O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-N-hydroxysuccinimide | 170590-83-7

• 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: O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-N-hydroxysuccinimide
• 英文别名: 2,3,4,6-tetra-O-acetyl-O-β-D-galactopyranosyl-N-oxysuccinimide；1-[(2,3,4,6-tetra-O-acetyl-β-D-galactosyl)oxy]-2,5-pyrrolidinedione；O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-N-oxysuccinimide；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,5-dioxopyrrolidin-1-yl)oxyoxan-2-yl]methyl acetate
• CAS: 170590-83-7
• 化学式: C₁₈H₂₃NO₁₂
• 分子量: 445.38
• InChiKey: FXFOHFDUFLAHFG-FMUWMXLXSA-N

物化性质

• 沸点：
  511.7±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-N-hydroxysuccinimide 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 O-(β-D-galactopyranosyl)hydroxylamine
  参考文献：
  名称：

  糖基氧基琥珀酰亚胺的立体选择性相转移催化合成及其向糖探针的转化

  摘要：

  D-半乳糖，D-葡萄糖，N-乙酰基-D-葡萄糖胺，乳糖，麦芽糖（7-11）和唾液酸（13）的糖基氧基琥珀酰亚胺是在PTC条件下由它们的糖基卤化物制备的。琥珀酰亚胺部分的开环发生与氢氧化钠或甲醇盐，以提供延长的糖苷配基，而用肼处理8提供O- galactopyranosylhydroxylamine 17。用三（2-氨基乙基）胺处理9得到二价簇20，其在用异硫氰酸荧光素进一步处理后提供二价糖探针21。

  DOI：

  10.1016/0040-4020(95)00325-3
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 氢溴酸 、 四丁基硫酸氢铵 、 乙酸酐 、 sodium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-N-hydroxysuccinimide
  参考文献：
  名称：

  Preparation and functional analysis of gossypols having two carbohydrate appendages with enaminooxy linkages

  摘要：

  We developed new gossypol (Gos)-based glycoconjugates through dehydration condensation of native Gos and chemically modified glycosides having aminooxy groups. The resultant glycoconjugates (glycoGos) were resistant to hydrolysis, although they were light-sensitive and slowly decomposed even under indoor lighting. The glycoGos also exhibited improved water solubility compared with native Gos, but their saturated concentrations in water were still low (6.4-17 mu M), due to their hydrophobic naphthyl rings. We also carried out WST-8 assays to assess the anticancer activity of the glycoGos on DLD-1 and HepG2 cells and found that the glycoGos having beta-lactosides and having beta-galactosides (specific ligands for asialoglycoprotein receptors) showed enhanced anticancer activity on HepG2 cells. (c) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2018.02.001

文献信息

• Multivalent presentation of carbohydrates by 3₁₄-helical peptide templates: synthesis, conformational analysis using CD spectroscopy and saccharide recognition
  作者：Nitin J. Pawar、Ulf Diederichsen、Dilip. D. Dhavale

  DOI：10.1039/c5ob01673h

  日期：——

  A tetrameric glycoconjugate template, SSFT 1, was coupled with a variety of six aminooxy sugars to achieve multivalent glycoconjugates 2–7.

  一个四聚糖结合物模板，SSFT 1，与多种六个氨氧基糖偶联，以实现多价糖结合物2-7。
• Aminooxy-, Hydrazide-, and Thiosemicarbazide-Functionalized Saccharides:  Versatile Reagents for Glycoconjugate Synthesis
  作者：Elena C. Rodriguez、Lisa A. Marcaurelle、Carolyn R. Bertozzi

  DOI：10.1021/jo981351n

  日期：1998.10.1
• Efficient synthesis of galactosylceramide analogues for iNKT cell stimulation
  作者：Wenlan Chen、Chengfeng Xia、Li Cai、Peng George Wang

  DOI：10.1016/j.bmcl.2010.05.045

  日期：2010.7

  Glycolipids are potential antigens for iNKT cells recognition and demonstrate important roles in both innate and adaptive immunity. However, the difficulties in the preparation of pure configuration defined glycolipids limit the exploration of their different profiles in activating iNKT cells. We report here a concise and stereospecific preparation of novel galactosylceramide analogues by oxime ligation. This strategy would provide an efficient way to generate varied glycolipid analogues with either synthetic or natural carbohydrates for biological evaluations. (c) 2010 Elsevier Ltd. All rights reserved.
• In Situ Preparation of β-<scp>d</scp>-1-<i>O</i>-Hydroxylamino Carbohydrate Polymers Mediated by Galactose Oxidase
  作者：Peter R. Andreana、Wenhua Xie、Huai N. Cheng、Lei Qiao、Dennis J. Murphy、Qu-Ming Gu、Peng G. Wang

  DOI：10.1021/ol0258379

  日期：2002.5.1

  [GRAPHICS]Galactose oxidase produced a C-6 aldehyde in various terminal-containing galactose hydroxylamines for the simultaneous in situ generation of an A-B type condensation for the construction of unique oxime polymers. Molecular weights of the corresponding polymers were determined to be in the range of 4200-8900 g/mol, respectively. This indicates that approximately 20-25 sugar units were incorporated in these unique polymers.
• Synthesis of glycoconjugated chlorin p6 cycloimide
  作者：Viktoriya S. Lebedeva、Ramzes D. Ruziev、Anton V. Popov、Yurii L. Sebyakin、Andrey F. Mironov

  DOI：10.1016/j.mencom.2007.06.008

  日期：2007.7