allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside | 1351452-34-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside
• 英文别名: allyl 6-O-tert-butyldiphenylsilyl-4-O-(2-methylnaphthyl)-2,3-O-isopropylidene-α-D-mannopyranoside
• CAS: 1351452-34-0
• 化学式: C₃₉H₄₆O₆Si
• 分子量: 638.876
• InChiKey: AHBNGAKNCRNAQG-DWCHZDDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside 在 甲醇 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 碘 、 sodium methylate 、 sodium hydride 、 戴斯-马丁氧化剂 、 magnesium 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 mercury dibromide 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 40.5h， 生成 allyl 6,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-α-D-mannoheptopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Campylobacter jejuni Lipo-oligosaccharide Core Domains to Examine Guillain–Barré Syndrome Serum Antibody Specificities

  摘要：

  Guillain-Barré syndrome is often caused by Campylobacter jejuni infection that has induced antibodies to the lipo-oligosaccharide (LOS) that cross-react with gangliosides at peripheral nerves causing polyneuropathy. To examine fine specificities of anti-ganglioside antibodies and develop a more robust platform for diagnosis and disease monitoring, we developed a chemoenzymatic approach that provided an unprecedented panel of oligosaccharides composed of the inner-core of the LOS of C. jejuni extended by various ganglioside mimics. The compounds and corresponding ganglio-oligosaccharides were printed as a microarray to examine binding specificities of lectins, anti-ganglioside antibodies, and serum antibodies of GBS patients. Although lectins and anti-ganglioside antibodies did not differentiate the ganglio-oligosaccharides and mimics, the patient serum samples bound much more strongly to the ganglioside mimics. The data indicate that antibodies have been elicited to a foreign epitope that includes a heptosyl residue unique of bacterial LOS and that these antibodies subsequently cross-react with lower affinity to gangliosides. The microarray detected anti-GM1a antibodies with high sensitivity and will be attractive for diagnosis, disease monitoring, and immunological research.

  DOI：

  10.1021/jacs.0c08583
• 作为产物：
  描述：

  甘露糖 在 咪唑 、 三氟甲磺酸 、 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 14.0h， 生成 allyl 2,3-O-isopropylidene-4-O-(2-naphthylmethyl)-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Campylobacter jejuni Lipo-oligosaccharide Core Domains to Examine Guillain–Barré Syndrome Serum Antibody Specificities

  摘要：

  Guillain-Barré syndrome is often caused by Campylobacter jejuni infection that has induced antibodies to the lipo-oligosaccharide (LOS) that cross-react with gangliosides at peripheral nerves causing polyneuropathy. To examine fine specificities of anti-ganglioside antibodies and develop a more robust platform for diagnosis and disease monitoring, we developed a chemoenzymatic approach that provided an unprecedented panel of oligosaccharides composed of the inner-core of the LOS of C. jejuni extended by various ganglioside mimics. The compounds and corresponding ganglio-oligosaccharides were printed as a microarray to examine binding specificities of lectins, anti-ganglioside antibodies, and serum antibodies of GBS patients. Although lectins and anti-ganglioside antibodies did not differentiate the ganglio-oligosaccharides and mimics, the patient serum samples bound much more strongly to the ganglioside mimics. The data indicate that antibodies have been elicited to a foreign epitope that includes a heptosyl residue unique of bacterial LOS and that these antibodies subsequently cross-react with lower affinity to gangliosides. The microarray detected anti-GM1a antibodies with high sensitivity and will be attractive for diagnosis, disease monitoring, and immunological research.

  DOI：

  10.1021/jacs.0c08583

文献信息

• A General Method for Synthesis of GPI Anchors Illustrated by the Total Synthesis of the Low-Molecular-Weight Antigen from Toxoplasma gondii
  作者：Yu-Hsuan Tsai、Sebastian Götze、Nahid Azzouz、Heung Sik Hahm、Peter H. Seeberger、Daniel Varon Silva

  DOI：10.1002/anie.201103483

  日期：2011.10.10

  Building blocks: A new, general synthetic strategy, which allows the construction of branched glycosylphosphatidylinositols (GPIs), enables the synthesis of parasitic glycolipid 1 from Toxoplasma gondii. In addition, the structure is further confirmed by recognition of monoclonal antibodies.

  组成部分：一种新的通用合成策略，该策略可以构建支链糖基磷脂酰肌醇（GPI），从而可以从弓形虫中合成寄生糖脂1 。另外，通过识别单克隆抗体进一步证实了该结构。