N-芴甲氧羰基-L-组氨酸 | 116611-64-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 组氨酸类衍生物
• 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: N-芴甲氧羰基-L-组氨酸
• 中文别名: N-FMOC-L-组氨酸；FMOC-L-组氨酸
• 英文名称: (9-fluorenylmethoxycarbonyl)-L-histidine
• 英文别名: Fmoc-His-OH；Fmoc-H；Fmoc-His；Fmoc-L-His-OH；Fmoc-histidine；Fmoc-His(Trt)-OH；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1H-imidazol-3-ium-5-yl)propanoate
• CAS: 116611-64-4
• 化学式: C₂₁H₁₉N₃O₄
• 分子量: 377.4
• InChiKey: SIRPVCUJLVXZPW-IBGZPJMESA-N

物化性质

• 熔点：
  171-174 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  706.7±60.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微）、DMF（轻微、超声处理）、甲醇（非常轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-His-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-His-OH
CAS number: 116611-64-4

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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: C21H19N3O4
Molecular weight: 377.4

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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

(9H-芴-9-基)甲氧基羰基-L-组氨酸是一种组氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  N-芴甲氧羰基-L-组氨酸 在 三甲基氯硅烷 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.25h， 生成 Fmoc-His(ϖ-2,6-dimethoxybenzoyl)-Val-OMe
  参考文献：
  名称：

  Nim-2,6-二甲氧基苯甲酰基组氨酸在固相肽合成中的应用

  摘要：

  Fmoc-组氨酸衍生物被 2,6-二甲氧基苯甲酰基 (2,6-Dmbz) 单元保护，在 τ- (1) 或 π-位 (2) 咪唑残基上，已制备并应用于合成二肽 Fmoc-His(2,6-Dmbz)-Val-OMe 具有高偶联效率（分别为 99% 和 95%）和低外消旋化（分别为 0.3% 和 0.1%），如通过完全受保护的二肽。此外，六肽 H-Ala-Ser-Val-His-Val-Phe-OH (I) 已在固体载体上合成，采用新型构件 1 和 2 以及市售的 Fmoc-His(τ-Trt )-OH (3)。粗脱保护产物通过反相 HPLC 和质谱分析，表明当使用 τ 保护的衍生物 1 和 3 时，产物的质量相当（93-94% 主峰）。用 π 保护的组氨酸 2 合成的六肽被对应于 2,6-Dmbz-His-Val-Phe-OH (12) 的产物污染，这可能是通过 2,6-Dmbz 的分子内酰基转移形成的在去除

  DOI：

  10.1002/ejoc.200200668
• 作为产物：
  描述：

  N-Fmoc-N'-三苯甲基-L-组氨酸 在 sodium thiosulfate 、 magnesium iodide 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 2.5h， 以93%的产率得到N-芴甲氧羰基-L-组氨酸
  参考文献：
  名称：

  MgI2-化学选择性切割可去除氨基酸保护基：肽合成的新视野

  摘要：

  在肽合成领域，成功接近合成靶标的关键在于保护基团的相关组合。他们的选择取决于他们的选择性去除条件。我们在这里介绍了肽化学中一些最常用的保护基团在实验裂解条件下的行为，结合了MgI 2和MW辐射，并使用2-Me-​​THF作为绿色溶剂。在这些实验条件下，可以在肽化学中重新考虑苄氧羰基保护基以及Merrifield树脂。

  DOI：

  10.1002/bip.22908

文献信息

• Alpha-Ketoamide Inhibitors Of Cysteine Proteases
  申请人：Phelix Therapeutics

  公开号：US20190085024A1

  公开（公告）日：2019-03-21

  The disclosure provides compounds comprising a α-ketoamide linkage that is terminated on each end by an amino acid, such as compounds of Formula (I), wherein RA-RC are defined herein. Also provided are compositions containing these compounds and methods of inhibiting calpain activity, treating a calpain-mediated disorder, inhibiting cathepsin-B, cathepsin-L, cathepsin-S, or cathepsin-L activity, and methods of treating a cathepsin-B, cathepsin-L, cathepsin-S, or cathepsin-L mediated disorder using these compounds and compositions.

  该披露提供了包含α-酮酰胺键的化合物，该键在每端由氨基酸终止，例如式(I)中的化合物，其中RA-RC在此处定义。还提供了含有这些化合物的组合物以及抑制钙蛋白酶活性、治疗钙蛋白酶介导的疾病、抑制卡托普西-B、卡托普西-L、卡托普西-S或卡托普西-L活性的方法，以及使用这些化合物和组合物治疗卡托普西-B、卡托普西-L、卡托普西-S或卡托普西-L介导的疾病的方法。
• Search for New Aggregable Fragments of Human Insulin
  作者：Monika Swiontek、Justyna Fraczyk、Joanna Wasko、Agata Chaberska、Lukasz Pietrzak、Zbigniew J. Kaminski、Lukasz Szymanski、Slawomir Wiak、Beata Kolesinska

  DOI：10.3390/molecules24081600

  日期：——

  In this study, three independent methods were used to identify short fragment of both chains of human insulin which are prone for aggregation. In addition, circular dichroism (CD) research was conducted to understand the progress of aggregation over time. The insulin fragments (deca- and pepta-peptides) were obtained by solid-phase synthesis using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium

  在这项研究中，使用了三种独立的方法来鉴定两条人胰岛素链中易于聚集的短片段。此外，还进行了圆二色性 (CD) 研究以了解聚合随时间的进展。胰岛素片段（十肽和肽肽）是通过固相合成获得的，使用 4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉鎓甲苯-4-磺酸盐（ DMT/NMM/TosO-) 作为偶联剂。系统研究允许鉴定新的片段，预计在生理条件下参与触发人胰岛素整个结构的聚集。发现聚集过程通过各种结构构象异构体发生并且可能有利于聚集物的纤维结构的形成。
• [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。
• Synthesis of an MUC1 Glycopeptide Dendrimer Based on β-Cyclodextrin by Click Chemistry
  作者：Yan-Mei Li、Pu-Guang Chen、Zhi-Hua Huang、Zhan-Yi Sun、Qian-Qian Li、Yong-Xiang Chen、Yu-Fen Zhao

  DOI：10.1055/s-0036-1590796

  日期：2017.9

  Glycopeptide dendrimers are attractive candidates for biomedical applications. Here, an efficient method for preparing multivalent MUC1 glycopeptide dendrimers based on β-cyclodextrin is described. By using copper(I) bromide and thioanisole as a catalyst system, precisely defined heptavalent conjugates were efficiently obtained. Using this heptavalent glycopeptide dendrimer, we observed multivalent

  糖肽树枝状聚合物是生物医学应用的有吸引力的候选者。在这里，描述了一种基于β-环糊精制备多价 MUC1 糖肽树枝状聚合物的有效方法。通过使用溴化铜 (I) 和苯硫醚作为催化剂体系，可以有效地获得精确定义的七价共轭物。使用这种七价糖肽树状聚合物，我们观察到抗体和表位相互作用中识别和关联过程中的多价效应，这可能具有生物医学应用。
• Postsynthetic Modification of Peptides: Chemoselective C-Arylation of Tryptophan Residues
  作者：Javier Ruiz-Rodríguez、Fernando Albericio、Rodolfo Lavilla

  DOI：10.1002/chem.200902676

  日期：2010.1.25

  Born to be mild: The general, direct and selective C2 arylation of native Trp‐containing peptides can be achieved by palladium‐catalyzed CH activation with aryl iodides in water, under microwave irradiation for a short time (see scheme). Under these mild conditions, the structural and stereochemical integrity of peptides is preserved.

  天生的温和：天然含色氨酸的肽的一般，直接和选择性的C2芳基化可以通过钯催化的C下实现 ħ活化与芳基碘在水，微波照射一个短的时间下（参见方案）。在这些温和条件下，肽的结构和立体化学完整性得以保留。