2,3,4,6-O-tetraacetyl-1-O-[3-(acryloylamino)propyl]-α-D-mannose | 848814-55-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,3,4,6-O-tetraacetyl-1-O-[3-(acryloylamino)propyl]-α-D-mannose
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[3-(prop-2-enoylamino)propoxy]oxan-2-yl]methyl acetate
• CAS: 848814-55-1
• 化学式: C₂₀H₂₉NO₁₁
• 分子量: 459.45
• InChiKey: ZNPDTGAXKFNJQZ-LGKHCZOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-O-tetraacetyl-1-O-[3-(acryloylamino)propyl]-α-D-mannose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到N-[3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl]prop-2-enamide
  参考文献：
  名称：

  Novel multivalent mannose compounds and their inhibition of the adhesion of type 1 fimbriated uropathogenic E. coli

  摘要：

  A series of multivalent mannose containing compounds were prepared varying in size from small divalent, to 16-valent glycodenrimers and 21-valent glycopolymers. The molecules were approached via a common mannose building block. As scaffolds dendrimers and dendrons based on the 3,5-di-(2-aminoethoxy)-benzoic acid branching unit were used along with commercially available PAMAM dendrimers. To include larger structures, linear glycopolymers with varying amounts of mannose were prepared via radical polymerization. The compounds were tested for their biological activity using a newly developed ELISA based inhibition assay, for their ability to inhibit the binding of recombinant type I fimbriated E. coli to a monolayer of T24 cell line derived from human urinary bladder epithelium. All compounds showed enhanced affinity as compared to mannose with IC50's down to the low micromolar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.014
• 作为产物：
  描述：

  1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 palladium on activated charcoal sodium azide 、 氢溴酸 、 氢气 、 一溴化碘 、 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 2,3,4,6-O-tetraacetyl-1-O-[3-(acryloylamino)propyl]-α-D-mannose
  参考文献：
  名称：

  Novel multivalent mannose compounds and their inhibition of the adhesion of type 1 fimbriated uropathogenic E. coli

  摘要：

  A series of multivalent mannose containing compounds were prepared varying in size from small divalent, to 16-valent glycodenrimers and 21-valent glycopolymers. The molecules were approached via a common mannose building block. As scaffolds dendrimers and dendrons based on the 3,5-di-(2-aminoethoxy)-benzoic acid branching unit were used along with commercially available PAMAM dendrimers. To include larger structures, linear glycopolymers with varying amounts of mannose were prepared via radical polymerization. The compounds were tested for their biological activity using a newly developed ELISA based inhibition assay, for their ability to inhibit the binding of recombinant type I fimbriated E. coli to a monolayer of T24 cell line derived from human urinary bladder epithelium. All compounds showed enhanced affinity as compared to mannose with IC50's down to the low micromolar range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.014

文献信息

• Synthesis of Monoconjugated and Multiply Conjugated Oligonucleotides by “Click Thiol” Thiol-Michael-Type Additions and by Combination with CuAAC “Click Huisgen”
  作者：Albert Meyer、Jean-Jacques Vasseur、François Morvan

  DOI：10.1002/ejoc.201201311

  日期：2013.1

  Monoconjugated and multiply conjugated oligonucleotides were efficiently synthesized by starting from mono-thiohexyl- or tetra-thiohexyl-oligonucleotides and treatment with acrylamide derivatives (carbohydrates, ferrocene, biotin, fluorescent dyes, deoxycholic acid). The thiol Michael-type additions (TMTAs) occurred during the deprotection and release of the oligonucleotides from the solid support

  通过从单-硫代己基-或四-硫代己基-寡核苷酸开始并用丙烯酰胺衍生物（碳水化合物、二茂铁、生物素、荧光染料、脱氧胆酸）处理，可以有效合成单缀合和多缀合寡核苷酸。硫醇迈克尔型添加 (TMTA) 发生在寡核苷酸从固体支持物脱保护和释放期间，因此不需要额外的缀合时间。铜催化的叠氮化物-炔环加成 (CuAAC) 在固体载体上然后是 TMTA 或 TMTA 然后是溶液中的 CuAAC 的顺序组合允许合成几种用两种不同生物分子装饰的寡核苷酸。