methyl 4-azido-2-O-methyl-4,6-dideoxy-α-D-mannopyranoside | 172603-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-azido-2-O-methyl-4,6-dideoxy-α-D-mannopyranoside
• 英文别名: methyl 4-azido-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside
• CAS: 172603-70-2
• 化学式: C₈H₁₅N₃O₄
• 分子量: 217.225
• InChiKey: WWXHEJASFWWQFA-HEIBUPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-2-O-methyl-4,6-dideoxy-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 3.0h， 生成 methyl 3-O-acetyl-4,6-dideoxy-4-(2,3-di-O-acetyl-D-glycero-propanamido)-2-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Syntheses of the l-manno and some other analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1

  摘要：

  Analogs of the methyl alpha -glycosides of the terminal residues of the O-specific polysaccharides (O-PS) of Vibrio cholerae O:1, serotype Inaba and Ogawa, have been prepared as probes to study their interaction with anti V. cholerae O:1 antibodies. They differ from the termini of the respective O-PSs in anomeric or absolute configuration of perosamine, position of the O-methyl group in D-perosamine, and nature of the N-acyl side chain. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00265-2
• 作为产物：
  描述：

  甲基 4-叠氮基-4,6-二脱氧吡喃甘露糖苷 在 sodium hydroxide 、 四丁基溴化铵 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 31.0h， 生成 methyl 4-azido-2-O-methyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-l-glycero-tetronamido) - 2-O-methyl-α-d-mannopyranoside, the methyl α-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa

  摘要：

  Methyl 4-azido-4,6-dideoxy-3-O-benzyl-alpha-D-mannopyranoside and its analogous 3-O-(4-methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were converted into methyl 4-amino-4,6-dideoxy-2-O-methyl-alpha-D-mannopyranoside. Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranose, the monosaccharide that is reported to be the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Ogawa. The unit cell packing of the compound, which crystallized as a monohydrate, differs from that of the previously described crystalline compound lacking the 2-O-methyl group. The unmethylated sugar is the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Inaba. The crystal structure of methyl 4,6-dideoxy-2-0-methyl-4-trifluoroacetamido-alpha-D-mannopyranoside is also described.

  DOI：

  10.1016/0008-6215(95)00147-l

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