N-乙酰基-N'-三苯甲基-L-组氨酸 | 183498-47-7

• 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 - 苯类化合物 - 三苯基化合物
• 中文名称: N-乙酰基-N'-三苯甲基-L-组氨酸
• 中文别名: N-乙酰基-N’-三苯甲基-L-组氨酸
• 英文名称: Ac-His(1-Trt)-OH
• 英文别名: Ac-His(Trt)-OH；(S)-2-Acetamido-3-(1-trityl-1H-imidazol-4-yl)propanoic acid；(2S)-2-acetamido-3-(1-tritylimidazol-4-yl)propanoic acid
• CAS: 183498-47-7
• 化学式: C₂₇H₂₅N₃O₃
• 分子量: 439.514
• InChiKey: MFOVFDBMJIPSLM-VWLOTQADSA-N

物化性质

• 沸点：
  680.1±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ac-His(1-Trt)-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: Ac-His(1-Trt)-OH
CAS number: 183498-47-7

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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: C27H25N3O3
Molecular weight: 439.5

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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-乙酰基-N'-三苯甲基-L-组氨酸 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 Ac-His-Lys-OMe bis(trifluoroacetate)
  参考文献：
  名称：

  一种对水溶液中肽中N-末端组氨酸具有亲和力的发光受体

  摘要：

  大小合适的冠醚是用于铵离子结合的完美人工宿主化合物，但在水溶液中的亲和力相当低，阻碍了它们在生理条件下的使用。我们在此报告了发光苯并冠醚的合成和性质，该醚具有侧链亚胺二乙酸铜配合物，与组氨酸具有高亲和力。在甲醇中存在铵离子时，苯并冠醚的发射强度显着增加。在 pH 7.5 的缓冲水中的生理条件下，这些相互作用太弱而无法检测到。如果分析物中存在铵离子和咪唑部分，例如在 His-Lys-OMe 或 His-OMe 中，则水溶液中的高结合亲和力会恢复。结合事件由发射强度的增加发出信号，甚至可以用肉眼观察到。这允许在生理条件下选择性检测所有其他氨基酸中含有 N 端组氨酸或组氨酸的小肽。

  DOI：

  10.1021/ja043930h

文献信息

• Design, Synthesis, and Evaluation of Proline and Pyrrolidine Based Melanocortin Receptor Agonists. A Conformationally Restricted Dipeptide Mimic Approach
  作者：Xinrong Tian、Timothy B. Field、Adrian G. Switzer、Adam W. Mazur、Frank H. Ebetino、John A. Wos、Steve M. Berberich、Lalith R. Jayasinghe、Cindy M. Obringer、Martin E. Dowty、Beth B. Pinney、Julie A. Farmer、Doreen Crossdoersen、Russell J. Sheldon

  DOI：10.1021/jm060384p

  日期：2006.7.1

  hMC4R. Potent cis-(2S,4R)-pyrrolidine based MCR agonists (35a-g) were subsequently developed by means of this design approach. A SAR study directed toward probing the effect of the two chiral centers in the pyrrolidine ring on biological activity revealed the importance of the (S) absolute configuration at the 2-position for binding affinity, agonist potency, and receptor selectivity. Among the four

  描述了一系列新型脯氨酸和吡咯烷类黑皮质素受体（MCR）激动剂的设计，合成和构效关系（SAR）。为了验证构象受限的Arg-Nal二肽类似物策略，我们首先合成并评估了顺-（2R，4R）-脯氨酸类似物（21a-g）的测试集。所有这些化合物在hMC1R，hMC3R和hMC4R上均显示出显着的结合和激动剂效能。随后通过这种设计方法开发了基于顺-（2S，4R）-吡咯烷的强效MCR激动剂（35a-g）。一项旨在探索吡咯烷环中两个手性中心对生物活性影响的SAR研究表明，在2位上的（S）绝对构型对于结合亲和力，激动剂效能和受体选择性很重要。
• Zinc Complexes of Amino Acids and Peptides, 8[]. Difunctional Dipeptides Containing Cysteine or Histidine: Solution Behavior and Zinc Complextion
  作者：Peter Gockel、Heinrich Vahrenkamp

  DOI：10.1002/cber.19961291016

  日期：1996.10

  The dipeptides Ac–Cys–Val–OH (1a) and Ac–His–Val–OH (1b), H–Gly–Cys–OEt (2a) and H–Val–His–OEt (2b) as well as Z–Asp–Cys–OH (3a) and Z–Asp–His–OH (3b) (Z = benzyloxycarbonyl) were prepared, and their zinc complexation was investigated by potentiometric methods. They have in common that in addition to the cysteine thiolate or the histidine imidazole the second amino acid offers one donor function. The

  二肽Ac–Cys–Val–OH（1a）和Ac–His–Val–OH（1b），H–Gly–Cys–OEt（2a）和H–Val–His–OEt（2b）以及Z–制备了Asp-Cys-OH（3a）和Z-Asp-His-OH（3b）（Z =苄氧羰基），并通过电位法研究了它们的锌络合作用。它们的共同之处在于，除了半胱氨酸硫醇盐或组氨酸咪唑以外，第二种氨基酸还提供一种供体功能。复杂的稳定性非常接近于单个氨基酸半胱氨酸或组氨酸的相应双功能衍生物的稳定性。这表明存在七至十元的螯合环。
• Solid phase synthesis of N-carboxy alkyl-containing peptides derived from enantiopure αketo-β-aminoacids
  作者：Concepción Fermández-García、Kai Prager、M Anthony McKervey、Brian Walker、Carvell H Williams

  DOI：10.1016/s0960-894x(98)00054-7

  日期：1998.3

  alpha-Keto-beta-aminoacids 5a-c can be reductively aminated with the peptide sequence H2N-Leu-Val-Phe-Phe on a solid support to afford N-carboxy alkyl peptides 1a-c. The N-carboxy alkyl lysine derivative 7 was subsequently extended from the N-terminus with glutamine and histidine residues.

  α-酮基-β-氨基酸5a-c可以在固体载体上被肽序列H2N-Leu-Val-Phe-Phe还原胺化，得到N-羧基烷基肽1a-c。N-羧基烷基赖氨酸衍生物7随后从具有谷氨酰胺和组氨酸残基的N-末端延伸。
• Design and synthesis of broad-Based mono- and bi- cyclic inhibitors of FIV and HIV proteases
  作者：Chi Ching Mak、Ashraf Brik、Danica L Lerner、John H Elder、Garrett M Morris、Arthur J Olson、Chi-Huey Wong

  DOI：10.1016/s0968-0896(03)00054-3

  日期：2003.5

  Based on the substrate transition state and our strategy to tackle the problem of drug resistance, a series of HIV/FIV protease (HIV/FIV PR) monocyclic inhibitors incorporating a 15- or 17-membered macrocycle with an equivalent P3 or P3' group and a unique unnatural amino acid, (2R, 3S)-3-amino-2-hydroxy-4-phenylbutyric acid, have been designed and synthesized. In addition, based on the structure of TL3 with small P3/P3' group, we have synthesized two conformationally restricted bicyclic inhibitors containing the macrocycle, which mimic the P1/P1'-P3/P3' tripeptide [Phe-Val-Ala] of TL3. We have found that the contribution of the macrocycle in our monocyclic inhibitors is important to the overall activity, but the ring size does not affect the activity to a significant extent. Several inhibitors that were developed in this work, exhibit low nanomolar inhibitory activity against the wild-type HIV/FIV PR and found to be highly effective against some drug-resistant as well as TL3-resistant mutants of HIV PRs. Compound 15, in particular, is the most effective cyclic inhibitor in hand to inhibit FIV replication in tissue culture at a concentration of 1.0 mug/mL (1.2 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.
• Design and synthesis of potent and selective 1,3,4-trisubstituted-2-oxopiperazine based melanocortin-4 receptor agonists
  作者：Xinrong Tian、Rajesh K. Mishra、Adrian G. Switzer、X. Eric Hu、Nick Kim、Adam W. Mazur、Frank H. Ebetino、John A. Wos、Doreen Crossdoersen、Beth B. Pinney、Julie A. Farmer、Russell J. Sheldon

  DOI：10.1016/j.bmcl.2006.05.087

  日期：2006.9

  The design and synthesis of a series of potent 1,3,4-trisubstituted-2-oxopiperazine based MC4 agonists are described. The tripeptidomimetic analogs (12a,b and 23) and the dipeptidomimetic 27 displayed single-nanomolar binding affinity and agonist potency for MC4,R and excellent selectivity for MC4R relative to MC1R. (c) 2006 Elsevier Ltd. All rights reserved.