O-{O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→2)-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→6)]-3,4-di-O-acetyl-α-D-mannopyranosyl}-trichloroacetamide | 1492048-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-{O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→2)-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→6)]-3,4-di-O-acetyl-α-D-mannopyranosyl}-trichloroacetamide
• 英文别名: TrocNH(-2d)Glc3Ac4Ac6Ac(b1-2)[TrocNH(-2d)Glc3Ac4Ac6Ac(b1-6)]Man3Ac4Ac(a)-O-C(NH)CCl3；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-[[(2R,3R,4S,5S,6R)-3,4-diacetyloxy-5-[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 1492048-31-3
• 化学式: C₄₂H₅₂Cl₉N₃O₂₆
• 分子量: 1333.96
• InChiKey: ZHJQULAQICUIQO-REBFJNCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  80
• 可旋转键数：
  31
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  366
• 氢给体数：
  3
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  O-{O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→2)-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→6)]-3,4-di-O-acetyl-α-D-mannopyranosyl}-trichloroacetamide 、 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 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以78%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-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→6)]-(3,4-di-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 {O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→2)-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→6)]}-3,4-O-(2',3'-dimethoxybutane-2’,3’-diyl)-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 17.67h， 生成 O-{O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→2)-O-[(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1→6)]-3,4-di-O-acetyl-α-D-mannopyranosyl}-trichloroacetamide
  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 as a designated standard in focused glycoproteomics to discover serum cancer biomarkers
  作者：K. V. Yogesh、Toshiya Kamiyama、Chikara Ohyama、Tohru Yoneyama、Kazuhiro Nouso、Satoshi Kimura、Hiroshi Hinou、Shin-Ichiro Nishimura

  DOI：10.1039/c8md00162f

  日期：——

  N-glycan structures that may be generated by direct tryptic digestion of serum glycoproteins. A preliminary selected reaction monitoring (SRM) assay using the synthetic model glycopeptide 1, 40Ser-Val-Gln-Glu-Ile-Gln-Ala-Thr-Phe-Phe-Tyr-Phe-Thr-Pro-Asn-Lys-Thr-Glu-Asp-Thr-Ile-Phe-Leu-Arg63 having an asialo tri-antennary N-glycan at the Asn54 residue as a designated calibration standard allowed for the

  先前对3500多种人体血清样品进行大规模糖组学研究表明，癌症患者的血清糖蛋白通常具有更多的显性和特异性糖型，即分支的三天线和四天线N聚糖，大多数癌症患者群体都比正常人多。对照组。我们在本文中建立了具有高度复杂的N-聚糖结构的糖肽的有效合成方案，其可以通过对血清糖蛋白的直接胰蛋白酶消化来产生。初步选择的反应使用合成模型糖肽监测（SRM）试验1，40丝氨酸-VAL-GLN-谷氨酸-ILE-GLN-ALA-THR-PHE-PHE-酪氨酸-苯丙氨酸-苏氨酸-脯氨酸-天冬酰胺-赖氨酸-苏氨酸-Glu-Asp-Thr-Ile-Phe-Leu-Arg 63在Asn54残基上具有去唾液酸三触角N-聚糖作为指定的校准标准，可以快速，绝对地定量源自血清α1-酸糖蛋白的胰蛋白酶消化片段，该片段携带着癌症患者和健康对照的N型糖蛋白。在200至1600 fmoleμL -1之间的范围内，目标糖蛋白没有任何富集过程。