5-(二甲氨基)-N-(6-羟基己基)萘-1-磺酰胺 | 110232-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-(二甲氨基)-N-(6-羟基己基)萘-1-磺酰胺
• 英文名称: 5-(dimethylamino)-N-(6-hydroxyhexyl)-1-naphthalenesulfonamide
• 英文别名: N-dansyl-6-aminohexanol；N-dansyl-6-aminohexan-1-ol；1-Naphthalenesulfonamide, 5-(dimethylamino)-N-(6-hydroxyhexyl)-；5-(dimethylamino)-N-(6-hydroxyhexyl)naphthalene-1-sulfonamide
• CAS: 110232-19-4
• 化学式: C₁₈H₂₆N₂O₃S
• 分子量: 350.482
• InChiKey: HERNPNXIVWMYSW-UHFFFAOYSA-N

物化性质

• 沸点：
  525.0±60.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  78
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(二甲氨基)-N-(6-羟基己基)萘-1-磺酰胺 在 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 Thioacetic acid S-[6-(5-dimethylamino-naphthalene-1-sulfonylamino)-hexyl] ester
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p
• 作为产物：
  描述：

  6-氨基-1-己醇 、 丹酰氯 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以94%的产率得到5-(二甲氨基)-N-(6-羟基己基)萘-1-磺酰胺
  参考文献：
  名称：

  水溶性脂质I荧光探针的化学合成

  摘要：

  肽聚糖（PG）是细菌特有的，因此，负责其生物合成的酶是有前途的抗菌药物靶标。由于合适的酶底物的制备需要耗时的生物转化或化学合成，因此PG中的膜嵌入酶在研究其机理方面仍面临重大挑战。脂质I（MurNAc（五肽）-焦磷酸基烯丙醇）是重要的PG生物合成中间体，用于研究中心酶，转位酶I（MraY / MurX）和MurG。从大自然中分离出来的脂质I含有C 50-或C 55-异戊二烯单元的水溶性极差，这使得对转位酶I和MurG酶的研究变得困难。我们已经研究了使用细菌膜级分和纯化的MraY酶对水溶性脂质I荧光探针进行的生物转化。在对MraY催化的脂质I合成中异戊二烯基磷酸酯的最低结构要求的研究中，我们发现（2 Z，6 E）-法呢基磷酸酯（C 15-磷酸酯）可以被大肠杆菌MraY识别以生成水。可溶性脂质I荧光探针产量高。在优化的条件下，使用Hydrogenivirga纯化的MraY进行相同的反应spp。

  DOI：

  10.1016/j.tetlet.2015.01.044

文献信息

• SYNTHESIS OF HAPTEN PHOSPHORAMIDITES
  作者：M. Adamczyk、D. D. Johnson、P. G. Mattingly、R. E. Reddy

  DOI：10.1080/00304940109356618

  日期：2001.10

  2-[3-(4-nitrophenyl)1 -adamantyl]acetic acid (1) was coupled with 6-amino1 -hexanol (2a) or 2-[(2-aminoethoxy)ethoxy]ethanol (2b)"x using HOBt and EDAC in dichloromethane to afford 3a and 3b in 80 and 8 I % yield respectively (Scheme I). The hydroxyl group in 3a and 3b was then converted to the 2-(cyanoethyl)-N,N-diisopropylphosphoramidite functionality by treatment with (2-cyanoethyl)-N,NN-diisopropylchlorophosphoramidite

  包含非放射性半抗原报告基团的寡核苷酸探针用于扩增核酸检测 (NAT) 检测，以识别患者样本中具有临床意义的序列。结构多样的半抗原和其他报告基团已被有效地引入到使用亚磷酰胺化学的自动合成仪上的寡核苷酸探针中。' 1996 年，我们描述了在 1,3-二醇框架中合成含有半抗原（如金刚烷、咔唑和丹酰）的亚磷酰胺探针。5 这些双功能试剂适用于在寡核苷酸的 3' 或 5' 末端掺入或在序列内。如果仅需要 5' 标记，则这种灵活性是无关紧要的。本文描述了基于相同半抗原（金刚烷 5a,b, 咔唑 9a,b, dansyl 12a,b) 但专为 5' 标记而设计。报道了具有 C-6 脂肪族和溶解度增强的含氧系链的亚磷酰胺。因此，2-[3-(4-硝基苯基)1-金刚烷基]乙酸(1)与6-氨基1-己醇(2a)或2-[(2-氨基乙氧基)乙氧基]乙醇(2b)"x使用HOBt 和 EDAC 在二氯甲烷中分别得到 3a 和
• 1-Deoxynojirimycins with dansyl capped N-substituents as probes for Morbus Gaucher affected cell lines
  作者：Richard F.G. Fröhlich、Richard H. Furneaux、Don J. Mahuran、Brigitte A. Rigat、Arnold E. Stütz、Michael B. Tropak、Jacqueline Wicki、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.carres.2010.04.015

  日期：2010.7

  Cyclization by double reductive amination of D-xylo-hexos-5-ulose with methyl 6-aminohexanoate gave (methoxycarbonyl)pentyl-1-deoxynojirimycin. Reaction of the terminal carboxylic acid with N-dansyl-1,6-diaminohexane provided the corresponding chain-extended fluorescent derivative. By reaction with bis(6-dansylaminohexyl)amine, the corresponding branched di-N-dansyl compound was obtained. Both compounds are strong inhibitors of D-glucosidases and could also be shown to distinctly improve, at sub-inhibitory concentrations, the activity of beta-glucocerebrosidase in a Gaucher fibroblast (N370S) cell-line through chaperoning of the enzyme to the lysosome. (C) 2010 Elsevier Ltd. All rights reserved.
• Chemoenzymatic syntheses of water-soluble lipid I fluorescent probes
  作者：Katsuhiko Mitachi、Shajila Siricilla、Lada Klaić、William M. Clemons、Michio Kurosu

  DOI：10.1016/j.tetlet.2015.01.044

  日期：2015.6

  requirements of the prenyl phosphates in MraY-catalyzed lipid I synthesis, we found that (2Z,6E)-farnesyl phosphate (C15-phosphate) can be recognized by Escherichia coli MraY to generate the water-soluble lipid I fluorescent probe in high-yields. Under the optimized conditions, the same reaction was performed by using the purified MraY from Hydrogenivirga spp. to afford the lipid I analog with high-yields

  肽聚糖（PG）是细菌特有的，因此，负责其生物合成的酶是有前途的抗菌药物靶标。由于合适的酶底物的制备需要耗时的生物转化或化学合成，因此PG中的膜嵌入酶在研究其机理方面仍面临重大挑战。脂质I（MurNAc（五肽）-焦磷酸基烯丙醇）是重要的PG生物合成中间体，用于研究中心酶，转位酶I（MraY / MurX）和MurG。从大自然中分离出来的脂质I含有C 50-或C 55-异戊二烯单元的水溶性极差，这使得对转位酶I和MurG酶的研究变得困难。我们已经研究了使用细菌膜级分和纯化的MraY酶对水溶性脂质I荧光探针进行的生物转化。在对MraY催化的脂质I合成中异戊二烯基磷酸酯的最低结构要求的研究中，我们发现（2 Z，6 E）-法呢基磷酸酯（C 15-磷酸酯）可以被大肠杆菌MraY识别以生成水。可溶性脂质I荧光探针产量高。在优化的条件下，使用Hydrogenivirga纯化的MraY进行相同的反应spp。
• Fluorophore-Labeled <i>S</i>-Nitrosothiols
  作者：Xinchao Chen、Zhong Wen、Ming Xian、Kun Wang、Niroshan Ramachandran、Xiaoping Tang、H. Bernhard Schlegel、Bulent Mutus、Peng George Wang

  DOI：10.1021/jo015658p

  日期：2001.9.1

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.