3-(5-dimethylaminonaphthalen-1-ylsulfonylamino)propyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside | 876857-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(5-dimethylaminonaphthalen-1-ylsulfonylamino)propyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-[3-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]propoxy]-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 876857-64-6
• 化学式: C₂₉H₄₃N₃O₁₃S
• 分子量: 673.739
• InChiKey: OAULJUMYWIDQFB-KDLURPGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  245
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  3-(5-dimethylaminonaphthalen-1-ylsulfonylamino)propyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside 、 GDP-fucose 在 manganese(ll) chloride calf intestine alkaline phosphatase 、 fucosyltransferase III 、 Na-cacodylate buffer 作用下， 以 水 为溶剂， 以88%的产率得到3-(5-dimethylaminonaphthalen-1-ylsulfonylamino)propyl β-D-galactopyranosyl-(1->3)-[α-L-fucopyranosyl-(1->4)]-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic Potential of Fucosyltransferase III for the Synthesis of Fluorescent‐labeled Milk Oligosaccharides

  摘要：

  Various fundamental biologic roles of milk oligosaccharides have been recognized; however, their structure-affinity relationship is still not fully revealed. Herein, we describe the synthesis of the fluorescent-labeled milk oligosaccharides 3-(5-dimethylaminonaphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-2-acetamido-2-deoxy-beta-D-glucopyranoside (1) and 3-(5-dimethylamino-naphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-beta-D-glucopyranoside (2) as useful tools for synthetic, analytic, and biologic applications. For the fucosylation of lactose and lacto- N -biose, the chemical and the enzymatic syntheses using fucosyltransferase III were compared.

  DOI：

  10.1080/07328300500341965
• 作为产物：
  描述：

  β-D-葡萄糖胺五乙酸酯 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.17h， 生成 3-(5-dimethylaminonaphthalen-1-ylsulfonylamino)propyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic Potential of Fucosyltransferase III for the Synthesis of Fluorescent‐labeled Milk Oligosaccharides

  摘要：

  Various fundamental biologic roles of milk oligosaccharides have been recognized; however, their structure-affinity relationship is still not fully revealed. Herein, we describe the synthesis of the fluorescent-labeled milk oligosaccharides 3-(5-dimethylaminonaphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-2-acetamido-2-deoxy-beta-D-glucopyranoside (1) and 3-(5-dimethylamino-naphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-beta-D-glucopyranoside (2) as useful tools for synthetic, analytic, and biologic applications. For the fucosylation of lactose and lacto- N -biose, the chemical and the enzymatic syntheses using fucosyltransferase III were compared.

  DOI：

  10.1080/07328300500341965

文献信息

• Synthetic Potential of Fucosyltransferase III for the Synthesis of Fluorescent‐labeled Milk Oligosaccharides
  作者：Said Rabbani、Federica Compostella、Laura Franchini、Beatrice Wagner、Luigi Panza、Beat Ernst

  DOI：10.1080/07328300500341965

  日期：2005.11.1

  Various fundamental biologic roles of milk oligosaccharides have been recognized; however, their structure-affinity relationship is still not fully revealed. Herein, we describe the synthesis of the fluorescent-labeled milk oligosaccharides 3-(5-dimethylaminonaphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-2-acetamido-2-deoxy-beta-D-glucopyranoside (1) and 3-(5-dimethylamino-naphthalene-1-sulfonylamino)propyl beta-D-galactopyranosyl-(1 -> 3)-[alpha-L-fucopyranosyl-(1 -> 4)]-beta-D-glucopyranoside (2) as useful tools for synthetic, analytic, and biologic applications. For the fucosylation of lactose and lacto- N -biose, the chemical and the enzymatic syntheses using fucosyltransferase III were compared.