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 | 214467-61-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: Bn(-3)[Bn(-4)][Bn(-6)]GlcNAc(b1-4)[Bn(-3)][Bn(-6)]GlcNAc(b)-N3；N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-2-azido-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 214467-61-5
• 化学式: C₅₁H₅₇N₅O₁₀
• 分子量: 900.041
• InChiKey: PHHZHLGKIMCLBV-MIPOLZBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  66.0
• 可旋转键数：
  22.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  180.8
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  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 在 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  大环肽抗生素酪氨酸A的N-糖基化衍生物的合成及抑菌活性

  摘要：

  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。

  DOI：

  10.1021/jm801577r
• 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 、 乙二胺 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 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

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 of a Glycosylated Peptide Thioester by the Boc Strategy and Its Application to Segment Condensation
  作者：Eiichiro HAGINOYA、Hironobu HOJO、Yuko NAKAHARA、Yoshiaki NAKAHARA、Kazuki NABESHIMA、Bryan P. TOOLE、Yasushi WATANABE

  DOI：10.1271/bbb.50621

  日期：2006.6.23

  The synthesis of a chitobiosylated peptide thioester by the t-butoxycarbonyl (Boc) strategy is demonstrated. Boc-Asn carrying benzyl-protected chitobiose was introduced during application of the Boc mode solid-phase method. HF treatment of the resulting protected peptide resin gave the desired chitobiosylated peptide thioester. This thioester was used to prepare the peptide sequence derived from extracellular matrix metalloproteinase inducers (emmprin) (34-94), (34-118) and (22-118) by the thioester segment condensation method. The conformation of these glycopeptides is characterized by circular dichroism (CD) spectral measurement.

  本文展示了通过叔丁氧羰基（Boc）策略合成壳寡糖化肽硫酯的过程。在应用 Boc 模式固相方法时，引入了携带苄基保护壳寡糖的 Boc-Asn。对得到的受保护肽树脂进行 HF 处理，可得到所需的壳寡糖化肽硫酯。利用这种硫酯通过硫酯段缩合法制备了源自细胞外基质金属蛋白酶诱导剂（emmprin）（34-94）、（34-118）和（22-118）的肽序列。这些糖肽的构象是通过圆二色性（CD）光谱测量确定的。