3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-β-D-glucopyranosyl-1’,1’,1’-trichloroacetimidate | 218961-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-β-D-glucopyranosyl-1’,1’,1’-trichloroacetimidate
• 英文别名: 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-D-glucopyranoside-trichloroacetimidate
• CAS: 218961-09-2
• 化学式: C₃₀H₂₅Cl₃N₂O₇
• 分子量: 631.897
• InChiKey: QJBJRRYXJDTITH-QZHDEGIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  42.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  107.38
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-β-D-glucopyranosyl-1’,1’,1’-trichloroacetimidate 在 盐酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.83h， 生成 phenyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalamido-β-D-glucopyranosyl-(1-4)-3,6-di-O-benzyl-2-deoxy-2-N-phthalamido-β-D-glucopyranoside
  参考文献：
  名称：

  ‘Naked’ and Hydrated Conformers of the Conserved Core Pentasaccharide of N-linked Glycoproteins and Its Building Blocks

  摘要：

  N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man(3)GlcNAc(2)- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-beta-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-alpha-1,3- and Man-alpha-1,6- branching units. Solvation stiffens the 'rod' but leaves the distal residues flexible, through a beta-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomolecular assemblies.

  DOI：

  10.1021/ja4056678
• 作为产物：
  描述：

  乙基3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 88.42h， 生成 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-β-D-glucopyranosyl-1’,1’,1’-trichloroacetimidate
  参考文献：
  名称：

  ‘Naked’ and Hydrated Conformers of the Conserved Core Pentasaccharide of N-linked Glycoproteins and Its Building Blocks

  摘要：

  N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man(3)GlcNAc(2)- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-beta-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-alpha-1,3- and Man-alpha-1,6- branching units. Solvation stiffens the 'rod' but leaves the distal residues flexible, through a beta-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomolecular assemblies.

  DOI：

  10.1021/ja4056678

文献信息

• [EN] NOVEL INTERMEDIATES FOR THE PREPARATION OF GBS POLYSACCHARIDE ANTIGENS<br/>[FR] NOUVEAUX INTERMÉDIAIRES POUR LA PRÉPARATION D'ANTIGÈNES DE POLYSACCHARIDE GBS
  申请人：GLAXOSMITHKLINE BIOLOGICALS SA

  公开号：WO2019012476A1

  公开（公告）日：2019-01-17

  The present invention generally refers to novel intermediate polysaccharide units, useful for the preparation of polysaccharide antigen of GBS Ia, Ib and III; the invention also refers to a process for their preparation and their use as intermediate for the preparation of conjugated derivatives useful in vaccines.

  本发明通常涉及新型中间聚糖单元，用于制备GBS Ia、Ib和III的多糖抗原；该发明还涉及一种用于其制备的过程以及它们作为用于疫苗中有用的共轭衍生物制备的中间体的用途。
• Regioselective Glycosylation Strategies for the Synthesis of Group Ia and Ib <i>Streptococcus</i> Related Glycans Enable Elucidating Unique Conformations of the Capsular Polysaccharides
  作者：Linda Del Bino、Ilaria Calloni、Davide Oldrini、Maria Michelina Raso、Rossella Cuffaro、Ana Ardá、Jeroen D. C. Codée、Jesús Jiménez‐Barbero、Roberto Adamo

  DOI：10.1002/chem.201903527

  日期：2019.12.18

  polysaccharides share high structural similarity. Both are composed of the same monosaccharide residues and differ only in the connection of the Neu5Acα2-3Gal side chain to the GlcNAc unit, which is a β1-4 linkage in serotype Ia and a β1-3 linkage in serotype Ib. The development of efficient regioselective routes for GlcNAcβ1-3[Glcβ1-4]Gal synthons is described, which give access to different group B Streptococcus

  B 组链球菌血清型 Ia 和 Ib 荚膜多糖是疫苗开发的关键目标。尽管它们具有免疫特异性，但这些多糖具有高度的结构相似性。两者均由相同的单糖残基组成，不同之处仅在于 Neu5Acα2-3Gal 侧链与 GlcNAc 单元的连接，在血清型 Ia 中为 β1-4 连接，在血清型 Ib 中为 β1-3 连接。描述了 GlcNAcβ1-3[Glcβ1-4]Gal 合成子的有效区域选择性途径的开发，该途径提供了不同 B 族链球菌 (GBS) Ia 和 Ib 重复单元移码的途径。这些聚糖用于探测两种多糖的构象和分子动力学，突出显示突出的 Neu5Acα2-3Gal 部分在多糖主链上的不同呈现方式，以及 Ib 聚合物相对于 Ia 具有更高的灵活性，这可能会影响表位暴露。
• Synthesis and Biological Evaluation of a Chitobiose-Based Peptide <i>N</i>-Glycanase Inhibitor Library
  作者：Martin D. Witte、Danielle Horst、Emmanuel J. H. J. Wiertz、Gijsbert A. van der Marel、Herman S. Overkleeft

  DOI：10.1021/jo801906s

  日期：2009.1.16

  Peptide N-glycanase (PNGase), the enzyme responsible for the deglycosylation of N-linked glycoproteins, has an active site related to that of cysteine proteases. Chitiobiose was equipped with electrophilic traps often used in cysteine protease inhibitors, and the resulting compounds were evaluated as PNGase inhibitors. We found that the electrophilic trap of the inhibitor has a great influence on the potency of the compounds with the chloromethyl ketone inhibitor being the first potent C-glycoside-based PNGase inhibitor.