N-[芴甲氧羰基]-1-甲基-L-组氨酸 | 202920-22-7

• 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]-1-甲基-L-组氨酸
• 中文别名: Fmoc-1-甲基-L-组氨酸
• 英文名称: Fmoc-His(1-Me)-OH
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1-methylimidazol-4-yl)propanoic acid
• CAS: 202920-22-7
• 化学式: C₂₂H₂₁N₃O₄
• 分子量: 391.426
• InChiKey: SLWOFHRSEVVUHM-FQEVSTJZSA-N

物化性质

• 沸点：
  686.7±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：10mg/mL； DMSO：10mg/mL； PBS（pH 7.2）：0.2 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-his(1-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-his(1-me)-oh
CAS number: 202920-22-7

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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: C22H21N3O4
Molecular weight: 391.4

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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

反应信息

• 作为反应物：
  描述：

  N-[芴甲氧羰基]-1-甲基-L-组氨酸 、 tert-butyl (S)-2-amino-6-diazo-5-oxohexanoate 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 为溶剂， 以83 %的产率得到tert-butyl (S)-2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-methyl-1H-imidazol-4-yl)propanamido)-6-diazo-5-oxohexanoate
  参考文献：
  名称：

  [EN] PRODRUGS OF 6-DIAZO-5-OXO-L-NORLEUCINE
  [FR] PROMÉDICAMENTS DE 6-DIAZO-5-OXO-L-NORLEUCINE

  摘要：

  本公开提供了6-重氮-5-氧代-L-异亮氨酸（DON）的前药，用于治疗或预防抑制谷氨酰胺利用酶有益的疾病、紊乱或状况。

  公开号：

  WO2022232565A1

文献信息

• Design and synthesis of peptide inhibitor conjugates as probes of the Cytochrome P450s from glycopeptide antibiotic biosynthesis
  作者：Clara Brieke、Theresa Maier、Martin Schröter、Max J. Cryle

  DOI：10.1039/c5md00332f

  日期：——

  The glycopeptide antibiotics are important clinical antibiotics that are currently employed against serious Gram-positive bacterial infections. Their chemical complexity means that their production is reliant upon the natural biosynthesis pathway, of which the key steps are the synthesis and side chain cyclisation of the peptide backbone. These processes rely upon a non-ribosomal peptide synthetase

  糖肽抗生素是重要的临床抗生素，目前已用于抵抗严重的革兰氏阳性细菌感染。它们的化学复杂性意味着它们的生产依赖于天然生物合成途径，其中关键步骤是肽骨架的合成和侧链环化。这些过程依赖于非核糖体肽合成酶（NRPS）和几种与NRPS结合的肽相互作用以产生活性糖苷配基的细胞色素P450酶。这些被称为Oxy酶的P450催化剂对于生物合成至关重要，然而，它们与底物肽相互作用的性质仍然知之甚少。在这项工作中面包车。与分离的GPA前体肽相比，这些化合物显示出改善的溶解度和结合特性，并提供了有关此类肽与P450活性位点结合的见解。这些探针可用于表征来自相关生物合成机械的其他P450，并且有望与Oxy酶共结晶。
• MODULATION OF STRUCTURED POLYPEPTIDE SPECIFICITY
  申请人：BICYCLE THERAPEUTICS LIMITED

  公开号：US20160046673A1

  公开（公告）日：2016-02-18

  The invention describes peptide ligands specific for human plasma Kallikrein.

  该发明描述了特异于人血浆卡利肽酶的肽配体。
• MACROCYCLIC COMPOUNDS FOR INHIBITION OF TUMOR NECROSIS FACTOR ALPHA
  申请人：Lee Jinbo

  公开号：US20100152099A1

  公开（公告）日：2010-06-17

  The invention provides macrocyclic compounds and methods for their synthesis and use. In particular, the invention provides macrocyclic compounds that modulate the activity of tumor necrosis factor alpha and/or are useful in the treatment of medical conditions, such as, rheumatoid arthritis, psoriasis, and asthma.

  该发明提供了大环化合物及其合成和使用方法。具体而言，该发明提供了调节肿瘤坏死因子α活性和/或用于治疗医学状况（如类风湿性关节炎、银屑病和哮喘）的大环化合物。
• Modulation of structured polypeptide specificity
  申请人：BICYCLE THERAPEUTICS LIMITED

  公开号：US10118947B2

  公开（公告）日：2018-11-06

  The invention describes peptide ligands specific for human plasma Kallikrein.

  本发明描述了人血浆 Kallikrein 的特异性肽配体。
• <i>In Vitro</i> and <i>in Vivo</i> Characterization of Novel ¹⁸F-Labeled Bombesin Analogues for Targeting GRPR-Positive Tumors
  作者：Linjing Mu、Michael Honer、Jessica Becaud、Miljen Martic、Pius A. Schubiger、Simon M. Ametamey、Timo Stellfeld、Keith Graham、Sandra Borkowski、Lutz Lehmann、Ludger Dinkelborg、Ananth Srinivasan

  DOI：10.1021/bc100222u

  日期：2010.10.20

  The gastrin-releasing peptide receptor (GRPR) is overexpressed on a number of human tumors and has been targeted with radiolabeled bombesin analogues for the diagnosis and therapy of these cancers. Seven bombesin analogues containing various linkers and peptide sequences were designed, synthesized, radiolabeled with F-18, and characterized in vitro and in vivo as potential PET imaging agents. Binding studies displayed nanomolar binding affinities toward human GRPR for all synthesized bombesin analogues. Two high-affinity peptide candidates 6b (K-i = 0.7 nM) and 7b (K-i = 0.1 nM) were chosen for further in vivo evaluation. Both tracers revealed specific uptake in GRPR-expressing PC-3 tumors and the pancreas. Compared to [F-18]6b, compound [F-18]7b was characterized by superior tumor uptake, higher specificity of tracer uptake, and more favorable tumor-to-nontarget ratios. In vivo PET imaging allowed for the visualization of PC-3 tumor in nude mice suggesting that [F-18]7b is a promising PET tracer candidate for the diagnosis of GRPR-positive tumors in humans.