丹磺酰-L-脯氨酸哌啶盐 | 1239-94-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 丹磺酰-L-脯氨酸哌啶盐
• 中文别名: 丹磺酰-L-脯氨酸；丹磺酰基-L-脯氨酸
• 英文名称: dansyl-L-proline
• 英文别名: dansylproline；(2S)-1-[5-(dimethylamino)naphthalen-1-yl]sulfonylpyrrolidine-2-carboxylic acid
• CAS: 1239-94-7
• 化学式: C₁₇H₂₀N₂O₄S
• 分子量: 348.423
• InChiKey: ZHJIWURDCGMVQE-HNNXBMFYSA-N

物化性质

• 熔点：
  150-153 °C
• 沸点：
  559.6±60.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

SDS

Version 1.4
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name DANSYL-L-PROLINE FREE ACID

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2 - Hazards Identification

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
DANSYL-L-PROLINE FREE ACID 1239-94-7 None None
Formula C17H20N2O4S
Molecular Weight 348,4000 AMU

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4 - First Aid Measures

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5 - Fire Fighting Measures

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6 - Accidental Release Measures

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7 - Handling and Storage

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STORAGE
Store at -20°C

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8 - Exposure Controls / Personal Protection

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9 - Physical and Chemical Properties

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pH N/A
BP/BP Range N/A
MP/MP Range N/A
Flash Point N/A
Flammability N/A
SIGMA www.molbase.com
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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11 - Toxicological Information

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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Caution: Substance not yet fully tested (EU).
COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
SIGMA www.molbase.com
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
SIGMA www.molbase.com

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  丹磺酰-L-脯氨酸哌啶盐 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (3S,3aR,6aS)-4-[((2S)-1-{[5-(dimethylamino)-1-naphthyl]sulfonyl}pyrrolidin-2-yl)carbonyl]-3-methylhexahydropyrrolo[3,2-b]pyrrol-2-one
  参考文献：
  名称：

  Design and Synthesis of Pyrrolidine-5,5-trans-lactams (5-Oxohexahydropyrrolo[3,2-b]pyrroles) as Novel Mechanism-Based Inhibitors of Human Cytomegalovirus Protease. 2. Potency and Chirality

  摘要：

  The stereospecific synthesis of a series of alpha-methylpyrrolidine-5,5-trans-lactam inhibitors of human cytomegalovirus (HCMV) protease is described. Examination of the SAR in this series has defined the size and chirality of the alpha-substituent, optimized the acyl substituent on the lactam nitrogen, and defined the steric constraint of this functionality. The SAR of the functionality on the pyrrolidine nitrogen of the trans-lactam has been investigated, and this has led to the discovery of potent serine protease inhibitors that are highly selective for the viral enzyme over the mammalian enzymes elastase, thrombin, and acetylcholine esterase. The mechanism of action of our lead compounds has been established by mass spectrometry, and enzymatic degradation of HCMV deltaAla protease acylated with these inhibitors showed that Ser 132 is the active site nucleophile. The crystal structure of HCMV protease was obtained and used to model the conformationally restricted, chiral (S)-proline-alpha-methyl-5,5-trans-lactams into the active site groove of the enzyme, enabling us to direct and rationalize the SAR in this series. The activity against HCMV deltaAla protease is the greatest with inhibitors based on the dansyl-(S)-proline alpha-methyl-5,5-trans-lactam template, which have low nanomolar activity against the viral enzyme.

  DOI：

  10.1021/jm0102203
• 作为产物：
  描述：

  dansylproline 在 L-亮氨酸 、 ammonium acetate 、 硼酸 、 zinc(II) sulfate 、 β-环糊精 作用下， 以 aq. buffer 为溶剂， 生成 丹磺酰-L-脯氨酸哌啶盐 、 dansyl D-proline
  参考文献：
  名称：

  基于Zn（ii）-1-亮氨酸配合物和β-环糊精的新型手性配体交换毛细管电泳系统及其在酪氨酸酶抑制剂筛选中的应用†

  摘要：

  酪氨酸酶在黑色素形成中起关键作用，并且与动物体内的色素沉着过多和食物中的酶促褐变密切相关。因此，筛选酪氨酸酶抑制剂具有重要意义。在这项工作中，基于Zn（II）-L-亮氨酸复合物和β-环糊精（β-CD）的协同作用，开发了一种新的手性配体交换-毛细管电泳（CLE-CE）系统，用于筛选酪氨酸酶抑制剂。β-CD的浓度的影响，缓冲液pH的比值，大号-亮氨酸对于Zn（II），并用DNS-复杂浓度进行了调查d，大号-酪氨酸，DNS- d，大号-缬氨酸和DNS- d，L-苯丙氨酸作为被测分析物。最佳的缓冲条件包括pH值为8.2的100.0 mM硼酸，5.0 mM乙酸铵，3.0 mM Zn（II），6.0 mM L-亮氨酸和4.0 mMβ-CD。已经发现六对Dns- D，L -AA可以被基线分离，并且五对Dns- D，L- AA被部分地对映分离。然后对L-酪氨酸进行了定量分析，并以12.95μM至413.3μM的浓度获得了良好的线性（r

  DOI：

  10.1039/c4ra09433f

文献信息

• Synthesis of <i>C</i>-Propargylic Esters of N-Protected Amino Acids and Peptides
  作者：Sean P. Bew、Glyn D. Hiatt-Gipson

  DOI：10.1021/jo100537q

  日期：2010.6.4

  critical importance of amino acids in organic synthesis as well as their myriad of applications in “click” chemistry it is interesting to note that the synthesis of C-propargyl derived amino acid esters has not been particularly well served. We report a convenient, straightforward, and high-yielding synthesis of structurally diverse C-propargyl-derived N-protected amino acid esters.

  近年来，人们对将炔烃衍生的基元用于所谓的“点击”化学反应产生了极大的兴趣。鉴于氨基酸在有机合成中的至关重要性及其在“点击”化学中的众多应用，值得注意的是，C-炔丙基衍生的氨基酸酯的合成并未得到很好的服务。我们报道了结构多样的C-炔丙基衍生的N-保护的氨基酸酯的方便，直接和高产率的合成。
• Nitrile derivatives that inhibit cathepsin K
  申请人：——

  公开号：US20010008901A1

  公开（公告）日：2001-07-19

  Compounds of the formula: 1 wherein R 1 to R 7 and Y are as defined in the specification, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof, are useful for treating diseases associated with cystein proteases, such as osteoporosis, osteoarthritis, rheumatoid arthritis, tumor metastasis, glomerulonephritis, atherosclerosis, myocardial infarction, angina pectoris, instable angina pectoris, stroke, plaque rupture, transient ischemic attacks, amaurosis fugax, peripheral arterial occlusive disease, restenosis after angioplasty and stent placement, abdominal aortic aneurysm formation, inflammation, autoimmune disease, malaria, ocular fundus tissue cytopathy and respiratory disease.

  该公式化合物：其中R1到R7和Y如规范中定义，并且其药用盐和/或药用酯是用于治疗与半胱氨酸蛋白酶相关的疾病，如骨质疏松症、骨关节炎、类风湿性关节炎、肿瘤转移、肾小球肾炎、动脉粥样硬化、心肌梗死、心绞痛、不稳定性心绞痛、中风、斑块破裂、短暂性缺血性发作、瞬间性视网膜动脉阻塞、外周动脉闭塞性疾病、血管成形术和支架植入术后再狭窄、腹主动脉瘤形成、炎症、自身免疫疾病、疟疾、眼底组织细胞病变和呼吸道疾病的有用化合物。
• Electrophoresis in Organogels
  作者：Shaul Mizrahi、Jenny Gun、Z. Gidon Kipervaser、Ovadia Lev

  DOI：10.1021/ac049606m

  日期：2004.9.1

  A new matrix for electrophoresis, a low molecular weight organogel, is described. Dansylated amino acids and peptides were separated by planar and capillary electrophoresis in acetonitrile gels of trans-(1S,2S)-1,2-bis(dodecylamido)cyclohexane. The superior separation ability of the organogel over its corresponding buffer solution in capillary electrophoresis is illustrated. Organogels provide all the advantages associated with planar matrixes with 100% efficient recovery and transfer of the analytes to a mass spectrometer. We demonstrate that the planar gel can be liquefied and injected as is into an ESI-MS to identify the separands.

  描述了一种新的电泳基质，即低分子量有机凝胶。通过平面和毛细管电泳在反式-(1S,2S)-1,2-双(十二烷基酰胺)环己烷乙腈凝胶中分离丹酰化氨基酸和肽。说明了有机凝胶在毛细管电泳中优于其相应缓冲溶液的分离能力。有机凝胶具有与平面基质相关的所有优点，可 100% 有效回收并将分析物转移至质谱仪。我们证明平面凝胶可以液化并按原样注入 ESI-MS 中以识别分离物。
• Microflow cell
  申请人：NIHON BUNKO KOGYO KABUSHIKI KAISHA

  公开号：EP0476248A1

  公开（公告）日：1992-03-25

  A microflow cell comprising an outer cylinder disposed on the outer periphery of a cylindrical flow cell and having a flat surface on at least a light-entering surface, and a filling material inserted between the outer cylinder and the flow cell and a capillary electrophoresis method using such a microflow cell. Since the outer cylinder is provided on the outer periphery of the cylindrical flow cell and the gap between the flow cell and the outer cylinder is filled up with a filling liquid, the quantity of scattered light is reduced, thereby enabling the adoption of fluorometry in the analysis of capillary electrophoresis.

  一种微流池，包括一个设置在圆柱形流动池外周的外筒，该外筒至少在入光面上有一个平坦的表面，以及一种插入外筒和流动池之间的填充材料，还有一种使用这种微流池的毛细管电泳方法。 由于外筒设置在圆柱形流动池的外周，且流动池与外筒之间的间隙被填充液填满，散射光量减少，因此可在毛细管电泳分析中采用荧光测定法。
• Termination of the structural confusion between plipastatin A1 and fengycin IX
  作者：Miho Honma、Kazuaki Tanaka、Katsuhiro Konno、Kenji Tsuge、Toshikatsu Okuno、Masaru Hashimoto

  DOI：10.1016/j.bmc.2012.04.040

  日期：2012.6

  Plipastatin A1 and fengycin IX were experimentally proven to be identical compounds, while these had been considered as diastereomers due to the permutation of the enantiomeric pair of Tyr in most papers. The H-1 NMR spectrum changed to become quite similar to that of plipastatin A1, when the sample which provided resembled spectrum of fengycin IX was treated with KOAc followed by LH-20 gel filtration. Our structural investigations disclosed that the structures of these molecules should be settled into that of plipastatin A1 by Umezawa (L-Tyr4 and D-Tyr10). (C) 2012 Elsevier Ltd. All rights reserved.