5'-methoxycarbonylpentyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-mannopyranoside | 1044594-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-methoxycarbonylpentyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
• 英文别名: methyl 6-[(2S,3S,4S,5S,6R)-5-azido-4-hydroxy-6-methyl-3-phenylmethoxyoxan-2-yl]oxyhexanoate
• CAS: 1044594-40-2
• 化学式: C₂₀H₂₉N₃O₆
• 分子量: 407.467
• InChiKey: CDCVRZSPLGVKAP-NSYSGPAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-methoxycarbonylpentyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 在 吡啶 、 20% palladium hydroxide-activated charcoal 、 硫化氢 、 氢气 、 sodium methylate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 93.0h， 生成 1-[(2'-aminoethylamido)carbonylpentyl α-D-mannopyranosyl(1→3)-4,6-dideoxy-4-formamido-α-D-mannopyranoside-2-butoxycyclobutene-3,4-dione]
  参考文献：
  名称：

  合成糖缀合物表征布鲁氏菌A和M单克隆抗体的优良特异性

  摘要：

  布鲁氏菌细菌的主要细胞壁抗原是光滑脂多糖的O-多糖成分。各种布鲁氏菌生物变种的感染会导致各种家畜和野生动物的流产和不育，并导致人类衰弱的疾病。诊断依赖于针对O-多糖中表达的A和M抗原的抗体的检测。该分子是稀有单糖4-甲酰胺基-4,6-二脱氧-D-甘露吡喃糖（Rha4NFo）的均聚物。A表位是由均匀的α1,2连接的内部聚合物序列产生的，该序列由限定M抗原的独特的四糖序列所覆盖。唯一的寡糖只能通过化学合成获得，并通过牛血清白蛋白的还原性和非还原性残基揭示了精细特异性的结构基础，该特异性可以区分这些密切相关的A和M表位。推断所有这三种M特异性单克隆抗体（mAb）具有在两端开放的凹槽型结合位点，并将α1,3连接的Rha4NFo二糖识别为三糖表位的一部分，在两个mAb中包括末端Rha4NFo残基。这些抗体之一的结合位点足够大，可以结合多达六个Rha4NFo残基，并且涉及对α1,2连接的Rha4NFo

  DOI：

  10.1039/c7ob00445a
• 作为产物：
  描述：

  5-methoxycarbonylpentyl 3-O-acetyl-4-azido-2-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以85%的产率得到5'-methoxycarbonylpentyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of spacer-equipped di-, tri-, and the tetrasaccharide fragments of the deacetylated O-PS1 of Citrobacter gillenii O9a,9b, and a related pentasaccharide

  摘要：

  The title rhamnooligosaccharides [alpha-D-Rhap4NAc-(1 -> 3)-O(-D-Rhap4NAc-1-O-(CH2)(5)COOMe, alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-(1 3)-alpha-D-Rhap4NAc-1-O-(CH2)(5)COOMe, alpha-D-Rhap4NAc-(1 -> 2)-alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-1-O-(CH2)(5)COOMe, and alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-(1-2)-(alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc(1 -> 3)-alpha-D-Rhap4NAc-1-O-(CH2)(5)COOMe] were synthesized in a stepwise fashion from 5-methoxycarbonylpentyl 4-azido-4, 6-dideoxy-2-O-benzyl-alpha-D-mannopyranoside and orthogonally protected 1-thioglycoside glycosyl donors. The amorphous, final products were fully characterized as corresponding per-O-acetyl derivatives. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2008.03.037

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.
• Synthetic glycoconjugates characterize the fine specificity of Brucella A and M monoclonal antibodies
  作者：Satadru Sekhar Mandal、N. Vijaya Ganesh、Joanna M. Sadowska、David R. Bundle

  DOI：10.1039/c7ob00445a

  日期：——

  The dominant cell wall antigen of Brucella bacteria is the O-polysaccharide component of the smooth lipopolysaccharide. Infection by various Brucella biovars causes abortions and infertility in a wide range of domestic and wild animals and debilitating disease in humans. Diagnosis relies on the detection of antibodies to the A and M antigens expressed in the O-polysaccharide. This molecule is a homopolymer

  布鲁氏菌细菌的主要细胞壁抗原是光滑脂多糖的O-多糖成分。各种布鲁氏菌生物变种的感染会导致各种家畜和野生动物的流产和不育，并导致人类衰弱的疾病。诊断依赖于针对O-多糖中表达的A和M抗原的抗体的检测。该分子是稀有单糖4-甲酰胺基-4,6-二脱氧-D-甘露吡喃糖（Rha4NFo）的均聚物。A表位是由均匀的α1,2连接的内部聚合物序列产生的，该序列由限定M抗原的独特的四糖序列所覆盖。唯一的寡糖只能通过化学合成获得，并通过牛血清白蛋白的还原性和非还原性残基揭示了精细特异性的结构基础，该特异性可以区分这些密切相关的A和M表位。推断所有这三种M特异性单克隆抗体（mAb）具有在两端开放的凹槽型结合位点，并将α1,3连接的Rha4NFo二糖识别为三糖表位的一部分，在两个mAb中包括末端Rha4NFo残基。这些抗体之一的结合位点足够大，可以结合多达六个Rha4NFo残基，并且涉及对α1,2连接的Rha4NFo
• Synthesis of spacer-equipped di-, tri-, and the tetrasaccharide fragments of the deacetylated O-PS1 of Citrobacter gillenii O9a,9b, and a related pentasaccharide
  作者：Rina Saksena、Anatoli Chernyak、Pavol Kováč

  DOI：10.1016/j.carres.2008.03.037

  日期：2008.7

  The title rhamnooligosaccharides [alpha-D-Rhap4NAc-(1 -> 3)-O(-D-Rhap4NAc-1-O-(CH2)(5)COOMe, alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-(1 3)-alpha-D-Rhap4NAc-1-O-(CH2)(5)COOMe, alpha-D-Rhap4NAc-(1 -> 2)-alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-1-O-(CH2)(5)COOMe, and alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc-(1-2)-(alpha-D-Rhap4NAc-(1 -> 3)-alpha-D-Rhap4NAc(1 -> 3)-alpha-D-Rhap4NAc-1-O-(CH2)(5)COOMe] were synthesized in a stepwise fashion from 5-methoxycarbonylpentyl 4-azido-4, 6-dideoxy-2-O-benzyl-alpha-D-mannopyranoside and orthogonally protected 1-thioglycoside glycosyl donors. The amorphous, final products were fully characterized as corresponding per-O-acetyl derivatives. Published by Elsevier Ltd.