5-sulfanylpentanyl 4,6-dideoxy-4-((R)-3-hydroxylbutanamido)-2-O-methyl-β-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-rhamnopyranoside | 1239318-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-sulfanylpentanyl 4,6-dideoxy-4-((R)-3-hydroxylbutanamido)-2-O-methyl-β-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-rhamnopyranoside
• 英文别名: (3R)-N-[(2R,3S,4S,5R,6S)-6-[(2S,3R,4R,5S,6S)-2-[(2S,3R,4R,5S,6S)-2-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-2-(5-sulfanylpentoxy)oxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl]oxy-4-hydroxy-5-methoxy-2-methyloxan-3-yl]-3-hydroxybutanamide
• CAS: 1239318-52-5
• 化学式: C₃₄H₆₁NO₁₈S
• 分子量: 803.92
• InChiKey: VHQVQCDLEGOUSJ-NYAROESHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  275
• 氢给体数：
  10
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  5-thioacetylpentyl 4,6-dideoxy-4-((R)-3-hydroxylbutanamido)-2-O-methyl-β-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-rhamnopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以96%的产率得到5-sulfanylpentanyl 4,6-dideoxy-4-((R)-3-hydroxylbutanamido)-2-O-methyl-β-D-glucopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Molecular Analysis of Carbohydrate−Antibody Interactions: Case Study Using a Bacillus anthracis Tetrasaccharide

  摘要：

  The process for selecting potent and effective carbohydrate antigens is not well-established. A combination of synthetic glycan microarray screening, surface plasmon resonance analysis, and saturation transfer difference NMR spectroscopy was used to dissect the antibody-binding surface of a carbohydrate antigen, revealing crucial binding elements with atomic-level detail. This analysis takes the first step toward uncovering the rules for structure-based design of carbohydrate antigens.

  DOI：

  10.1021/ja104027w

文献信息

• Molecular Analysis of Carbohydrate−Antibody Interactions: Case Study Using a <i>Bacillus anthracis</i> Tetrasaccharide
  作者：Matthias A. Oberli、Marco Tamborrini、Yu-Hsuan Tsai、Daniel B. Werz、Tim Horlacher、Alexander Adibekian、Dominik Gauss、Heiko M. Möller、Gerd Pluschke、Peter H. Seeberger

  DOI：10.1021/ja104027w

  日期：2010.8.4

  The process for selecting potent and effective carbohydrate antigens is not well-established. A combination of synthetic glycan microarray screening, surface plasmon resonance analysis, and saturation transfer difference NMR spectroscopy was used to dissect the antibody-binding surface of a carbohydrate antigen, revealing crucial binding elements with atomic-level detail. This analysis takes the first step toward uncovering the rules for structure-based design of carbohydrate antigens.