2-aminoethyl β-D-mannopyranosyl-(1→2)-β-D-mannopyranosyl-(1→2)-α-D-mannopyranoside | 1583320-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-aminoethyl β-D-mannopyranosyl-(1→2)-β-D-mannopyranosyl-(1→2)-α-D-mannopyranoside
• 英文别名: beta-D-Manp-(1->2)-beta-D-Manp-(1->2)-alpha-D-Manp-O[CH2]2NH2；(2S,3S,4S,5S,6R)-2-[(2S,3S,4S,5S,6R)-2-[(2S,3S,4S,5S,6R)-2-(2-aminoethoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1583320-54-0
• 化学式: C₂₀H₃₇NO₁₆
• 分子量: 547.511
• InChiKey: BWBSAHNMKJGTFW-LLDPRYFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  284
• 氢给体数：
  11
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  方酸二正丁酯 、 2-aminoethyl β-D-mannopyranosyl-(1→2)-β-D-mannopyranosyl-(1→2)-α-D-mannopyranoside 以 甲醇 为溶剂， 反应 1.0h， 以81%的产率得到2-(2-butoxycyclobutene-3,4-dione-1-ylamino)ethyl-β-D-mannopyranosyl-(1→2)-β-D-mannopyranosyl-(1→2)-α-D-mannopyranoside
  参考文献：
  名称：

  Oligosaccharides and Peptide Displayed on an Amphiphilic Polymer Enable Solid Phase Assay of Hapten Specific Antibodies

  摘要：

  Copovidone, a copolymer of vinyl acetate and N-vinyl-2-pyrrolidone, was synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization, and after deacetylation the polymer was functionalized by introduction of amino, azide, and alkyne pendant groups to allow attachment of glycans and peptide. Candida albicans beta-mannan trisaccharides 1 and 2 and M. tuberculosis arabinan hexasaccharide 3 with appropriate tethers were conjugated to the polymers by squarate or click chemistry. C. albicans T-cell peptide 4 bearing a C-terminal epsilon-azidolysine was also conjugated to copovidone by click chemistry. The resulting conjugates provide convenient non-protein-based antigens that are readily adsorbed on ELISA plates, and display excellent characteristics for assay of antibody binding to the haptenic group of interest. Copovidone and BSA glycoconjugates exhibited similar adsorption characteristics when used to coat ELISA plates, and both conjugates were optimal when used as coating solutions at low nanogram/mL concentrations. Provided that the copovidone conjugated glycan is stable to acid, assay plates can be easily processed for reuse at least three times without detectable variation or degradation in ELISA readout.

  DOI：

  10.1021/bc400486w
• 作为产物：
  描述：

  2-azidoethyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1→2)-3-O-benzyl-4,6-O-benzylidene-(1→2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 在 palladium 10% on activated carbon 、 氢气 、 palladium hydroxide 10 wt. % on activated carbon 作用下， 以 甲苯 、 水 、 溶剂黄146 为溶剂， 反应 0.5h， 以69%的产率得到2-aminoethyl β-D-mannopyranosyl-(1→2)-β-D-mannopyranosyl-(1→2)-α-D-mannopyranoside
  参考文献：
  名称：

  Oligosaccharides and Peptide Displayed on an Amphiphilic Polymer Enable Solid Phase Assay of Hapten Specific Antibodies

  摘要：

  Copovidone, a copolymer of vinyl acetate and N-vinyl-2-pyrrolidone, was synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization, and after deacetylation the polymer was functionalized by introduction of amino, azide, and alkyne pendant groups to allow attachment of glycans and peptide. Candida albicans beta-mannan trisaccharides 1 and 2 and M. tuberculosis arabinan hexasaccharide 3 with appropriate tethers were conjugated to the polymers by squarate or click chemistry. C. albicans T-cell peptide 4 bearing a C-terminal epsilon-azidolysine was also conjugated to copovidone by click chemistry. The resulting conjugates provide convenient non-protein-based antigens that are readily adsorbed on ELISA plates, and display excellent characteristics for assay of antibody binding to the haptenic group of interest. Copovidone and BSA glycoconjugates exhibited similar adsorption characteristics when used to coat ELISA plates, and both conjugates were optimal when used as coating solutions at low nanogram/mL concentrations. Provided that the copovidone conjugated glycan is stable to acid, assay plates can be easily processed for reuse at least three times without detectable variation or degradation in ELISA readout.

  DOI：

  10.1021/bc400486w

文献信息

• Synthesis of antifungal vaccines by conjugation of β-1,2 trimannosides with T-cell peptides and covalent anchoring of neoglycopeptide to tetanus toxoid
  作者：Jonathan Cartmell、Eugenia Paszkiewicz、Sebastian Dziadek、Pui-Hang Tam、Thanh Luu、Susmita Sarkar、Tomasz Lipinski、David R. Bundle

  DOI：10.1016/j.carres.2014.06.024

  日期：2015.2

  Selective strategies for the construction of novel three component glycoconjugate vaccines presenting Candida albicans cell wall glycan (beta-1,2 mannoside) and polypeptide fragments on a tetanus toxoid carrier are described. The first of two conjugation strategies employed peptides bearing an N-terminal thiopropionyl residue for conjugation to a trisaccharide equipped with an acrylate linker and a C- terminal S-acetyl thioglycolyl moiety for subsequent linking of neoglycopeptide to bromoacetylated tetanus toxoid. Michael addition of acrylate trisaccharides to peptide thiol under mildly basic conditions gave a mixture of N- and C-terminal glyco-peptide thioethers. An adaptation of this strategy coordinated S-acyl protection with anticipated thioester exchange equilibria. This furnished a single chemically defined fully synthetic neoglycopeptide conjugate that could be anchored to a tetanus toxoid carrier and avoids the introduction of exogenous antigenic groups. The second strategy retained the N-terminal thiopropionyl residue but replaced the C-terminal S-acetate functionality with an azido group that allowed efficient, selective formation of neoglycopeptide thioethers and subsequent conjugation of these with propargylated tetanus toxoid, but introduced potentially antigenic triazole linkages. (C) 2014 Elsevier Ltd. All rights reserved.
• Oligosaccharides and Peptide Displayed on an Amphiphilic Polymer Enable Solid Phase Assay of Hapten Specific Antibodies
  作者：David R. Bundle、Pui-Hang Tam、Huu-Anh Tran、Eugenia Paszkiewicz、Jonathan Cartmell、Joanna M. Sadowska、Susmita Sarkar、Maju Joe、Pavel I. Kitov

  DOI：10.1021/bc400486w

  日期：2014.4.16

  Copovidone, a copolymer of vinyl acetate and N-vinyl-2-pyrrolidone, was synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization, and after deacetylation the polymer was functionalized by introduction of amino, azide, and alkyne pendant groups to allow attachment of glycans and peptide. Candida albicans beta-mannan trisaccharides 1 and 2 and M. tuberculosis arabinan hexasaccharide 3 with appropriate tethers were conjugated to the polymers by squarate or click chemistry. C. albicans T-cell peptide 4 bearing a C-terminal epsilon-azidolysine was also conjugated to copovidone by click chemistry. The resulting conjugates provide convenient non-protein-based antigens that are readily adsorbed on ELISA plates, and display excellent characteristics for assay of antibody binding to the haptenic group of interest. Copovidone and BSA glycoconjugates exhibited similar adsorption characteristics when used to coat ELISA plates, and both conjugates were optimal when used as coating solutions at low nanogram/mL concentrations. Provided that the copovidone conjugated glycan is stable to acid, assay plates can be easily processed for reuse at least three times without detectable variation or degradation in ELISA readout.