3-(benzyloxycarbonylamino)propyl 2-acetylamino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside | 876905-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 3-(benzyloxycarbonylamino)propyl 2-acetylamino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS: 876905-87-2
• 化学式: C₂₆H₃₂N₂O₈
• 分子量: 500.549
• InChiKey: UOZGPMCCXXYARC-VRVGQERDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  124.58
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonylamino)propyl 2-acetylamino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.17h， 生成
  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：

  3-(苄氧羰基氨基)-1-丙醇 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-(benzyloxycarbonylamino)propyl 2-acetylamino-4,6-O-benzylidene-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

• Stabilization of Branched Oligosaccharides: Lewis^x Benefits from a Nonconventional C–H···O Hydrogen Bond
  作者：Mirko Zierke、Martin Smieško、Said Rabbani、Thomas Aeschbacher、Brian Cutting、Frédéric H.-T. Allain、Mario Schubert、Beat Ernst

  DOI：10.1021/ja4054702

  日期：2013.9.11

  this C-H···O hydrogen bond is the most prominent factor in stabilization, contributing 40% of the total stabilization energy. We therefore propose that the nonconventional hydrogen bond contributing to a reduction of the conformational flexibility of the Le(x) core represents a novel element of the glycocode. Its relevance to the stabilization of related branched oligosaccharides is currently being studied

  尽管动物凝集素通常对聚糖结构表现出高度的特异性，但它们的单位点结合亲和力通常较弱，这一缺陷在生物系统中通常通过碳水化合物表位的寡价呈现得到补偿。对于单价糖模拟物的设计，有关碳水化合物铅的溶液和结合构象的结构信息代表了一个有价值的起点。在本文中，我们关注三糖 Le(x) (Gal[Fucα(1-3)]β(1-4)GlcNAc) 的构象。主要是由于不利的翻滚机制，到目前为止，通过 NMR 阐明 Le(x) 的溶液构象仅部分成功。因此，Le(x) 与 (13)C,(15)N 标记的蛋白质相连。(13)C, (15) N 过滤的 NOESY NMR 技术在超高场允许增加最大的 NOE 增强，导致每个糖苷键的大量距离限制，因此，一个明确的结构。除了已知的 Le(x) 结构构象限制因素（外异构效应、由与 L-岩藻糖连接位置相邻的 NHAc 基团引起​​的空间压缩，以及 L-岩藻糖与 β- D-半乳糖），鉴定了