benzyl 2-acetamido-6-azido-2,6-dideoxy-3-O--α-D-glucopyranoside | 77268-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-6-azido-2,6-dideoxy-3-O--α-D-glucopyranoside
• 英文别名: methyl (2R)-2-[(2R,3R,4R,5R,6S)-5-acetamido-2-(azidomethyl)-3-hydroxy-6-phenylmethoxyoxan-4-yl]oxypropanoate
• CAS: 77268-46-3
• 化学式: C₁₉H₂₆N₄O₇
• 分子量: 422.438
• InChiKey: LUGJMKYBVPPHCX-CAOSTJHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-6-azido-2,6-dideoxy-3-O--α-D-glucopyranoside 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 benzyl 2-acetamido-4,6-diazido-2,4,6-trideoxy-3-O--α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of some carbohydrate analogs of N-acetylmuramoyl-l-alanyl-d-isoglutamine

  摘要：

  DOI：

  10.1016/s0008-6215(00)80688-6
• 作为产物：
  描述：

  benzyl 2-acetamido-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-α-D-glucopyranoside 在 吡啶 、 甲基磺酰氯 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到benzyl 2-acetamido-6-azido-2,6-dideoxy-3-O--α-D-glucopyranoside
  参考文献：
  名称：

  Membrane Association Dictates Ligand Specificity for the Innate Immune Receptor NOD2

  摘要：

  The human gut must regulate its immune response to resident and pathogenic bacteria, numbering in the trillions. The peptidoglycan component of the bacterial cell wall is a dense and rigid structure that consists of polymeric carbohydrates and highly cross-linked peptides which offers protection from the host and surrounding environment. Nucleotide-binding oligomerization domain-containing protein 2 (NOD2), a human membrane-associated innate immune receptor found in the gut epithelium and mutated in an estimated 30% of Crohn's disease patients, binds to peptidoglycan fragments and initiates an immune response. Using a combination of chemical synthesis, advanced analytical assays, and protein biochemistry, we tested the binding of a variety,of synthetic peptidoglycan fragments to wild-type (WT)-NOD2. Only when the protein was presented in the native membrane did binding measurements correlate with a NOD2-dependent nuclear factor kappa-light-chain-enhancer of activated B cells (NF-KB) response, supporting the hypothesis that the native-membrane environment confers ligand specificity to the NOD2 receptor for NF-KB signaling. While N-acetyl-muramyl dipeptide (MDP) has been thought to be the minimal peptidoglycan fragment necessary to activate a NOD2-dependent immune response, we found that fragments with and without the dipeptide moiety are capable of binding and activating, a NOD2-dependent NF-KB response, suggesting that the carbohydrate moiety of the peptidoglycan fragments is the minimal functional epitope. This work highlights the necessity of studying NOD2-ligand binding in systems that resemble the receptor's natural environment, as the cellular membrane and/or NOD2 interacting, partners appear to play a crucial role in ligand binding and in triggering an innate immune response.

  DOI：

  10.1021/acschembio.7b00469