5'-methoxycarbonylpentyl 4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-Dmannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-methoxycarbonylpentyl 4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-Dmannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranoside
• 英文别名: alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFo-(1->2)-alpha-D-Rhap4NFoO[CH2]5CO2Me；methyl 6-[(2S,3S,4S,5S,6R)-5-formamido-3-[(2R,3S,4S,5S,6R)-5-formamido-3-[(2R,3S,4S,5S,6R)-5-formamido-3-[(2R,3S,4S,5S,6R)-5-formamido-3-[(2R,3S,4S,5S,6R)-5-formamido-3-[(2R,3S,4S,5S,6R)-5-formamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxyhexanoate
• 化学式: C₄₉H₈₀N₆O₂₇
• 分子量: 1185.2
• InChiKey: YMFIWPINWGXZIM-OZAYIRNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  82
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  453
• 氢给体数：
  13
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  5'-methoxycarbonylpentyl 4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-Dmannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranoside 、 乙二胺 反应 48.0h， 以97%的产率得到(2'-aminoethylamido)carbonylpentyl 4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranoside
  参考文献：
  名称：

  Molecular Recognition of Brucella A and M Antigens Dissected by Synthetic Oligosaccharide Glycoconjugates Leads to a Disaccharide Diagnostic for Brucellosis

  摘要：

  The cell wall O-polysaccharides of pathogenic Brucella species are homopolymers of the rare sugar 4,6-dideoxy-4-formamido-alpha-D-mannopyranose. Despite the apparent simplicity of the polysaccharide it appears to be a "block copolymer" composed of A and M polysaccharide sequences expressed as a single molecule. The simultaneous presence of both in the cell wall has complicated the understanding of the molecular recognition of these antigens by antibodies present in the serum of infected animals and humans and by monoclonal antibodies. Since presumptive diagnosis of brucellosis, a serious disease in domestic livestock, wild animals, and humans, is based on detection of these antibodies it is important to separate the two antigenic epitopes, one of which is also found in other bacteria. Chemical synthesis provides the only means to achieve this outcome. A series of six oligosaccharides from di to hexasaccharides 1-6 were synthesized and conjugated to proteins to provide glycoconjugate antigens and conjugate vaccines. These chemically defined antigens identified the M antigenic determinant and provided a structural basis for understanding the fine specificity of monoclonal and polyclonal antibodies that bind the M antigen. This resulted in the discovery of a disaccharide that shows considerable potential as an unambiguous diagnostic antigen for detecting brucellosis in humans and animals and two hexasaccharide conjugate vaccine candidates that produce high levels of O-polysaccharide specific antibodies in mice.

  DOI：

  10.1021/ja5081184
• 作为产物：
  描述：

  在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以0.052 g的产率得到5'-methoxycarbonylpentyl 4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-Dmannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranosyl-(1→2)-4,6-dideoxy-4-formamido-α-D-mannopyranoside
  参考文献：
  名称：

  Molecular Recognition of Brucella A and M Antigens Dissected by Synthetic Oligosaccharide Glycoconjugates Leads to a Disaccharide Diagnostic for Brucellosis

  摘要：

  The cell wall O-polysaccharides of pathogenic Brucella species are homopolymers of the rare sugar 4,6-dideoxy-4-formamido-alpha-D-mannopyranose. Despite the apparent simplicity of the polysaccharide it appears to be a "block copolymer" composed of A and M polysaccharide sequences expressed as a single molecule. The simultaneous presence of both in the cell wall has complicated the understanding of the molecular recognition of these antigens by antibodies present in the serum of infected animals and humans and by monoclonal antibodies. Since presumptive diagnosis of brucellosis, a serious disease in domestic livestock, wild animals, and humans, is based on detection of these antibodies it is important to separate the two antigenic epitopes, one of which is also found in other bacteria. Chemical synthesis provides the only means to achieve this outcome. A series of six oligosaccharides from di to hexasaccharides 1-6 were synthesized and conjugated to proteins to provide glycoconjugate antigens and conjugate vaccines. These chemically defined antigens identified the M antigenic determinant and provided a structural basis for understanding the fine specificity of monoclonal and polyclonal antibodies that bind the M antigen. This resulted in the discovery of a disaccharide that shows considerable potential as an unambiguous diagnostic antigen for detecting brucellosis in humans and animals and two hexasaccharide conjugate vaccine candidates that produce high levels of O-polysaccharide specific antibodies in mice.

  DOI：

  10.1021/ja5081184

文献信息

• Molecular Recognition of <i>Brucella</i> A and M Antigens Dissected by Synthetic Oligosaccharide Glycoconjugates Leads to a Disaccharide Diagnostic for Brucellosis
  作者：N. Vijaya Ganesh、Joanna M. Sadowska、Susmita Sarkar、Laurence Howells、John McGiven、David R. Bundle

  DOI：10.1021/ja5081184

  日期：2014.11.19

  The cell wall O-polysaccharides of pathogenic Brucella species are homopolymers of the rare sugar 4,6-dideoxy-4-formamido-alpha-D-mannopyranose. Despite the apparent simplicity of the polysaccharide it appears to be a "block copolymer" composed of A and M polysaccharide sequences expressed as a single molecule. The simultaneous presence of both in the cell wall has complicated the understanding of the molecular recognition of these antigens by antibodies present in the serum of infected animals and humans and by monoclonal antibodies. Since presumptive diagnosis of brucellosis, a serious disease in domestic livestock, wild animals, and humans, is based on detection of these antibodies it is important to separate the two antigenic epitopes, one of which is also found in other bacteria. Chemical synthesis provides the only means to achieve this outcome. A series of six oligosaccharides from di to hexasaccharides 1-6 were synthesized and conjugated to proteins to provide glycoconjugate antigens and conjugate vaccines. These chemically defined antigens identified the M antigenic determinant and provided a structural basis for understanding the fine specificity of monoclonal and polyclonal antibodies that bind the M antigen. This resulted in the discovery of a disaccharide that shows considerable potential as an unambiguous diagnostic antigen for detecting brucellosis in humans and animals and two hexasaccharide conjugate vaccine candidates that produce high levels of O-polysaccharide specific antibodies in mice.