N-methyl-O-(propyl-3-thiol)-N-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl] hydroxylamine | 1152438-45-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methyl-O-(propyl-3-thiol)-N-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl] hydroxylamine
• 英文别名: N-[(2R,3R,4R,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxymethyl]-4,5-dihydroxy-2-[methyl(3-sulfanylpropoxy)amino]oxan-3-yl]acetamide
• CAS: 1152438-45-3
• 化学式: C₄₄H₇₆N₆O₂₆S
• 分子量: 1137.18
• InChiKey: MAHRTHKKYIRRCL-ZYXOHFJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.8
• 重原子数：
  77
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  465
• 氢给体数：
  17
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  N-methyl-O-(propyl-3-thiol)-N-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl] hydroxylamine 在 sodium hydroxide 、 Cleland's reagent 作用下， 以 水 为溶剂， 反应 48.0h， 以90%的产率得到
  参考文献：
  名称：

  Efficient synthesis and protein conjugation of β-(1→6)-d-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin

  摘要：

  A wide variety of medically important biofilm forming bacteria produce similar polysaccharide intracellular adhesins (PIAs). The PIA structures consist of partially de-N-acetylated beta-(1 -> 6)-N-acetylglucosamine polymers. These exopolysaccharides are key components of the bacterial biofilm matrix. Here, we describe the efficient synthesis of PIA oligosaccharides using an acid reversion reaction of N-acetylglucosamine in HF pyridine. The PIA oligosaccharides produced by this reaction can be purified to homogeneity by size exclusion chromatography. Chemistry was developed to conjugate the PIA oligosaccharides to bovine serum albumin using a new heterobifunctional linker containing a thiol and an N-methylhydroxylamine functional group. These glycoconjugates may serve as useful precursors for the development of defined conjugate vaccines against PIA producing bacterial strains. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.021
• 作为产物：
  描述：

  1,2-bis(N-methyl-O-propyl-hydroxylamine)disulfide 、 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-D-glucopyranose 在 三乙胺 、 Cleland's reagent 作用下， 以 N,N-二甲基甲酰胺 、 水 、 溶剂黄146 为溶剂， 反应 0.5h， 以55%的产率得到N-methyl-O-(propyl-3-thiol)-N-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranosyl] hydroxylamine
  参考文献：
  名称：

  Efficient synthesis and protein conjugation of β-(1→6)-d-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin

  摘要：

  A wide variety of medically important biofilm forming bacteria produce similar polysaccharide intracellular adhesins (PIAs). The PIA structures consist of partially de-N-acetylated beta-(1 -> 6)-N-acetylglucosamine polymers. These exopolysaccharides are key components of the bacterial biofilm matrix. Here, we describe the efficient synthesis of PIA oligosaccharides using an acid reversion reaction of N-acetylglucosamine in HF pyridine. The PIA oligosaccharides produced by this reaction can be purified to homogeneity by size exclusion chromatography. Chemistry was developed to conjugate the PIA oligosaccharides to bovine serum albumin using a new heterobifunctional linker containing a thiol and an N-methylhydroxylamine functional group. These glycoconjugates may serve as useful precursors for the development of defined conjugate vaccines against PIA producing bacterial strains. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.021