(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6R)-6-Amino-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol | 160836-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6R)-6-Amino-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• 英文别名: Glc(a1-4)Glc(a1-4)b-Glc1N；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-amino-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 160836-61-3
• 化学式: C₁₈H₃₃NO₁₅
• 分子量: 503.458
• InChiKey: FAMLWIBGQOXKDJ-WUZXSGHDSA-N

物化性质

• 沸点：
  868.1±65.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -7.1
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  275
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6R)-6-Amino-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 哌啶 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Amino-N-{(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl}-acetamide
  参考文献：
  名称：

  Tight binding ligand approach to oligosaccharide-grafted protein

  摘要：

  A novel type of artificial glycoprotein was developed, by using dihydrofolate reductase (DHFR) and methotrexate (MTX) as a protein-ligand pair. Various oligosaccharides linked to MTX were shown to bind tightly with DHFR and afforded oligosaccharide-grafted protein, which could be isolated easily by lectin beads. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.106
• 作为产物：
  描述：

  maltotriose 在 碳酸氢铵 作用下， 生成 (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6R)-6-Amino-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Novel sequential solid-phase synthesis of N-linked glycopeptides from natural sources

  摘要：

  本报告展示了一种从天然来源固相合成 N-连接糖肽的实用且多功能的方法。该方法基于温和的肼解程序，以完整的未还原形式从天然糖蛋白（如胎盘素和核糖核酸酶 B）中释放出 N-连接寡糖，随后形成相应的糖基胺。用碳酸氢铵在水或二甲基亚砜（DMSO）中的饱和溶液处理还原糖 1-7，几乎可以得到定量的糖基胺 8-14。将未受保护的糖基胺 8-14 与侧链激活的天冬氨酸衍生物 Fmoc-Asp(ODhbt)-OBut 16 偶联，可得到 N-糖基化的天冬酰胺衍生物 17-23。随后通过三氟乙酸（TFA）处理对碳水化合物羟基进行乙酰化并裂解叔丁酯，可得到糖基化的 N-连接构筑模块 31-37。然后，将这些结构单元 31-37 加入小鼠血红蛋白衍生的十肽 Hb（67-76）VITAFNEGLK 的糖肽 T 细胞表位类似物 40-46 的多柱肽合成方案中。十肽序列 VITAFNEGLK 与 MHC II 类 Ek 分子结合良好，对 CBA/J 小鼠无免疫原性。本文介绍了在十肽 Hb（67-76）上进行几种天然和非天然糖基化，如 N-乙酰葡糖胺、N,N′-二乙酰壳寡糖、葡萄糖、麦芽三糖、麦芽庚糖以及二元和三元泛酰复合寡糖，从而得到 N-连接的糖肽 40-46。通过 1D- 和 2D-1H 和 13C NMR 光谱以及 ES-MS 对 N-连接的糖肽 40-46 进行了全面鉴定。

  DOI：

  10.1039/a705528e

文献信息

• <i>N</i> -Linked Glycosyl Auxiliary-Mediated Native Chemical Ligation on Aspartic Acid: Application towards <i>N</i> -Glycopeptide Synthesis
  作者：Hua Chai、Kim Le Mai Hoang、Minh Duy Vu、Kalyan Pasunooti、Chuan-Fa Liu、Xue-Wei Liu

  DOI：10.1002/anie.201605597

  日期：2016.8.22

  A practical approach towards N‐glycopeptide synthesis using an auxiliary‐mediated dual native chemical ligation (NCL) has been developed. The first NCL connects an N‐linked glycosyl auxiliary to the thioester side chain of an N‐terminal aspartate oligopeptide. This intermediate undergoes a second NCL with a C‐terminal thioester oligopeptide. Mild cleavage provides the desired N‐glycopeptide.

  已经开发了一种使用辅助介导的双重天然化学连接（NCL）合成N糖肽的实用方法。第一个NCL将N连接的糖基助剂连接到N末端天冬氨酸寡肽的硫酯侧链。该中间体经过第二次NCL和C末端的硫酯寡肽。轻度裂解可提供所需的N糖肽。
• An Efficient Synthetic Route to Glycoamino Acid Building Blocks for Glycopeptide Synthesis
  作者：Mallesham Bejugam、Sabine L. Flitsch

  DOI：10.1021/ol048342n

  日期：2004.10.1

  requires access to gram quantities of glycosylated amino acid building blocks. Hence, the efficiency of synthesis of such building blocks is of great importance. Here, we report a fast and highly efficient synthetic route to Fmoc-protected asparaginyl glycosides from unprotected sugars in three steps with high yields. The glycosylated amino acids were successfully incorporated into target glycopeptides

  [反应：见正文]化学糖肽合成需要获得克量的糖基化氨基酸构件。因此，这种结构单元的合成效率非常重要。在这里，我们报告了一种快速高效的合成路线，可分三步以高收率从未保护的糖中合成Fmoc保护的天冬酰胺基糖苷。通过标准的Fmoc固相肽合成，将糖基化的氨基酸成功地掺入靶糖肽7和8中。
• A Facile Synthesis of<i>N</i>^γ-Glycosyl Asparagine Conjugates and Short<i>N</i>-Linked Glycopeptides
  作者：Jie Xue、Min Guo、Guofeng Gu、Zhongwu Guo

  DOI：10.1080/07328303.2011.633723

  日期：2012.2

  Both free and protected glycosyl azides were efficiently coupled to the side chain of aspartate by the Staudinger reaction for the synthesis of N γ-glycosyl asparagine conjugates and short N-linked glycopeptides that can be employed to construct complex N-linked glycopeptides. In the process, a facile two-step protocol was developed for free glycosyl azide synthesis, which includes reported direct transformation

  游离和保护的糖基叠氮化物通过用于合成的施陶丁格反应中有效地耦合到天冬氨酸的侧链Ñ γ α-糖基天冬酰胺的共轭和短ñ -连接的可被采用来构建复杂的糖肽ñ -连接的糖肽。在此过程中，开发了一种用于游离糖基叠氮化物合成的简便的两步方案，该方法包括据报道通过与碳酸氢铵反应将游离寡糖直接转化为糖基胺，然后进行立体定向重氮转移反应将糖基胺转化为糖基叠氮化物。
• Ueda, Taichi; Tomita, Kazuyoshi; Notsu, Yoshihide, Journal of the American Chemical Society, 2009, vol. 131, p. 6237 - 6245
  作者：Ueda, Taichi、Tomita, Kazuyoshi、Notsu, Yoshihide、Ito, Takaomi、Fumoto, Masataka、et al.

  DOI：——

  日期：——
• Efficient Synthesis of Complex Glycopeptides Based on Unprotected Oligosaccharides
  作者：Jie Xue、Zhongwu Guo

  DOI：10.1021/jo020570c

  日期：2003.4.1

  N-Glycopeptides containing 1 to 4 trisaccharide chains, with the carbohydrates vicinal to each other in the multivalent glycopeptides, were efficiently synthesized by using the glycosylated Fmoc-asparagine as a key building block. While the couplings of amino acids with glycopeptides could be achieved in the homogeneous solutions in N-methylpyrrolidinone (NMP) to give excellent yields, all products were conveniently isolated from the reaction mixtures through a precipitation method by using the free carbohydrate chains as phase tags. Commercially available pentafluorophenyl (Pfp) esters of amino acids were employed for the glycopeptide elongation. Longer glycopeptides were constructed by means of a highly convergent synthetic design that is based on the coupling of glycopeptide/peptide fragments. Hydrogen bond interactions between free oligosaccharides were proposed to explain the exceptionally high efficiency of the couplings between two glycosylated building blocks.