2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-[p-(n-decanamido)benzyl]-β-D-glucopyranoside | 210423-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-[p-(n-decanamido)benzyl]-β-D-glucopyranoside
• CAS: 210423-90-8
• 化学式: C₂₁H₂₈N₂O₉
• 分子量: 452.461
• InChiKey: AGWSJEAOFJITNF-PFAUGDHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  152.48
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-[p-(n-decanamido)benzyl]-β-D-glucopyranoside 在 sodium methylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-Acryloylamino-hexanoic acid [4-((2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-phenyl]-amide
  参考文献：
  名称：

  Chemoenzymatic oligosaccharide synthesis on a soluble polymeric carrier

  摘要：

  A facile and efficient method for the chemical and enzymatic syntheses of oligosaccharides using a new type of soluble polymeric sugar acceptor substrate is described. The water soluble glycopolymers having N-acetyl-D-glucosamine (GlcNAc) branches derived from a p-substituted benzyl glycosides were galactosylated with bovine milk galactosyl transferase. The flexible GlcNAc branches of the polymer chains allow quantitative galactosylation and subsequent hydrogenolysis proceeded smoothly to release the desired N-acetyl-lactosamine from the polymer support in high yield.

  DOI：

  10.1016/s0040-4039(00)77272-8
• 作为产物：
  描述：

  nitrobenzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-[p-(n-decanamido)benzyl]-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic oligosaccharide synthesis on a soluble polymeric carrier

  摘要：

  A facile and efficient method for the chemical and enzymatic syntheses of oligosaccharides using a new type of soluble polymeric sugar acceptor substrate is described. The water soluble glycopolymers having N-acetyl-D-glucosamine (GlcNAc) branches derived from a p-substituted benzyl glycosides were galactosylated with bovine milk galactosyl transferase. The flexible GlcNAc branches of the polymer chains allow quantitative galactosylation and subsequent hydrogenolysis proceeded smoothly to release the desired N-acetyl-lactosamine from the polymer support in high yield.

  DOI：

  10.1016/s0040-4039(00)77272-8

文献信息

• Intra- and intermolecular hydrogen bonds enhance the fluoride-responsiveness of functionalized glycolipid-based gelators
  作者：Cheng-Che Tsai、Wei-Tsung Chuang、Yow-Fu Tsai、Jyun-Ting Li、Yu-Fa Wu、Chun-Chen Liao

  DOI：10.1039/c2tb00150k

  日期：——

  We propose a facile approach toward enhancing the efficiency of fluoride-responsive gels through the positioning of functionalized receptor units, allowing tunable intra- and intermolecular hydrogen bonding, in the gelator molecules. We prepared the new glycolipid-based gelator 2 and its hydroxy and methoxy derivatives 2a and 2b, respectively, to study the effects of three types modes of supramolecular assembly: solely intermolecular hydrogen bonding in 2, solely intramolecular hydrogen bonding in 2b, and both inter- and intramolecular hydrogen bonding in 2a. 1H NMR spectra confirmed the self-assembly interactions of these glycolipid-based gelators. We measured the minimum gel concentrations and sol–gel transitions and recorded X-ray diffraction patterns and electron micrographs to characterize the gelation behavior and structural organization of each of these supramolecular gels. Among these three gelators, only 2 and 2a could form organogels in the test solvents, indicating that intermolecular hydrogen bonding plays a determinant role in the supramolecular assemblies leading to gelation. The self-assembly of 2 resulted in a bilayer-packed lamellar structure within ribbon-like fibers, whereas that of 2a resulted in hexagonally packed cylindrical micelles within tree-like fibers. A minimum amount of 0.3 equivalent of F− was required for complete disruption of the gel formed from 2a, which was approximately four times lower than that required for the gel formed from 2. Thus, the incorporation of a β-hydroxy motif—the only difference in the chemical structures of 2 and 2a—led to interesting variations in the resulting gel morphologies and enhanced the gel's fluoride-responsiveness.

  我们提出了一种简便的方法，通过在凝胶剂分子中定位功能化受体单元，增强氟响应凝胶的效率，实现可调节的分子内和分子间氢键。我们制备了新的基于糖脂的凝胶剂2及其羟基和甲氧基衍生物2a和2b，来研究三种超分子组装模式的影响：仅分子间氢键的2，仅分子内氢键的2b，以及同时具备分子间和分子内氢键的2a。1H NMR光谱证实了这些基于糖脂的凝胶剂的自组装相互作用。我们测量了最低凝胶浓度和凝胶-溶液转变，并记录了X射线衍射图谱和电子显微镜图像，以表征每种超分子凝胶的成胶行为和结构组织。在这三种凝胶剂中，只有2和2a能够在测试溶剂中形成有机凝胶，这表明分子间氢键在导致成胶的超分子组装中起着决定性作用。2的自组装形成了带状纤维内的双层堆叠层状结构，而2a的自组装则在树状纤维中形成了六角堆叠的圆柱形胶束。完整破坏由2a形成的凝胶需要最少0.3当量的F−，这大约是形成由2生成的凝胶所需量的四分之一。因此，β-羟基基团的引入——这是2和2a的化学结构中唯一的差异——导致了所形成的凝胶形态的有趣变化，并增强了凝胶的氟响应性。
• High performance polymer supports for enzyme-assisted synthesis of glycoconjugates
  作者：Kuriko Yamada、Eriko Fujita、Shin-Ichiro Nishimura

  DOI：10.1016/s0008-6215(97)10051-9

  日期：1997.12

  Efficient and practical methodology for the construction of carbohydrates, including oligosaccharide derivatives and sphingoglycolipids, was established on the basis of a water-soluble polymer supports having unique linkers that can be cleaved by specific conditions. Novel glycomonomers for the construction of polymer supports were synthesized and copolymerized with acrylamide to give three types of water-soluble glycopolymers having primer sugars through the specific linkers containing (i) p-substituted benzyl group, (ii) L-phenylalanine residue, and (iii) ceramide-mimetic L-serine derivative, respectively. These glycopolymers were employed for sugar elongation reactions with glycosyl transferases such as GlcNAc beta 1,4-galactosyl transferase, beta Gal1-->3/4GlcNAc alpha-2,6-sialyl transferase, and beta Gal1-->3/4GlcNAc alpha-2,3-sialyl transferase in the presence of each sugar nucleotide as glycosyl donor to afford polymers having N-acetyllactosamine, sialyl alpha-(2-->6) N-acetyllactosamine, and sialyl alpha-(2-->3) lactose residues in excellent yield. Subsequent hydrogenolysis, hydrolysis with alpha-chymotrypsin, or transglycosylation to ceramide with ceramide glycanase proceeds smoothly to give N-acetyllactosamine, a versatile sialyl alpha-(2-->6) N-acetyllactosamine derivative having a terminal amino group, and ganglioside GM3 in high yield. (C) 1998 Elsevier Science Ltd.
• Synthesis and modification of spacered glycosides of N-acetylglucosamine
  作者：A. E. Zemlyakov、V. O. Kur'yanov、E. A. Sidorova、T. A. Chupakina、V. Ya. Chirva

  DOI：10.1007/bf02254805

  日期：1997.9