phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside | 1492048-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
• CAS: 1492048-38-0
• 化学式: C₆₆H₇₇Cl₃N₄O₂₆S
• 分子量: 1480.77
• InChiKey: SMOMLLODUKKTIR-ZESVHXHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  100.0
• 可旋转键数：
  30.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  377.65
• 氢给体数：
  3.0
• 氢受体数：
  28.0

反应信息

• 作为反应物：
  描述：

  O-[(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)]-(1→2)-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl) trichloroacetimidate 、 phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到phenyl {(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-[(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→6)-2-O-benzyl-β-D-mannopyranosyl]}-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A New Approach for the Synthesis of Hyperbranched N-Glycan Core Structures from Locust Bean Gum

  摘要：

  A novel protocol for the synthesis of general N-glycan core structures was established by means of Man beta(1 -> 4)Man peracetate derived from a naturally abundant locust bean gum as a key starting material. Phenyl (2-O-benzy1-4,6-O-benzylidine-beta-D-mannopyranosyl)-(1 -> 4)-3,6-di-O-benzyl-2-azido-2-deoxy-1-thio-beta-D-glucopyranoside facilitated the synthesis of key intermediates leading to hyperbranched N-glycan core structures.

  DOI：

  10.1021/ol403140h
• 作为产物：
  描述：

  phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidine-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside 在 水 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到phenyl [(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1→3)-2-O-benzyl-β-D-mannopyranosyl]-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A New Approach for the Synthesis of Hyperbranched N-Glycan Core Structures from Locust Bean Gum

  摘要：

  A novel protocol for the synthesis of general N-glycan core structures was established by means of Man beta(1 -> 4)Man peracetate derived from a naturally abundant locust bean gum as a key starting material. Phenyl (2-O-benzy1-4,6-O-benzylidine-beta-D-mannopyranosyl)-(1 -> 4)-3,6-di-O-benzyl-2-azido-2-deoxy-1-thio-beta-D-glucopyranoside facilitated the synthesis of key intermediates leading to hyperbranched N-glycan core structures.

  DOI：

  10.1021/ol403140h

文献信息

• Synthetic Glycopeptides Allow for the Quantitation of Scarce Nonfucosylated IgG Fc <i>N</i>-Glycans of Therapeutic Antibody
  作者：Kazuki Hammura、Akari Ishikawa、Ravi Kumar H. V.、Risho Miyoshi、Yasuhiro Yokoi、Masakazu Tanaka、Hiroshi Hinou、Shin-Ichiro Nishimura

  DOI：10.1021/acsmedchemlett.8b00127

  日期：2018.9.13

  IgGs remains elusive. The present study communicates that selected reaction monitoring (SRM)-based assay of tryptic IgG Fc glycopeptides is a promising approach for the characterization of antibodies when combined with structure-defined synthetic Fc peptides having a focused N-glycoform as a calibration standard. We describe a novel synthetic approach to the human IgG1 Fc peptide having a bisected decasaccharide

  连接至IgG Fc结构域的聚糖强烈影响生物学活性，例如治疗性抗体的抗体依赖性细胞毒性（ADCC）和补体依赖性细胞毒性（CDC）。然而，IgG的糖基依赖性功能调节的分子机制仍然难以捉摸。本研究表明，胰蛋白酶IgG Fc糖肽的基于反应监测（SRM）的选择测定是一种有潜力的表征抗体的方法，当与结构集中的合成Fc肽结合使用时，该Fc肽具有聚焦的N-糖型作为校准标准。我们描述了一种新的合成方法，将人IgG1 Fc肽分为两等分的十糖及其非等分的对应化合物，涉及具有罕见N的Fc结构域的抗体的签名-聚糖期望显示出比大量IgG N-聚糖高得多的ADCC / CDC ，并将其应用于基于SRM的定量糖蛋白组学中。关键中间体，苯基的使用（2- ø -苄基-4,6- ö -benzylidine-β- d -mannopyranosyl） - （1→4）-3,6-二- ø -苄基-2-叠氮基-2-刺槐豆胶半乳甘露聚糖衍生的-deoxy