2-aminoethyl 5-thio-α-D-mannopyranoside | 1148027-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 2-aminoethyl 5-thio-α-D-mannopyranoside
• 英文别名: 5SManEtN；(2S,3S,4S,5S,6R)-2-(2-aminoethoxy)-6-(hydroxymethyl)thiane-3,4,5-triol
• CAS: 1148027-66-0
• 化学式: C₈H₁₇NO₅S
• 分子量: 239.293
• InChiKey: FRYKKMDWURTOKO-HEIBUPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 水 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以32 mg的产率得到2-aminoethyl 5-thio-α-D-mannopyranoside
  参考文献：
  名称：

  A Facile Latex Agglutination Lectin Assay (LALA) for Weakly Binding Ligands

  摘要：

  To apply the latex agglutination lectin assay (LALA) to carbohydrate ligands, monosaccharide derivatives were incorporated onto latex beads by various methods, and the usefulness of the resulting beads was evaluated. The best outcome, which resulted in aggregation with lectin concentrations of 1 to 4 g/mL, was obtained when latex beads coated with bovine serum albumin were treated with divinylsulfone, a linker agent, and then with 2-aminoethyl glycosides. Monosaccharides with an amino or anomeric hydroxyl group other than N-acetylglucosamine were applicable in this direct LALA. For example, mannose- and 5-thiomannose-coupled latex beads showed aggregation with minimum concanavalin (ConA) concentrations of 4 and 32 g/mL, respectively. An inhibition assay was more versatile than the direct LALA, and the standardized inhibition activity (EC050) was determined for several compounds. Representative EC050 data for mannose, methyl mannoside, and p-nitrophenyl mannoside (1, 0.12, and 0.06 mM, respectively) are consistent with those reported with other methods. We obtained EC050 values for some synthetic compounds with slightly different binding abilities to ConA, demonstrating a semiquantitative character of this method. The inhibition LALA can be performed without instrumentation or tedious derivatization and is thus suitable for the rapid evaluation of monovalent ligands prior to assemblage into multivalent ligands.

  DOI：

  10.1080/07328300802696207