2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetaldehyde | 193156-88-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetaldehyde
• 英文别名: 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)ethanal；[(2R,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-(2-oxoethyl)oxan-2-yl]methyl acetate
• CAS: 193156-88-6
• 化学式: C₁₆H₂₂O₁₀
• 分子量: 374.345
• InChiKey: FFERSWWEXDRJFC-RBGFHDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetaldehyde 在 poly(ethylene glycol) supported L-proline 作用下， 以 甲醇 为溶剂， 以99%的产率得到2-(2,3,4,6-tetraacetyl-β-D-galactopyranosyl)acetaldehyde
  参考文献：
  名称：

  合成和亲和力评价的小双齿霍乱毒素配体库：面向不可水解的神经节苷脂模拟物。

  摘要：

  合成并测试了一个以半乳糖和唾液酸为药效学碳水化合物残基的GM1神经节苷脂的不可水解模拟物的小型文库。所有化合物都是使用高效反应（包括点击化学方案）和避免O-糖苷键的高效反应前体合成的。一些活性最高的分子还具有进一步衍生化的特征，可用于与多价糖苷配基结合。通过弱亲和色谱法评估了它们对霍乱毒素的亲和力，从而可以系统地评估和选择最佳候选物。与单个药效团糖残基的亲和力相比，亲和力可以提高一个或两个数量级。

  DOI：

  10.1002/chem.200902469
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetaldehyde
  参考文献：
  名称：

  通过氯肟-硫醇偶联合成糖偶联物

  摘要：

  引入聚糖是改善治疗性生物分子药理学特性的一种有效化学方法。在此，我们报道了通过氯肟-硫醇偶联物高效合成糖缀合物的方法。衍生自吡喃糖或呋喃糖的反应性糖基氯肟很容易与多种含巯基的底物偶联，包括肽、糖和硫酚。该方法具有反应条件温和、动力学快速的特点。水性介质和克级合成的能力证明了该方法在糖类与生物活性分子的生物偶联中的潜力。

  DOI：

  10.1021/acs.joc.4c00356

文献信息

• Synthesis of new C-glycosyl aza-β3-amino acids building blocks
  作者：Manuel Andreini、Anne-Sophie Felten、Hoang-Trang Tran Thien、Claude Taillefumier、Nadia Pellegrini-Moïse、Yves Chapleur

  DOI：10.1016/j.tetlet.2012.03.072

  日期：2012.5

  building blocks have been prepared from C-glycosyl aldehydes of gluco and galacto configuration by reductive amination and subsequent N-alkylation. These moieties were elaborated to β-dipeptides by elongation at the C- or the N-terminus establishing their ability to be incorporated in original glycosylated foldamers.

  新C-糖基化Ñ β -保护的氮杂- β 3 -氨基酸构建块已经从制备Ç的α-糖基醛葡糖和半乳糖构型通过还原胺化和随后的N-烷基化。这些部分通过在C或N端延伸而被精制为β-二肽，从而确立了它们被掺入原始糖基化折叠子的能力。
• First round of a focused library of cholera toxin inhibitors
  作者：Črtomir Podlipnik、Ingrid Velter、Barbara La Ferla、Gilles Marcou、Laura Belvisi、Francesco Nicotra、Anna Bernardi

  DOI：10.1016/j.carres.2007.06.006

  日期：2007.9

  C-Galactosides have been used as scaffolds to design a library of non-hydrolysable inhibitors of cholera toxin (CT). Test elements from the library were synthesized and found to inhibit CT binding to an asialofetuin-coated SPR chip with micromolar affinity. Preliminary results are reported.

  C-半乳糖苷已被用作支架来设计霍乱毒素（CT）的不可水解抑制剂库。合成了来自该文库的测试元件，发现其以微摩尔亲和力抑制CT结合去唾液铁蛋白包被的SPR芯片。报告了初步结果。
• Stereoselective synthesis of neo-C-glycopeptide building blocks: Towards a flexible and control-oriented design as probes for carbohydrate-protein interactions
  作者：Prabhat Arya、Sylvain Dion、George K.H Shimizu

  DOI：10.1016/s0960-894x(97)00255-2

  日期：1997.6

  Neo-C-glycopeptides (1-4) have been synthesized as building blocks to obtain higher neo-C-glycopeptides as probes for studying carbohydrate-protein interactions. A convergent approach for the synthesis of 4 has been developed, in which two galactose units are attached to a glycine derivative in a stepwise procedure (reductive amination followed by amide coupling) and finally coupling to the protected dipeptide having a free amino group on the side chain. (C) 1997 Elsevier Science Ltd.
• α-Galactose based neoglycopeptides. Inhibition of verotoxin binding to globotriosylceramide
  作者：Prabhat Arya、Kristina M.K. Kutterer、Huiping Qin、Johanne Roby、Michael L. Barnes、Shuqiong Lin、Clifford A. Lingwood、Markus G. Peter

  DOI：10.1016/s0968-0896(99)00226-6

  日期：1999.12

  Solution and solid phase strategies for the synthesis of a-galactose based neoglycopeptide derivatives 2-13 were developed. Neoglycopeptides generated were tested for the inhibition of verotoxin binding to globotriosylceramide (Gb3) using ELISA. Among all of the compounds tested, only the lipid derivatives of neoglycopeptides, 11, 12 and 13 were found to be inhibitors, IC50 = 2.0 mM (11b and 12c) and 0.2 mM (11c and 13c). All of the inhibitors (11b, 11c, 12c and 13c) have a similar branching of the two alpha-galactosyl units at the N-terminal glycine residue of a short peptide and a lipid moiety attached at the C-terminal site. Both of these factors seem to be crucial for the inhibition. It is interesting to note that the inhibitors have only a portion of the natural trisaccharide ligand. The secondary groups either may contribute in sub-site oriented interactions with the protein receptors or may mimic the internal sugar units of the cell-surface ligand, Gb3. (C) 1999 Elsevier Science Ltd. All rights reserved.
• <i>C</i>-Linked Galactosyl Serine AFGP Analogues as Potent Recrystallization Inhibitors
  作者：Suhuai Liu、Robert N. Ben

  DOI：10.1021/ol050677x

  日期：2005.6.1

  A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.