dansyl-D-leucine | 99388-22-4

• 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
• 英文名称: dansyl-D-leucine
• 英文别名: dansyl-D-Leu；Dns-D-Leu；(2R)-2-[5-(dimethylamino)naphthalene-1-sulfonamido]-4-methylpentanoic acid；(2R)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-4-methylpentanoic acid
• CAS: 99388-22-4
• 化学式: C₁₈H₂₄N₂O₄S
• 分子量: 364.466
• InChiKey: XBMQRPDOXIPUFG-OAHLLOKOSA-N

物化性质

• 沸点：
  545.0±60.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  单-6-O-氨基-Β-环糊精 、 dansyl-D-leucine 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以40%的产率得到6-(N-dansyl-D-leucylamino)-6-deoxy-β-cyclodextrin
  参考文献：
  名称：

  Fluorescent Cyclodextrins for Molecule Sensing:  Fluorescent Properties, NMR Characterization, and Inclusion Phenomena of N-Dansylleucine-Modified Cyclodextrins

  摘要：

  Fluorophore-amino acid-cyclodextrin (CD) triad systems, N-dansyl-L-leucine-modified and N-dansyl-D-leucine-modified beta-CD (1, 2) and N-dansyl-L-leucine-modified and N-dansyl-D-leucine-modified gamma-CD (3, 4), were synthesized and characterized as fluorescent indicators of molecular recognition. Fluorescence decay analyses of these CD derivatives indicated that there exist two lifetime components, being in equilibrium with each other in aqueous solution, with the dansyl moiety included in its own cavity (self-inclusion) for the larger lifetime component while located outside the cavity for the shorter lifetime one. The structural analyses of beta-CD derivatives 1 and 2 undertaken by combined use of 1D and 2D MVIR spectra indicate that the dansyl moiety of 2 is more deeply included in the CD cavity than that of 1. The leucine residue between the dansyl and the CD moieties of these hosts was more effective in enhancing the binding abilities for various guests when compared with the glycine residue of the corresponding hosts; The difference in the enantiomeric configuration of the leucine residue caused the difference in the binding constants with larger values for 1 than 2 and with the opposite trend for the gamma-CD derivatives 3 and 4. Upon guest addition, the fluorescence intensities of 1 and 2 decreased, reflecting the exclusion of the dansyl moiety from inside to outside of the beta-CD cavity, while the fluorescence intensities of the gamma-CD derivatives 3 and 4 depended on the guest as shown by the increase induced by cyclohexanol and the decrease by (-)-borneol and other larger guests. These guest-responsive variations of the fluorescence intensity enabled these hosts to be used as effective fluorescent indicators of molecular recognition.

  DOI：

  10.1021/ja960183i
• 作为产物：
  描述：

  D-亮氨酸 、 丹酰氯 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以30%的产率得到dansyl-D-leucine
  参考文献：
  名称：

  Fluorescent Cyclodextrins for Molecule Sensing:  Fluorescent Properties, NMR Characterization, and Inclusion Phenomena of N-Dansylleucine-Modified Cyclodextrins

  摘要：

  Fluorophore-amino acid-cyclodextrin (CD) triad systems, N-dansyl-L-leucine-modified and N-dansyl-D-leucine-modified beta-CD (1, 2) and N-dansyl-L-leucine-modified and N-dansyl-D-leucine-modified gamma-CD (3, 4), were synthesized and characterized as fluorescent indicators of molecular recognition. Fluorescence decay analyses of these CD derivatives indicated that there exist two lifetime components, being in equilibrium with each other in aqueous solution, with the dansyl moiety included in its own cavity (self-inclusion) for the larger lifetime component while located outside the cavity for the shorter lifetime one. The structural analyses of beta-CD derivatives 1 and 2 undertaken by combined use of 1D and 2D MVIR spectra indicate that the dansyl moiety of 2 is more deeply included in the CD cavity than that of 1. The leucine residue between the dansyl and the CD moieties of these hosts was more effective in enhancing the binding abilities for various guests when compared with the glycine residue of the corresponding hosts; The difference in the enantiomeric configuration of the leucine residue caused the difference in the binding constants with larger values for 1 than 2 and with the opposite trend for the gamma-CD derivatives 3 and 4. Upon guest addition, the fluorescence intensities of 1 and 2 decreased, reflecting the exclusion of the dansyl moiety from inside to outside of the beta-CD cavity, while the fluorescence intensities of the gamma-CD derivatives 3 and 4 depended on the guest as shown by the increase induced by cyclohexanol and the decrease by (-)-borneol and other larger guests. These guest-responsive variations of the fluorescence intensity enabled these hosts to be used as effective fluorescent indicators of molecular recognition.

  DOI：

  10.1021/ja960183i

文献信息

• Direct Resolution of Optically Active Isomers on Chiral Packings Containing Ergoline Skeletons. 5. Enantioseparation of Amino Acid Derivatives
  作者：A. Messina、A. M. Girelli、M. Flieger、M. Sinibaldi、P. Sedmera、L. Cvak

  DOI：10.1021/ac950698c

  日期：1996.4.1

  alkaloid-based chiral stationary phase preparation is described. Synthesis is based on bonding the allyl derivative of terguride to mercaptopropylsilanized silica gel. The packing exhibits higher content of chiral selector, stability, reproducibility, and enantioselectivity toward amino acids compared to that previously studied. The chromatographic behavior of amino acids with different side chains and substituent

  描述了一种基于麦角生物碱的手性固定相制备的新方法。合成是基于将特固脲的烯丙基衍生物与巯基丙基硅烷化的硅胶结合。与先前研究的相比，该填料表现出更高的手性选择剂含量，稳定性，可再现性和对氨基酸的对映选择性。研究了具有不同侧链和取代基的氨基酸的色谱行为，以便更深入地了解对映鉴别机理，并确定特固利作为此类化合物的手性选择剂的局限性和强度。检查了多种因素，包括流动相参数，例如pH，离子强度，有机改性剂的含量和性质以及温度。
• Preparation and evaluation of a triazole‐bridged <i>bis</i> (β‐cyclodextrin)–bonded chiral stationary phase for HPLC
  作者：Yazhou Shuang、Yuqin Liao、Hui Wang、Yuanxing Wang、Laisheng Li

  DOI：10.1002/chir.23147

  日期：2020.2

  spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β‐blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and

  通过6-叠氮基-β-环糊精和6-丙炔基氨基-β-环糊精之间的高产率Click化学反应合成了三唑桥联的双（β-环糊精），然后将其键合到有序硅胶SBA-15上获得新颖的三唑桥双（β-环糊精）-键合手性固定相（TBCDP）。通过红外光谱，质谱，元素分析和热重分析对桥联的环糊精和TBCDP的结构进行了表征。通过使用手性农药和药物（包括三唑，黄烷酮，丹酰氨基酸和β受体阻滞剂）作为探针，评估了TBCDP的手性性能。以不同方式研究了流动相中的组成和pH值对对映体的影响。在反相色谱下成功分离了9种三唑，8种黄烷酮和8种丹磺酰基氨基酸，其分辨率为六康唑，2'-羟基黄酮和dansyl- DL酪氨酸，在30分钟内分别为2.49、5.40和3.25。十种β受体阻滞剂在极性有机模式下也被分离，阿替洛尔的分辨率达到1.71。初步讨论了一些相关的分离机制。与天然环糊精固定相（CDSP）相比，TBCDP具有更高的对映选择
• Cationic β-cyclodextrin-modified hybrid magnetic microspheres as chiral selectors for selective chiral absorption of dansyl amino acids
  作者：Jingwei Wu、Ping Su、Danhua Guo、Jun Huang、Yi Yang

  DOI：10.1039/c4nj00030g

  日期：——

  Chirally selective functionalized magnetic microspheres show great potential in enantiomeric separations. In this study, a novel class of chiral magnetic selectors was developed by immobilization of vinylimidazolium-β-cyclodextrin chloride (VIMCD-Cl) on 3-methacryloxypropyltrimethoxysilane-modified iron oxide magnetic microspheres through a radical polymerization. The prepared chiral materials have

  手性选择性官能化的磁性微球在对映体分离中显示出巨大的潜力。在这项研究中，通过自由基聚合将乙烯基咪唑鎓-β-环糊精氯化物（VIMCD-Cl）固定在3-甲基丙烯酰氧基丙基三甲氧基硅烷改性的氧化铁磁性微球上，开发了一类新型的手性磁性选择剂。制备的手性材料具有规则的三维核-壳结构，平均粒径约为580 nm，高磁化饱和度约为51 emu g -1。傅立叶变换红外光谱（FT-IR），热重分析（TGA）和元素分析证实了VIMCD-Cl在磁性微球表面成功聚合。然后将所制备的功能性磁性材料应用微分批技术应用于三种丹磺酰基氨基酸的选择性手性吸收。结果表明，固定的VIMCD-Cl磁性微球（VIMCD-MNPs）对三个丹磺酰基氨基酸具有良好的对映选择性，并且在手性吸附过程中表现出与L-对映体更强的相互作用。此外，这些官能化的手性磁性材料具有优异的可回收性，并且可用作手性分离的有效手性磁性选择剂。
• [EN] COMPOUNDS USEFUL AS REVERSIBLE INHIBITORS OF CATHEPSIN S<br/>[FR] COMPOSES UTILES EN TANT QU'INHIBITEURS REVERSIBLES DE LA CATHEPSINE S
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2000051998A1

  公开（公告）日：2000-09-08

  Disclosed are novel cathepsin S reversible inhibitory compounds of formulas (I),(Ia) and (II),(IIa) as defined herein. The compou nds are useful for treating autoimmune diseases. Also disclosed are processes for making such novel compounds.

  本发明揭示了具有以下公式（I）、（Ia）和（II）、（IIa）的新型cathepsin S可逆抑制化合物。所述化合物可用于治疗自身免疫性疾病。本发明还揭示了制备这种新型化合物的方法。
• Compounds useful as reversible inhibitors of cathepsin S
  申请人：——

  公开号：US20020091259A1

  公开（公告）日：2002-07-11

  Disclosed are cathepsin S reversible inhibitory compounds of the formulas (I),(Ia) and (II),(IIa) as defined herein. The compounds are useful for treating autoimmune diseases. Also disclosed are processes for making such novel compounds. 1

  本发明公开了具有以下式子(I)、(Ia)和(II)、(IIa)的卡特普西林S可逆抑制化合物。这些化合物可用于治疗自身免疫性疾病。本发明还公开了制备这些新型化合物的方法。