芴甲氧羰基-L-半胱氨酸 | 135248-89-4

• 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: 芴甲氧羰基-L-半胱氨酸
• 中文别名: FMOC-L-半胱氨酸；Fmoc-L-半胱氨酸
• 英文名称: N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine
• 英文别名: Fmoc-(Cys)-OH；Fmoc-Cys；Fmoc-L-cysteine；(((9H-fluoren-9-yl)methoxy)carbonyl)-L-cysteine；N-(9-fluorenylmethoxycarbonyl)-L-cysteine；N-Fmoc-L-cysteine；Fmoc-Cysteine-OH；Fmoc-cysteine；(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-mercaptopropanoic acid；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-sulfanylpropanoic acid
• CAS: 135248-89-4
• 化学式: C₁₈H₁₇NO₄S
• 分子量: 343.403
• InChiKey: RMTDKXQYAKLQKF-INIZCTEOSA-N

物化性质

• 熔点：
  98-102oC
• 沸点：
  574.4±50.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)
• 溶解度：
  丙酮（微溶）、DMF（微溶）、DMSO（微溶）、甲醇（微溶、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76.6
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光、干燥密闭保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-cys-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-oh
CAS number: 135248-89-4

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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, 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: C18H17NO4S
Molecular weight: 343.4

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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

制备方法与用途

(9H-芴-9-基)甲氧基羰基-L-半胱氨酸是一种半胱氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  芴甲氧羰基-L-半胱氨酸 在 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 亚磷酸三乙酯 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 0.5h， 以84%的产率得到Fmoc-L-丙氨酸
  参考文献：
  名称：

  可见光光氧化还原催化的含硫醇和二硫键的氨基酸和小肽的脱硫。

  摘要：

  通过使用可见光，光催化剂Ir（dF（CF 3）ppy）2（dtb-bpy）PF 6对半胱氨酸进行脱硫的可扩展方案已经开发了在两相反应条件下的亚磷酸三乙酯。催化剂的负载量可低至0.01 mol％，可在后处理过程中有效去除（≤0.3 ppm），从而以高收率得到相应的脱硫产物。该方法也已应用于胱氨酸，青霉胺以及还原和氧化的谷胱甘肽。已发现脱硫对pH敏感，半胱氨酸衍生物和谷胱甘肽的最佳pH值分别为6.5和7.0。此外，在含有半胱氨酸和蛋氨酸的十肽脱硫过程中，已观察到两个含硫残基同时氧化为二硫键和亚砜。所以，尽管所提出的方案通过使用非常低的催化剂负载量和具有成本效益的亚磷酸三烷基酯作为硫代自由基捕获剂，可以对可见光进行简单的硫醇直接脱硫，但需要仔细验证其在复杂底物上的应用。版权所有©2017欧洲多肽协会和John Wiley＆Sons，Ltd.

  DOI：

  10.1002/psc.3016
• 作为产物：
  描述：

  Fmoc-L-Cys(Thp)-OH 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以99%的产率得到芴甲氧羰基-L-半胱氨酸
  参考文献：
  名称：

  四氢吡喃基，Fmoc肽化学的一种非芳香族酸不稳定的半胱氨酸保护基

  摘要：

  四氢吡喃基（THP），其利用的是一个概念小号，ö -acetal非芳香族保护基为半胱氨酸，已被证明优于TRT，DPM，ACM，和S吨在使用Fmoc固相肽合成BU / t Bu策略。因此，当Cys被Thp保护时，Cys外消旋作用和C末端3-（1-哌啶基）丙氨酸的形成被最小化。该非芳族保护基团还改善了含Cys的被保护肽的溶解性。

  DOI：

  10.1021/acs.orglett.5b00444
• 作为试剂：
  描述：

  (E)-cyclooct-4-enol 在 芴甲氧羰基-L-半胱氨酸 作用下， 以 氘代甲醇 为溶剂， 22.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 (Z)-(R)-Cyclooct-4-enol
  参考文献：
  名称：

  Site-Specific Antibody Functionalization Using Tetrazine–Styrene Cycloaddition

  摘要：

  生物制剂，如抗体-药物偶连物，正逐渐成为主流治疗方法。因此，开发在不破坏其天然特性的情况下功能化生物制剂的方法，对于识别、表征和将候选生物制剂从实验室转化到临床应用至关重要。在此，我们提出了一种对单链抗体片段（scFv）进行特定位点、羧基末端修饰的方法。通过将内肽介导的表达蛋白连接（EPL）与反向电子需求Diels–Alder（IEDDA）环加成结合，分离并功能化了显示在酵母表面的scFv，采用的是苯乙烯-四氮唑配对。触发EPL所需的高硫醇浓度可能会妨碍后续的化学选择性连接反应；因此，使用EPL反应将苯乙烯附加到scFv上，从而限制了四氮唑暴露于有害硫醇中。随后，将苯乙烯功能化的scFv与四氮唑偶联化合物进行IEDDA环加成反应，生成保留其天然结合活性的功能化scFv。以定点方式快速功能化酵母表面衍生的scFv，可能在许多下游实验室和临床前应用中具有实用性。

  DOI：

  10.1021/acs.bioconjchem.8b00114

文献信息

• THIOL-ENE CLICK CHEMISTRY FOR DRUG CONJUGATES
  申请人：SYSCHEM, INC.

  公开号：US20130323169A1

  公开（公告）日：2013-12-05

  The present invention relates to linker molecules that readily conjugate cellular recognition ligand at one end and drug payload at the other, and are useful in treating or preventing cancer, an autoimmune disease, an inflammatory condition, a central nervous system disorder or an infection. The linker inker molecules of the invention are represented by Formula I, II and III; Linker-Drug compounds represented by Formula IV, V and VI; and Ligand-Linker-Drug conjugates represented by Formula VII, VIII and IX:

  本发明涉及易于在一端结合细胞识别配体和在另一端结合药物载荷的连接分子，并且在治疗或预防癌症、自身免疫疾病、炎症症状、中枢神经系统紊乱或感染方面具有用处。该发明的连接分子由公式I、II和III表示；由公式IV、V和VI表示的连接-药物化合物；以及由公式VII、VIII和IX表示的配体-连接-药物共轭物。
• Visible‐Light‐Mediated S−H Bond Insertion Reactions of Diazoalkanes with Cysteine Residues in Batch and Flow
  作者：Long‐Zhou Qin、Xin Yuan、Yu‐Sheng Cui、Qi Sun、Xiu Duan、Kai‐Qiang Zhuang、Lin Chen、Jiang‐Kai Qiu、Kai Guo

  DOI：10.1002/adsc.202000716

  日期：2020.11.18

  diazoacetates with cysteine residues that enabled metal‐free, S−H functionalization under visible‐light conditions. Moreover, this process could be intensified by a continuous‐flow photomicroreactor on the acceleration of the reaction (6.5 min residence time). The batch and flow protocols described were applied to obtain a wide range of functionalized cysteine derivatives and cysteine‐containing dipeptides

  我们描述了芳基重氮乙酸酯与半胱氨酸残基的S-H键插入反应的应用，该反应可在可见光条件下实现无金属的S-H功能化。此外，连续反应光微反应器可加快反应速度（6.5分钟的停留时间），从而增强该过程。所描述的批次和流程方案可用于获得各种功能化的半胱氨酸衍生物和含半胱氨酸的二肽，从而为其在温和条件下的功能化提供了一个简单而通用的平台。
• [EN] FIBRIN-BINDING COMPOUNDS FOR IMAGING AND TREATMENT<br/>[FR] COMPOSÉS DE LIAISON À LA FIBRINE POUR IMAGERIE ET TRAITEMENT
  申请人：COLLAGEN MEDICAL LLC

  公开号：WO2021081430A1

  公开（公告）日：2021-04-29

  This disclosure relates to compounds of Formula IV: for fibrin imaging, wherein the compounds comprise an imaging or therapeutic radioisotope.

  这项披露涉及到公式IV的化合物：用于纤维蛋白成像，其中化合物包含成像或治疗放射性同位素。
• Glutamic Acid Selective Chemical Cleavage of Peptide Bonds
  作者：Joseph M. Nalbone、Neelam Lahankar、Lyssa Buissereth、Monika Raj

  DOI：10.1021/acs.orglett.6b00317

  日期：2016.3.4

  hydrolysis of peptide bonds at glutamic acid under neutral aqueous conditions is reported. The method relies on the activation of the backbone amide chain at glutamic acid by the formation of a pyroglutamyl (pGlu) imide moiety. This activation increases the susceptibility of a peptide bond toward hydrolysis. The method is highly specific and demonstrates broad substrate scope including cleavage of various bioactive

  据报道在中性水性条件下谷氨酸上肽键的位点特异性水解。该方法依赖于通过形成焦谷氨酰基（pGlu）酰亚胺部分而在谷氨酸上激活主链酰胺链。这种活化增加了肽键对水解的敏感性。该方法是高度特异性的，并证明了广泛的底物范围，包括具有非天然氨基酸残基的各种生物活性肽的裂解，所述非天然氨基酸残基是不适合酶促水解的底物。
• Synthesis of natural and non natural orthogonally protected lanthionines from N-tritylserine and allo-threonine derivatives
  作者：Christophe Dugave、André Ménez

  DOI：10.1016/s0957-4166(97)00109-2

  日期：1997.5

  This strategy was applied to the synthesis of lanthionines, the monosulfide analogs of cystine. Orthogonally protected sulfide adducts from L- and D-cysteines, threo-β-methyl-L-cysteine and D-penicillamine were isolated in 81–88% yield (ee>98%). This strategy was applied to the prepration of lanthionine and cyclolanthionine suitably protected for peptide synthesis.

  衍生自亲电子的反应性Ñ -tritylserine，苏氨酸和异基因朝向选择的亲核试剂的苏氨酸酯进行了研究。用N-三苯并碘丙氨酸和软亲核试剂（例如硫醇）可获得替代产品的最佳收率。该策略被用于合成胱氨酸的单硫醚类似物羊毛硫氨酸。从L-和d-半胱氨酸，正交保护的加合物硫化物苏- β -甲基-L-半胱氨酸和d青霉胺在81-88％的产率（ee值> 98％）中分离得到。将该策略应用于适当保护用于肽合成的羊毛硫氨酸和环羊毛硫氨酸的制备。