ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside | 115216-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-5-azido-2-ethylsulfanyl-6-methyl-4-phenylmethoxyoxan-3-ol
• CAS: 115216-48-3
• 化学式: C₁₅H₂₁N₃O₃S
• 分子量: 323.416
• InChiKey: CYOOMROQUXVORY-JSFFLRCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87.45
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 在 silver trifluoromethanesulfonate 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 methyl O-(2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-O-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  布鲁氏菌A和M抗原的抗原决定簇三，四和五糖的4,6-二脱氧-4-甲酰胺基-α-D-甘露糖的合成

  摘要：

  已经开发了基于使用硫代糖苷生成1,2-反式-糖苷键的合成策略，该策略已使五聚体α-1,2连接的4,6-二脱氧-4-甲酰胺基-α - D-甘露糖有效合成。均聚物以及包含α-1,3键的结构。

  DOI：

  10.1039/c39870001648
• 作为产物：
  描述：

  1,2-di-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranose 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Peters, Thomas; Bundle, David R., Canadian Journal of Chemistry, 1989, vol. 67, p. 491 - 496

  摘要：

  DOI：

文献信息

• 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
• Design and Synthesis of a Universal Antigen to Detect Brucellosis
  作者：Julie Guiard、Eugenia Paszkiewicz、Joanna Sadowska、David R. Bundle

  DOI：10.1002/anie.201302303

  日期：2013.7.8

  Upgrading diagnostics: A universal antigen has been prepared for the detection of brucellosis caused by any Brucella species that express a smooth lipopolysaccharide. This nonasaccharide, which encompasses Brucella A‐ and M‐antigenic determinants, is uniquely available only by chemical synthesis.

  诊断升级：已准备了一种通用抗原，用于检测由表达光滑脂多糖的任何布鲁氏菌属引起的布鲁氏菌病。这种包含布鲁氏菌A和M抗原决定簇的九糖，只有通过化学合成才能唯一获得。
• The design and synthesis of antibody binding site probes: three pentasaccharide analogues of the Brucella A antigen prepared by activation in situ of thioglycosides with bromine
  作者：Jan Kihlberg、Eva Eichler、David R. Bundle

  DOI：10.1016/0008-6215(91)84146-6

  日期：1991.4

  formamido group replaced by a hydroxyl group, have been prepared as their methyl glycosides. Mono- and di-saccharide thioglycosides of D-rhamnose and 4-azido-4,6-dideoxy-D-mannose were used as glycosyl donors for the preparation of protected pentasaccharide derivatives with trisaccharides as intermediates. Glycosylations were performed by activation in situ of the thioglycosides with bromine in the presence

  已制备了布鲁氏菌A抗原[---- 2）-alpha-D-Rhap4NFo-（1 ----）的三个五糖类似物，每个类似物均被一个甲基取代，并带有一个甲酰胺基。用D-鼠李糖和4-叠氮基-4,6-二脱氧-D-甘露糖的-和二糖硫糖苷作为糖基供体，以三糖为中间体制备受保护的五糖衍生物，通过原位活化糖基化来进行糖基化。在糖基受体和三氟甲磺酸银作为助催化剂存在下，用溴将硫代糖苷与溴化；用硫化氢还原叠氮基；用甲酸乙酯进行N-甲酰化，然后氢解得到目标五糖。
• 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.
• Synthesis of Tetrasaccharide Repeating Unit of the O‐Antigen from Enterohemorrhagic <i>Escherichia coli</i> O157 in the form of its 2‐(trimethylsilyl)ethyl Glycoside
  作者：Kakali Sarkar、Nirmolendu Roy

  DOI：10.1080/07328300500495878

  日期：2006.1.1

  Two alpha-linked disaccharide derivatives, ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl-(1 -> 2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-alpha-D-mannopyranoside (10) and 2-(trimethylsilyl)ethyl 3-O-acetyl-4-O-benzoyl-2-O-benzyl-alpha-L-fucopyranosyl-(1 -> 4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-beta-D-glucopyranoside (16), were prepared from appropriate monosaccharide synthons. The disaccharide 16 was deacetylated and debenzoylated to afford the acceptor 17, which was allowed to react with the donor 10 to afford a tetrasaccharide derivative 18. This tetrasaccharide was transformed in three steps into 21, the desired repeating unit of the antigen from enterohemorrhagic E. coli type O157.