4-aminophenyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 135253-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-aminophenyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: p-aminophenyl-2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactoside；per-O-acetyl-p-aminophenyl-β-lactoside；4-aminophenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tetra-O-acetyl-β-D-glucopyranoside；Gal2Ac3Ac4Ac6Ac(b1-4)Glc2Ac3Ac6Ac(b)-O-Ph(4-NH2)；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-(4-aminophenoxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 135253-84-8
• 化学式: C₃₂H₄₁NO₁₈
• 分子量: 727.673
• InChiKey: LNDOOFKKBRYBJN-TZDACTGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  51
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  247
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  4-aminophenyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 亚硝酸特丁酯 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以100%的产率得到4-[4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy]phenyldiazonium tetrafluoroborate
  参考文献：
  名称：

  Synthesis of Amphiphilic Phenylazophenyl Glycosides and a Study of Their Liquid Crystal Properties

  摘要：

  Several 4-(4'-N,N-didodecylaminophenylazo)phenyl 1,2-trans glycosides 5a-e with various carbohydrate heads (beta-D-gluco, beta-D-galacto, beta-lacto, beta-D-xylo, and alpha-D-manno) have been synthesized. The key step was the formation of phenyldiazonium tetrafluoroborates 2a-e from the per-O-acetylated 4-aminophenyl glycosides 1a-e. These salts were condensed with N,N-didoclecylaniline under phase transfer conditions and the per-O-acetylated 4-(4'-N,N-didodecylaminophenylazo)phenyl 1,2-trans glycosides 4a-e were fully de-O-acetylated by the Zemplen method. The self-organizing liquid crystal properties of the compounds were investigated by a variety of techniques, including polarized light microscopy, differential scanning calorimetry, and X-ray diffraction. All but one of the materials exhibited smectic A, lamellar phases. Remarkably, the glucose derivative exhibited a rectangular disordered columnar phase. This result has implications with respect to the induced curvature created by the recognition processes of the glucose headgroup relative to the other sugar moieties and to the prevalence of various glycolipids in cell membranes.

  DOI：

  10.1021/ja037347x
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 三氟化硼乙醚 、 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 4-aminophenyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosylated lanthanide cyclen complexes as luminescent probes for monitoring glycosidase enzyme activity

  摘要：

  已经制备并研究了糖基化镧系环氮化合物，作为糖苷酶酶活性和凝集素结合的发光探针。

  DOI：

  10.1039/c6ob01712f

文献信息

• Syntheses and transformations of glycohydrolase substrates into protein conjugates based on Michael additions
  作者：Ren� Roy、Fran�ois D. Tropper、Tara Morrison、Janusz Boratynski

  DOI：10.1039/c39910000536

  日期：——

  The glycosyl chloride 1 and bromides 2 and 3 were stereospecifically transformed into p-nitrophenyl glycosides by phase transfer catalysis; these glycohydrolase substrates were reduced and N-acryloylated to afford Michael acceptors which reacted with amine functions of proteins.

  通过相转移催化，糖基氯化物 1 和溴化物 2 及 3 被立体定向转化为对硝基苯基糖苷；这些糖水解酶底物被还原和 N-丙烯酰化，从而产生迈克尔受体，与蛋白质的胺功能发生反应。
• High-Throughput Evaluation System based on Fluorescence Intensity Distribution Analysis-Polarization to Investigate Carbohydrate–Carbohydrate Interactions
  作者：Maho Iwamura、Ryoichi Koyama、Yuki Nonaka、Fumiko Dai、Ryoji Matsuoka、Masaki Nakamura、Haruo Iwabuchi、Takahiro Okada、Teruaki Hasegawa

  DOI：10.1246/bcsj.20150369

  日期：2016.5.15

  We synthesized rhodamine-labeled β-lactoside and assessed its rotatory diffusion rates in aqueous media containing various oligosaccharides through fluorescence intensity distribution analysis-polarization measurements to find that its rotatory diffusion rates decrease in the presence of the coexisting oligosaccharides. Especially, the coexisting lactose lowered the rotatory diffusion rate more effectively than the other disaccharides did. This restrained rotatory diffusion arises from intermolecular carbohydrate–carbohydrate interactions between the rhodamine-labeled β-lactoside and the coexisting lactose. We also detected intermolecular bindings between the rhodamine-labeled β-lactoside and monosialyl-disaccharides (3′- and 6′-sialyllactoses). These data clearly show that the fluorescence intensity distribution analysis-polarization-based system is quite advantageous to probe carbohydrate–carbohydrate interactions.

  我们合成了罗丹明标记的β-乳糖苷，并通过荧光强度分布分析-偏振测量评估了其在含有各种寡糖的水介质中的旋转扩散速率，发现其旋转扩散速率在共存寡糖的存在下降低。特别是，共存的乳糖比其他二糖更有效地降低了旋转扩散速率。这种受限制的旋转扩散是由罗丹明标记的β-乳糖苷和共存的乳糖之间的分子间碳水化合物-碳水化合物相互作用引起的。我们还检测到罗丹明标记的 β-乳糖苷和单唾液酸二糖（3'-和 6'-唾液酸乳糖）之间的分子间结合。这些数据清楚地表明，基于偏振的荧光强度分布分析系统对于探测碳水化合物-碳水化合物相互作用非常有利。
• Synthetic multivalent ligands for cholera & cholera-like toxins: Protected cyclic neoglycopeptides
  作者：Vajinder Kumar、Narender Yadav、K.P. Ravindranathan Kartha

  DOI：10.1016/j.carres.2016.05.011

  日期：2016.8

  Synthesis of a set of novel glycopeptide analogues as potential cholera/cholera-like toxin inhibitors in their protected form is described. They include di-, tri-, tetra- and pentavalent scaffolds. The synthetic steps were achieved using a combination of solvent-free mechanochemical as well as the conventional solution-phase reactions. During the conventional DIC-HOBt-mediated peptide coupling followed

  描述了合成一组新的糖肽类似物作为其保护形式的潜在霍乱/霍乱样毒素抑制剂。它们包括二价，三价，四价和五价支架。合成步骤是结合使用无溶剂的机械化学反应和常规的溶液相反应来完成的。在常规的DIC-HOBt介导的肽偶联过程中，随后用于制备某些糖肽类似物，观察到有趣的原位Fmoc去保护作用，其已被证明具有合成具有延伸的聚酰胺链的糖肽/新糖肽的潜力。
• Synthesis and Inhibitory Activity Evaluation of 2,6-Disubstituted Purine Derivatives
  作者：Hongxia Liu、Libo Li、Shaikh Qurat-ul-ain、Tao Jiang

  DOI：10.1002/jhet.1959

  日期：2015.3

  novel 2,6‐disubstituted purine derivatives were designed and synthesized from 2,6‐dichloropurine. The structures of target compounds were determined by 1H‐NMR, 13C‐NMR, and HRMS. The synthesized compounds were evaluated for their inhibitory activities against lung cancer cell lines of A549 and liver cancer cell lines of Bel‐7402. 2‐(4‐Benzyloxy‐phenylamino)‐6‐(cyclohexylamino)purine(3), 2‐(4‐chloro‐phe

  由2,6-二氯嘌呤设计并合成了一系列新颖的2,6-二取代嘌呤衍生物。目标化合物的结构由1 H-NMR，13 C-NMR和HRMS确定。评估了合成的化合物对A549肺癌细胞系和Bel-7402肝癌细胞系的抑制活性。2-（4-苄氧基-苯基氨基）-6-（环己基氨基）嘌呤（3），2-（4-氯-苯基氨基）-6-（正丁基氨基）嘌呤（5），2-（4-吗啉代氨基）- 6-（4-羟基-苯基氨基）嘌呤（9）和2-（4 - O-半乳糖基-苯基氨基）-6-（环己基氨基）嘌呤（12）表现出中等的抑制活性。
• Glycosylated tris-bipyridine ferrous complexes to provide dynamic combinatorial libraries for probing carbohydrate–carbohydrate interactions
  作者：Motomi Nakamura、Mayuka Tsutsumi、Yoshiaki Ishikawa、Haruka Umemiya、Toki Hasegawa、Kazumi Izawa、Haruka Abe、Yosuke Togashi、Tatsuya Kinone、Sho Sekiguchi、Mihiro Igumi、Kanako Ide、Teruaki Hasegawa

  DOI：10.1016/j.tet.2013.01.095

  日期：2013.4

  2,2-Bipyridines having beta-lactoside, beta-D-glucoside, beta-D-galactoside, and N-acetyl-beta-D-glucosaminide were prepared and then, complexed with ferrous ion to afford trivalent glycoclusters having tris-bipyridine ferrous complex cores. Each glycocluster provides a dynamic combinatorial library composed of four diastereomeric stereoisomers (Delta mer, Delta fac, Delta mer, and Delta fac) whose ratios depend on their relative stabilities. CD spectral analyses of these glycoclusters showed that various cations (Na+, Mg2+, K+ or Ca2+) enriched Delta-forms of the glycocluster having beta-lactosides and N-acetyl-beta-D-glucosaminides possibly by cations-induced intramolecular carbohydrate-carbohydrate interactions. (C) 2013 Elsevier Ltd. All rights reserved.