GlcNAc-LC-biotin | 1200232-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: GlcNAc-LC-biotin
• 英文别名: 1-(6-biotinamidohexanoylamino)-1-deoxy-2-acetamido-2-deoxy-β-D-glucopyranose
• CAS: 1200232-74-1
• 化学式: C₂₄H₄₁N₅O₈S
• 分子量: 559.684
• InChiKey: QJADCZONOFOTIQ-LAHBGAKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.55
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  198.35
• 氢给体数：
  8.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  CT-ox 、 GlcNAc-LC-biotin 在 EndoM-N₁₇₅A 作用下， 反应 8.0h， 以72%的产率得到CT-GlcNAc2-LC-biotin
  参考文献：
  名称：

  Chemoenzymatic Synthesis and Lectin Array Characterization of a Class of N-Glycan Clusters

  摘要：

  N-Glycans are major components of many glycoproteins. These sugar moieties are frequently involved in important physiological and disease processes via their interactions with a variety of glycan-binding proteins (GBP). Clustering effect is an important feature in many glycan-lectin interactions. We describe in this paper a chemoenzymatic synthesis of novel N-glycan clusters using a tandem endoglycosidase-catalyzed transglycosylation. It was found that the internal beta-1,2-linked GlcNAc moieties in the N-glycan core, once exposed in the nonreducing terminus, was able to serve as acceptors for transglycosylation catalyzed by Endo-A and EndoM-N175A. This efficient chemoenzymatic method allows a quick extension of the sugar chains to form a class of glycan clusters in which sugar residues are all connected by native glycosidic linkages found in natural N-glycans. In addition, a discriminative enzymatic reaction at the two GlcNAc residues could be fulfilled to afford novel hybrid clusters. Lectin microarray studies revealed unusual properties in glyco-epitope expression by this panel of structurally well-defined synthetic N-glycans. These new compounds are likely valuable for functional glycomics studies to unveil new functions of both glycans and carbohydrate-binding proteins.

  DOI：

  10.1021/ja9078539
• 作为产物：
  描述：

  2-乙酰氨基-1-氨基-1,2-二脱氧-beta-D-吡喃葡萄糖 、 生物素化-epsilon-氨基己酸-N-羟基丁二酰亚胺活化酯 以 二甲基亚砜 、 乙腈 为溶剂， 以17 mg的产率得到GlcNAc-LC-biotin
  参考文献：
  名称：

  Chemoenzymatic Synthesis and Lectin Array Characterization of a Class of N-Glycan Clusters

  摘要：

  N-Glycans are major components of many glycoproteins. These sugar moieties are frequently involved in important physiological and disease processes via their interactions with a variety of glycan-binding proteins (GBP). Clustering effect is an important feature in many glycan-lectin interactions. We describe in this paper a chemoenzymatic synthesis of novel N-glycan clusters using a tandem endoglycosidase-catalyzed transglycosylation. It was found that the internal beta-1,2-linked GlcNAc moieties in the N-glycan core, once exposed in the nonreducing terminus, was able to serve as acceptors for transglycosylation catalyzed by Endo-A and EndoM-N175A. This efficient chemoenzymatic method allows a quick extension of the sugar chains to form a class of glycan clusters in which sugar residues are all connected by native glycosidic linkages found in natural N-glycans. In addition, a discriminative enzymatic reaction at the two GlcNAc residues could be fulfilled to afford novel hybrid clusters. Lectin microarray studies revealed unusual properties in glyco-epitope expression by this panel of structurally well-defined synthetic N-glycans. These new compounds are likely valuable for functional glycomics studies to unveil new functions of both glycans and carbohydrate-binding proteins.

  DOI：

  10.1021/ja9078539