6-(2,3,4,6-tetra-O-(2-cyanoethyl)-β-D-glucopyranosylamino)-6-oxohexanoic acid benzyl ester | 1015045-05-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-(2,3,4,6-tetra-O-(2-cyanoethyl)-β-D-glucopyranosylamino)-6-oxohexanoic acid benzyl ester
• 英文别名: 6-(2,3,4,6-tetra-O-(2-cyanoethyl)-β-D-glucopyranosylamino)-oxohexanoic acid benzyl ester；benzyl 6-oxo-6-[[(2R,3R,4S,5R,6R)-3,4,5-tris(2-cyanoethoxy)-6-(2-cyanoethoxymethyl)oxan-2-yl]amino]hexanoate
• CAS: 1015045-05-2
• 化学式: C₃₁H₃₉N₅O₈
• 分子量: 609.679
• InChiKey: FMCBMNOOLYXABL-KLBVUYHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  44
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  197
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-(2,3,4,6-tetra-O-(2-cyanoethyl)-β-D-glucopyranosylamino)-6-oxohexanoic acid benzyl ester 、 二碳酸二叔丁酯 在 sodium tetrahydroborate 、 cobalt(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 6-(2,3,4,6-tetra-O-[3-(butoxycarbonylamino)propyl]-β-D-glucopyranosylamino)-oxohexanoic acid benzyl ester
  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：

  3,3',3''-(((2R,3R,4S,5R,6R)-2-amino-6-((2-cyanoethoxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl)tris(oxy))tripropanenitrile 、 己二酸单苄酯 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以1.51 g的产率得到6-(2,3,4,6-tetra-O-(2-cyanoethyl)-β-D-glucopyranosylamino)-6-oxohexanoic acid benzyl ester
  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

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.