3-<2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosylthio>propionic acid | 152435-15-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-<2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosylthio>propionic acid
• 英文别名: 3-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosylthio]propionic acid；3-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanylpropanoic acid
• CAS: 152435-15-9
• 化学式: C₂₉H₄₀O₁₉S
• 分子量: 724.691
• InChiKey: OHZAKAVDHPPMAZ-CVWDROHSSA-N

物化性质

• 沸点：
  753.9±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  49
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  274
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  3-<2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosylthio>propionic acid 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以96%的产率得到3-(4-O-β-D-galactopyranosyl-β-D-glucopyranosylthio)propionic acid
  参考文献：
  名称：

  可以与固相共价连接的水溶性丝氨酸基新糖脂的合成。

  摘要：

  用过苯甲酰化的乳糖基溴化物使Nα-Fmoc-丝氨酸五氟苯基酯糖基化。将所得产物与用6-氨基己酸官能化的树脂偶联，然后将Nα-酰化，以得到基于丝氨酸的乳糖基神经酰胺类似物。水溶性新糖脂通过其羧基共价连接至微量滴定板，并在ELISA中被乳糖结合凝集素识别。

  DOI：

  10.1016/0008-6215(94)84080-6
• 作为产物：
  描述：

  lactose octaacetate 、 3-巯基丙酸 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以66%的产率得到3-<2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosylthio>propionic acid
  参考文献：
  名称：

  Cyclodextrin‐based carbohydrate clusters by amide bond formation

  摘要：

  摘要以原生ß-环糊精为原料，通过四个步骤高效地制备了Per-6-氨基-2,3-二甲基-ß-环糊精盐酸盐，总收率为89%。在 BF3-OEt2 催化下，ß-D-葡萄糖五乙酸酯和ß-乳糖八乙酸酯分别与 3-巯基丙酸发生硫代糖基化反应，制备出 O-乙酰基保护的ß-D-硫代葡萄糖和ß-D-硫代乳糖衍生物。以形成酰胺键为关键步骤，将这些硫代-ß-D-葡萄糖基和乳糖基衍生物与过-6-氨基-2,3-二甲基-ß-环糊精偶联，经脱保护后得到分别含有七个硫代-ß-D-葡萄糖基和七个ß-乳糖基附属物的全官能化ß-环糊精基团簇。对这两种ß-环糊精基团簇的分子建模显示，葡萄糖和乳糖团簇的直径分别约为 23 Å 和 27 Å，高度约为 19 Å。通过紫外可见分光光度滴定法发现，在 0.01 M 磷酸盐缓冲盐溶液（pH 7.4）中，ß-环糊精、过-2,3-二甲基ß-环糊精和ß-环糊精的乳糖簇与消炎药萘普生的络合常数分别为 374 ± 75 M-1、351 ± 70 M-1 和 165 ± 33 M-1。

  DOI：

  10.1560/26tf-06hg-eqjj-w85j

文献信息

• Lanthanide(<scp>III</scp>) Complexes of DOTA-Glycoconjugates: A Potential New Class of Lectin-Mediated Medical Imaging Agents
  作者：João P. André、Carlos F. G. C. Geraldes、José A. Martins、André E. Merbach、Maria I. M. Prata、Ana C. Santos、João J. P. de Lima、Éva Tóth

  DOI：10.1002/chem.200400187

  日期：2004.11.19

  The synthesis and characterization of a new class of DOTA (1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane) monoamide-linked glycoconjugates (glucose, lactose and galactose) of different valencies (mono, di and tetra) and their Sm(III), Eu(III) and Gd(III) complexes are reported. The 1H NMR spectrum of Eu(III)-DOTALac2 shows the predominance of a single structural isomer of square antiprismatic

  新型DOTA（1,4,7,10-四（羧甲基）-1,4,7,10-四氮杂环十二烷）单酰胺连接的糖价（葡萄糖，乳糖和半乳糖）连接的糖共轭物的合成与表征，二和四）及其Sm（III），Eu（III）和Gd（III）配合物。Eu（III）-DOTALac2的1H NMR谱图显示了DOTA螯合部分的方形反棱角几何结构的单个结构异构体的优势，并且绕着与靶向糖树状聚合物连接的酰胺键快速旋转。通过1H核磁弛豫分散液（NMRD）研究了Gd（III）-糖基共轭物的体外弛豫性，得出的参数接近于其他DOTA单酰胺所报道的参数。
• Lanthanide( <scp>III</scp> ) Chelates of DTPA Bis(amide) Glycoconjugates: Potential Imaging Agents Targeted at the Asyaloglycoprotein Receptor
  作者：Paula Baía、João P. André、Carlos F. G. C. Geraldes、José A. Martins、André E. Merbach、Éva Tóth

  DOI：10.1002/ejic.200400766

  日期：2005.6

  effects of racemisation of the central nitrogen atom in the NMR spectra show that this process is fast at 60 °C for the SmIII complexes and slow at 7 °C for the EuIII complexes. The in vitro r1 nuclear magnetic relaxation dispersion (NMRD) of the water protons of the GdIII–DTPA bis(amide) glycoconjugate containing two lactosyl moieties [GdIII–DTPALac2] was studied, yielding the molecular parameters

  合成和表征了一类新的 DTPA 双（酰胺）连接的不同糖类 [乳糖 (Lac) 和半乳糖 (Gal)] 和价态（二和四）及其 LnIII 复合物的糖缀合物的表征。DTPAGal2、DTPAGal4 和 DTPALac2 的 SmIII 和 EuIII 复合物的 1H NMR 谱在 7 到 80°C 之间获得，表明存在由三个结合的 DTPA 氮原子的手性产生的四种可能的非对映异构结构对中的几种在溶液中，具有不同的相对种群。核磁共振谱中中心氮原子外消旋化的动态效应表明，SmIII 配合物在 60°C 时该过程快速，而 EuIII 配合物在 7°C 时缓慢。研究了含有两个乳糖基部分 [GdIII-DTPALac2] 的 GdIII-DTPA 双（酰胺）糖缀合物的水质子的体外 r1 核磁弛豫分散度（NMRD），产生了控制其弛豫性的分子参数。在 25 °C 和 20 MHz 下，其 r1 值比报告的低分子量
• Solid-phase synthesis and conformational studies of glycosylated derivatives of helper-T-cell immunogenic peptides from hen-egg lysozyme
  作者：Mikael Elofsson、Sarbari Roy、Björn Wase、Jan Kihlberg

  DOI：10.1016/0008-6215(93)84026-3

  日期：1993.8

  unprotected carboxyl groups, were stereospecifically glycosylated in 62-82% yields, using saccharide 1,2-trans peracetates and Lewis acid catalysis. The resulting glycosylated building blocks were used in the synthesis of derivatives of helper-T-cell stimulating peptides, with the carbohydrate moiety located at the amino terminus, or internally in the peptide chain. 1H NMR spectroscopy in Me2SO-d6 showed

  使用糖1,2-反式过乙酸盐和路易斯酸催化，将具有未保护羧基的3-巯基丙酸和Nα-Fmoc丝氨酸立体定向糖基化，收率为62-82％。所得的糖基化结构单元用于合成辅助性T细胞刺激肽的衍生物，碳水化合物部分位于氨基末端或肽链内部。Me2SO-d6中的1H NMR光谱表明，糖肽呈随机构象，不受糖基化或肽部分中氨基酸的单取代的影响。
• Synthesis of Glycodendrimers by Modification of Poly(propylene imine) Dendrimers
  作者：Peter R. Ashton、Sue E. Boyd、Christopher L. Brown、Sergey A. Nepogodiev、E. W. Meijer、H. W. I. Peerlings、H. W. I. Peerlings、J. Fraser Stoddart

  DOI：10.1002/chem.19970030620

  日期：1997.6

  AbstractThe use of preformed poly‐(propylene imine) dendrimers (DAB‐dendr‐(NH2)x) for the rapid and facile construction of high molecular weight carbohydrate‐coated dendrimers (glyco‐dendrimers) is presented. An efficient attachment of spacer‐armed derivatives of D‐galactose and lactose to the primary amino end groups of DAB‐dendr‐(NH2)x has been achieved by means of amide bond formation, using the N‐hydroxysuccinimide coupling procedure. Acetate protecting groups have been employed in order to avoid side reactions at the coupling stage. Deacetylation leads to the target glycodendrimers. The reactivity of all the available DAB‐dendr‐(NH2)x (generations 1–5) has been investigated and a series of homologous carbohydrate‐coated dendrimers have been synthesized. In addition, the attachment of larger saccharide moieties has been demonstrated by the condensation of a trisgalactoside cluster with DAB‐dendr‐(NH2)x carrying both four and eight primary amino groups. The regularity of the glycodendrimers has been proven by NMR spectroscopy, and the molecular weights of the low‐generation carbohydrate‐coated dendrimers have been determined by mass spectrometry. Modifications of DAB‐dendr‐(NH2)x with biologically active carbohydrates affords a new and simple approach to high molecular weight compounds that may be considered as neoglycoconjugates with perfectly symmetrical structures and that offer much promise as multivalent ligands involved in carbohydrate‐protein interactions.
• Dynamic Multivalent Lactosides Displayed on Cyclodextrin Beads Dangling from Polymer Strings
  作者：Alshakim Nelson、J. Fraser Stoddart

  DOI：10.1021/ol0353464

  日期：2003.10.1

  [GRAPHICS]Lactose-appended cyclodextrin derivatives have been synthesized and threaded onto hydrophobic polymers in aqueous solution to form dynamic multivalent lactosides for binding to lectins. The threading process, which proceeds quickly, can be observed by one- and two-dimensional NMR spectroscopies.