methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside | 172603-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-5-azido-2,3-dimethoxy-6-methyl-4-phenylmethoxyoxane
• CAS: 172603-65-5
• 化学式: C₁₅H₂₁N₃O₄
• 分子量: 307.349
• InChiKey: NYGOWLVAGJFTAB-IKSZGEOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 硫化氢 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 生成 methyl 4-amino-4,6-dideoxy-2-O-methyl-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
• 作为产物：
  描述：

  methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 、 碘甲烷 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以95%的产率得到methyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-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
• OLIGOSACCHARIDE CONJUGATES AND METHODS OF USE
  申请人：THE SECRETARY OF STATE FOR ENVIRNMENT, FOOD AND RURAL AFFAIRS

  公开号：US20160067345A1

  公开（公告）日：2016-03-10

  There is provided a method of detecting in a sample the presence of an anti-M and/or anti-A and/or anti-C/Y anti-body, the method comprising contacting the sample with a diagnostic conjugate provided according to the invention, comprising an oligosaccharide which comprises at least two units of 4,6-dideoxy-4-acylamido-α-pyranose and comprising at least one -(1-3)-link between adjacent 4,6-dideoxy-4-acylamido-α-pyranose units, in which the carbon at position 5 in the pyranose is linked to an R group, where R is independently selected from —CH 2 OH, —H or an alkyl group having at least one C atom, the oligosaccharide being covalently linked to a non-saccharide molecule or to a surface.

  本发明提供了一种检测样品中抗-M和/或抗-A和/或抗C/Y抗体存在的方法，该方法包括将样品与根据本发明提供的诊断共轭物接触，所述诊断共轭物包括寡糖，其包含至少两个4,6-二脱氧-4-酰胺基-α-吡喃糖单元，并且包含至少一个相邻的4,6-二脱氧-4-酰胺基-α-吡喃糖单元之间的-(1-3)-键，其中在吡喃糖的5号碳与R基连接，其中R独立选择自-CH2OH，-H或至少具有一个C原子的烷基基团，所述寡糖与非糖分子或表面共价连接。
• Oligosaccharide conjugates and methods of use
  申请人：THE SECRETARY OF STATE FOR ENVIRONMENT, FOOD AND RURAL AFFAIRS

  公开号：US10207006B2

  公开（公告）日：2019-02-19

  There is provided a method of detecting in a sample the presence of an anti-M and/or anti-A and/or anti-C/Y antibody, the method comprising contacting the sample with a diagnostic conjugate provided according to the invention, comprising an oligosaccharide which comprises at least two units of 4,6-dideoxy-4-acylamido-α-pyranose and comprising at least one -(1-3)- link between adjacent 4,6-dideoxy-4-acylamido-α-pyranose units, in which the carbon at position 5 in the pyranose is linked to an R group, where R is independently selected from —CH2OH, —H or an alkyl group having at least one C atom, the oligosaccharide being covalently linked to a non-saccharide molecule or to a surface.

  本发明提供了一种检测样品中是否存在抗-M 和/或抗-A 和/或抗-C/Y 抗体的方法，该方法包括将样品与根据本发明提供的诊断共轭物接触，该诊断共轭物由寡糖组成，寡糖包括至少两个 4,6-二脱氧-4-酰氨基-α-吡喃糖单元，相邻的 4、6-二脱氧-4-酰氨基-α-吡喃糖单元之间至少有一个-(1-3)-连接，其中吡喃糖第 5 位的碳与一个 R 基相连，其中 R 独立地选自-CH2OH、-H 或至少有一个 C 原子的烷基，寡糖与非糖分子或表面共价连接。
• Polysaccharide and methods
  申请人：THE SECRETARY OF STATE FOR ENVIRONMENT, FOOD AND RURAL AFFAIRS

  公开号：US11033632B2

  公开（公告）日：2021-06-15

  There is provided a molecule comprising a chain of seven or more contiguous units of 4,6-dideoxy-4-acylamido-α-pyranose, each pair of units joined by a C1-C2 or a C1-C3 link, the chain having a terminal end and a reducing end, wherein the pyranose ring in the unit of the chain most distal from the reducing end is linked to a cap structure. The cap structure is not a 4,6-dideoxy-4-acylamido-α-pyranose. There are also provided vaccine compositions comprising the molecule and methods of vaccinating an animal NI against infection by a Brucella organism, including methods of distinguishing between a vaccinated and an infected animal. There are further provided novel methods of detecting the presence in a sample of an anti-Brucella antibody.

  本发明提供了一种分子，该分子包括由七个或七个以上连续的 4,6-二脱氧-4-酰氨基-α-吡喃糖单元组成的链，每对单元通过一个 C1-C2 或一个 C1-C3 链节连接，该链具有一个末端和一个还原端，其中离还原端最远的链单元中的吡喃糖环与一个帽结构相连。帽结构不是 4,6-二脱氧-4-酰氨基-α-吡喃糖。还提供了包含该分子的疫苗组合物和接种动物 NI 以防止布鲁氏菌感染的方法，包括区分接种疫苗的动物和受感染的动物的方法。还提供了检测样品中是否存在抗布鲁氏菌抗体的新方法。
• Synthesis of Some Analogs of the Methyl α-Glycoside of the Presumed Antigenic Determinant of the O-Specific Polysaccharide of<i>Vibrio cholerae</i>O:1, Serotype Ogawa
  作者：Jian Zhang、Pavol Kováč

  DOI：10.1080/07328309808002896

  日期：1998.4

  The following analogs of the title determinant, methyl 4,6-dideoxy-4-(3 -deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, have been prepared: methyl 3,4,6,-trideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(4-hydroxybutyramido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(3,4-dideoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(3-deoxy-D-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(2-deoxy-L-glycero-tetronamido)2-O-methyl-alpha-D-mannopyranoside, methyl 4-acetamido-4,6-dideoxy-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(3 -deoxy-L-glycero-tetronamido)-2-O-ethyl-alpha-D-mannopyranoside, and methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-propyl-alpha-D-mannopyranoside.