O-(-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide | 214467-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• 英文别名: 2-[(2R,3R,4R,5S,6R)-2-azido-5-[(2S,3R,4R,5S,6R)-3-(1,3-dioxoisoindol-2-yl)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 214467-65-9
• 化学式: C₆₃H₅₇N₅O₁₂
• 分子量: 1076.17
• InChiKey: QKTWBHXWYIFIGD-SJWSMRJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.65
• 重原子数：
  80.0
• 可旋转键数：
  22.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  197.36
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  O-(-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 在 乙二胺 作用下， 生成 O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

  摘要：

  Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding glycosyl azides with trimethylsilyl azide in the presence of methyl triflate. The beta-mannosidic linkage was created by C-2 epimerization of the initially introduced beta-D-gluco-unit via oxidation followed by stereoselective reduction with tetrabutylammonium borohydride. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01540-8
• 作为产物：
  描述：

  ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 O-(-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

  摘要：

  Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding glycosyl azides with trimethylsilyl azide in the presence of methyl triflate. The beta-mannosidic linkage was created by C-2 epimerization of the initially introduced beta-D-gluco-unit via oxidation followed by stereoselective reduction with tetrabutylammonium borohydride. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01540-8

文献信息

• Synthesis and CD structural studies of CD52 peptides and glycopeptides
  作者：Benjamin M. Swarts、Yu-Cheng Chang、Honggang Hu、Zhongwu Guo

  DOI：10.1016/j.carres.2008.08.024

  日期：2008.11

  peptides and glycopeptides of the CD52 antigen are described. Solid phase peptide synthesis was employed in the construction of the target compounds from Fmoc-protected commercial amino acids and synthetic glycan-asparagine conjugates. Circular dichroism studies of the synthetic targets showed that they exist as random coils in solution, and no significant change in secondary structure was observed

  描述了CD52抗原的五个天然和N末端乙酰化肽和糖肽的合成。固相肽合成用于由Fmoc保护的商业氨基酸和合成的聚糖-天冬酰胺偶联物构建目标化合物。合成目标物的圆二色性研究表明，它们以无规卷曲形式存在于溶液中，当CD52肽在N端被乙酰化或在Asn（3）残基处被二糖糖基化时，二级结构没有观察到显着变化。或含岩藻糖的支链三糖。
• Synthesis and Antibacterial Activities of <i>N</i>-Glycosylated Derivatives of Tyrocidine A, a Macrocyclic Peptide Antibiotic
  作者：Honggang Hu、Jie Xue、Benjamin M. Swarts、Qianli Wang、Qiuye Wu、Zhongwu Guo

  DOI：10.1021/jm801577r

  日期：2009.4.9

  method for macrocyclic glycopeptide synthesis was developed and utilized to synthesize tyrocidine A and its glycosylated derivatives. The method is based on solid-phase peptide synthesis using 2-chlorotrityl resin as the solid-phase support and glycosyl amino acids as building blocks. After glycopeptides with fully protected glycans and side chains were released from the acid-labile resin, their C- and

  开发了一种有效且实用的大环糖肽合成方法，并将其用于合成酪氨酸A及其糖基化衍生物。该方法基于固相肽合成，其中2-氯三苯甲基树脂为固相载体，糖基氨基酸为结构单元。从酸不稳定的树脂中释放出具有完全保护的聚糖和侧链的糖肽后，它们的C-和N-末端在溶液中分子内偶联，以定量产率提供环状糖肽。该合成方法通常应适用于各种大环糖肽。合成酪氨酸A衍生物的生物学研究表明，将聚糖直接连接到酪氨酸A的Asn残基上可减少其抗菌活性，但通过简单的间隔子将聚糖连接到Asn却没有。这些结果揭示了聚糖对糖肽抗生素的活性，可能还有其结构的重要影响。