• 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-cys(me)-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-cys(me)-oh
CAS number: 138021-87-1

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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: C19H19NO4S
Molecular weight: 357.4

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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, sulfur 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：

  N-芴甲氧羰基-S-甲基-L-半胱氨酸 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (R)-N-acetyl-S-methyl-L-cysteine methyl ester
  参考文献：
  名称：

  Identification of novel N-acetylcysteine derivatives for the treatment of hepatocellular injury

  摘要：

  N-乙酰半胱氨酸（NAC）衍生物被合成并筛选，用于对抗两种不同细胞模型的抗肝细胞损伤活性，其中衍生物6a和6b表现出最强效果，可降低丙二醛（MDA）水平。

  DOI：

  10.1039/c7md00409e
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 trifluoroacetate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 N-芴甲氧羰基-S-甲基-L-半胱氨酸
  参考文献：
  名称：

  Sc（OTf）3介导的硫醚的轻度和高度化学选择性氧化。

  摘要：

  [反应：见正文]催化Sc（OTf）（3）大大提高了过氧化氢介导的烷基芳基硫醚和甲基半胱氨酸肽的单氧化效率。该方法收率高，可与许多广泛使用的保护基团兼容，适用于固相应用，且过氧化反应最少。

  DOI：

  10.1021/ol026947i

文献信息

• [EN] NOVEL HEPCIDIN MIMETICS AND USES THEREOF<br/>[FR] NOUVEAUX MIMÉTIQUES D'HEPCIDINE ET LEURS UTILISATIONS
  申请人：BAYER HEALTHCARE LLC

  公开号：WO2018128828A1

  公开（公告）日：2018-07-12

  The present invention relates to novel peptides acting as hepcidin mimetics, as well as analogues and derivatives thereof. The invention further relates to compositions comprising the peptides of the present invention, and to the use of the peptides in the prophylaxis and treatment of hepcidin-associated disorders, including prophylaxis and treatment of iron overload diseases such as hemochromatosis, iron-loading anemias such as thalassemia, and diseases being associated with ineffective or augmented erythropoiesis, as well as further related conditions and disorders described herein.

  本发明涉及作为赫普西定类似物的新型肽，以及其类似物和衍生物。该发明还涉及包含本发明肽的组合物，以及在预防和治疗赫普西定相关疾病中使用这些肽，包括预防和治疗铁过载疾病如血色病、铁负荷性贫血如地中海贫血，以及与效率低下或增强的红细胞生成相关的疾病，以及本文所述的进一步相关病症和疾病。
• Decarbonylative Approach to the Synthesis of Enamides from Amino Acids: Stereoselective Synthesis of the (<i>Z</i>)-Aminovinyl-<scp>d</scp>-Cysteine Unit of Mersacidin
  作者：Pablo García-Reynaga、Angela K. Carrillo、Michael S. VanNieuwenhze

  DOI：10.1021/ol203399x

  日期：2012.2.17

  The Pd- and Ni-promoted decarbonylation of amino acid thioesters proceeds smoothly to yield enamides. The synthesis of the (S)-(Z)-AviMeCys subunit of mersacidin, an MRSA-active lantibiotic, via this approach, is described.

  Pd 和 Ni 促进的氨基酸硫酯脱羰反应顺利进行，生成烯酰胺。描述了通过这种方法合成MRSA 活性羊毛硫抗生素 mersacidin的 ( S )-( Z )-AviMeCys 亚基。
• An efficient method for racemization free attachment of 9-fluorenylmethyloxycarbonyl-amino acids to peptide synthesis supports
  作者：Michael S. Bernatowicz、Thomas Kearney、Richard S. Neves、Hubert Köster

  DOI：10.1016/s0040-4039(00)99355-9

  日期：1989.1

  An efficient, general, and racemization free method of covalently attaching N α -Fmoc protected amino acids to solid supports for peptide synthesis is described. The process involves the preparation of 2,4-dichlorophenyl-N α -Fmoc-aminoacyl-4-oxymethyl-phenoxy acetates which can be used to directly and efficiently acylate amine functionalized polymers.

  描述了将Nα-Fmoc保护的氨基酸共价附接至固体支持物以进行肽合成的有效，通用且无外消旋的方法。该方法涉及2，4-二氯苯基-Nα-Fmoc-氨基酰基-4-氧甲基-苯氧基乙酸酯的制备，该乙酸酯可用于直接和有效地酰化胺官能化的聚合物。
• Synthesis of <i>e</i><i>nt</i>-Alantrypinone
  作者：David J. Hart、Nabi A. Magomedov

  DOI：10.1021/ja010066+

  日期：2001.6.1

  This paper presents a synthesis of ent-alantrypinone (ent-6), the enantiomer of a natural product produced by the fungus Penicillium thymicola. The synthesis revolves around the Li[Me(3)AlSPh]-promoted isomerization of iminobenzoxazine 33 to quinazolinone 34, an N-acyliminium ion cyclization that converts enamide 9 to bridged indole 35, and rearrangement of 35 to oxindole ent-6. Ancillary chemistry

  本文介绍了 ent-alantrypinone (ent-6) 的合成，它是由真菌 Penicillium thymicola 产生的天然产物的对映异构体。合成围绕 Li[Me(3)AlSPh] 促进的亚氨基苯并恶嗪 33 异构化为喹唑啉酮 34、N-acyliminium 离子环化将烯酰胺 9 转化为桥接吲哚 35，以及 35 重排为 oxindole ent-6。还描述了涉及亚氨基苯并恶嗪热裂解为腈叶立德和 Me(2)AlSPh 介导的肟醚酯 22 环化为吡咯烷酮 23 的辅助化学。
• Novel peptides as NS3-serine protease inhibitors of hepatitis C virus
  申请人：——

  公开号：US20030036501A1

  公开（公告）日：2003-02-20

  The present invention discloses novel peptide compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such peptides as well as methods of using them to treat disorders associated with the HCV protease.

  本发明揭示了具有HCV蛋白酶抑制活性的新型肽化合物，以及制备这些化合物的方法。在另一实施方案中，本发明揭示了包含这些肽段的药物组合物，以及使用它们治疗与HCV蛋白酶相关疾病的方法。