FMOC-D-组氨酸 | 157355-79-8

• 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: FMOC-D-组氨酸
• 中文别名: N-芴甲氧羰基-D-组氨酸；Fmoc-D-组氨酸
• 英文名称: Fmoc-D-His-OH
• 英文别名: (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1H-imidazol-3-ium-5-yl)propanoate
• CAS: 157355-79-8
• 化学式: C₂₁H₁₉N₃O₄
• mdl: MFCD00237022
• 分子量: 377.4
• InChiKey: SIRPVCUJLVXZPW-LJQANCHMSA-N

物化性质

• 熔点：
  >128oC (dec.)
• 沸点：
  706.7±60.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)
• 溶解度：
  乙酸（少量溶解）、碱水（少量溶解）、DMSO（少量溶解）

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-D-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-D-His-OH
CAS number: 157355-79-8

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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-D-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 、 FMOC-D-组氨酸 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 cyclo-Leu-N-methyl-3-(4-thiazoyl)Ala-D-Leu-D-3-(4-thiazoyl)Ala-3,3-biphenyl-D-Ala
  参考文献：
  名称：

  击中一个移动的目标：N-甲基对生物活性有何影响？

  摘要：

  在解决特定的蛋白质间相互作用作为治疗目标时，大环化合物相对于小分子药物具有多个优势。在这里，我们报告了七个新的环肽分子的合成及其生物学活性。设计这些大环化合物是为了了解围绕肽主链移动N-甲基部分如何影响生物活性。由于铅的非甲基化结构抑制了致癌调节物热休克蛋白90（Hsp90），因此对两个最有效的类似物的Hsp90抑制活性进行了评估。我们证明结合了N甲基部分控制着大环的构象，这极大地影响了对Hsp90的细胞毒性和结合亲和力。因此，在大环内放置一个N-甲基化氨基酸会对该化合物的构象产生不可预测的变化，从而导致其生物活性发生不可预测的变化。

  DOI：

  10.1002/cmdc.201500572
• 作为产物：
  描述：

  N-芴甲氧羰基-N'-三苯甲基-D-组氨酸 在 三氟乙酸 作用下， 反应 3.0h， 生成 FMOC-D-组氨酸
  参考文献：
  名称：

  用FMOC-组氨酸4-烷氧基苄醇树脂的酯化（N IM三苯甲基）-N-羧酸酐

  摘要：

  4-烷氧基苄醇树脂（Wang树脂）的酯化是在高产率和当FMOC-组氨酸（N没有可检测的外消旋化迅速完成即时三苯）-NCA是冷凝试剂。

  DOI：

  10.1016/s0040-4039(00)76938-3

文献信息

• Synthesis, stability and mechanistic studies of potent anticryptococcal hexapeptides
  作者：Kitika Shenmar、Krishna K. Sharma、Nishima Wangoo、Indresh K. Maurya、Vinod Kumar、Shabana I. Khan、Melissa R. Jacob、Kulbhushan Tikoo、Rahul Jain

  DOI：10.1016/j.ejmech.2017.03.046

  日期：2017.5

  which has been exploited in the present study by synthesizing a series of hexapeptides that exhibits promising activity against a panel of Gram-negative and Gram-positive bacteria and various pathogenic fungal strains; the most exemplary activity was observed against Cryptococcus neoformans. The peptides 3, 24, 32 and 36 displayed potent anticryptococcal activity (IC50 = 0.4-0.46 μg/mL, MIC = 0.63-1.25

  免疫功能低下患者中隐球菌病的发病率不断增长，因此需要一种能够根除该病的新型药物疗法。与传统治疗剂相比，基于肽的药物治疗具有许多优势，传统治疗剂已在本研究中得到利用，其方法是合成一系列六肽，这些六肽对一组革兰氏阴性和革兰氏阳性细菌以及各种病原性真菌菌株显示出有希望的活性; 观察到了对新型隐球菌的最典型的活性。肽3、24、32和36表现出强大的抗隐球菌活性（IC50 = 0.4-0.46μg/ mL，MIC = 0.63-1.25μg/ mL，MFC = 0.63-1.25μg/ mL），并且在蛋白水解条件下具有稳定性。除此之外，其他几种肽还显示出对病原菌的抑制作用。突出的肽包括表现出IC50值在2.1和3.6μg/ mL之间的肽18-20和26，针对金黄色葡萄球菌和耐甲氧西林的S的MIC为5-20μg/ mL和MBC为10-20μg/ mL。金黄色的。通过扫描电子显微镜和透射电子显微镜研究证
• Evaluation of Readily Accessible Azoles as Mimics of the Aromatic Ring of D-Phenylalanine in the Turn Region of Gramicidin S
  作者：Matthijs van der Knaap、Lianne T. Lageveen、Henk J. Busscher、Roos Mars-Groenendijk、Daan Noort、José M. Otero、Antonio L. Llamas-Saiz、Mark J. van Raaij、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1002/cmdc.201000539

  日期：2011.5.2

  d‐phenylalanine residue with substituted and unsubstituted azoles on the structure and biological activity of the antibiotic gramicidin S was investigated against a representative panel of Gram‐positive and Gram‐negative bacteria strains. Substituted triazole derivatives, obtained using a convergent synthetic strategy, are as active as gramicidin S, provided that any substituent on the triazole moiety is

  更换d‐的影响针对具有代表性的革兰氏阳性和革兰氏阴性细菌菌株，研究了抗生素短杆菌肽S的结构和生物学活性上带有取代和未取代的唑的苯丙氨酸残基。如果三唑部分上的取代基不太大，则采用收敛合成策略获得的取代三唑衍生物的活性与短杆菌肽S相同。未取代的三唑衍生物的生物学活性低于母体天然产物短杆菌肽S。一般来说，三唑系列的溶血活性可能与抗菌活性相关，即，抗菌活性越高，对血液的毒性越高。细胞。有趣的是，它的咪唑对应物显示出很高的抗菌活性，
• 一种海洋真菌来源的抗病毒喹啉酮生物碱类 衍生物的制备方法
  申请人：扬州蓝色生物医药科技有限公司

  公开号：CN106554307B

  公开（公告）日：2019-09-27

  本发明涉及一种海洋真菌来源的抗病毒喹啉酮生物碱类衍生物的制备方法，包括由式A化合物与R1OH反应制备式I‑1化合物的步骤：式A化合物与任选取代的氨基酸R1OH，在有机溶剂中，发生缩合反应，得到式I‑1化合物；其中R1为羧基端脱掉羟基的氨基酸残基，R2为H、C1‑C4烷基、C3‑C6环烷基、C1‑C4卤代烷基、C1‑C4烷基酰基、C1‑C4卤代烷基酰基、C3‑C6环烷基酰基、C2‑C4烯基、C5‑C10芳基烷基，“‑‑‑‑‑”表示单键或不存在，表示指向纸面里的键或指向纸面外的键
• PRODRUGS OF CYTOTOXIC ACTIVE AGENTS HAVING ENZYMATICALLY CLEAVABLE GROUPS
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20190077752A1

  公开（公告）日：2019-03-14

  The invention relates to novel prodrugs or conjugates of the general formula (Ia) in which cytotoxic drugs, for example kinesin spindle protein inhibitors, are masked with legumain-cleavable groups and hence release the drug, and to the use of these prodrugs or conjugates for treatment and/or prevention of diseases, and to the use of these prodrugs or conjugates for production of medicaments for treatment and/or prevention of diseases, especially of hyperproliferative and/or angiogenic disorders, for example cancers.

  该发明涉及通式(Ia)的新型前药或结合物，其中细胞毒性药物，例如动力蛋白抑制剂，被腿蛋白酶可切割基团掩蔽，从而释放药物，并且涉及使用这些前药或结合物用于治疗和/或预防疾病，以及使用这些前药或结合物用于生产用于治疗和/或预防疾病的药物，特别是治疗和/或预防高增殖和/或血管生成异常的疾病，例如癌症。
• Selection of DNA‐Encoded Dynamic Chemical Libraries for Direct Inhibitor Discovery
  作者：Yuqing Deng、Jianzhao Peng、Feng Xiong、Yinan Song、Yu Zhou、Jianfu Zhang、Fong Sang Lam、Chao Xie、Wenyin Shen、Yiran Huang、Ling Meng、Xiaoyu Li

  DOI：10.1002/anie.202005070

  日期：2020.8.24

  that can identify full ligand structures from large‐scale DEDLs. This method is also able to convert unbiased libraries into focused ones targeting specific protein classes. We demonstrated this method by selecting DEDLs against five proteins, and novel inhibitors were identified for all targets. Notably, several selective BD1/BD2 inhibitors were identified from the selections against bromodomain 4 (BRD4)

  动态组合库（DCL）是生物医学研究中配体发现的强大工具。但是，DCL的低多样性阻碍了它们的应用。最近，DCL中已经采用了DNA编码的概念来创建DNA编码的动态库（DEDL）。但是，当前所有的DEDL都仅限于片段识别，并且在选择后需要一个具有挑战性的片段链接过程。我们报告了一种锚定的DEDL方法，该方法可以从大规模DEDL中识别出完整的配体结构。这种方法还能够将无偏文库转换为针对特定蛋白质类别的集中文库。我们通过选择针对五种蛋白质的DEDLs证明了这种方法，并为所有靶标确定了新型抑制剂。值得注意的是 从针对重要的抗癌药物靶标bromodomain 4（BRD4）的选择中鉴定出了几种选择性的BD1 / BD2抑制剂。这项工作可以为抑制剂发现提供广泛适用的方法。