每周分子 | Molecule of the Week
每周分子 | Molecule of the Week
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每周分子： 对氰基-L-苯丙氨酸
Molecule of the Week:
p -Cyano-L-phenylalanine
对氰基-L-苯丙氨酸 (pCNPhe) 是一种非天然氨基酸，可用于蛋白质成像光学探针。1994年，Diatide公司 (美国新罕布什尔州伦敦德里) 的Richard T. Dean及共同发明人在全球专利申请中介绍了对氰基-L-苯丙氨酸，他们在手术中将其用作放射性锝-99m的螯合剂，用于检测血凝块 (血栓)。提交这项专利申请后，于1996年在 Journal of Medicinal Chemistry 上发表了相关文章 。
自这一发现以来，pCNPhe在其他应用场合展示了多功能性。在2009年的一份报告中，纽约州立大学石溪分校和富兰克林与马歇尔学院 (美国宾夕法尼亚州兰卡斯特) 的Daniel P. Raleigh、Isaac Carrico及其合著者使用这一分子作为荧光、红外 (IR) 和Förster共振能量转移 (FRET) 探针来研究蛋白质折叠、蛋白质-膜相互作用、蛋白质-蛋白质相互作用和淀粉样变性。他们的研究结果表明，特别是FRET，可以直接用于探测蛋白质的构象变化 。
2019年，印第安纳大学 (美国伯明顿和印第安纳波利斯) 的Megan C. Thielges及其同事介绍了使用pCNPhe作为红外探针来以高空间和时间分辨率表征蛋白质动力学。他们将探针应用于Src 1 同源3结构域的6个位点，发现这种方法揭示了广泛的微环境和对配体结合的不同反应 。
去年11月，加州大学洛杉矶分校和富兰克林与马歇尔学院的Paul S. Nerenberg、Christine M. Phillips-Piro、Scott H. Brewer及其合作者再次证明了pCNPhe的实用性，这次在模型系统超折叠绿色荧光蛋白 (sfGFP) 中用作“振动指示剂”。他们结合了温度相关红外光谱、X射线晶体学和分子动力学模拟来研究蛋白质中腈基的局部环境。在一个实例中，他们发现，sfGFP的一个内部位点由腈基周围的三个不同局部环境组成，包括非特异性范德华相互作用、与结构化水的氢键作用以及与组氨酸侧链的氢键作用 。
1. 一种原癌基因酪氨酸蛋白激酶。
对氰基-L-苯丙氨 信息速览
CAS 登记号 |
167479-78-9 |
CAS SciFinder命名 |
L-Phenylalanine, 4-cyano- |
分子式 |
C 10 H 10 N 2 O 2 |
摩尔质量 |
190.20 g/mol |
外观 |
白色晶体或粉末 |
熔点 |
未报告 |
水溶性 |
100 g/L (估算值） |
对氰基-L-苯丙氨危害信息
GHS分类：急性毒性，经口，分类4 |
|
H302-吞咽有害 |
|
GHS分类：急性毒性，经皮，分类4 |
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H312-皮肤接触有害 |
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GHS分类：皮肤腐蚀/刺激，分类2 |
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H315-造成皮肤刺激 |
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GHS分类：严重眼损伤/眼刺激，分类2A |
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H372-造成严重眼刺激 |
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GHS分类：急性毒性，吸入，分类4 |
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H332-吸入有害 |
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GHS分类：特异性靶器官毒性–单次接触，呼吸系统，分类3 |
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H335-可引起呼吸道刺激 |
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【 关于每周分子 】
自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的CAS SciFinder n 中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。 发送邮件至motw@acs.org推荐您感兴趣的分子吧 。
p -Cyano-l-phenylalanine (pCNPhe) is an unnatural amino acid used in optical probes for imaging proteins. It was introduced in a 1994 world patent application by Richard T. Dean and co-inventors at Diatide (Londonderry, NH), who used it as a chelator for the radionuclide technetium-99m in a procedure for detecting blood clots (thrombi). The patent application was followed by a 1996 Journal of Medicinal Chemistry article .
Since that finding, pCNPhe showed its versatility in other applications. In a 2009 report, Daniel P. Raleigh, Isaac Carrico, and coauthors at the State University of New York at Stony Brook and Franklin & Marshall College (Lancaster, PA) used the molecule as a fluorescence, infrared (IR), and Förster resonance energy transfer (FRET) probe to study protein folding, protein−membrane interactions, protein−protein interactions, and amyloid formation. They concluded that FRET, in particular, can be used directly to probe conformational changes in proteins .
In 2019, Megan C. Thielges and colleagues at Indiana University (Bloomington and Indianapolis) described the use of pCNPhe as an IR probe to characterize protein dynamics with high spatial and temporal resolution. They applied the probe at six sites in a Src 1 homology 3 domain and found that their method revealed a wide range of microenvironments and distinct responses to ligand binding.
This past November, Paul S. Nerenberg, Christine M. Phillips-Piro, Scott H. Brewer, and collaborators at California State University, Los Angeles, and Franklin & Marshall once again demonstrated the utility of pCNPhe, this time as a “vibrational reporter” in the model system superfolder green fluorescent protein (sfGFP). They combined temperature-dependent IR spectroscopy, X-ray crystallography, and molecular dynamics simulations to investigate the local environment of the nitrile group in the protein. In one instance, they found that an interior site in sfGFP consists of three distinct local environments around the nitrile group, including nonspecific van der Waals interactions, hydrogen bonding to a structural water, and hydrogen bonding to a histidine side chain.
1. A proto-oncogene tyrosine–protein kinase.
p -Cyano-L-phenylalanine fast facts
CAS Reg. No. |
167479-78-9 |
|
SciFinder nomenclature |
L-Phenylalanine, 4-cyano- |
|
Empirical formula |
C 10 H 10 N 2 O 2 |
Molar mass |
190.20 g/mol |
Appearance |
White crystals or powder |
Melting point |
Not reported |
Watersolubility |
100 g/L(est.) |
p -Cyano-L-phenylalanine hazard information
Acute toxicity, oral, category 4 |
|
H302-Harmful if swallowed |
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Acute toxicity, dermal, category 4 |
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H312-Harmful in contact with skin |
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Skin corrosion/irritation, category 2 |
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H315-Causes skin irritation |
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Serious eye damage/eye irritation, category 2A |
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H372-Causes serious eye irritation |
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Acute toxicity, inhalation, category 4 |
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H332-Harmful if inhaled |
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Specific target organ toxicity-single exposure, respiratory system, category 3 |
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H335-May cause respiratory irritation |
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About Molecule of the Week
MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using CAS SciFinder n . Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org .
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