2,3,4,6-tetra-O-(2-cyanoethyl)-β-D-glucopyranosyl azide | 1015044-93-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-(2-cyanoethyl)-β-D-glucopyranosyl azide
• 英文别名: 3-[[(2R,3R,4S,5R,6R)-6-azido-3,4,5-tris(2-cyanoethoxy)oxan-2-yl]methoxy]propanenitrile
• CAS: 1015044-93-5
• 化学式: C₁₈H₂₃N₇O₅
• 分子量: 417.425
• InChiKey: LEFCSVMHMJOWSH-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-(2-cyanoethyl)-β-D-glucopyranosyl azide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 3,3',3''-(((2R,3R,4S,5R,6R)-2-amino-6-((2-cyanoethoxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl)tris(oxy))tripropanenitrile
  参考文献：
  名称：

  Synthesis of a Streptococcus pyogenes vaccine candidate based on the M protein PL1 epitope

  摘要：

  Group A streptococcus is a Gram-positive bacteria that causes a range of infectious diseases. Targeting the bacteria, a new self-adjuvanting vaccine candidate, incorporating a carbohydrate carrier and an amino acid-based adjuvant, was synthesised utilising carbohydrate chemistry and solid-phase peptide synthesis procedures. Characterisation of the candidate was achieved using reverse-phase HPLC and electrospray ionisation mass spectrometry. The successful synthesis and characterisation of the vaccine candidate may contribute to the discovery of a therapeutically and clinically viable vaccine against group A streptococcus. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.013
• 作为产物：
  描述：

  D-glucopyranosyl azide 、 丙烯腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以66%的产率得到2,3,4,6-tetra-O-(2-cyanoethyl)-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Development of a Liposaccharide-Based Delivery System and Its Application to the Design of Group A Streptococcal Vaccines

  摘要：

  Group A streptococcus (GAS) is associated with many human diseases, ranging in severity from benign to life-threatening. A promising strategy for developing vaccines against GAS involves the use of carbohydrates as carriers for peptide antigens. This study describes the optimized synthesis of D-glucose and D-galactose derived carriers, bearing an adipate linker and four tert-butoxycarbonyl protected aminopropyl groups. Prophylactic GAS vaccine candidates were synthesized by conjugating multiple copies of a single GAS M protein derived peptide antigen (either J8 or J14) onto the carbohydrate carriers. These antigens contain peptide sequences, which are highly conserved and offer the potential to prevent infections caused by up to 70% of GAS strains. Lipophilic amino acids were also conjugated to the D-glucose anomeric carbon to produce a self-adjuvanting liposaccharide vaccine. High serum IgG antibody titers against each of the incorporated peptide epitopes were detected following subcutaneous immunization of B10.BR (H-2(k)) mice with the liposaccharide vaccine candidates.

  DOI：

  10.1021/jm701410p

文献信息

• Development of a Liposaccharide-Based Delivery System and Its Application to the Design of Group A Streptococcal Vaccines
  作者：Pavla Simerska、Abu-Baker M. Abdel-Aal、Yoshio Fujita、Peter M. Moyle、Ross P. McGeary、Michael R. Batzloff、Colleen Olive、Michael F. Good、Istvan Toth

  DOI：10.1021/jm701410p

  日期：2008.3.13

  Group A streptococcus (GAS) is associated with many human diseases, ranging in severity from benign to life-threatening. A promising strategy for developing vaccines against GAS involves the use of carbohydrates as carriers for peptide antigens. This study describes the optimized synthesis of D-glucose and D-galactose derived carriers, bearing an adipate linker and four tert-butoxycarbonyl protected aminopropyl groups. Prophylactic GAS vaccine candidates were synthesized by conjugating multiple copies of a single GAS M protein derived peptide antigen (either J8 or J14) onto the carbohydrate carriers. These antigens contain peptide sequences, which are highly conserved and offer the potential to prevent infections caused by up to 70% of GAS strains. Lipophilic amino acids were also conjugated to the D-glucose anomeric carbon to produce a self-adjuvanting liposaccharide vaccine. High serum IgG antibody titers against each of the incorporated peptide epitopes were detected following subcutaneous immunization of B10.BR (H-2(k)) mice with the liposaccharide vaccine candidates.
• Synthesis of a Streptococcus pyogenes vaccine candidate based on the M protein PL1 epitope
  作者：Pavla Simerska、Hao Lu、Istvan Toth

  DOI：10.1016/j.bmcl.2008.12.013

  日期：2009.2

  Group A streptococcus is a Gram-positive bacteria that causes a range of infectious diseases. Targeting the bacteria, a new self-adjuvanting vaccine candidate, incorporating a carbohydrate carrier and an amino acid-based adjuvant, was synthesised utilising carbohydrate chemistry and solid-phase peptide synthesis procedures. Characterisation of the candidate was achieved using reverse-phase HPLC and electrospray ionisation mass spectrometry. The successful synthesis and characterisation of the vaccine candidate may contribute to the discovery of a therapeutically and clinically viable vaccine against group A streptococcus. (C) 2008 Elsevier Ltd. All rights reserved.