2-aminoethyl 2-acetamido-2-deoxy-α-D-mannopyranoside | 497096-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl 2-acetamido-2-deoxy-α-D-mannopyranoside
• 英文别名: N-[(2S,3S,4R,5S,6R)-2-(2-aminoethoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 497096-00-1
• 化学式: C₁₀H₂₀N₂O₆
• 分子量: 264.279
• InChiKey: QCTRCKYGWQLWGS-ZOZBQHSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  134
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-hydroxysuccinimidyl hexa-4,6-dienoate 、 2-aminoethyl 2-acetamido-2-deoxy-α-D-mannopyranoside 以 甲醇 为溶剂， 反应 0.17h， 生成 (E)-Hepta-4,6-dienoic acid [2-((2S,3S,4R,5S,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-amide
  参考文献：
  名称：

  Towards a Synthetic Glycoconjugate Vaccine Against Neisseria meningitidis A

  摘要：

  Albumin conjugates of synthetic fragments of the capsular polysaccharide of the Gram-negative bacterium Neisseria meningitidis serogroup A were prepared. The fragments include monosaccharides 1 [alpha-D-ManpNAc(1--> 0)-(CH2)(2)NH2] and 2 [6-O-P(O)-(O-)(2)-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2] ,disaccharide 3 [alpha-D-ManpNAc[1-->O-P(O)(O-) --> 6]-alpha-D-ManpNAc(1 --> O)-(CH2)(2)NH2], and trisaccharide 4 [alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2]. Two monosaccharide blocks were employed as key intermediates. The reduc-ing-end mannose unit featured the NHAc group at C-2, and contained the aminoethyl spacer as the aglycon for the final bioconjugation. The interresidual phosphodiester linkages were fashioned from an anomerically positioned H-phosphonate group in a 2-azido-man-nose building block. The spacer-linked saccharides 1-4 were N-acylated with hepta-4,6-dienoic acid and the resulting conjugated diene-equipped saccharides were subjected to Diels-Alder-type addition with maleimidobutyryl-group functionalized human serum albumin to form covalent conjugates containing up to 26 saccharide haptens per albumin molecule. Complete H-1, C-13, and P-31 NMR assignments for 1-4 are given. Antigenicity of the neoglycoconjugates containing 1-4 was demonstrated by a double immunodiffusion assay which indicated that a fragment as small as a monosaccharide is recognized by a polyclonal meningococcus group A antiserum and that the O-acetyl group(s) present in the natural capsular material is not essential for antigenicity.

  DOI：

  10.1002/1521-3765(20021004)8:19<4424::aid-chem4424>3.0.co;2-1
• 作为产物：
  描述：

  6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranose 在 10percent Pd/C sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 nickel dichloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 23.0 ℃ 、1.38 MPa 条件下， 反应 129.0h， 生成 2-aminoethyl 2-acetamido-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Towards a Synthetic Glycoconjugate Vaccine Against Neisseria meningitidis A

  摘要：

  Albumin conjugates of synthetic fragments of the capsular polysaccharide of the Gram-negative bacterium Neisseria meningitidis serogroup A were prepared. The fragments include monosaccharides 1 [alpha-D-ManpNAc(1--> 0)-(CH2)(2)NH2] and 2 [6-O-P(O)-(O-)(2)-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2] ,disaccharide 3 [alpha-D-ManpNAc[1-->O-P(O)(O-) --> 6]-alpha-D-ManpNAc(1 --> O)-(CH2)(2)NH2], and trisaccharide 4 [alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2]. Two monosaccharide blocks were employed as key intermediates. The reduc-ing-end mannose unit featured the NHAc group at C-2, and contained the aminoethyl spacer as the aglycon for the final bioconjugation. The interresidual phosphodiester linkages were fashioned from an anomerically positioned H-phosphonate group in a 2-azido-man-nose building block. The spacer-linked saccharides 1-4 were N-acylated with hepta-4,6-dienoic acid and the resulting conjugated diene-equipped saccharides were subjected to Diels-Alder-type addition with maleimidobutyryl-group functionalized human serum albumin to form covalent conjugates containing up to 26 saccharide haptens per albumin molecule. Complete H-1, C-13, and P-31 NMR assignments for 1-4 are given. Antigenicity of the neoglycoconjugates containing 1-4 was demonstrated by a double immunodiffusion assay which indicated that a fragment as small as a monosaccharide is recognized by a polyclonal meningococcus group A antiserum and that the O-acetyl group(s) present in the natural capsular material is not essential for antigenicity.

  DOI：

  10.1002/1521-3765(20021004)8:19<4424::aid-chem4424>3.0.co;2-1

文献信息

• HIGH AFFINITY SIGLEC LIGANDS
  申请人：Paulson, James

  公开号：EP1951740A2

  公开（公告）日：2008-08-06
• High Affinity Siglec Ligands
  申请人：Paulson James

  公开号：US20090238837A1

  公开（公告）日：2009-09-24

  The invention relates to high affinity Siglec ligands that are useful for isolating cells that express Siglecs and for delivering agents to cells that express Siglecs. In one embodiment, the invention provides a method for treating cancer in a mammal that involves administering a Siglec ligand of the invention to the mammal, where the Siglec ligand is linked to a therapeutic agent.
• US8357671B2
  申请人：——

  公开号：US8357671B2

  公开（公告）日：2013-01-22
• [EN] MICROARRAYS FOR ANALYTE DETECTION<br/>[FR] JEUX ORDONNES DE MICROECHANTILLONS POUR LA DETECTION D'ANALYTES
  申请人：SWISS FED INST OF TECHNOLOGY

  公开号：WO2006055925A2

  公开（公告）日：2006-05-26

  [EN] On embodiment of the present invention describes the use of microarrays to investigate the carbohydrate binding specificities of bacteria, to detect pathogens, and to screen anti-adhesion therapeutics is reported. This system is ideal for whole cell applications because microarrays present carbohydrate ligands in a manner that mimics interactions at cell-cell interfaces. Other advantages include assay miniaturization, since minimal amounts (e.g., on the order of picomoles) of a ligand (i.e., a biological recognition element) are required to observe binding, and high-throughput, since thousands of compounds can be placed on an array and analyzed in parallel. Pathogen detection experiments can be completed in complex mixtures of cells or protein using the known carbohydrate binding epitopes of the pathogens in question. The non-destructive nature of the arrays allows the pathogen to be harvested and tested for antibacterial susceptibility. These investigations allow microarray-based screening of biological samples for contaminants and combinatorial libraries for anti-adhesion therapeutics.
  [FR] Un mode de réalisation de la présente invention décrit l'utilisation de jeux ordonnés de microéchantillons afin d'étudier les spécificités de liaison de bactéries aux glucides, de détecter des pathogènes et de cribler les traitements anti-adhésion. Ce système est idéal pour des applications de cellules entières parce que les jeux ordonnés de microéchantillons présentent des ligands aux glucides de façon à imiter les interactions au niveau des interfaces cellule-cellule. D'autres avantages comprennent la miniaturisation d'analyse, étant donné que des quantités minimales (par exemple, de l'ordre des picomoles) d'un ligand (c'est-à-dire, un élément de reconnaissance biologique) sont nécessaires pour observer la liaison et un haut rendement, étant donné que des milliers de composés peuvent être placés sur un réseau et analysés en parallèle. Des expériences de détection de pathogènes peuvent être réalisées dans des mélanges complexes de cellules ou de protéines au moyen d'épitopes connus de liaison des pathogènes en question aux glucides. La nature non destructive des jeux ordonnés permet de moissonner le pathogène et de tester sa sensibilité antibactérienne. Ces recherches permettent de réaliser un criblage d'échantillons biologiques basé sur des jeux ordonnés de microéchantillons afin de rechercher des contaminants et des bibliothèques combinatoires et d'effectuer un traitement anti-adhésion.
• [EN] HIGH AFFINITY SIGLEC LIGANDS<br/>[FR] LIGANDS DE SIGLEC A HAUTE AFFINITE
  申请人：PAULSON JAMES

  公开号：WO2007056525A2

  公开（公告）日：2007-05-18

  [EN] The invention relates to high affinity Siglec ligands that are useful for isolating cells that express Siglecs and for delivering agents to cells that express Siglecs. In one embodiment, the invention provides a method for treating cancer in a mammal that involves administering a Siglec ligand of the invention to the mammal, where the Siglec ligand is linked to a therapeutic agent.
  [FR] L'invention concerne des ligands de Siglec à haute affinité qui sont utiles pour isoler des cellules exprimant des Siglec et pour administrer des agents sur des cellules exprimant des Siglec. Dans un mode de réalisation, l'invention concerne un procédé de traitement du cancer chez un mammifère, lequel implique l'administration d'un ligand de Siglec selon l'invention au mammifère, le ligand de Siglec étant lié à un agent thérapeutique.